Bevenopran

Bevenopran (INN, USAN) (former developmental code names CB-5945, ADL-5945, MK-2402, OpRA III) is a peripherally acting μ-opioid receptor antagonist that also acts on δ-opioid receptors and was under development by Cubist Pharmaceuticals for the treatment of chronic opioid-induced constipation.[1][2][3] It reached phase III clinical trials for this indication before being discontinued.[4][5]

Bevenopran

Legal status
Legal status	Investigational
Identifiers
IUPAC name 5-[2-Methoxy-4-[[2-(oxan-4-yl)ethylamino]methyl]phenoxy]pyrazine-2-carboxamide
CAS Number	676500-67-7
PubChem CID	10452732
ChemSpider	8628148
UNII	IC58Q2EHPJ
KEGG	D10349
CompTox Dashboard (EPA)	DTXSID90217963
Chemical and physical data
Formula	C20H26N4O4
Molar mass	386.452 g·mol^−1
3D model (JSmol)	Interactive image
SMILES COC1=C(C=CC(=C1)CNCCC2CCOCC2)OC3=NC=C(N=C3)C(=O)N
InChI InChI=1S/C20H26N4O4/c1-26-18-10-15(11-22-7-4-14-5-8-27-9-6-14)2-3-17(18)28-19-13-23-16(12-24-19)20(21)25/h2-3,10,12-14,22H,4-9,11H2,1H3,(H2,21,25) Key:ZGCYVRNZWGUXNQ-UHFFFAOYSA-N

See also

• Alvimopan
• Axelopran
• Eluxadoline
• Methylnaltrexone
• Naldemedine
• Naloxegol

References

1. Diego L, Atayee R, Helmons P, Hsiao G, von Gunten CF (2011). "Novel opioid antagonists for opioid-induced bowel dysfunction". Expert Opin Investig Drugs. 20 (8): 1047–56. doi:10.1517/13543784.2011.592830. PMID 21663526.
2. Siemens W, Gaertner J, Becker G (2015). "Advances in pharmacotherapy for opioid-induced constipation - a systematic review". Expert Opin Pharmacother. 16 (4): 515–32. doi:10.1517/14656566.2015.995625. PMID 25539282.
3. Annual Reports in Medicinal Chemistry. Elsevier Science. 13 September 2013. pp. 451–. ISBN 978-0-12-417151-0.
4. Combating Opioid-Induced Constipation: New and Emerging Therapies
5. Bevenopran