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Levorphanol information


Levorphanol
Structural formula
Ball-and-stick model
Clinical data
Trade namesLevo-Dromoran
Other namesRo 1-5431[1]
AHFS/Drugs.comMonograph
MedlinePlusa682020
Routes of
administration
Oral, intravenous, subcutaneous, intramuscular
ATC code
  • None
Legal status
Legal status
  • AU: S8 (Controlled drug)
  • BR: Class A1 (Narcotic drugs)[2]
  • CA: Schedule I
  • DE: Anlage II (Authorized trade only, not prescriptible)
  • UK: Class A
  • US: Schedule II
Pharmacokinetic data
Bioavailability70% (oral); 100% (IV)
Protein binding40%
MetabolismHepatic
Elimination half-life11–16 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 checkY
PubChem CID
  • 5359272
IUPHAR/BPS
  • 7595
DrugBank
  • DB00854 checkY
ChemSpider
  • 16736212 checkY
UNII
  • 27618J1N2X
KEGG
  • D08123 checkY
ChEMBL
  • ChEMBL592 ☒N
CompTox Dashboard (EPA)
  • DTXSID3023213 Edit this at Wikidata
ECHA InfoCard100.000.912 Edit this at Wikidata
Chemical and physical data
FormulaC17H23NO
Molar mass257.377 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 checkY
  • Key:JAQUASYNZVUNQP-USXIJHARSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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]

  1. ^ 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.
  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.
  3. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 606–. ISBN 978-3-88763-075-1.
  4. ^ Morton IK, Hall JM (December 6, 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Medi a. pp. 165–. ISBN 978-94-011-4439-1.
  5. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 527. ISBN 978-3-527-60749-5.
  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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Levorphanol

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Levorphanol (brand name Levo-Dromoran) is an opioid medication used to treat moderate to severe pain. It is the levorotatory enantiomer of the compound...

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Dextrorphan

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dextrorotatory enantiomer of racemorphan; the levorotatory enantiomer is levorphanol. Dextrorphan is produced by O-demethylation of dextromethorphan by CYP2D6...

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Levomethorphan

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about five times stronger than morphine. Levomethorphan is a prodrug to levorphanol, analogously to DXM acting as a prodrug to dextrorphan or codeine behaving...

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Butamirate

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Codeine; Pholcodine Dextromethorphan; Dimemorfan Racemorphan; Dextrorphan; Levorphanol Pentoxyverine Tipepidine Cloperastine; Levocloperastine Germouty J, Weibel...

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Racemorphan

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antitussive and dissociative hallucinogen (NMDA receptor antagonist) Levorphanol – an opioid analgesic Racemorphan itself is under international control...

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Butorphanol

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by Bristol-Myers. Butorphanol is most closely structurally related to levorphanol. Butorphanol is available as the tartrate salt in injectable, tablet...

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Methorphan

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clinically developed; a prodrug of the powerful opioid agonist analgesic levorphanol (Levo-Dromoran). Racemethorphan is the racemic mixture of both of these...

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Equianalgesic

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half-life and the bioavailability of a drug. For example, the narcotic levorphanol is 4–8 times stronger than morphine, but also has a much longer half-life...

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Dextromethorphan

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dextrorotatory enantiomer of levomethorphan, which is the methyl ether of levorphanol, both opioid analgesics. It is named according to IUPAC rules as...

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have significantly incomplete cross-tolerance with morphine such as levorphanol, ketobemidone, piritramide, and methadone and its derivatives; all of...

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Hydrocodone (+paracetamol, +ibuprofen, +aspirin) Hydromorphinol Hydromorphone Levorphanol Metopon Nalbuphine Nicocodeine Nicodicodine Nicomorphine Oxycodone (+paracetamol...

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Analgesic

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original on 13 April 2014. Retrieved 8 April 2014. Prommer E (March 2007). "Levorphanol: the forgotten opioid". Supportive Care in Cancer. 15 (3): 259–64. doi:10...

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LSD

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Paracetamol

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