Structure via PubChem · Public domain (PubChem)
sinomenine
Sign in to saveSinomenine or cocculine is an alkaloid found in the root of the climbing plant Sinomenium acutum which is native to Japan and China. The plant is traditionally used in herbal medicine in these countries for rheumatism and arthritis. However, analgesic action against other types of pain seems to be limited. Sinomenine is a morphinan derivative that is related to the common cough suppressant dextromethorphan. The drug's anti-rheumatic effects are thought to be primarily mediated via release of histamine, but other effects such as inhibition of prostaglandin, leukotriene and nitric oxide synthesi
Chemical data
- Formula
- C19H23NO4
- Molecular weight
- 329.4 g/mol
- IUPAC name
- (1R,9S,10S)-3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,11-tetraen-13-one
- SMILES
- CN1CC[C@@]23CC(=O)C(=C[C@@H]2[C@@H]1CC4=C3C(=C(C=C4)OC)O)OC
- InChIKey
- INYYVPJSBIVGPH-QHRIQVFBSA-N
- XLogP
- 2.2
- Polar surface area
- 59 Ų
- H-bond donors
- 1
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
- Indications
- osteoarthritis, knee
via ChEMBL · EBI
Wikidata facts
- Mass
- 329.162708
Show 5 more facts
- found in taxon
- Stephania cephalantha
- chemical formula
- C₁₉H₂₃NO₄
- isomeric SMILES
- CN1CC[C@@]23CC(=O)C(=C[C@@H]2[C@@H]1CC4=C3C(=C(C=C4)OC)O)OC
- canonical SMILES
- CN1CCC23CC(=O)C(=CC2C1CC4=C3C(=C(C=C4)OC)O)OC
- subject has role
- disease-modifying antirheumatic drug
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
Sinomenine or cocculine is an alkaloid found in the root of the climbing plant Sinomenium acutum which is native to Japan and China. The plant is traditionally used in herbal medicine in these countries for rheumatism and arthritis. However, analgesic action against other types of pain seems to be limited. Sinomenine is a morphinan derivative that is related to the common cough suppressant dextromethorphan. The drug's anti-rheumatic effects are thought to be primarily mediated via release of histamine, but other effects such as inhibition of prostaglandin, leukotriene and nitric oxide synthesis may also be involved.
== See also == Hasubanan Oreobeiline
Excerpted from Wikipedia’s “sinomenine” article, available under the CC BY-SA 4.0 licence.