Levorphanol

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Levorphanol
Structural formula
Ball-and-stick model
Systematic (IUPAC) name
17-methylmorphinan-3-ol
Clinical data
Trade names Levo-dromoran
AHFS/Drugs.com Monograph
MedlinePlus a682020
Pregnancy
category
  • US: C (Risk not ruled out)
Dependence
liability		 High
Routes of
administration		 oral, intravenous, subcutaneous, intramuscular
Legal status
Legal status
Pharmacokinetic data
Bioavailability 70% (oral); 100% (IV)
Protein binding 40%
Metabolism Hepatic
Biological half-life 11-16 hours
Identifiers
CAS Number 77-07-6 YesY
ATC code None
PubChem CID 5359272
IUPHAR/BPS 7595
DrugBank DB00854 YesY
ChemSpider 16736212 YesY
UNII 27618J1N2X YesY
KEGG D08123 YesY
ChEMBL CHEMBL592 N
Chemical data
Formula C17H23NO
Molar mass 257.371 g/mol
3D model (Jmol) Interactive image
 NYesY (what is this?)  (verify)

Levorphanol /lɛvaʊrfɑːnɒl/ (brand name 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 racemorphan, first described in Germany in 1948 as an orally-active morphine-like analgesic.[2] It has been in clinical use in the U.S. since 1953.[3]

Levorphanol acts predominantly as an agonist of the μ-opioid receptor, but is also an agonist of the δ-opioid, κ-opioid, and nociceptin receptors, as well as an NMDA receptor antagonist and a serotonin-norepinephrine reuptake inhibitor.[3] Levorphanol, similarly to certain other opioids, also acts as a glycine receptor antagonist and GABA receptor antagonist at very high concentrations.[4]

Relative to morphine, levorphanol lacks complete cross-tolerance [1] and possesses greater intrinsic activity at the MOR.[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.[5]

Levorphanol shows a high rate of psychotomimetic effects such as hallucinations and delirium, which have been attributed to by its binding to and activation of the κ-opioid receptor.[6] However, activation of this receptor as well as of the δ-opioid receptor have been determined to contribute to its analgesic effects.[6]

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) [7]

See also[edit]

References[edit]

  1. ^ a b c 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. 
  2. ^ DE 1014545 
  3. ^ a b Gudin, Jeffrey; Fudin, Jeffrey; Nalamachu, Srinivas (2015). "Levorphanol Use: Past, Present and Future". Postgraduate Medicine. doi:10.1080/00325481.2016.1128308. ISSN 0032-5481. 
  4. ^ Neville N. Osborne (22 October 2013). Selected Topics from Neurochemistry. Elsevier Science. pp. 244–. ISBN 978-1-4832-8635-8. 
  5. ^ Prommer, E (2007). "Levorphanol: the forgotten opioid.". Supportive Care in Cancer. 15 (3): 259–264. doi:10.1007/s00520-006-0146-2. PMID 17039381. 
  6. ^ a b Eduardo D. Bruera; Russell K. Portenoy (12 October 2009). Cancer Pain: Assessment and Management. Cambridge University Press. pp. 215–. ISBN 978-0-521-87927-9. 
  7. ^ http://www.deadiversion.usdoj.gov/quotas/conv_factor/index.html


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