Levorphanol

Levorphanol
Clinical data
Trade names	Levo-Dromoran
Other names	Ro 1-5431
AHFS/Drugs.com	Monograph
MedlinePlus	a682020
Routes of; administration	Oral, intravenous, subcutaneous, intramuscular
ATC code	None;
Legal status
Legal status	AU: S8 (Controlled drug); BR: Class A1 (Narcotic drugs); CA: Schedule I; DE: Anlage II (Authorized trade only, not prescriptible); UK: Class A; US: Schedule II;
Pharmacokinetic data
Bioavailability	70% (oral); 100% (IV)
Protein binding	40%
Metabolism	Hepatic
Elimination half-life	11–16 hours
Identifiers
	IUPAC name (1R,9R,10R)-17-Methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-ol;
CAS Number	77-07-6 ;
PubChem CID	5359272;
IUPHAR/BPS	7595;
DrugBank	DB00854 ;
ChemSpider	16736212 ;
UNII	27618J1N2X;
KEGG	D08123 ;
ChEMBL	ChEMBL592 ;
CompTox Dashboard (EPA)	DTXSID3023213 ;
ECHA InfoCard	100.000.912
Chemical and physical data
Formula	C17H23NO
Molar mass	257.377 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1CC[C@]23CCCC[C@H]2[C@H]1Cc4c3cc(O)cc4;
	InChI InChI=1S/C17H23NO/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17/h5-6,11,14,16,19H,2-4,7-10H2,1H3/t14-,16+,17+/m0/s1 ; Key:JAQUASYNZVUNQP-USXIJHARSA-N ;
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Levorphanol (brand name Levo-Dromoran) is an opioid medication used to treat moderate to severe pain.^[1]^[3]^[4] It is the levorotatory enantiomer of the compound racemorphan. Its dextrorotatory counterpart is dextrorphan.

It was first described in Germany in 1946.^[5] The drug has been in medical use in the United States since 1953.^[6]

^ ^a ^b Elks J (November 14, 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 656–. ISBN 978-1-4757-2085-3.
^ Anvisa (March 31, 2023). "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 April 4, 2023). Archived from the original on August 3, 2023. Retrieved August 16, 2023.
^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 606–. ISBN 978-3-88763-075-1.
^ Morton IK, Hall JM (December 6, 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 165–. ISBN 978-94-011-4439-1.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 527. ISBN 978-3-527-60749-5.
^ Gudin J, Fudin J, Nalamachu S (January 2016). "Levorphanol Use: Past, Present and Future". Postgraduate Medicine. 128 (1): 46–53. doi:10.1080/00325481.2016.1128308. PMID 26635068. S2CID 3912175.

[Elks2014-1] Elks J (November 14, 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 656–. ISBN 978-1-4757-2085-3.

[2] Anvisa (March 31, 2023). "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 April 4, 2023). Archived from the original on August 3, 2023. Retrieved August 16, 2023.

[IndexNominum2000-3] Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 606–. ISBN 978-3-88763-075-1.

[MortonHall2012-4] Morton IK, Hall JM (December 6, 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 165–. ISBN 978-94-011-4439-1.

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

[GudinFudin2015-6] Gudin J, Fudin J, Nalamachu S (January 2016). "Levorphanol Use: Past, Present and Future". Postgraduate Medicine. 128 (1): 46–53. doi:10.1080/00325481.2016.1128308. PMID 26635068. S2CID 3912175.

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