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Levorphanol
Systematic (IUPAC) name
17-methylmorphinan-3-ol
Identifiers
CAS number 77-07-6
ATC code none
PubChem 5359272
DrugBank APRD00764
Chemical data
Formula C 17H23NO 
Mol. mass 257.371 g/mol
SMILES eMolecules & PubChem
Physical data
Melt. point 23 °C (73 °F)
Pharmacokinetic data
Bioavailability  ?
Protein binding 40%
Metabolism  ?
Half life 11-16 hours
Excretion  ?
Therapeutic considerations
Pregnancy cat. C(US)
Legal status Schedule II (US)
Routes oral, intravenous, intramuscular, subcutaneous
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Levorphanol (Levo-Dromoran) is an opioid medication used to treat severe pain. It is the laevorotary stereoisomer of the synthetic morphinan (Dromoran) and a pure opioid agonist, first described in Germany in 1946 as an orally active morphine-like analgesic. Morphinan is the parent drug and prototype of a large series of opioid and/or NMDA antagonists and opioid agonists used in medicine including nalbuphine, butorphanol, dextromethorphan, and others.

Levorphanol has the same properties as morphine with respect to the potential for habituation, tolerance, physical dependence and withdrawal syndrome. It is 4 to 8 times as potent as morphine and has a longer half-life. Approximately 30 mg of oral morphine is roughly equianalgesic to 4 mg of oral levorphanol.[1] The laevo isomer is the source of the narcotic properties of the racemic drug Dromoran, but the dextro isomers are also useful in medicine: in addition to acting on sigma receptors, the O-methyl derivative of its dextrorotary isomer, dextromethorphan, acts as an NMDA receptor antagonist.[2] Oral doses of levorphanol come in 2 mg and 4 mg strengths or subcutaneous injection every 6 to 8 hours.

Levorphanol has affinity to μ, κ, and δ opioid receptors, but lacks complete cross-tolerance with morphine. 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 and ketobemidone, make levorphanol useful for types of pain that other analgesics may not be as effective against; levorphanol's sigma receptor, SNRI and SSRI properties make it even more useful particularly for neuropathic pain.[3]

See also

References

  1. ^ www.globalrph.com/narcoticonv.htm
  2. ^ Brookoff D. Hospital Practice. 2000;35:45-59.
  3. ^ Prommer E. Levorphanol: the forgotten opioid. Supportive Care in Cancer. 2007 Mar;15(3):259-64. PMID 17039381







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