Butorphanol

Butorphanol
Clinical data
Trade names	Stadol, others
Other names	BC 2627
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a682667
Pregnancy; category	C/D (United States);
Routes of; administration	IV, intranasal, oral
ATC code	N02AF01 (WHO) QR05DA90 (WHO);
Legal status
Legal status	AU: S8 (Controlled drug); BR: Class A1 (Narcotic drugs); CA: Schedule IV; UK: Controlled Drug; US: Schedule IV;
Pharmacokinetic data
Bioavailability	Nasal: 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.
Metabolism	Liver hydroxylated & glucuronidated
Elimination half-life	4-7 hours
Excretion	Kidney, 75%; Biliary, 11-14%; Fecal, 15%
Identifiers
	IUPAC name (4bR, 8aR, 9S)-11-(cyclobutylmethyl)-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano) phenanthrene-3,8a-diol;
CAS Number	42408-82-2 ;
PubChem CID	5361092;
IUPHAR/BPS	7591;
DrugBank	DB00611 ;
ChemSpider	16735714 ;
UNII	QV897JC36D;
KEGG	D00837 ;
ChEBI	CHEBI:3242 ;
ChEMBL	ChEMBL33986 ;
CompTox Dashboard (EPA)	DTXSID1022714 ;
ECHA InfoCard	100.050.717
Chemical and physical data
Formula	C21H29NO2
Molar mass	327.468 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES OC1=CC2=C(C=C1)C[C@H]3N(CC[C@@]24CCCC[C@@]34O)CC5CCC5;
	InChI 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 ; Key:IFKLAQQSCNILHL-QHAWAJNXSA-N ;
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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]

^ 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.
^ US 3819635, "14-hydroxymorphinan derivatives."
^ US 3775414, "Process for the preparation of 14-hydroxymorphinan derivatives."
^ 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.
^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 154–. ISBN 978-3-88763-075-1.
^ 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.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 529. ISBN 978-3-527-60749-5.

[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."

[Elks2014-4] 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.

[IndexNominum2000-5] Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 154–. ISBN 978-3-88763-075-1.

[MortonHall2012-6] 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.

[Fis2006-7] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 529. ISBN 978-3-527-60749-5.

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