Document Detail


Biotransformation of an alpha4beta2 nicotinic acetylcholine receptor partial agonist in sprague-dawley rats and the dispositional characterization of its N-carbamoyl glucuronide metabolite.
MedLine Citation:
PMID:  19339375     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The metabolism and disposition of (1S,5R)-2,3,4,5-tetrahydro-7-(trifluoromethyl)-1,5-methano-1H-3-benzazepine (1), an alpha(4)beta(2) nicotinic acetylcholine receptor partial agonist, was determined in Sprague-Dawley rats after oral administration of [(14)C]1. In intact animals, mass balance was achieved within 48 h, with 5 times more radioactivity excreted in urine than in feces. Compound 1 underwent renal and metabolic clearance equally and exhibited a very long half-life attributable to a secondary peak occurring 8 h postdose in its serum concentration-time curve. In bile duct-cannulated (BDC) rats, mass balance was also achieved within 48 h with 73.7, 23.4, and 5.5% of the dose detected in bile, urine, and feces, respectively. Rats metabolized 1 by two primary routes: four-electron oxidation to either four amino acids or a lactam and formation of an N-carbamoyl glucuronide (M6), which was only detected in bile. The presence of M6 solely in bile and the double-humped serum concentration-time curve of 1 suggested the indirect enterohepatic cycling of 1 via M6 after oral administration. To explore this mechanistic hypothesis further, intravenous studies were conducted with 1 in both intact and BDC rats to determine the extent of 1 undergoing indirect enterohepatic cycling via M6. Compared with the pharmacokinetics in intact rats, total serum clearance was higher (1.7-fold) and volume of distribution was lower (1.6-fold) in BDC rats, resulting in a correspondingly shorter (2.5-fold) half-life, with 56% of administered 1 undergoing recirculation, an amount consistent with that (68% of dose) of M6 observed in bile from rats dosed orally with [(14)C]1.
Authors:
Christopher L Shaffer; Tim F Ryder; Karthik Venkatakrishnan; Ilana K Henne; Thomas N O'Connell
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Publication Detail:
Type:  Journal Article     Date:  2009-04-01
Journal Detail:
Title:  Drug metabolism and disposition: the biological fate of chemicals     Volume:  37     ISSN:  1521-009X     ISO Abbreviation:  Drug Metab. Dispos.     Publication Date:  2009 Jul 
Date Detail:
Created Date:  2009-06-22     Completed Date:  2009-09-28     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9421550     Medline TA:  Drug Metab Dispos     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1480-9     Citation Subset:  IM    
Affiliation:
Pharmacokinetics, Dynamics and Metabolism, Pfizer Global Research and Development, Groton/New London Laboratories, Pfizer Inc., Eastern Point Road, MS 8220-4186, Groton, CT 06340, USA. christopher.l.shaffer@pfizer.com
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MeSH Terms
Descriptor/Qualifier:
Administration, Oral
Animals
Bile / drug effects,  physiology
Biotransformation
Carbon Radioisotopes / administration & dosage
Chromatography, High Pressure Liquid
Glucuronides / metabolism
Half-Life
Rats
Rats, Sprague-Dawley
Receptors, Nicotinic / drug effects,  genetics,  metabolism*
Chemical
Reg. No./Substance:
0/Carbon Radioisotopes; 0/Glucuronides; 0/Receptors, Nicotinic; 0/nicotinic receptor alpha4beta2

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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