Structure via PubChem · Public domain (PubChem)
naloxazone
Sign in to saveNaloxazone is an irreversible μ-opioid receptor antagonist which is selective for the μ1 receptor subtype. Naloxazone produces very long lasting antagonist effects as it forms a covalent bond to the active site of the μ-opioid receptor, thus making it impossible for the molecule to unbind and blocking the receptor permanently until the receptor is recycled by endocytosis.
Chemical data
- Formula
- C19H23N3O3
- Molecular weight
- 341.4 g/mol
- IUPAC name
- (4R,4aS,7E,7aR,12bS)-7-hydrazinylidene-3-prop-2-enyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,9-diol
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 341.17394159599996
Show 4 more facts
- canonical SMILES
- C=CCN1CCC23C4C(=NN)CCC2(C1CC5=C3C(=C(C=C5)O)O4)O
- chemical formula
- C₁₉H₂₃N₃O₃
- Commons category
- Naloxazone
- isomeric SMILES
- C=CCN1CC[C@]23c4c5ccc(O)c4O[C@H]2/C(=N/N)CC[C@@]3(O)[C@H]1C5
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
Naloxazone is an irreversible μ-opioid receptor antagonist which is selective for the μ1 receptor subtype. Naloxazone produces very long lasting antagonist effects as it forms a covalent bond to the active site of the μ-opioid receptor, thus making it impossible for the molecule to unbind and blocking the receptor permanently until the receptor is recycled by endocytosis.
Naloxazone is the hydrazone analog of naloxone. It has been reported that naloxazone is unstable in acidic solution, dimerizing into the more stable and much more potent antagonist naloxonazine via the free NH2 of the hydrazone to form an azine linkage. Under conditions in which no naloxonazine formation could be detected, naloxazone did not display irreversible μ opioid receptor binding.
Excerpted from Wikipedia’s “naloxazone” article, available under the CC BY-SA 4.0 licence.