Alvimopan

Alvimopan
Clinical data
Trade names	Entereg
Other names	Alvimopan, Entereg
AHFS/Drugs.com	Monograph
MedlinePlus	a608051
License data	US FDA: Alvimopan;
Routes of; administration	Oral
ATC code	A06AH02 (WHO) ;
Legal status
Legal status	US: WARNINGRx-only;
Pharmacokinetic data
Bioavailability	6%
Protein binding	80% (parent drug), 94% (metabolite)
Metabolism	Gut microflora-mediated hydrolysis to active metabolite
Elimination half-life	10-17 hours
Excretion	Faeces, urine (35%)
Identifiers
	IUPAC name 2-([(2S)-2-([(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]methyl) -3-phenylpropanoyl]amino)acetic acid;
CAS Number	156053-89-3 ;
PubChem CID	5488548;
IUPHAR/BPS	7471;
DrugBank	DB06274 ;
ChemSpider	4589864 ;
UNII	Q153V49P3Z;
ChEMBL	ChEMBL270190 ;
CompTox Dashboard (EPA)	DTXSID60166035 ;
Chemical and physical data
Formula	C25H32N2O4
Molar mass	424.541 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(O)CNC(=O)[C@@H](Cc1ccccc1)CN3CC[C@@](c2cccc(O)c2)([C@H](C3)C)C;
	InChI InChI=1S/C25H32N2O4/c1-18-16-27(12-11-25(18,2)21-9-6-10-22(28)14-21)17-20(24(31)26-15-23(29)30)13-19-7-4-3-5-8-19/h3-10,14,18,20,28H,11-13,15-17H2,1-2H3,(H,26,31)(H,29,30)/t18-,20-,25+/m0/s1 ; Key:UPNUIXSCZBYVBB-JVFUWBCBSA-N ;
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Alvimopan (trade name Entereg) is a drug which behaves as a peripherally acting μ-opioid receptor antagonist. With the limited ability to cross the blood–brain barrier and reach the μ-opioid receptors of the central nervous system, the clinically undesirable effects of centrally acting opioid antagonists (like reversal of opioid-mediated analgesia) are avoided without affecting the intended blockade of μ-opioid receptors in the gastrointestinal tract.^[2]^[3] It is currently only Food and Drug Administration approved for the treatment of postoperative ileus which it received in May 2008.^[4]^[5]

^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
^ Neary P, Delaney CP (April 2005). "Alvimopan". Expert Opinion on Investigational Drugs. 14 (4): 479–488. doi:10.1517/13543784.14.4.479. PMID 15882122. S2CID 219293329.
^ Schmidt WK (November 2001). "Alvimopan* (ADL 8-2698) is a novel peripheral opioid antagonist". American Journal of Surgery. 182 (5A Suppl): 27S – 38S. doi:10.1016/S0002-9610(01)00784-X. PMID 11755894.
^ FDA press release - FDA Approves Entereg to Help Restore Bowel Function Following Surgery
^ Sharma A, Jamal MM (July 2013). "Opioid induced bowel disease: a twenty-first century physicians' dilemma. Considering pathophysiology and treatment strategies". Current Gastroenterology Reports. 15 (7): 334. doi:10.1007/s11894-013-0334-4. PMID 23836088. S2CID 32265790.