Alvimopan

Title: Alvimopan
CAS Registry Number: 156053-89-3
CAS Name: N-[(2S)-2-[[(3R,4R)-4-(3-Hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl]-1-oxo-3-phenylpropyl]glycine
Additional Names: [[2(S)-[[4(R)-(3-hydroxyphenyl)-3(R),4-dimethyl-1-piperidinyl]methyl]-1-oxo-3-phenylpropyl]amino]acetic acid
Manufacturers' Codes: ADL-8-2698; LY-246736
Trademarks: Entereg (Adolor)
Molecular Formula: C25H32N2O4
Molecular Weight: 424.53
Percent Composition: C 70.73%, H 7.60%, N 6.60%, O 15.07%
Literature References: Peripheral mu-opioid receptor antagonist. Prepn: B. E. Cantrell et al., EP 506478; eidem, US 5250542 (1992, 1993 both to Lilly); D. M. Zimmerman et al., J. Med. Chem. 37, 2262 (1994). Improved synthesis: J. A. Werner et al., J. Org. Chem. 61, 587 (1996). Clinical pharmacology: S. S. Liu et al., Clin. Pharmacol. Ther. 68, 66 (2000). Clinical trial in postoperative ileus: A. Taguchi et al., N. Engl. J. Med. 345, 935 (2001); E. R. Viscusi et al., Surg. Endosc. 20, 64 (2006). Review of clinical experience: W. K. Schmidt, Am. J. Surg. 182, Suppl., 27S-38S (2001); and pharmacology: P. Neary, C. P. Delaney, Expert Opin. Invest. Drugs 14, 479-488 (2005).
Derivative Type: Dihydrate
CAS Registry Number: 170098-38-1
Properties: Crystals, mp 210-213°. [a]D25 +51.8° (c = 1.0 in DMSO).
Melting point: mp 210-213°
Optical Rotation: [a]D25 +51.8° (c = 1.0 in DMSO)
Therap-Cat: Gastroprokinetic.
Keywords: Gastroprokinetic.
Amanitin Amanozine Amantadine Amantanium Bromide Amaranth (Dye)

Alvimopan
Alvimopan.svg
Systematic (IUPAC) name
2-([(2S)-2-([(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]methyl) -3-phenylpropanoyl]amino)acetic acid
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a608051
Licence data US FDA:link
Legal status  ?
Routes Oral
Identifiers
CAS number 156053-89-3 N
ATC code A06AH02
PubChem CID 5488548
DrugBank DB06274
ChemSpider 4589864 YesY
UNII Q153V49P3Z N
ChEMBL CHEMBL270190 YesY
Synonyms Alvimopan, Entereg
Chemical data
Formula C25H32N2O4 
Mol. mass 424.53 g/mol
 N (what is this?)  (verify)

Alvimopan (trade name Entereg) is a drug which behaves as a peripherally acting μ-opioid antagonist. With limited ability to cross the blood–brain barrier, many of the undesirable side-effects of the opioid agonists such as constipation are minimized without affecting analgesia or precipitating withdrawals[disambiguation needed].[1][2] The Food and Drug Administration reviewed the safety and efficacy data for alvimopan and approved its use in May 2008.[3]