Structure via PubChem · Public domain (PubChem)
butorphanol
Sign in to saveAlso known as butorphanol tartrate, LEVO-BC-2627, (-)-N-cyclobutylmethyl-3,14-dihydroxymorphinan, (-)-17-(cyclobutylmethyl)morphinan-3,14-diol, (-)-butorphanol, (-)-Butorphanol, Butorfanol
Butorphanol is a morphinan-type synthetic agonist–antagonist opioid analgesic developed by Bristol-Myers. Butorphanol is most closely structurally related to levorphanol. Butorphanol is available as the tartrate salt in injectable, tablet, and intranasal spray formulations. The tablet form is only used in dogs, cats and horses due to low bioavailability in humans.
Key facts
- Drug.H
- 29
- Drug.N
- 1
- Drug.O
- 2
- Drug.C
- 21
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 459988204
- Drug.IUPAC_name
- (4bR, 8aR, 9S)-11-(cyclobutylmethyl)-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano) phenanthrene-3,8a-diol
- Drug.image
- Butorphanol2DCSDT.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 210px
- Drug.alt
- Structural formula
- Drug.image2
- Butorphanol molecule ball.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 240px
- Drug.alt2
- Ball-and-stick model
- Drug.synonyms
- BC 2627
- Drug.tradename
- Stadol, others
via Wikipedia infobox
Chemical data
- Formula
- C21H29NO2
- Molecular weight
- 327.5 g/mol
- IUPAC name
- (1S,9R,10S)-17-(cyclobutylmethyl)-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene-4,10-diol
- SMILES
- C1CC[C@]2([C@H]3CC4=C([C@]2(C1)CCN3CC5CCC5)C=C(C=C4)O)O
- InChIKey
- IFKLAQQSCNILHL-QHAWAJNXSA-N
- XLogP
- 3.8
- Polar surface area
- 43.7 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
2,111 papers- Butorphanol.Drug and alcohol dependence · 1985
- Butorphanol effectively prevents etomidate-induced myoclonus: a pooled analysis of 788 patients.The Journal of international medical research · 2019
- Transnasal butorphanol.American family physician · 1994
- Effect of butorphanol on etomidate-induced myoclonus: a systematic review and meta-analysis.Drug design, development and therapy · 2019
- Butorphanol: effects of a prototypical agonist-antagonist analgesic on kappa-opioid receptors.Journal of pharmacological sciences · 2005
via PubMed
Wikidata facts
- Mass
- 327.22
Show 6 more facts
- defined daily dose
- 12
- chemical formula
- C₂₁H₂₉NO₂
- World Health Organisation international non-proprietary name
- butorphanol
- isomeric SMILES
- C1CC[C@]2([C@H]3CC4=C([C@]2(C1)CCN3CC5CCC5)C=C(C=C4)O)O
- canonical SMILES
- C1CCC2(C3CC4=C(C2(C1)CCN3CC5CCC5)C=C(C=C4)O)O
- Commons category
- Butorphanol
Sources (6)
via Wikidata · CC0
~5 min read
Article
9 sectionsContents
- Medical uses
- Pharmacology
- Society and culture
- Name
- Legal status
- Veterinary use
- Use in horses
- See also
- References
Butorphanol is a morphinan-type synthetic agonist–antagonist opioid analgesic developed by Bristol-Myers. Butorphanol is most closely structurally related to levorphanol. Butorphanol is available as the tartrate salt in injectable, tablet, and intranasal spray formulations. The tablet form is only used in dogs, cats and horses due to low bioavailability in humans.
It was patented in 1971 and approved for medical use in 1979.