107 - Alvimopan  pp. 420-423


By Victor A. II Filadora and Sidney Allison

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Generic Name: alvimopan

Trade Name: Entereg™

Drug Class: peripheral opioid antagonist

Manufacturer: Adolor Corporation, Exton, PA 19341–1127

Chemical Structure: see Figure 107.1

Chemical Name: [[2(S)-[[4(R)-(3-hydroxyphenyl)-3(R),4-dimethyl-1-piperidinyl]methyl]-1-oxo-3-phenylpropyl]amino]acetic acid dihydrate

Chemical Formula: C25H32N2O4•2H2O; molecular wt 460.6


Alvimopan is a peripheral μ opioid receptor antagonist. It was first synthesized at Lilly Research Laboratories, and introduced in May 2008 by Adolor Corporation and GlaxoSmithKline under the brand name Entereg. Its indication is to accelerate upper and lower gastrointestinal recovery time following partial large or small bowel resection surgery with primary anastomosis. It is the first pharmacotherapy approved by the US FDA for this application.

Alvimopan's activity is peripherally restricted because at physiological pH, its large zwitterionic form and polarity limit gastrointestinal absorption and prevent passage through the blood–brain barrier. It competitively antagonizes the effects of morphine on gastrointestinal contractility without reversing the central analgesic effects of μ opioid agonists. No dosage adjustments are required in patients with co-administration of morphine or acid blockers. Patients with recent exposure to opioids are more sensitive to μ opioid receptor antagonists. This sensitivity is limited to gastrointestinal tract discomfort, which may include abdominal pain, nausea and vomiting, and diarrhea.

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