Ketorfanol

Ketorfanol (INN, USAN) (developmental code name SBW-22), or ketorphanol, is an opioid analgesic of the morphinan family that was found to possess "potent antiwrithing activity" in animal assays but was never marketed.[1][2] It is a 17-cycloalkylmethyl derivative of morphinan and as such, is closely related structurally to butorphanol, cyclorphan, oxilorphan, proxorphan, and xorphanol, which act preferentially as κ-opioid receptor agonists and to a lesser extent as μ-opioid receptor partial agonists/antagonists.[3]

Ketorfanol
Clinical data
ATC code
  • None
Identifiers
IUPAC name
  • 17-(Cyclopropylmethyl)-4-hydroxymorphinan-6-one
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC20H25NO2
Molar mass311.425 g·mol−1
3D model (JSmol)
SMILES
  • C1CC1CN2CCC34CC(=O)CCC3C2CC5=C4C(=CC=C5)O
InChI
  • InChI=1S/C20H25NO2/c22-15-6-7-16-17-10-14-2-1-3-18(23)19(14)20(16,11-15)8-9-21(17)12-13-4-5-13/h1-3,13,16-17,23H,4-12H2/t16-,17+,20-/m0/s1
  • Key:ORMBBVGVPWUEMQ-QKLQHJQFSA-N

See also

References
  1. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 720–. ISBN 978-1-4757-2085-3.
  2. Korolkovas A (16 August 1988). Essentials of Medicinal Chemistry. Wiley. p. 243. ISBN 978-0-471-88356-2.
  3. Neumeyer JL, Bidlack JM, Zong R, Bakthavachalam V, Gao P, Cohen DJ, et al. (January 2000). "Synthesis and opioid receptor affinity of morphinan and benzomorphan derivatives: mixed kappa agonists and mu agonists/antagonists as potential pharmacotherapeutics for cocaine dependence". Journal of Medicinal Chemistry. 43 (1): 114–22. doi:10.1021/jm9903343. PMID 10633042.
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