6β-Naltrexol

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6β-Naltrexol
File:6beta-Naltrexol.svg
Systematic (IUPAC) name
(5α,6β)-17-(Cyclopropylmethyl)-4,5-epoxymorphinan-3,6,14-triol
Pharmacokinetic data
Biological half-life 12–18 hours[1]
Identifiers
CAS Number 49625-89-0
ATC code None
PubChem CID: 5486554
ChemSpider 4588965
UNII J0W963M37T YesY
Chemical data
Formula C20H25NO4
Molecular mass 343.417 g/mol
  • c1cc(c2c3c1C[C@@H]4[C@]5([C@]3(CCN4CC6CC6)[C@@H](O2)[C@@H](CC5)O)O)O
  • InChI=1S/C20H25NO4/c22-13-4-3-12-9-15-20(24)6-5-14(23)18-19(20,16(12)17(13)25-18)7-8-21(15)10-11-1-2-11/h3-4,11,14-15,18,22-24H,1-2,5-10H2/t14-,15-,18+,19+,20-/m1/s1
  • Key:JLVNEHKORQFVQJ-PYIJOLGTSA-N

6β-Naltrexol, or 6α-hydroxynaltrexone, is a major active metabolite of naltrexone formed by hepatic dihydrodiol dehydrogenase which acts as a potent, peripherally-selective opioid neutral antagonist.[2][3] Relative to naltrexone, 6β-naltrexol has about half the affinity for the μ-opioid receptor,[1] but is present at approximately 10–30-fold higher concentrations at steady state due to extensive first-pass metabolism of the parent drug.[4] 6β-Naltrexol was itself investigated as an opioid antagonist, specifically for the treatment of opioid-induced constipation, and was found to be effective and well-tolerated, but was not further pursued.[2]

See also

References

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  1. ↑ 1.0 1.1 Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ 2.0 2.1 Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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