VOLUME  6 5 ,   NO.  1,  JANUARY/FEBRUARY  2 0 0 4  Bioequivalence  Study  o f   T w o   Formulations  o f  Enalapril,  at  a  Single  Oral  Dose  o f   20  mg (Tablets):  A  Randomized,  T w o - W a y ,   Open-Label, Crossover  Study  in  H e a l t h y   Volunteers A n t o n i o   Portol~s,  M D ,   PhD, 1 A n a   Terleira,  M D ,   PhD, 1  Susana  A l m e i d a ,   P h a r m D ,  2 M a r   Garcfa-Arenillas,  M D ,   PhD, ~  M a r i - C r u z   Caturla,  PhD, 3 A u g u s t   Filipe,  M D ,   MSc, 2  and  Emilio  Vargas,  M D ,   PhD ~ Z Unidad  de  Estudios de Farmacologfa Clfnica, Servicio de  Farmacologfa, Clfnica Hospital  Clfnico San  Carlos, Madrid,  Spain, 2Medical  Department,  Tecnimede Sociedade Tdcnico-Medicinal S.A., Prior  Velho, Portugal,  and 3MCC Analftica, Barcelona, Spain A B S T R A C T  Background: Enalapril  m a l e a t e   is  t h e   m o n o e t h y l  e s t e r   p r o d r u g   of  enalapril- at,  a n   a n g i o t e n s i n - c o n v e r t i n g  e n z y m e  i n h i b i t o r  i n d i c a t e d  in  t h e   m a n a g e m e n t  of e s s e n t i a l   a n d   r e n o v a s c u l a r   h y p e r t e n s i o n ,   a n d   in  t h e   t r e a t m e n t   of  c o n g e s t i v e  h e a r t   f a i l u r e  a n d   in a s y m p t o m a t i c  p a t i e n t s  w i t h  left v e n t r i c u l a r  d y s f u n c t i o n  a n d  a n   e j e c t i o n   f r a c t i o n   of  ->35%.  Enalapril  h a s   little  p h a r m a c o l o g i c   a c t i v i t y   until h y d r o l y z e d  in  v i v o   t o   e n a l a p r i l a t .  Objective:  T h e   a i m   of  t h e   p r e s e n t   s t u d y  w a s   t o   c o m p a r e   t h e   b i o a v a i l a b i l i t y  a n d   t o l e r a b i l i t y   of  2  c o m m e r c i a l   b r a n d s   ( t e s t   a n d   r e f e r e n c e   f o r m u l a t i o n s )   of e n a l a p r i l   t a b l e t s   (20  mg),  d e s c r i b e d   as  t h e   r a t e   a n d   e x t e n t   of a b s o r p t i o n   of t h e  a c t i v e   m o i e t y ,   t o   a s s e s s   t h e i r   b i o e q u i v a l e n c e .  Methods:  This  s i n g l e - d o s e ,   r a n d o m i z e d ,   2-way,  open-label,  c r o s s o v e r   s t u d y  in  h e a l t h y  v o l u n t e e r s   a g e d   18  t o   40  y e a r s   w a s   c o n d u c t e d   a t   t h e   Clinical  Phar- m a c o l o g y   S t u d y   Unit,  H o s p i t a l   Clfnico  San  Carlos  (Madrid,  Spain).  S u b j e c t s  w e r e   r a n d o m i z e d   t o   r e c e i v e   ( u n d e r   f a s t i n g  c o n d i t i o n s )   e i t h e r   t h e   t e s t   o r   refer- e n c e   f o r m u l a t i o n  of e n a l a p r i l   (20-mg  t a b l e t )   at  s t u d y  p e r i o d   1 a n d   t h e   o p p o s i t e  f o r m u l a t i o n   a t   s t u d y   p e r i o d   2.  S t u d y   p e r i o d s   w e r e   s e p a r a t e d   b y   a  w a s h o u t  p e r i o d   of at  l e a s t   7 d a y s .  During  e a c h   s t u d y  p e r i o d ,   15 p l a s m a   e x t r a c t i o n s  w e r e  m a d e   t o   d e t e r m i n e   e n a l a p r i l   a n d   e n a l a p r i l a t   p l a s m a   c o n c e n t r a t i o n s   a n d   t o   cal- c u l a t e   t h e   p h a r m a c o k i n e t i c   (PK)  p r o p e r t i e s   ( m a x i m a l   p l a s m a   d r u g   c o n c e n t r a -  t i o n   [C . . . . .   ] ,   t i m e   t o   C . . . . .   [ T  . . . . .   ],  a r e a   u n d e r   t h e   p l a s m a   c o n c e n t r a t i o n -  t i m e   c u r v e   [AUC] t o   t h e   l a s t   m e a s u r a b l e   c o n c e n t r a t i o n   [AUCt], AUC  f r o m  t i m e  0  t o   i n f i n i t y   [AUC0_~], m e a n   r e s i d e n c e   time,  a n d   e l i m i n a t i o n   half-life  [tl/2] )  of b o t h .   P h y s i c a l   e x a m i n a t i o n ,   s u b j e c t   i n t e r v i e w ,   l a b o r a t o r y   a n a l y s e s ,   e l e c t r o c a r -  d i o g r a m ,   a n d   b l o o d   p r e s s u r e   (BP)  w e r e   u s e d   t o   a s s e s s   t o l e r a b i l i t y .  Accepted for publication November 21, 2003. Printed in  the  USA. Reproduction in whole or part is not  permitted.  0011-393X/04/$19.00 34  Copyright  © 2004 Excerpta Medica, Inc. 
A.  Portol~s  et  aL Results:  T w e n t y - f o u r   s u b j e c t s   w e r e   i n c l u d e d   i n   t h e   s t u d y   (12  m e n ,  12  w o m e n ;   m e a n   [SD]  age,  22.8  [2.2]  y e a r s   [range,  19-30  y e a r s ] ) .   Of  t h e s e ,  1  s u b j e c t   (4.2%)  w i t h d r e w   f r o m   t h e   s t u d y   f o r   p e r s o n a l   r e a s o n s ;   t h u s ,   PK  a n d  s t a t i s t i c a l  a n a l y s e s  i n c l u d e d  r e s u l t s  f r o m  23 s u b j e c t s .   No s t a t i s t i c a l l y  s i g n i f i c a n t  s e q u e n c e   o r   p e r i o d   e f f e c t   w a s   f o u n d .   T . . . .   w a s   n o t   s t a t i s t i c a l l y   d i f f e r e n t   be- t w e e n   t h e   2  f o r m u l a t i o n s ,  a n d   t h e   90%  CI c a l c u l a t e d   f o r   T . . . .   for t h e   d i f f e r e n c e  of  t h e   m e d i a n s   w a s   w i t h i n   t h e   p r e d e f i n e d   r a n g e .   T h e   90%  CIs  of  t h e   l o g a r i t h -  mically t r a n s f o r m e d  c o n c e n t r a t i o n - d e r i v e d  p a r a m e t e r s   (C . . . . .   AUCt, a n d   AUC0_~) a l s o  w e r e   w i t h i n  t h e   p r e d e f i n e d   range;  t h u s ,   t h e   2  f o r m u l a t i o n s  a r e   c o n s i d e r e d  b i o e q u i v a l e n t .  For b o t h   f o r m u l a t i o n s ,  s y s t o l i c  a n d   d i a s t o l i c  BPs  s h o w e d   signifi- c a n t  r e d u c t i o n s  c o m p a r e d  w i t h  b a s e l i n e  v a l u e s  (P < 0.05).  Seven a d v e r s e  e f f e c t s  w e r e   r e c o r d e d ,   all  of  t h e m   t r a n s i e n t   a n d   n o n e   of  s e v e r e   i n t e n s i t y .  Conclusions:  In  t h i s   s t u d y   of  2  c o m m e r c i a l   b r a n d s   ( t e s t   a n d   r e f e r e n c e   for- m u l a t i o n s )   of  e n a l a p r i l   in  h e a l t h y   s u b j e c t s ,   d e s i g n e d   a n d   c o n d u c t e d   u n d e r  Good  Clinical  P r a c t i c e   g u i d e l i n e s ,   a  s i m i l a r   r a t e   a n d   e x t e n t   of  a b s o r p t i o n   for b o t h   f o r m u l a t i o n s  w e r e  f o u n d  t o   b e  b i o e q u i v a l e n t .  B o t h  f o r m u l a t i o n s  p r o d u c e d  a  s i g n i f i c a n t  d e c r e a s e  in BP v a l u e s   a n d   w e r e   g e n e r a l l y  well t o l e r a t e d .   (Curr Ther Res  Clin Exp.  2004;65:34--46)  C o p y r i g h t  ©  2004  E x c e r p t a   Medica,  Inc. K e y   w o r d s :   b i o e q u i v a l e n c e ,   b i o a v a i l a b i l i t y ,   p h a r m a c o k i n e t i c s ,   e n a l a p r i l ,  e n a l a p r i l a t ,   h e a l t h y  v o l u n t e e r s ,   clinical  trial,  b l o o d   p r e s s u r e .  I N T R O D U C T I O N  T h e   u s e   of  g e n e r i c   d r u g s   is  of i n c r e a s i n g   i m p o r t a n c e ,   in  t e r m s   of  efficiency, in t h e   s e l e c t i o n   of  t h e r a p e u t i c   a l t e r n a t i v e s .   But  t h e i r   u s e   in  clinical  p r a c t i c e   de- p e n d s   n o t   o n l y  o n   t h e i r   " e s s e n t i a l  s i m i l a r i t y "  (in  t e r m s   of f o r m u l a t i o n ,  c o m p o -  sition,  a n d   b i o e q u i v a l e n c e   as  c o n s i d e r e d   b y   r e g u l a t o r y   a g e n c i e s ) ,   b u t   m o s t l y  o n   t h e   c o n v i c t i o n  of t h e i r   i n t e r c h a n g e a b i l i t y  w i t h  t h e i r   r e f e r e n c e  c o u n t e r p a r t s .  T h u s ,   t h e   p u b l i c a t i o n  of t h e   c o m p a r a t i v e   b i o a v a i l a b i l i t i e s  of t e s t   a n d   r e f e r e n c e  f o r m u l a t i o n s   is  s i g n i f i c a n t   for  t h e   k n o w l e d g e   a n d   a p p r o p r i a t e   a s s e s s m e n t   b y  t h e  s c i e n t i f i c  c o m m u n i t y  of w h a t   t h e y  a r e   d e a l i n g  w i t h .  W h e n   2 f o r m u l a t i o n s  of t h e   s a m e   d r u g   p r e s e n t   s i m i l a r   b i o a v a i l a b i l i t i e s  t o   t h e   e x t e n t   t h a t   t h e y   a r e   con- s i d e r e d   b i o e q u i v a l e n t  b y  c e r t a i n  c r i t e r i a   (ie,  t h o s e   d e s c r i b e d   b y  t h e   C o m m i t t e e  for  P r o p r i e t a r y   M e d i c i n a l   P r o d u c t s  1 [CPMP]),  it  is  a s s u m e d   t h a t   w h e n   a d m i n -  i s t e r e d   in  t h e   s a m e   m o l a r   d o s e ,   t h e y  will  p r o v i d e   t h e   s a m e   t h e r a p e u t i c   effect, o r   t h e y  will  b e   t h e r a p e u t i c a l l y  e q u i v a l e n t .  2 Enalapril m a l e a t e  is t h e  m o n o e t h y l  e s t e r  p r o d r u g  of enalaprilat, an  angiotensin- c o n v e r t i n g  e n z y m e  (ACE) inhibitor,  t h a t   a c t s   b y   d e c r e a s i n g  p l a s m a   a n g i o t e n s i n  II a n d   a l d o s t e r o n e   l e v e l s ,   c o n s e q u e n t l y   d e c r e a s i n g   b l o o d   p r e s s u r e   (BP)  b y  d e c r e a s i n g   p e r i p h e r a l   v a s c u l a r   r e s i s t a n c e .  3'4 It is  i n d i c a t e d   in  t h e   m a n a g e m e n t  of  all  g r a d e s   of  e s s e n t i a l   a n d   r e n o v a s c u l a r   h y p e r t e n s i o n ,   as  well  as  in  t h e  t r e a t m e n t   of  c o n g e s t i v e   h e a r t   f a i l u r e   a n d   in  a s y m p t o m a t i c   p a t i e n t s   w i t h   left v e n t r i c u l a r   d y s f u n c t i o n  a n d   a n   e j e c t i o n   f r a c t i o n   of  ~35%. 4  3 5  
CURRENT THERAPEUTIC RESEARCH @ Enalapril  h a s   little  p h a r m a c o l o g i c   a c t i v i t y  until  h y d r o l y z e d  in  v i v o   t o   enala- prilat.  Unlike e n a l a p r i l a t ,  t h e  p r o d r u g   is well a b s o r b e d   a f t e r  o r a l   a d m i n i s t r a t i o n ,  w i t h   a n   o r a l   a b s o r p t i o n   of  55%  t o   75%  c o m p a r e d   w i t h   3%  t o   12%  f o r   enalapril- at. 3'4 T h e  m a x i m a l  p l a s m a  d r u g  c o n c e n t r a t i o n  (Cma~) for t h e  p r o d r u g   is r e a c h e d  w i t h i n   -1  h o u r   a f t e r   o r a l   a d m i n i s t r a t i o n ,  w h e r e a s   C . . . .   for  e n a l a p r i l a t   is  s o m e -  w h a t   d e l a y e d   (3-4  h o u r s   a f t e r   o r a l   a d m i n i s t r a t i o n ) .  3'4  P l a s m a   e n a l a p r i l a t   con- c e n t r a t i o n s   a r e   r e p o r t e d l y   l i n e a r l y   r e l a t e d   t o   t h e   a d m i n i s t e r e d   d o s e   o v e r   t h e  t h e r a p e u t i c   r a n g e   (2.5-40.0  m g ) .  3  E n a l a p r i l a t   is  -50%  b o u n d   t o   p l a s m a   pro- t e i n s .  3  Renal  e x c r e t i o n   is  t h e   p r i m a r y   r o u t e   of  e l i m i n a t i o n .   T h e   e l i m i n a t i o n  half-life (tl/2)  of u n c h a n g e d   e n a l a p r i l  is >2  h o u r s   in h e a l t h y  s u b j e c t s .  3 For  enala- prilat,  p o l y p h a s i c   e l i m i n a t i o n   k i n e t i c   p r o p e r t i e s   h a v e   b e e n   r e p o r t e d ,   w i t h   a n  initial tl/2  of - 5   h o u r s   a n d   a  r e p o r t e d   t e r m i n a l   half-life of  30  t o   35  h o u r s  3 or,  in o t h e r   c a s e s ,  4 35  t o   38  h o u r s   ( r a n g e ,   30-87  h o u r s ) ,   p r o b a b l y   r e f l e c t i n g  its  bind- ing  t o   t h e   high-affinity,  l o w - c a p a c i t y   b i n d i n g   s i t e   of  c i r c u l a t i n g   s e r u m   ACE. 4 S o m e  e v i d e n c e  s h o w s   a  c o r r e l a t i o n  b e t w e e n   p l a s m a  e n a l a p r i l a t  c o n c e n t r a t i o n s  a n d   p l a s m a  ACE a c t i v i t y  a n d   a  p o s s i b l e   c o r r e l a t i o n  b e t w e e n   t h e s e   p l a s m a  con- c e n t r a t i o n s   a n d   d e c r e a s e s   in  BP. 5 A d v e r s e   e f f e c t s  (AEs)  t h a t   o c c u r  w i t h   e n a l a p r i l   t h e r a p y  u s u a l l y  a r e   mild  a n d  t r a n s i e n t ,   o c c u r r i n g  in <10% of p a t i e n t s .  6 T h e   m o s t   t y p i c a l  AEs  a s s o c i a t e d  w i t h  e n a l a p r i l  u s e  i n c l u d e  h e a d a c h e ,   d i z z i n e s s ,  fatigue, d i a r r h e a ,  n a u s e a  a n d / o r  vom- iting,  r a s h ,   c o u g h ,   a n d   h y p o t e n s i o n .  6 In  3%  t o   6%  of  p a t i e n t s ,   t h e r a p e u t i c   dis- c o n t i n u a n c e  o c c u r s   as  a c o n s e q u e n c e  of d r y ,  p e r s i s t e n t  c o u g h ,  f o l l o w e d  b y  r a r e  c a s e s   (<1%)  of  a n g i o e d e m a ,   h y p o t e n s i o n ,  h y p e r k a l e m i a ,   o r   a c u t e   r e n a l   failure. In  t h e   p r e s e n t   s t u d y ,   t h e   b i o e q u i v a l e n c e   of  2  c o m m e r c i a l   b r a n d s   ( t e s t   a n d  r e f e r e n c e )   of  e n a l a p r i l   t a b l e t s   (20  mg)  w a s   a s s e s s e d   b y   c o m p a r i s o n   of  t h e i r  p h a r m a c o k i n e t i c   (PK)  p r o p e r t i e s   t h a t   d e s c r i b e   t h e   r a t e   a n d   e x t e n t   o f  a b s o r p t i o n - - a r e a  u n d e r  t h e  p l a s m a  c o n c e n t r a t i o n - t i m e  c u r v e   (AUC),  C . . . . .   a n d  t i m e   t o   C . . . . .   ( T m a x ) .  SUBJECTS AND  METHODS S t u d y   D e s i g n  T h i s   s i n g l e - d o s e ,   r a n d o m i z e d ,   2-way,  o p e n - l a b e l ,   c r o s s o v e r   s t u d y   w a s   con- d u c t e d   a t   t h e   Clinical  P h a r m a c o l o g y   S t u d y   Unit,  H o s p i t a l   Clinico  San  Carlos (Madrid,  Spain).  T h e  p r o t o c o l  w a s   a p p r o v e d   b y  t h e  h o s p i t a l  Ethical  C o m m i t t e e  a n d   w a s   a u t h o r i z e d   b y   t h e   S p a n i s h   M i n i s t r y   of  Health.  It  w a s   d e v e l o p e d   ac- c o r d i n g   t o   t h e   r e v i s e d   p r i n c i p l e s   of t h e   D e c l a r a t i o n  of Helsinki  (World  Medical A s s o c i a t i o n  r e v i s e d   S o m e r s e t  West,  1996)  a n d  t h e   Good Clinical P r a c t i c e   Guide- lines  ( I n t e r n a t i o n a l   C o n f e r e n c e  o n   H a r m o n i z a t i o n ,   1996). Subjects S u b j e c t s   w e r e   s e l e c t e d   f r o m   a  p a n e l   of  h e a l t h y   v o l u n t e e r s   r e c r u i t e d   b y   t h e  Clinical  P h a r m a c o l o g y   S t u d y   Unit.  I n c l u s i o n   c r i t e r i a   w e r e   age  18  t o   40  y e a r s ,  b o d y  w e i g h t  50 t o   100 kg,  a n d  b o d y  m a s s   i n d e x   18 t o   27 k g / m  2. All s u b j e c t s  w e r e  36 
A.  Portol~s et aL e x a m i n e d   t o   v e r i f y   t h e i r   h e a l t h y   s t a t u s ;   t h e s e   e x a m i n a t i o n s   i n c l u d e d   m e d i c a l  h i s t o r y   taking,  vital  s i g n   m e a s u r e m e n t s ,   e l e c t r o c a r d i o g r a p h y   (ECG),  b l o o d  s a m p l e   a n a l y s i s   ( b a s i c   profile,  c o m p l e t e   b l o o d   cell  c o u n t ,   p r o t h r o m b i n   time, viral  s e r o l o g y ) ,   a n d   u r i n a l y s i s  ( s e d i m e n t ,   d r u g s ,   p r e g n a n c y  t e s t ) .   S u b j e c t s   w i t h  r e l e v a n t   clinical,  a n a l y t i c a l ,  o r   ECG a b n o r m a l i t i e s  w e r e   e x c l u d e d  f r o m  t h e   trial. A d d i t i o n a l   e x c l u s i o n   c r i t e r i a   w e r e   as  follows:  s m o k i n g ;   h i s t o r y   of  a l c o h o l   o r  o t h e r   d r u g   a b u s e ;   h i g h  c o n s u m p t i o n  (>8 c u p s / d )   of s t i m u l a t i n g  b e v e r a g e s ;   con- s u m p t i o n   of  m e d i c a t i o n   t h a t   c o u l d   a f f e c t   t h e   d r u g   u n d e r   s t u d y   (eg,  a n t a c i d s ,  a n t i d e p r e s s a n t s ) ;   r e g u l a r  c o n s u m p t i o n  of a n y  m e d i c a t i o n  in t h e   2 w e e k s  b e f o r e  e n r o l l m e n t ;   c o n s u m p t i o n   of  a n y   e n z y m e   i n h i b i t o r s   o r   i n d u c e r s   in  t h e   m o n t h  b e f o r e   e n r o l l m e n t ;  p a r t i c i p a t i o n   in  a  clinical trial  in  t h e   2 m o n t h s   b e f o r e   enroll- m e n t   o r   4  t i m e s   in  t h e   y e a r   b e f o r e   e n r o l l m e n t ;   h i s t o r y   of  c l i n i c a l l y  i m p o r t a n t  illness o r   m a j o r  s u r g e r y  in t h e   3 m o n t h s  b e f o r e  e n r o l l m e n t ;  i n a b i l i t y  t o  r e l a t e  t o  a n d / o r   c o o p e r a t e   w i t h   t h e   i n v e s t i g a t o r s ;   m e d i c a t i o n   allergy; i l l n e s s e s   o r   disor- d e r s   t h a t   c o u l d   a f f e c t   t h e   a b s o r p t i o n ,   d i s t r i b u t i o n ,   m e t a b o l i s m ,   a n d / o r   excre- t i o n   of  d r u g s   (eg,  m a l a b s o r p t i o n ,   e d e m a s ,   r e n a l   a n d / o r   h e p a t i c   failure);  a  his- t o r y  of p o s i t i v e  s e r o l o g y  f o r  h e p a t i t i s   B o r   C ( n o t   d u e   t o   i m m u n i z a t i o n )  o r   HIV; b l o o d   l o s s   o r   d o n a t i o n   >200  mL  in  t h e   3  m o n t h s   b e f o r e   e n r o l l m e n t ;   b l o o d   o r  b l o o d - d e r i v a t i v e  t r a n s f u s i o n  in t h e   6 m o n t h s  b e f o r e  e n r o l l m e n t ;  a n d   e x h a u s t i n g  p h y s i c a l   e x e r c i s e   in  t h e   72  h o u r s   b e f o r e   e n r o l l m e n t .   P r e g n a n t ,   p o s s i b l y   preg- n a n t ,   o r   b r e a s t f e e d i n g  w o m e n   w e r e   e x c l u d e d   f r o m   t h e   s t u d y .   W o m e n   of  child- b e a r i n g   a g e   w e r e   r e q u i r e d   t o   u s e   a n   e f f e c t i v e  m e t h o d   of  b i r t h   c o n t r o l   ( e x c e p t  o r a l   a n o v u l a t o r y   d r u g s )   t h r o u g h o u t   t h e   s t u d y .   All  eligible  s u b j e c t s   p r o v i d e d  w r i t t e n   i n f o r m e d   c o n s e n t   t o   p a r t i c i p a t e .  M e t h o d s  S u b j e c t s   w e r e   a d m i t t e d   t o   t h e   s t u d y   u n i t   at  - 8   PM o n   e a c h   of  t h e   2  e v e n i n g s  b e f o r e  s t u d y  d r u g   a d m i n i s t r a t i o n .  Clinical e n t r y  c o n t r o l s   ( p h y s i c a l  e x a m i n a t i o n  a n d   s u b j e c t   i n t e r v i e w )   w e r e   p e r f o r m e d ,   a n d   all  s u b j e c t s   r e c e i v e d   a  s t a n d a r d  d i n n e r   ( b a l a n c e d   c o m p o s i t i o n  w i t h   -25%  of  d a i l y  c a l o r i e s ) .   S u b j e c t s   f a s t e d   for at  l e a s t   10  h o u r s   b e f o r e   a n d   4  h o u r s   a f t e r   s t u d y   d r u g   a d m i n i s t r a t i o n .  S u b j e c t s   w e r e   r a n d o m i z e d ,   a c c o r d i n g   t o   a  c o m p u t e r - g e n e r a t e d   r a n d o m i z a -  t i o n   t a b l e   of s e q u e n c e s ,   t o   r e c e i v e   e i t h e r   t h e   t e s t *   o r   r e f e r e n c e  ~ f o r m u l a t i o n  of e n a l a p r i l   (20-mg t a b l e t )   a t  s t u d y  p e r i o d   1 a n d   t h e  o p p o s i t e   f o r m u l a t i o n  a t  s t u d y  p e r i o d   2.  S t u d y  p e r i o d s   w e r e   s e p a r a t e d   b y   a  w a s h o u t   p e r i o d   of a t   l e a s t   7  d a y s .  Drug  a d m i n i s t r a t i o n   s t a r t e d   a t   8  AM,  a n d   v o l u n t e e r s   r e c e i v e d   t h e   m e d i c a t i o n  w i t h   150  mL of  w a t e r   at  r o o m   t e m p e r a t u r e   b y   a  n u r s e .  D r u g   Analysis Blood s a m p l e s  of - 1 0   mL e a c h  w e r e   d r a w n  b y  a n u r s e   a t   15 t i m e  p o i n t s :  b a s e l i n e  ( i m m e d i a t e l y   b e f o r e   s t u d y   d r u g   a d m i n i s t r a t i o n ) ;   30,  45,  60,  75,  105,  135,  180, *Trademark:  Enalapril Farmoz ® (Tecnimede  Sociedade T~cnico-Medicinal  S.A., Prior Velho,  Portugal). tTrademark:  Renitec ® (Merck  Sharp &  Dohme,  Lda., Pa(~o de Arcos, Portugal).  37 
CURRENT THERAPEUTIC RESEARCH ® 195,  a n d   225  m i n u t e s ;   a n d   5,  8,  12,  24,  a n d   36  h o u r s   a f t e r   s t u d y   d r u g   a d m i n i s -  t r a t i o n .   S a m p l e s   w e r e   c e n t r i f u g e d   at  3000  r p m   for  10  m i n u t e s   ( a t   4°C),  a n d   t h e  o b t a i n e d   p l a s m a   s a m p l e s   w e r e   s e p a r a t e d   in  t w o   1.5-mL a l i q u o t s   a n d   s t o r e d   in s u i t a b l y  l a b e l e d ,   t i g h t l y  s e a l e d   t u b e s   at -30°C.  After 24 h o u r s ,   t h e  s a m p l e s  w e r e  t r a n s f e r r e d   t o   -80°C.  V o l u n t e e r s   r e m a i n e d   u n d e r   m e d i c a l   s u p e r v i s i o n   a t   t h e  s t u d y   c e n t e r   u n t i l   12  h o u r s   a f t e r   s t u d y   d r u g   a d m i n i s t r a t i o n ,   a n d   r e t u r n e d   at 24  a n d   36  h o u r s   a f t e r   a d m i n i s t r a t i o n  for  t h e   l a s t   e x t r a c t i o n s .  A n a l y t i c a l  d e t e r m i n a t i o n  of p l a s m a  d r u g  a n d  m e t a b o l i t e  c o n c e n t r a t i o n s  w e r e  p e r f o r m e d  b y  MCC AnaHtica S.A. ( B a r c e l o n a ,   Spain)  a n d   f o l l o w e d  a n   a c i d  s o l i d -  liquid  e x t r a c t i o n   w i t h   a  r e v e r s e d - p h a s e   h i g h - p r e s s u r e   liquid  c h r o m a t o g r a p h y  s e p a r a t i o n   a n d   m a s s   s p e c t r o m e t r y   d e t e c t o r .   Lisinopril w a s   u s e d   as  a n   i n t e r n a l  s t a n d a r d .   T h e   m e t h o d   of  a n a l y s i s   w a s   v a l i d a t e d   u n d e r   t h e   p r i n c i p l e s   of  Good L a b o r a t o r y   P r a c t i c e   t h r o u g h   t h e   f o l l o w i n g   p a r a m e t e r s :   l i n e a r i t y ,   p r e c i s i o n ,  i n t r a - a s s a y  a n d   i n t e r a s s a y  a c c u r a c y ,   limit of q u a n t i f i c a t i o n  (LOQ),  v a l i d a t i o n  of t h e   d i l u t i o n  f a c t o r ,  s p e c i f i c i t y ,  s t a b i l i t y ,  a n d  r e c o v e r y .  T h e   a n a l y t i c a l  p a r t   of t h e  s t u d y  w a s   d e v e l o p e d   b l i n d l y .  Pharmacokinetic  Analysis PK p r o p e r t i e s   w e r e   c a l c u l a t e d   b y   a  n o n c o m p a r t m e n t a l   a p p r o a c h   f r o m   p l a s m a  c o n c e n t r a t i o n s   of  e n a l a p r i l   a n d   e n a l a p r i l a t ,   u s i n g   WinNonlin P r o   s o f t w a r e  ver- s i o n  2.1  ( P h a r s i g h t  C o r p o r a t i o n ,  M o u n t a i n  View,  California). C . . . .  w a s   e s t i m a t e d  d i r e c t l y   f r o m   o b s e r v e d   c o n c e n t r a t i o n s ,   a n d   T .....  as  t h e   c o r r e s p o n d i n g   t i m e  p o i n t   at  w h i c h   C .....  o c c u r r e d .   AUCt w a s   c a l c u l a t e d   b y   t h e   l i n e a r   t r a p e z o i d a l  m e t h o d   until  t h e   l a s t   m e a s u r a b l e   p l a s m a   d r u g   c o n c e n t r a t i o n ,   a n d   AUC  f r o m  t i m e   0  t o   i n f i n i t y  (AUC0_~) w a s   c a l c u l a t e d   as: AUC0_~ =  AUC t  +  Ct/K e, w h e r e   Ct  is  t h e   p l a s m a   d r u g   c o n c e n t r a t i o n   a t   t i m e   t  a n d   Ke  is  t h e   e l i m i n a t i o n  r a t e   c o n s t a n t .   T h e   m e a n   r e s i d e n c e   t i m e   (MRT0_~) a n d   tl/2  a l s o  w e r e   c a l c u l a t e d  a n d   p r e s e n t e d   for  d e s c r i p t i v e   p u r p o s e s .   Given t h e   i n a c t i v e  n a t u r e   of  enalapril, t h e   PK  p r o p e r t i e s   of  e n a l a p r i l a t   w e r e   d e f i n e d   as  p r i m a r y   a s s e s s m e n t   c r i t e r i a .  AUC  is  c o n s i d e r e d   t h e   m o s t   r e p r e s e n t a t i v e   p a r a m e t e r   of  b i o e q u i v a l e n c e .  Tolerability  Assessment For  t o l e r a b i l i t y  a s s e s s m e n t ,   clinical  c o n t r o l s   (vital  c o n s t a n t s ,   eg,  BP,  t e m p e r a -  t u r e ,   o r   h e a r t   r a t e ,   a n d   t h e   q u e s t i o n   o n   AE)  w e r e   p e r f o r m e d   a t   5,  12,  24,  a n d  36  h o u r s   a f t e r   s t u d y   d r u g   a d m i n i s t r a t i o n .   L a b o r a t o r y   a n a l y s e s   a n d   ECG  a l s o  w e r e   p e r f o r m e d   a t   p r e s t u d y   a n d   p o s t s t u d y   t i m e s .   T o l e r a b i l i t y  of  t h e   2  f o r m u -  l a t i o n s   w a s   t h e   s e c o n d a r y   a s s e s s m e n t   c r i t e r i o n ;   t h u s ,   o n l y   d e s c r i p t i v e   s t a t i s -  t i c s   w e r e   f o r e s e e n   a n d   p e r f o r m e d .  Statistical  Analysis T h e  s a m p l e  s i z e  n e e d e d  f o r  >90% p o w e r  w a s   d e t e r m i n e d  u s i n g  PC-SIZE s o f t w a r e  v e r s i o n   1.0  ( S t a t T o o l s  TM, P a l i s a d e   C o r p o r a t i o n ,   Newfield,  New  York)  a n d   vari- a b i l i t y   d a t a   f r o m   a  p r e v i o u s l y  p u b l i s h e d   s t u d y .  7 38 
A.  Portol(~s  et  aL C o n c e n t r a t i o n - d e r i v e d  p a r a m e t e r s  w e r e  a n a l y z e d  (WinNonlin, P h a r s i g h t  Cor- p o r a t i o n ,   M o u n t a i n  View,  California) u s i n g   a  p a r a m e t r i c   m e t h o d ,   c o n d u c t e d  b y  m e a n s   of a n a l y s i s  of v a r i a n c e   (ANOVA), u s i n g   as  d e p e n d e n t  v a r i a b l e s   t h e   loga- r i t h m i c   t r a n s f o r m a t i o n s   (Ln)  of  t h e   t e s t / r e f e r e n c e   r a t i o s   of  t h e   p a r a m e t e r s  AUC0_~, AUC t,  C . . . . .   a n d   Cmax/AUC0_~. In  t h e   a n a l y s i s ,   t h e   following m o d e l   ef- f e c t s   w e r e   c o n s i d e r e d :   form,  p e r i o d ,   s e q u e n c e ,   a n d   v o l u n t e e r   ( s e q u e n c e ) .   T h e  90%  CIs w e r e   c a l c u l a t e d   for  t h e s e   r a t i o s   a n d   u s e d   as  b i o e q u i v a l e n c e - a s s e s s m e n t  c r i t e r i a .   A c c e p t a n c e   c r i t e r i a   f o r   t h e   90%  CIs  w e r e   p r o s p e c t i v e l y   d e f i n e d   in  t h e  s t u d y  p r o t o c o l   as  80%  t o   125% f o r   Ln AUC  r a t i o s   a n d   70%  t o   143% for  Ln  C . . . .  r a t i o s .   T h e   T . . . . .   s  f r o m  b o t h   f o r m u l a t i o n s  w e r e   c o m p a r e d   u s i n g   a  n o n p a r a m e t -  ric  m e t h o d   (CI  of  t h e   m e d i a n   of  t h e   d i f f e r e n c e s   b y   t h e   W i l c o x o n   s i g n e d   r a n k  t e s t ) ,   a n d   t h e   a c c e p t a n c e   c r i t e r i o n   f o r   t h i s   p a r a m e t e r   w a s   70%  t o   130%. RESULTS Subjects T w e n t y - f o u r   w h i t e   h e a l t h y   v o l u n t e e r s   w e r e   i n c l u d e d   in  t h e   s t u d y   (12  m e n ,  12 w o m e n ;  m e a n   [SD] age, 22.8  [2.2]  y e a r s   [range,  19-30 y e a r s ] ;  m e a n   [SD] b o d y  w e i g h t ,   65.1  [12.4]  kg  [men,  75.3  (9.1)  kg;  w o m e n ,   54.9  (4.6)  kg];  m e a n   [SD] h e i g h t ,   173.0  [10.2]  c m   [men,  182.7  (4.6)  cm;  w o m e n ,   163.9  (3.6)  c m ] ) .   One s u b j e c t   (4.2%)  w i t h d r e w   b e t w e e n   s t u d y   p e r i o d s   f o r   p e r s o n a l   r e a s o n s .   T h e   re- s u i t s   of  23  s u b j e c t s   w e r e   i n c l u d e d   in  t h e   PK  a n a l y s i s .  Analytical  Assay A s s e s s m e n t   of  PK  p a r a m e t e r s   d e t e r m i n e d   t h e   a d e q u a c y   of  t h e   a n a l y t i c a l  m e t h o d   f o r   t h e   d e t e r m i n a t i o n   of  p l a s m a   d r u g   a n d   m e t a b o l i t e   c o n c e n t r a t i o n s .  T h e   LOQ  w a s   s e t   at  1 n g / m L  f o r   b o t h   e n a l a p r i l   a n d   e n a l a p r i l a t .  M e a n   p l a s m a   d r u g   c o n c e n t r a t i o n s   of  e n a l a p r i l   a n d   e n a l a p r i l a t   f o r   b o t h   t h e  t e s t   a n d   r e f e r e n c e   f o r m u l a t i o n s   a r e   p r e s e n t e d   in  F i g u r e   1.  No  p r e d o s e   d e t e c t -  a b l e   levels  w e r e   f o u n d   in  a n y   of  t h e   s u b j e c t s   in  e i t h e r   t r e a t m e n t   p e r i o d .  P h a r m a c o k i n e t i c  Analysis T h e   PK  p r o p e r t i e s   of  e n a l a p r i l   a n d   e n a l a p r i l a t   a r e   s u m m a r i z e d   in  T a b l e   I  a n d  T a b l e   II.  M e a n   (SD)  C ..... s  of  118.58  (52.38)  n g / m L   a n d   134.63  (56.28)  n g / m L  ( e n a l a p r i l )   a n d   70.02  (31.90)  n g / m L   a n d   73.60  (30.31)  n g / m L   ( e n a l a p r i l a t )   for t e s t   o r   r e f e r e n c e   f o r m u l a t i o n s ,   r e s p e c t i v e l y ,   w e r e   a t t a i n e d   a t   m e d i a n   T ..... s  of 0.96  a n d   0.90  h o u r s   ( e n a l a p r i l )   a n d   3.25  a n d   3.39  h o u r s   ( e n a l a p r i l a t )   ( r e s p e c -  tively,  f o r   t e s t   a n d   r e f e r e n c e   f o r m u l a t i o n s ) .   R e s u l t s   of  MRT0_~ a n d   tl/2  a r e  s h o w n   in  T a b l e s   I  a n d   II.  All  s u b j e c t s   (100.0%)  p r e s e n t e d   a n   AUCt/AUC0_~ r a t i o   >80%, a n d   t h e   ANOVA of  Ln  C . . . . .   AUC t,  a n d   AUC0_~ s h o w e d   n o   s t a t i s t i -  c a l l y   s i g n i f i c a n t   s e q u e n c e   o r   p e r i o d   effect.  T h e   o b t a i n e d   90%  CIs  for  t h e   pa- r a m e t e r   r a t i o s   a r e   p r e s e n t e d   in  T a b l e   III. T h e   r a t i o s   a n d   t h e i r   90%  CIs  c a l c u l a t e d   for  t h e   L n - t r a n s f o r m e d  p a r a m e t e r s  for e n a l a p r i l  w e r e   Ln C . . . . .   88.90%  (77.35%-102.16%);  Ln AUCt, 94.08% (87.14%- 39 
CURRENT THERAPEUTIC RESEARCH ® 1 4 0 -  ,007   A , . I  e  I o  - ;   17  ~ k -   EnalapriI-R --o-  EnalapriI-T - O -   Enalaprilat-R Enalaprilat-T 2'4  36 T i m e   A f t e r   S t u d y   D r u g   A d m i n i s t r a t i o n   ( h )  Figure  1.  Plasma  d r u g   concentrations  of  the  test  (T;  trademark:  Enalapril  Farmoz ®,  Tec- nimede  Sociedade  T~cnico-Medicinal  S.A.,  Prior  Velho,  Portugal)  and  reference  (R;  trade- mark:  Renitec ®,  Merck  Sharp  &  Dohme,  Lda.,  Pa(~o de  Arcos,  Portugal)  formulations  of enalapril  ( p r o d r u g )   and  enalaprilat  (active  metabolite)  (N  =  23  subjects). 101.58%);  a n d   Ln  AUC0_~, 94.19% (87.42%-101.49%).  T h e   r e s p e c t i v e   v a l u e s   f o r  e n a l a p r i l a t  w e r e   92.98%  (83.56%-103.46%)  f o r  Ln C . . . . .   95.87%  (88.60%-103.74%) f o r   Ln AUCt, a n d   96.27%  (89.20%-103.91%)  for  Ln AUC0_~. All  of  t h e   c a l c u l a t e d  i n t e r v a l s   w e r e   w i t h i n   t h e   p r e d e f i n e d   b i o e q u i v a l e n c e   r a n g e s ;   also,  90%  CIs  ob- t a i n e d   f o r   t h e   m e d i a n   of  d i f f e r e n c e s  of  T . . . .   w e r e   w i t h i n   p r e d e f i n e d   r a n g e s   f o r  b o t h   e n a l a p r i l   (86.14%-113.86%)  a n d   e n a l a p r i l a t   (88.90%-100.00%). T o l e r a b i l i t y  All  24  s u b j e c t s   w e r e   i n c l u d e d   in  t h e   t o l e r a b i l i t y  a s s e s s m e n t .   During t h e   c o u r s e  of  t h e   s t u d y ,   7  AEs  w e r e   r e p o r t e d .   Five  p o s s i b l y   t r e a t m e n t - r e l a t e d   AEs  w e r e  r e c o r d e d   ( d i z z i n e s s ,   2  s u b j e c t s   [8.3%];  fatigue,  h e a d a c h e ,   a n d   s o m n o l e n c e ,  1 s u b j e c t   e a c h   [4.2%]).  One s u b j e c t   (4.2%) e x p e r i e n c e d   an AE w i t h  d o u b t f u l  treat- m e n t   r e l a t i o n s h i p   ( d i a r r h e a ) ,   a n d   1 s u b j e c t   (4.2%)  e x p e r i e n c e d   a n   AE t h a t   w a s  n o t   t r e a t m e n t   r e l a t e d   ( d i z z i n e s s ) .   All AEs  w e r e   mild  e x c e p t   1 c a s e   of d i z z i n e s s ,  w h i c h   w a s   m o d e r a t e .   All AEs  r e s o l v e d   c o m p l e t e l y  a n d   s p o n t a n e o u s l y .  Six  AEs o c c u r r e d   d u r i n g   a d m i n i s t r a t i o n   of  t h e   r e f e r e n c e   f o r m u l a t i o n ,   a n d   1  o c c u r r e d  d u r i n g   a d m i n i s t r a t i o n  of  t h e   t e s t   f o r m u l a t i o n .   No  s a f e t y  c o n c e r n s   a r o s e .  40 
T a b l e   I.  P h a r m a c o k i n e t i c   p r o p e r t i e s  o f   enalapril  ( p r o d r u g )   f r o m   t h e   test*  and  reference ~ (Ref)  f o r m u l a t i o n s   (N  =  23  subjects). AUCt,  n g / m L ,   h  AUCo_~ ,  n g / m L ,   h Parameter  Test  Ref  Test  Ref  Test  Ref  Test  Ref  Test  Ref  Test  Ref C . . . .   n g / m L   T . . . .   h  MRTo_~ ,  h  t l / 2 ,   h M e a n   1 1 8 . 5 8   1 3 4 . 6 3   0 . 9 6   0 . 9 0   1 8 9 . 4 0   2 0 0 . 6 5   1 9 2 . 0 7   2 0 3 . 6 2   1.67  1.61  0 . 8 7   0.82 SD  5 2 . 3 8   5 6 . 2 8   0 . 3 4   0 . 2 6   8 5 . 5 2   7 9 . 9 8   8 5 . 5 0   8 1 . 0 2   0.33  0 . 3 4   0.33  0.22 M i n i m u m   4 8 . 2 8   4 8 . 4 3   0 . 5 0   0 . 5 0   1 0 2 . 6 7   9 0 . 7 0   1 0 4 . 5 3   9 1 . 9 2   1.23  1.07  0.59  0 . 5 4  M e d i a n   1 0 8 . 9 5   132.51  1.00  0.75  1 7 1 . 4 8   198.81  1 7 5 . 0 8   2 0 1 . 5 8   1.61  1.60  0.79  0 . 7 4  M a x i m u m   2 9 1 . 9 4   2 5 1 . 5 4   2.25  1.75  4 8 3 . 8 6   3 9 0 . 7 7   487.01  3 9 5 . 0 7   2 . 6 0   2.85  1.76  1.37 CV%  4 4 . 1 7   41.81  35.81  2 8 . 6 3   4 5 . 1 5   3 9 . 8 6   44.51  3 9 . 7 9   19.71  2 1 . 2 7   3 7 . 4 7   2 6 . 3 7  G e o m e t r i c   mean  1 0 9 . 6 7   1 2 2 . 9 8   0.91  0 . 8 7   1 7 5 . 3 7   1 8 5 . 8 7   1 7 8 . 1 8   1 8 8 . 6 8   1.64  1.58  0.83  0 . 8 0  H a r m o n i c   mean  1 0 1 . 9 7   1 1 1 . 3 7   0 . 8 7   0.85  1 6 4 . 4 5   1 7 1 . 8 9   1 6 7 . 2 9   1 7 4 . 5 4   1.61  1.56  0.79  0 . 7 8  C m a  x  =  maximum plasma drug concentration;  Tma x = time to maximal plasma drug concentration;  AUC t = area under the plasma concentration-time curve  to  the  last measurable concentration; AUC o ~  =  area under the  plasma concentration-time curve  from  time  0  to  infinity;  MRT o ~  =  mean residence time;  tl/2  = elimination half-life;  CV% = coefficient  of variation. *Trademark:  Enalapril Farmoz ® (Tecnimede  Sociedade T~cnico-Medicinal  S.A., Prior Velho,  Portugal). tTrademark:  Renitec ® (Merck  Sharp &  Dohme,  Lda., Pa(~o de Arcos,  Portugal). 
NI  -q -q T a b l e   II.  P h a r m a c o k i n e t i c  p r o p e r t i e s  o f   e n a l a p r i l a t  (active  m e t a b o l i t e )  f r o m   t h e   test*  and  reference t  (Ref)  f o r m u l a t i o n s  o f   e n a l a p r i l  ( p r o d r u g )   (N  =  23  subjects). C . . . .   n g / m L   T . . . .   h  AUCt,  n g / m L ,   h  AUCo_~ ,  n g / m L ,   h  MRTo_~ ,  h  t l / 2 ,   h Parameter  Test  Ref  Test  Ref  Test  Ref  Test  Ref  Test  Ref  Test  Ref M e a n   7 0 . 0 2   7 3 . 6 0   3.25  3.39  5 6 3 . 4 8   5 8 8 . 6 9   5 8 7 . 1 0   61 0.07  9 . 6 4   9 . 3 7   6 . 0 6   5 . 9 8  SD  3 1 . 9 0   30.31  0.71  0.82  2 2 6 . 5 0   2 3 4 . 0 0   2 3 7 . 9 5   2 4 1 . 3 8   3.1 0  2.91  2 . 0 4   2.01 M i n i m u m   2 1 . 4 2   1 7.89  2.25  1.75  233.41  2 5 2 . 2 8   2 4 9 . 2 3   269.81  4.91  4 . 2 8   2 . 5 4   2.1 3 M e d i a n   7 3 . 9 9   6 9 . 6 2   3.00  3.25  4 8 3 . 3 4   5 2 9 . 6 5   5 2 3 . 0 9   5 4 9 . 8 7   9.1 6  9 . 2 7   5.52  6.01 M a x i m u m   1 5 2 . 5 7   1 3 6 . 8 8   5.00  5.00  1 0 5 6 . 2 2   1 0 8 9 . 0 9   1 0 9 9 . 6 5   1 1 5 5 . 5 8   1 6 . 1 2   1 5 . 9 0   9.93  9.81 CV%  4 5 . 5 6   4 1 . 1 8   2 1 . 8 8   2 4 . 2 3   4 0 . 2 0   3 9 . 7 5   4 0 . 5 3   3 9 . 5 7   3 2 . 1 4   3 1 . 0 8   3 3 . 6 5   3 3 . 6 9  G e o m e t r i c   mean  62.51  6 7 . 0 3   3.18  3.30  5 2 4 . 1 9   5 4 5 . 6 0   5 4 6 . 4 4   566.51  9.1 7  8.93  5 . 7 0   5 . 6 0  H a r m o n i c   mean  5 4 . 5 7   59.41  3.12  3.20  4 8 8 . 9 4   5 0 4 . 5 2   51 0.84  5 2 5 . 6 3   8 . 7 0   8 . 4 6   5.33  5.1 6 C m a   x  =  maximum plasma drug concentration;  Tma x = time to maximal plasma drug concentration;  AUC t = area under the plasma concentration-time curve  to  the  last measurable concentration; AUC o ~  =  area under the  plasma concentration-time curve  from  time  0  to  infinity;  MRT o ~  =  mean residence time;  tl/2  = elimination half-life;  CV% = coefficient  of variation. *Trademark:  Enalapril Farmoz ® (Tecnimede  Sociedade T~cnico-Medicinal  S.A., Prior Velho,  Portugal). tTrademark:  Renitec ® (Merck  Sharp &  Dohme,  Lda., Pa(~o de Arcos,  Portugal). 
A.  Portol~s  et  aL T a b l e   III.  Differences in  p h a r m a c o k i n e t i c   properties  o f   enalapril ( p r o d r u g )   and  e n a l a p r i l a t  (active  m e t a b o l i t e )   b e t w e e n   t h e   test*  and  reference t  f o r m u l a t i o n s   (N  =  23  subjects). Property  Enalapril  Enalaprilat Ln  Cma x Difference,  mean  (SE)  - 0 . 1 2   (0.08)  - 0 . 0 7   ( 0 . 0 6 )  Ratio,  %  8 8 . 9 0   9 2 . 9 8  9 0 %   CI,  %  7 7 . 3 5   t o   1 0 2 . 1 6   8 3 . 5 6   t o   1 0 3 . 4 6  Ln  AUC t Difference,  mean  (SE)  - 0 . 0 6   (0.04)  - 0 . 0 4   ( 0 . 0 5 )  Ratio,  %  9 4 . 0 8   9 5 . 8 7  9 0 %   CI,  %  8 7 . 1 4   t o   1 0 1 . 5 8   8 8 . 6 0   t o   1 0 3 . 7 4  Ln  AUCo_~ Difference,  mean  (SE)  - 0 . 0 6   (0.04)  - 0 . 0 4   ( 0 . 0 4 )  Ratio,  %  9 4 . 1 9   9 6 . 2 7  9 0 %   CI,  %  8 7 . 4 2   t o   1 0 1 . 4 9   8 9 . 2 0   t o   103.91 T m a x  :~ Differences,  m e d i a n ,   h  0.0  - 0 . 1 2 5  9 0 %   CI,  difference,  h  -  d e c i m a l   - 0 . 1 2 5   t o   0 . 1 2 5   - 0 . 3 7 5   t o   0 . 0  9 0 %   CI,  difference, %  ( w i t h   respect  t o   mean  o f   reference f o r m )   8 6 . 1 4   t o   1 1 3 . 8 6   8 8 . 9 0   t o   1 0 0 . 0 0  Ln  =  logarithmically (e-base) transformed;  C m a  x  =  maximal plasma drug  concentration;  AUC t  =  area under the plasma concentration-time curve to the last measurable concentration; AUCo~ = area under the  plasma concentration-time curve  from  time  0  to  infinity;  Tma x  --  time  to  maximal  plasma  drug concentration. *Trademark:  Enalapril Farmoz ® (Tecnimede  Sociedade T~cnico-Medicinal  S.A., Prior Velho,  Portugal). tTrademark:  Renitec ® (Merck  Sharp &  Dohme,  Lda., Pa(~o de Arcos, Portugal). SNo significant  differences were found  between  the test  and  reference formulations. L a b o r a t o r y   a n a l y s i s   f o r   t o l e r a b i l i t y  r e v e a l e d   s o m e   m o d i f i c a t i o n s  in  t h e   bio- c h e m i c a l   a n d   h e m a t o l o g i c  r e s u l t s ,   n a m e l y :   (1)  d e c r e a s e d   r e d   b l o o d   ceil  c o u n t  (9  s u b j e c t s   [37.5%]),  (2)  s l i g h t   e l e v a t i o n s   in  a  b i o c h e m i c a l   p a r a m e t e r   ( t o t a l  bilirubin,  2  s u b j e c t s   [8.3%]),  (3)  r e d u c t i o n s   in  o t h e r   b i o c h e m i c a l   p a r a m e t e r s  (alkaline  p h o s p h a t a s e ,   1 s u b j e c t   [4.2%];  u r i c   acid,  4  [16.7%];  a n d   t o t a l   c h o l e s -  t e r o l ,   3  [12.5%]),  a n d   (4)  p r e s e n c e   of  u r i n e   s e d i m e n t   a n o m a l i e s   ( o x a l a t e s ,  2 s u b j e c t s   [8.3%];  a n d  w h i t e  b l o o d  ceils,  1 [4.2%]).  S y m p t o m s  w e r e  n o t  d e t e c t e d  in a n y  of t h e s e  c a s e s ,   a n d   all of t h e s e  l a b o r a t o r y  a b n o r m a l i t i e s  w e r e  c o n s i d e r e d  c l i n i c a l l y  n o n s i g n i f i c a n t .  T h e   m e a n   v a l u e s   o b t a i n e d   f o r   s y s t o l i c   a n d   d i a s t o l i c   BP  a r e   p r e s e n t e d   in F i g u r e   2.  After  5  h o u r s ,   t h e   m e a n   v a l u e s   o b t a i n e d   for  b o t h   f o r m u l a t i o n s  w e r e  s i g n i f i c a n t l y  l o w e r   t h a n   b a s e l i n e   v a l u e s   ( b o t h   P  <  0.05),  c o r r e s p o n d i n g   t o   a m i n i m u m  in t h e  s y s t o l i c  a n d   d i a s t o l i c  BPs, w i t h  m e a n   (SD)  s y s t o l i c  BP v a l u e s  of 102 (18)  m m  Hg for t h e  r e f e r e n c e  f o r m u l a t i o n  a n d  of  101  (11)  m m  Hg for t h e  t e s t  f o r m u l a t i o n .   43 
CURRENT THERAPEUTIC RESEARCH ®  - ! -   SBP-T - 0 -   SBP-R DBP-T - ~ -   DBP-R 1 4 0   L a.  6 0   .:  . . . . . . . . . .  4 O  2  o  ";"  l'z  14 T i m e   A f t e r   S t u d y   D r u g   A d m i n i s t r a t i o n   ( h )  Figure  2.  Systolic  and  diastolic  blood  pressures  (SBP and  DBP, respectively)  of  the  test  (T; trademark:  Enalapril  Farmoz ®,  Tecnimede  Sociedade  T~cnico-Medicinal  S.A.,  Prior  Velho, Portugal)  and  reference (R; trademark:  Renitec ®, Merck  Sharp &  Dohme,  Lda., Pa(~o de Arcos, Portugal)  formulations  of  enalapril  (N  =  23  subjects).  *P  <  0.05  5  hours  versus baseline. D I S C U S S I O N  B o t h   t h e   t e s t   a n d   r e f e r e n c e   f o r m u l a t i o n s   of  e n a l a p r i l   e x h i b i t e d   o v e r l a p p i n g  p l a s m a   p r o f i l e s .  T h e   f a c t   t h a t   n o   m o d e l   e f f e c t s  ( p e r i o d   o r   s e q u e n c e )   o r   d e t e c t -  a b l e  p r e d o s e  p l a s m a   d r u g  c o n c e n t r a t i o n s  w e r e  f o u n d  i n d i c a t e s   t h e   a d e q u a c y  of t h e   p r o p o s e d   s t u d y   d e s i g n   a n d   of  t h e   s t u d y   c o n d u c t i o n .  T o   e n s u r e   a  r e l i a b l e   e s t i m a t e   of t h e   e x t e n t  of a b s o r p t i o n ,   a  c o l l e c t i o n  p e r i o d  of  a t   l e a s t   3  tl/2S  is  r e c o m m e n d e d   b y   US  F o o d   a n d   Drug  A d m i n i s t r a t i o n  8 a n d  CPMP 1 g u i d e l i n e s .   T h i s   r e q u i s i t e   w a s   fulfilled,  a n d   t h e   m e a n   e x t r a p o l a t e d   a r e a  w a s   well b e l o w   20% f o r  b o t h   f o r m u l a t i o n s ,   i n d i c a t i n g   t h a t   t h e   e x t r a c t i o n  p e r i o d  w a s   a d e q u a t e   t o   fully  c h a r a c t e r i z e   t h e   PK  p r o p e r t i e s   of  t h e   p r o d r u g   a n d   its a c t i v e   m e t a b o l i t e .  T a k i n g   i n t o   a c c o u n t   t h e   PK  c h a r a c t e r i s t i c s   of  t h e   p r o d r u g   a n d   of  its  a c t i v e  m e t a b o l i t e ,   a  s i n g l e - d o s e   PK  s t u d y   w a s   d e e m e d   as  a p p r o p r i a t e .   T h e   c h o s e n  d o s e   fails  w i t h i n   t h e   r a n g e   of  c l i n i c a l l y   a d m i n i s t e r e d   d o s e s .   T h e   s t u d y   w a s  c o n d u c t e d   u n d e r   f a s t i n g  c o n d i t i o n s   t o   r e d u c e   t h e   p o s s i b l e   i n t e r f e r e n c e  of f o o d  o v e r   a b s o r p t i o n   k i n e t i c s .  44 
A.  Portol~s  et  aL B e c a u s e   t h e   a s s e s s e d   v a r i a b l e s   w e r e   PK  p r o p e r t i e s ,   it  w a s   r e g a r d e d   u n n e c -  e s s a r y   t o   u s e   a  b l i n d e d   d e s i g n .   N e v e r t h e l e s s ,   as  m e n t i o n e d   e a r l i e r ,   t h e   a n a l y t i -  cal  p a r t   of  t h e   s t u d y   w a s   c o n d u c t e d   b l i n d l y .  T h e   d e s i g n   w e   c h o s e   c o m p l i e s   w i t h   E u r o p e a n  1  a n d   US 8  g u i d e l i n e s   o n  b i o a v a i l a b i l i t y / b i o e q u i v a l e n c e  s t u d i e s .   T h e   s t u d y   d e s i g n   is  s u i t e d   t o   its  o b j e c -  t i v e s ,   a n d   t h e   s t u d y   w a s   c a r r i e d   o u t   w i t h   n o   s i g n i f i c a n t   d e v i a t i o n s   f r o m   t h e  p r o t o c o l .  T h e   c a l c u l a t e d   PK  p a r a m e t e r s   a r e   s i m i l a r   t o   t h o s e   p r e v i o u s l y   d e s c r i b e d :  T . . . .   f o r   e n a l a p r i l   a n d   e n a l a p r i l a t  w e r e   in  a c c o r d a n c e  w i t h   p r e v i o u s l y  r e p o r t e d  v a l u e s .  3 In  o u r   s t u d y ,   t h e   tu2  f o r   e n a l a p r i l   w a s   r e l a t i v e l y  s h o r t   f o r   b o t h   f o r m u -  l a t i o n s   ( m e d i a n s :   t e s t ,   0.79  h o u r ;   r e f e r e n c e ,   0.74  h o u r ) ;   f o r   e n a l a p r i l a t ,   t h e   m e -  d i a n   tl/2s  w e r e   5.52  a n d   6.01  h o u r s   f o r   t h e   t e s t   a n d   r e f e r e n c e   f o r m u l a t i o n s ,  r e s p e c t i v e l y .  A l t h o u g h   p o l y p h a s i c   e l i m i n a t i o n   k i n e t i c   p r o p e r t i e s   h a v e   b e e n   de- s c r i b e d   f o r   e n a l a p r i l ,   w i t h   m e a n   t e r m i n a l   half-lives  - 3 0   h o u r s ,   s i m i l a r   half- l i v e s   f o r   e n a l a p r i l a t   h a v e   b e e n   r e p o r t e d   in  a  s e p a r a t e   b i o e q u i v a l e n c e  s t u d y   b y   R i b e i r o   e t   al.7  T h i s   d i f f e r e n c e  in  t h e   e s t i m a t e d   half-lives  is  p r o b a b l y  r e l a t e d   t o   t h e   s a m p l i n g   p e r i o d   ( i n   o u r   c a s e ,   u p   t o   36  h o u r s   a f t e r   s t u d y  d r u g   a d m i n i s t r a t i o n ,   a n d   in  t h e   s t u d y   b y   R i b e i r o   e t   al, 7 u p   t o   24  h o u r s   a f t e r  a d m i n i s t r a t i o n ) .  A l t h o u g h   t h e   CPMP  g u i d e l i n e s  ~ r e c o m m e n d   t h a t   b i o e q u i v a l e n c e   s h o u l d   b e  a s s e s s e d   b y   c o m p a r i n g   t h e   b i o a v a i l a b i l i t y   o f   t h e   p a r e n t   c o m p o u n d   a d m i n i s -  t e r e d ,   in  t h i s   c a s e ,   g i v e n   t h a t   t h e   p a r e n t   c o m p o u n d   is  i n a c t i v e   a n d   its  m e t a b o -  lite  is  in  f a c t   t h e   c o m p o u n d   e x h i b i t i n g   p h a r m a c o l o g i c   a c t i v i t y ,   it  w a s   c o n s i d -  e r e d   a p p r o p r i a t e   t o   c o m p a r e   t h e   b i o a v a i l a b i l i t y   o f   t h e   m e t a b o l i t e   in  b o t h  f o r m u l a t i o n s .  All  90%  CIs  o b t a i n e d   f o r   e n a l a p r i l   ( t h e   p r o d r u g )   a n d   e n a l a p r i l a t   ( t h e   a c t i v e  m e t a b o l i t e )   w e r e   w i t h i n   t h e   p r e d e f i n e d   r a n g e s   o f   b i o e q u i v a l e n c e   a c c e p t a n c e ;  t h u s ,   t h e   2  f o r m u l a t i o n s   a r e   c o n s i d e r e d   b i o e q u i v a l e n t .   A l t h o u g h   a  r e l a t i v e l y  h i g h   v a r i a b i l i t y  w a s   f o u n d   f o r   s o m e   p a r a m e t e r s   o f   e a c h   f o r m u l a t i o n ,   t h a t   w a s  n o t   t h e   c a s e   in  t h e   c o m p a r i s o n   of  t h e   i n t r a s u b j e c t   d i f f e r e n c e s   a n d   r a t i o s .  In  g e n e r a l ,   e n a l a p r i l   w a s   well  t o l e r a t e d .   No  u n e x p e c t e d   AEs  o c c u r r e d ,   a n d  t h e   r e p o r t e d   p o s s i b l y   t r e a t m e n t - r e l a t e d   AEs  c o u l d   b e   e x p l a i n e d   b y   t h e   h y p o -  t e n s i v e   e f f e c t  of t h e   d r u g .   T h e   h e m a t o l o g i c  c h a n g e s   in  t h e   r e d   b l o o d   cell  c o u n t  w e r e   a t t r i b u t a b l e   t o   t h e   b l o o d   e x t r a c t i o n   d u r i n g   t h e   s t u d y .   No  p r o b l e m s   c o n -  c e r n i n g   s a f e t y   of  t h e   f o r m u l a t i o n   w e r e   d e t e c t e d .  R e s u l t s   f o r   BP  w e r e   c o l l e c t e d   t o   a s s e s s   t h e   t o l e r a b i l i t y   of  t h e   f o r m u l a t i o n s  a n d   n o t   t h e i r  p h a r m a c o d y n a m i c  p r o p e r t i e s .   A c c o r d i n g l y ,  t h e   a s s e s s m e n t   t i m e s  a n d   t h e   s t u d y   d e s i g n   d i d   n o t   allow  f o r   a  c l o s e r   m o n i t o r i n g   o f  t h e   BP  as  w o u l d  b e   n e c e s s a r y   f o r   a  p h a r m a c o d y n a m i c   a s s e s s m e n t .   H o w e v e r ,   u n l i k e   w h a t   w a s  r e p o r t e d  b y  R i b e i r o  e t   al7  o n   t h e   a b s e n c e  of a n   e v a l u a b l e  e f f e c t  (BP)  of e n a l a p r i l  in  h e a l t h y   v o l u n t e e r s ,   w e   f o u n d   s i g n i f i c a n t   r e d u c t i o n s   in  m e a n   BPs  ( P   <  0.05), w h i c h   r e t u r n e d   t o   b a s e l i n e   v a l u e s   a t   t h e   f o l l o w i n g   m e a s u r e m e n t   ( a s s e s s e d   a t  12  h o u r s   a f t e r   s t u d y   d r u g   a d m i n i s t r a t i o n ) .   T h i s   f i n d i n g   is  in  a c c o r d a n c e   w i t h  t h e   r e p o r t e d  r e d u c t i o n  in  BP f o u n d  in  a n o t h e r  s t u d y  4 in  n o r m o t e n s i v e  i n d i v i d u -  45 
CURRENT THERAPEUTIC RESEARCH @ a l s ,   a n d   s u g g e s t s   t h a t ,   f o r   t h i s   g r o u p   o f   d r u g s   ( H y p o t e n s i v e s ) ,   a  m o r e   d e t a i l e d  a s s e s s m e n t   o f   p h a r m a c o d y n a m i c   p r o p e r t i e s   c o u l d   b e   p e r f o r m e d   in  h e a l t h y  s u b j e c t s   u s i n g   a  m o r e   s p e c i f i c   s t u d y   d e s i g n   (ie,  B P   m o n i t o r i n g ) .  C O N C L U S I O N S  I n  t h i s   s t u d y   o f   2  c o m m e r c i a l   b r a n d s   ( t e s t   a n d   r e f e r e n c e   f o r m u l a t i o n s )   o f   e n a l a -  p r i l   i n   h e a l t h y   s u b j e c t s ,   d e s i g n e d   a n d   c o n d u c t e d   u n d e r   G o o d   C l i n i c a l   P r a c t i c e  g u i d e l i n e s ,   a  s i m i l a r   r a t e   a n d   e x t e n t   o f   d r u g   a b s o r p t i o n   f o r   b o t h   f o r m u l a t i o n s  w e r e   f o u n d   t o   b e   b i o e q u i v a l e n t .   B o t h   f o r m u l a t i o n s   p r o d u c e d   a  s i g n i f i c a n t   d e -  c r e a s e   i n   B P   v a l u e s   a n d   w e r e   g e n e r a l l y   w e l l   t o l e r a t e d .  A C K N O W L E D G M E N T  W e   t h a n k   t h e   m e d i c a l ,   n u r s i n g ,   a n d   a d m i n i s t r a t i v e   p e r s o n n e l   o f   t h e   C l i n i c a l  P h a r m a c o l o g y   S t u d i e s   U n i t   ( H o s p i t a l   C l f n i c o   S a n   C a r l o s ,   M a d r i d ,   S p a i n )   f o r  t h e i r   e n t h u s i a s t i c   c o o p e r a t i o n .  REFERENCES 1.  C o m m i t t e e  for  P r o p r i e t a r y   Medicinal  P r o d u c t s .   Note  for Guidance  on  the Investigation o f  Bioavailability  and Bioequivalence;  2001.  Available  at:  www.emea.eu.int.  A c c e s s e d  N o v e m b e r   1,  2003. 2.  Chow  SC,  Liu  JP.  Design  and  Analysis  o f  Bioavailability  and  Bioequivalence  Studies. New  York:  Marcel  Dekker;  2000. 3.  T o d d   PA,  Goa KL. Enalapril.  A r e a p p r a i s a l   of its  p h a r m a c o l o g y  a n d   t h e r a p e u t i c   u s e   in h y p e r t e n s i o n .   Drugs.  1992;43:346-381. 4.  Drug Information.  B e t h e s d a ,   Md:  A m e r i c a n   Hospital  F o r m u l a r y   Service,  A m e r i c a n   So- c i e t y   of  Health-System P h a r m a c i s t s ,   Inc;  2001. 5.  Donnelly R, Meredith  PA,  Elliott  HL, Reid JL.  Kinetic-dynamic r e l a t i o n s   a n d   individual r e s p o n s e s   t o   enalapril.  Hypertension.  1990; 15:301-309. 6.  T o d d   PA,  Heel  RC.  Enalapril.  A r e v i e w   of its  p h a r m a c o d y n a m i c   a n d   p h a r m a c o k i n e t i c  p r o p e r t i e s ,   a n d   t h e r a p e u t i c   u s e   in  h y p e r t e n s i o n   a n d   c o n g e s t i v e   h e a r t   failure.  Drugs. 1986;31:198-248. 7.  Ribeiro  W,  M u s c a r ~   MN,  Martins  AR,  et  al.  B i o e q u i v a l e n c e   s t u d y   of  t w o   enalapril m a l e a t e  t a b l e t  f o r m u l a t i o n s   in h e a l t h y  m a l e  v o l u n t e e r s .   P h a r m a c o k i n e t i c  v e r s u s   p h a r -  m a c o d y n a m i c   a p p r o a c h .   Eur J  Clin Pharmacol.  1996;50:399-405. 8.  US  Food  a n d   Drug  Administration.  Guidance  for  industry:  Bioavailability  a n d   bio- e q u i v a l e n c e   s t u d i e s   for  orally  a d m i n i s t e r e d   d r u g   p r o d u c t s - - G e n e r a l   c o n s i d e r a t i o n s .  2003.  Available at:  www.fda.gov/cder/guidance/index/htm.  Accessed  N o v e m b e r   1,  2003. A d d r e s s   c o r r e s p o n d e n c e   t o :   A n t o n i o   P o r t o l ~ s ,   MD,  P h D ,   S e r v i c i o   d e   F a r m a -  c o l o g f a   C l f n i c a ,   H o s p i t a l   C l f n i c o   S a n   C a r l o s ,   c / o   P r o f .   M a r t f n   L a g o s   s / n ,   M a d r i d ,  S p a i n   28040.  E-mail:  a p o r t o l e s . h c s c @ s a l u d . m a d r i d . o r g  4 6