Levorphanol

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Levorphanol
Levorphanol2DCSD2.svg
Levorphanol3DanJ.gif
Systematic (IUPAC) name
17-methylmorphinan-3-ol
Clinical data
Trade namesLevo-dromoran
AHFS/Drugs.commonograph
MedlinePlusa682020
Pregnancy cat.C (US)
Legal statusControlled (S8) (AU) Schedule I (CA) Schedule II (US) Class A (UK)
Dependence liabilityHigh
Routesoral, intravenous, subcutaneous, intramuscular
Pharmacokinetic data
Bioavailability70% (oral); 100% (IV)
Protein binding40%
MetabolismHepatic
Half-life11-16 hours
Identifiers
CAS number77-07-6 YesY
ATC codeNone
PubChemCID 5359272
DrugBankDB00854
ChemSpider16736212 YesY
UNII27618J1N2X YesY
KEGGD08123 YesY
ChEMBLCHEMBL592 N
Chemical data
FormulaC17H23NO 
Mol. mass257.371 g/mol
 N (what is this?)  (verify)
 
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Levorphanol
Levorphanol2DCSD2.svg
Levorphanol3DanJ.gif
Systematic (IUPAC) name
17-methylmorphinan-3-ol
Clinical data
Trade namesLevo-dromoran
AHFS/Drugs.commonograph
MedlinePlusa682020
Pregnancy cat.C (US)
Legal statusControlled (S8) (AU) Schedule I (CA) Schedule II (US) Class A (UK)
Dependence liabilityHigh
Routesoral, intravenous, subcutaneous, intramuscular
Pharmacokinetic data
Bioavailability70% (oral); 100% (IV)
Protein binding40%
MetabolismHepatic
Half-life11-16 hours
Identifiers
CAS number77-07-6 YesY
ATC codeNone
PubChemCID 5359272
DrugBankDB00854
ChemSpider16736212 YesY
UNII27618J1N2X YesY
KEGGD08123 YesY
ChEMBLCHEMBL592 N
Chemical data
FormulaC17H23NO 
Mol. mass257.371 g/mol
 N (what is this?)  (verify)

Levorphanol /lɛvrfɑːnɒl/ (Levo-Dromoran) is an opioid medication used to treat moderate to severe pain. Chemically it is (-)-3-hydroxy-N-methyl-morphinan.[1] It is the levorotatory stereoisomer of the synthetic morphinan (Dromoran) and a pure opioid agonist, first described in Germany in 1948[2] as an orally active morphine-like analgesic. It has been in clinical use in the U.S. since the 1950s.[1] Levorphanol has opioid, NMDA antagonist and monoamine reuptake inhibitor activity; it binds strongly to the mu opioid receptor and less strongly to the kappa and delta opioid receptors but lacks complete cross-tolerance with morphine.[1] It possesses greater intrinsic activity at the MOR than morphine.[1] The duration of action is generally long compared to other comparable analgesics and varies from 4 hours to as much as 15 hours. For this reason levorphanol is useful in palliation of chronic pain and similar conditions. Levorphanol has an oral to parenteral effectiveness ratio of 2:1, one of the most favourable of the strong narcotics. Its NMDA actions, similar to those of the phenylheptylamine open-chain narcotics such as methadone or the phenylpiperidine ketobemidone, make levorphanol useful for types of pain that other analgesics may not be as effective against, such as neuropathic pain.[3]

Levorphanol is listed under the Single Convention On Narcotic Drugs 1961 and is regulated like morphine in most countries. In the United States it is a Schedule II Narcotic controlled substance with a DEA ACSCN of 9220 and 2013 annual aggregate manufacturing quota of 4.5 kilos. The salts in use are the tartrate (free base conversion ratio 0.58) and hydrobromide (0.76) [4]

See also[edit]

References[edit]

  1. ^ a b c d Davis, MP; Glare, PA; Hardy, J (2009) [2005]. Opioids in Cancer Pain (2nd ed.). Oxford, UK: Oxford University Press. ISBN 978-0-19-157532-7.  edit
  2. ^ DE Patent 1014545
  3. ^ Prommer, E (2007). "Levorphanol: the forgotten opioid.". Supportive Care in Cancer 15 (3): 259–264. doi:10.1007/s00520-006-0146-2. PMID 17039381. 
  4. ^ http://www.deadiversion.usdoj.gov/quotas/conv_factor/index.html