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
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H26N4O4
Molar mass386.452 g·mol−1
3D model (JSmol)
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

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. S2CID 207475985.
  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. S2CID 34614812.
  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



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