Bevenopran

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;

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]

References

^ 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.
^ 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.
^ Annual Reports in Medicinal Chemistry. Elsevier Science. 13 September 2013. pp. 451–. ISBN 978-0-12-417151-0.
^ Combating Opioid-Induced Constipation: New and Emerging Therapies
^ Bevenopran

v t e Drugs for constipation (laxatives and cathartics) (A06)
Stool softeners	Docusate
Stimulant laxatives	Bisacodyl Bisoxatin Cascara Castor oil Dantron Oxyphenisatine Phenolphthalein Senna glycosides Sodium picosulfate
Bulk-forming laxatives	Dietary fiber Ethulose Ispaghula Methylcellulose Polycarbophil calcium Sterculia Triticum Syrup of figs
Lubricant laxatives	Liquid paraffin Mineral oil
Osmotic laxatives	Lactitol Lactulose Laminarid Magnesium carbonate Magnesium citrate Magnesium hydroxide (milk of magnesia) Magnesium oxide Magnesium peroxide Magnesium sulfate Mannitol Pentaerythritol Polyethylene glycol (macrogol) Sodium phosphate Sodium sulfate Sodium tartrate Sorbitol
Enemas	Bisacodyl Dantron Glycerol Oil Sodium laurilsulfate Sodium lauryl sulfoacetate Sodium phosphate Sorbitol
Opioid antagonists	Naloxone (Oxycodone/naloxone) PAMORAs Alvimopan Axelopran Bevenopran Methylnaltrexone Naldemedine Naloxegol
Others	Linaclotide Lubiprostone Oxyphenisatine Plecanatide Prucalopride Tegaserod Tenapanor Ulimorelin

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