Levallorphan

Levallorphan (INN, BAN) (brand names Lorfan, Naloxifan, Naloxiphan), also known as levallorphan tartrate (USAN), is an opioid modulator of the morphinan family used as an opioid analgesic and opioid antagonist/antidote.[1][2][3] It acts as an antagonist of the μ-opioid receptor (MOR) and as an agonist of the κ-opioid receptor (KOR),[4] and as a result, blocks the effects of stronger agents with greater intrinsic activity such as morphine whilst simultaneously producing analgesia.[5]

Levallorphan
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
IUPAC name
  • (−)-17-allylmorphinan-3-ol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.005.273
Chemical and physical data
FormulaC19H25NO
Molar mass283.415 g·mol−1
3D model (JSmol)
SMILES
  • Oc1ccc3c(c1)[C@@]24[C@H]([C@H](N(CC2)C\C=C)C3)CCCC4
InChI
  • InChI=1S/C19H25NO/c1-2-10-20-11-9-19-8-4-3-5-16(19)18(20)12-14-6-7-15(21)13-17(14)19/h2,6-7,13,16,18,21H,1,3-5,8-12H2/t16-,18-,19-/m0/s1 Y
  • Key:OZYUPQUCAUTOBP-WDSOQIARSA-N Y
 NY (what is this?)  (verify)

Levallorphan was formerly widely used in general anesthesia, mainly to reverse the respiratory depression produced by opioid analgesics and barbiturates used for induction of surgical anaesthesia whilst maintaining a degree of analgesia (via KOR agonism). It is now less commonly employed for this purpose as the newer drug naloxone tends to be used instead. Levallorphan was also used in combination with opioid analgesics to reduce their side effects, mainly in obstetrics, and a very small dose of levallorphan used alongside a full agonist of the MOR can produce greater analgesia than when the latter is used by itself.[6] The combination of levallorphan with pethidine (meperidine) was indeed used so frequently, a standardized formulation was made available, known as Pethilorfan.[7]

As an agonist of the KOR, levallorphan can produce severe mental reactions at sufficient doses including hallucinations, dissociation, and other psychotomimetic effects, dysphoria, anxiety, confusion, dizziness, disorientation, derealization, feelings of drunkenness, delusions, paranoia, and bizarre, unusual, or disturbing dreams.[8][9][10]

See also

References
  1. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 731–. ISBN 978-1-4757-2085-3.
  2. Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. ISBN 978-3-88763-075-1.
  3. Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 164–. ISBN 978-94-011-4439-1.
  4. Goodman & Gilman (2001). The Pharmacological Basis of Therapeutics (10th ed.). McGraw Hill Medical Publishing. p. 602. ISBN 978-0-07-135469-1.
  5. Codd EE, Shank RP, Schupsky JJ, Raffa RB (September 1995). "Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception". The Journal of Pharmacology and Experimental Therapeutics. 274 (3): 1263–70. PMID 7562497.
  6. Bullough J (October 1959). "Use of premixed pethidine and antagonists in obstetrical analgesia; with special reference to cases in which levallorphan was used". British Medical Journal. 2 (5156): 859–62. doi:10.1136/bmj.2.5156.859. PMC 1990381. PMID 13805887.
  7. Williams G, Cope I (September 1962). "An evaluation of a combination of pethidine and levallorphan ("pethilorfan") in labour". The Medical Journal of Australia. 49 (2): 499–503. doi:10.5694/j.1326-5377.1962.tb20494.x. PMID 14000851.
  8. Hall RC (6 December 2012). Psychiatric Presentations of Medical Illness: Somatopsychic Disorders. Springer Science & Business Media. pp. 364–. ISBN 978-94-011-7677-4.
  9. American Hospital Formulary Service Drug Information. authority of the Board of Directors of the American Society of Hospital Pharmacists. 1984. p. 664.
  10. Williams JB (1963). Narcotics. Wm. C. Brown Company. p. 203.
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