Levallorphan

Levallorphan
Systematic (IUPAC) name
(−)-17-allylmorphinan-3-ol
Clinical data
AHFS/Drugs.com International Drug Names
Routes of
administration		 Oral
Legal status
Legal status
  • ℞ (Prescription only)
Identifiers
CAS Number 152-02-3 YesY
ATC code none
PubChem CID 5359371
IUPHAR/BPS 7209
DrugBank DB00504 N
ChemSpider 4514267 YesY
UNII 353613BU4U YesY
ChEMBL CHEMBL1254682 N
Chemical data
Formula C19H25NO
Molar mass 283.4079 g/mol
 NYesY (what is this?)  (verify)

Levallorphan (INN, BAN) (brand names Lorfan, Naloxifan, Naloxiphan), also known as levallorphan tartate (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 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 an 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, and bizarre, unusual, or disturbing dreams.[8][9][10]

See also

References

  1. ↑ J. Elks (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 3-88763-075-0.
  3. ↑ I.K. Morton; Judith M. Hall (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. The Pharmacological Basis of Therapeutics (10th ed.). McGraw Hill Medical Publishing. p. 602. ISBN 978-0-07-135469-1.
  5. ↑ Codd, E. E.; Shank, R. P.; Schupsky, J. J.; Raffa, R. B. (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): 1263–1270. PMID 7562497.
  6. ↑ Bullough, J. (1959). "Use of premixed pethidine and antagonists in obstetrical analgesia; with special reference to cases in which levallorphan was used" (pdf). British Medical Journal 2 (5156): 859–862. doi:10.1136/bmj.2.5156.859. PMC: 1990381. PMID 13805887.
  7. ↑ Williams, G.; Cope, I. (1962). "An evaluation of a combination of pethidine and levallorphan ("pethilorfan") in labour". The Medical Journal of Australia 49 (2): 499–503. PMID 14000851.
  8. ↑ R.C.W. Hall (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. ↑ John B. Williams (1963). Narcotics. Wm. C. Brown Company. p. 203.



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