Levallorphan

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Levallorphan
Levallorphan.svg
Systematic (IUPAC) name
(−)-17-allylmorphinan-3-ol
Clinical data
AHFS/Drugs.com International Drug Names
Legal status
  • ℞ (Prescription only)
Routes of
administration
Oral
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
Molecular mass 283.4079 g/mol
  • Oc1ccc3c(c1)[C@@]24[C@H]([C@H](N(CC2)C\C=C)C3)CCCC4
  • 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 YesY
  • Key:OZYUPQUCAUTOBP-WDSOQIARSA-N YesY
 NYesY (what is this?)  (verify)

Levallorphan (Lorfan, Naloxiphan) is a drug of the morphinan family used as an opioid modulator and antidote.[1] It acts as an antagonist on μ-opioid receptor and agonist on kappa receptor,[2] and as a result, blocks the effects of stronger agents with greater intrinsic activity such as morphine or endogenous β-endorphin.[3]

Levallorphan was formerly widely used in general anaesthesia, mainly to reverse the respiratory depression produced by the opioid analgesics and barbiturates used for induction of surgical anaesthesia while maintaining a degree of analgesia (via kappa opioid receptor agonization) although it is now less common as the newer drug naloxone tends to be used, instead.

It was also used in combination with opioids to reduce their side effects, mainly in obstetrics, and a very small dose of levallorphan used alongside an opioid full agonist can produce greater analgesia than when the agonist is used by itself.[4] The combination of levallorphan with pethidine (meperidine) was indeed used so frequently, a standardized formulation was made available, known as Pethilorfan.[5]

See also

References

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