Butorphanol

Butorphanol
Structural formula
Ball-and-stick model
Clinical data
Trade namesStadol, others
Other namesBC 2627
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa682667
Pregnancy
category
  • C/D (United States)
Routes of
administration
IV, intranasal, oral
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityNasal: 60-70%, Sublingual/Buccal 25%-35%. PO < OR= to 10%. * Try to use IN route best used out of the hospital setting or both choices. has longer duration of action ~ 5 hours. IV 2-4 hours. Avoid oral route unless stronger advised by a physician.
MetabolismLiver hydroxylated & glucuronidated
Elimination half-life4-7 hours
ExcretionKidney, 75%
Biliary, 11-14%
Fecal, 15%
Identifiers
  • (4bR, 8aR, 9S)-11-(cyclobutylmethyl)-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano) phenanthrene-3,8a-diol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.050.717 Edit this at Wikidata
Chemical and physical data
FormulaC21H29NO2
Molar mass327.468 g·mol−1
3D model (JSmol)
  • OC1=CC2=C(C=C1)C[C@H]3N(CC[C@@]24CCCC[C@@]34O)CC5CCC5
  • InChI=1S/C21H29NO2/c23-17-7-6-16-12-19-21(24)9-2-1-8-20(21,18(16)13-17)10-11-22(19)14-15-4-3-5-15/h6-7,13,15,19,23-24H,1-5,8-12,14H2/t19-,20+,21-/m1/s1 checkY
  • Key:IFKLAQQSCNILHL-QHAWAJNXSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Butorphanol is a morphinan-type synthetic agonist–antagonist opioid analgesic developed by Bristol-Myers.[2][3][4][5][6] 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.[7]

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ^ US 3819635, "14-hydroxymorphinan derivatives." 
  3. ^ US 3775414, "Process for the preparation of 14-hydroxymorphinan derivatives." 
  4. ^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 200–. ISBN 978-1-4757-2085-3.
  5. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 154–. ISBN 978-3-88763-075-1.
  6. ^ Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 58–. ISBN 978-94-011-4439-1.
  7. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 529. ISBN 978-3-527-60749-5.