Levorphanol

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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
Hepatic
Elimination half-life11–16 hours
Identifiers
  • (1R,9R,10R)-17-Methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-ol
JSmol)
  • CN1CC[C@]23CCCC[C@H]2[C@H]1Cc4c3cc(O)cc4
  • 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

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]

Pharmacology

Levorphanol acts predominantly as an

serotonin-norepinephrine reuptake inhibitor (SNRI).[6] Levorphanol, similarly to certain other opioids, also acts as a glycine receptor antagonist and GABA receptor antagonist at very high concentrations.[7] As per the World Health Organization, levorphanol is a step 3 opioid and is considered eight times more potent than morphine at the MOR (2 mg levorphanol is equivalent to 15 mg morphine).[citation needed
]

Relative to morphine, levorphanol lacks complete

phenylpiperidine ketobemidone, make levorphanol useful for types of pain that other analgesics may not be as effective against, such as neuropathic pain.[9] 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.[10]

Levorphanol shows a high rate of

psychotomimetic side effects such as hallucinations and delirium, which have been attributed to its binding to and activation of the KOR.[11] At the same time however, activation of this receptor as well as of the DOR have been determined to contribute to its analgesic effects.[11]

Chemistry

Levorphanol and its stereoisomer dextrorphan, the enantiomers of the racemic mixture racemorphan.

Chemically, levorphanol belongs to the

racemethorphan along with levomethorphan
, the latter of which has similar properties to those of levorphanol.

Society and culture

Name

Levorphanol is the

Roche was Ro 1-5431.[1][4]

Availability

As the tartrate salt, levorphanol is marketed by Hikma Pharmaceuticals USA Inc.[12] and Virtus Pharmaceuticals in the U.S., and Canada under the brand name Levo-Dromoran.[3]

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).[13]

See also

References

  1. ^
    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. ^
    ISBN 978-3-88763-075-1
    .
  4. ^
    ISBN 978-94-011-4439-1
    .
  5. ISBN 978-3-527-60749-5
    .
  6. ^
    S2CID 3912175
    .
  7. ISBN 978-1-4832-8635-8
    .
  8. ^
    ISBN 978-0-19-157532-7
    .
  9. S2CID 10916508
    .
  10. doi:10.1016/j.jpain.2016.01.056
    .
  11. ^
    ISBN 978-0-521-87927-9
    .
  12. ^ "LEVORPHANOL TARTRATE tablet". National Library of Medicine. National Institutes of Health.
  13. ^ "Conversion Factors for Controlled Substances". Diversion Control Division. U.S. Department of Justice • Drug Enforcement Administration.