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-8635, ADL-8635, 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 207475985.1047-56&rft.date=2011&rft_id=https://api.semanticscholar.org/CorpusID:207475985#id-name=S2CID&rft_id=info:pmid/21663526&rft_id=info:doi/10.1517/13543784.2011.592830&rft.aulast=Diego&rft.aufirst=L&rft.au=Atayee, R&rft.au=Helmons, P&rft.au=Hsiao, G&rft.au=von Gunten, CF&rfr_id=info:sid/en.wikipedia.org:Bevenopran" class="Z3988">
^ 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 34614812.515-32&rft.date=2015&rft_id=https://api.semanticscholar.org/CorpusID:34614812#id-name=S2CID&rft_id=info:pmid/25539282&rft_id=info:doi/10.1517/14656566.2015.995625&rft.aulast=Siemens&rft.aufirst=W&rft.au=Gaertner, J&rft.au=Becker, G&rfr_id=info:sid/en.wikipedia.org:Bevenopran" class="Z3988">
^ 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

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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