Product Code Database
Levorphanol (brand name Levo-Dromoran) is an opioid medication used to treat moderate to severe pain. It is the levorotatory enantiomer of the compound racemorphan. Its dextrorotatory counterpart is dextrorphan.
It was first described in Germany in 1946. The drug has been in medical use in the United States since 1953.
Relative to morphine, levorphanol lacks complete cross-tolerance
Levorphanol shows a high rate of psychotomimetic such as and delirium, which have been attributed to its binding to and activation of the KOR. At the same time however, activation of this receptor as well as of the DOR have been determined to contribute to its analgesic effects.
(2025). 9780191575327, Oxford University Press. ISBN 9780191575327 and possesses greater intrinsic activity at the MOR. 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 favorable of the strong narcotics. Its antagonism of the NMDA receptor, similar to those of the phenylheptylamine open-chain opioids 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. Levorphanol's exceptionally high analgesic efficacy in the treatment of neuropathic pain is also conferred by its action on serotonin and norepinephrine transporters, similar to the opioids tramadol and tapentadol, and mutually complements the analgesic effect of its NMDA receptor antagonism.
Chemistry
Chemically, levorphanol belongs to the morphinan class and is (−)-3-hydroxy- N-methyl-morphinan. It is the "left-handed" (levorotatory) stereoisomer of racemorphan, the racemic mixture of the two stereoisomers with differing pharmacology. The "right-handed" (dextrorotatory) enantiomer of racemorphan is dextrorphan (DXO), an antitussive, potent dissociative hallucinogen (NMDA receptor antagonist), and weakly active opioid. DXO is an active metabolite of the pharmaceutical drug dextromethorphan (DXM), which, analogously to DXO, is an enantiomer of the racemic mixture racemethorphan along with levomethorphan, the latter of which has similar properties to those of levorphanol.
Society and culture
Name
Levorphanol is the INN, BAN, and DCF. As the medically used tartrate salt, the drug is also known as levorphanol tartrate (USAN, BANM). The former developmental code name of levorphanol at Roche was Ro 1-5431.
Availability
As the tartrate salt, levorphanol is marketed by Hikma Pharmaceuticals USA Inc. and Virtus Pharmaceuticals in the U.S., and Canada under the brand name Levo-Dromoran.
Legality
Levorphanol is listed under the Single Convention On Narcotic Drugs 1961 and is regulated like morphine in most countries. In the U.S., it is a Schedule II Narcotic controlled substance with a DEA ACSCN of 9220 and 2013 annual aggregate manufacturing quota of 4.5 kilograms. The salts in use are the tartrate (free base conversion ratio 0.58) and hydrobromide (0.76).
See also
Categories: Delta-opioid Receptor Agonists, Dissociative Drugs, Enantiopure Drugs, Euphoriants, Gaba Receptor Antagonists, German Inventions, Glycine Receptor Antagonists, Kappa-opioid Receptor Agonists, Morphinans, Mu-opioid Receptor Agonists, Nmda Receptor Antagonists, Nociceptin Receptor Agonists, Hydroxyarenes, Serotonin–norepinephrine Reuptake Inhibitors, Synthetic Opioids
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