Structure via PubChem · Public domain (PubChem)
xorphanol
Sign in to saveXorphanol (INN; also known as xorphanol mesylate (USAN); developmental codes TR-5379 or TR-5379M) is an opioid analgesic of the morphinan family that was never marketed.
Chemical data
- Formula
- C23H31NO
- Molecular weight
- 337.5 g/mol
- IUPAC name
- (1R,9R,10R,11S)-17-(cyclobutylmethyl)-11-methyl-13-methylidene-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-ol
- SMILES
- C[C@H]1CC(=C)C[C@@]23[C@@H]1[C@@H](CC4=C2C=C(C=C4)O)N(CC3)CC5CCC5
- InChIKey
- AZJPPZHRNFQRRE-AZIXLERZSA-N
- XLogP
- 5
- Polar surface area
- 23.5 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 337.241
Show 4 more facts
- Commons category
- Xorphanol
- chemical formula
- C₂₃H₃₁NO
- canonical SMILES
- CC1CC(=C)CC23C1C(CC4=C2C=C(C=C4)O)N(CC3)CC5CCC5
- isomeric SMILES
- C[C@H]1CC(=C)C[C@@]23[C@@H]1[C@@H](CC4=C2C=C(C=C4)O)N(CC3)CC5CCC5
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
Xorphanol (INN; also known as xorphanol mesylate (USAN); developmental codes TR-5379 or TR-5379M) is an opioid analgesic of the morphinan family that was never marketed.
Xorphanol is a mixed agonist–antagonist of opioid receptors, acting preferentially as a high-efficacy partial agonist/near-full agonist of the κ-opioid receptor (Ki = 0.4 nM; EC50 = 3.3 nM; = 49%; = 0.84) and to a lesser extent as a partial agonist of the μ-opioid receptor (Ki = 0.25 nM; IC50 = 3.4 nM; = 29%) with lower relative intrinsic activity and marked antagonistic potential (including the ability to antagonize morphine-induced effects and induce opioid withdrawal in opioid-dependent individuals). The drug has also been found to act as an agonist of the δ-opioid receptor (Ki = 1.0 nM; IC50 = 8 nM; = 76%).
Excerpted from Wikipedia’s “xorphanol” article, available under the CC BY-SA 4.0 licence.