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CHEBI:7459 - naloxone

ChEBI IDCHEBI:7459
ChEBI Namenaloxone
Stars
DefinitionA synthetic morphinane alkaloid that is morphinone in which the enone double bond has been reduced to a single bond, the hydrogen at position 14 has been replaced by a hydroxy group, and the methyl group attached to the nitrogen has been replaced by an allyl group. A specific opioid antagonist, it is used (commonly as its hydrochloride salt) to reverse the effects of opioids, both following their use of opioids during surgery and in cases of known or suspected opioid overdose.
Last Modified22 February 2017
DownloadsMolfile
FormulaC19H21NO4
Net Charge0
Average Mass327.380
Monoisotopic Mass327.14706
SMILESC=CCN1CC[C@]23c4c5ccc(O)c4O[C@H]2C(=O)CC[C@@]3(O)[C@H]1C5
InChIInChI=1S/C19H21NO4/c1-2-8-20-9-7-18-15-11-3-4-12(21)16(15)24-17(18)13(22)5-6-19(18,23)14(20)10-11/h2-4,14,17,21,23H,1,5-10H2/t14-,17+,18+,19-/m1/s1
InChIKeyUZHSEJADLWPNLE-GRGSLBFTSA-N
Wikipedia
Roles Classification
Biological Roles:
mu-opioid receptor antagonist  Any compound that exhibits antagonist activity at the μ-opioid receptor
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
antidote to opioid poisoning  A role borne by a molecule that acts to counteract or neutralise the deleterious effects of opioids.
mu-opioid receptor antagonist  Any compound that exhibits antagonist activity at the μ-opioid receptor
central nervous system depressant  A loosely defined group of drugs that tend to reduce the activity of the central nervous system.
ChEBI Ontology
Outgoing Relation(s)
naloxone (CHEBI:7459) has parent hydride morphinan (CHEBI:35649)
naloxone (CHEBI:7459) has role antidote to opioid poisoning (CHEBI:90755)
naloxone (CHEBI:7459) has role central nervous system depressant (CHEBI:35488)
naloxone (CHEBI:7459) has role μ-opioid receptor antagonist (CHEBI:50137)
naloxone (CHEBI:7459) is a morphinane alkaloid (CHEBI:25418)
naloxone (CHEBI:7459) is a organic heteropentacyclic compound (CHEBI:38164)
naloxone (CHEBI:7459) is a tertiary alcohol (CHEBI:26878)
naloxone (CHEBI:7459) is conjugate base of naloxone(1+) (CHEBI:90756)
Incoming Relation(s)
naloxegol (CHEBI:82975) has functional parent naloxone (CHEBI:7459)
naloxone(1+) (CHEBI:90756) is conjugate acid of naloxone (CHEBI:7459)
IUPAC Name 
3,14-dihydroxy-17-(prop-2-en-1-yl)-4,5α-epoxymorphinan-6-one
INNs  Source
naloxonaDrugBank
naloxonumDrugBank
naloxoneChemIDplus
naloxoneWHO MedNet
Synonyms  Source
17-allyl-3,14-dihydroxy-4,5α-epoxymorphinan-6-oneChEBI
1-N-Allyl-14-hydroxynordihydromorphinoneChemIDplus
(−)-naloxoneChEBI
Manual XrefsDatabases
C07252KEGG COMPOUND
DB01183DrugBank
GB939287Patent
US3254088Patent
NaloxoneWikipedia
D08249KEGG DRUG
HMDB0015314HMDB
LSM-3504LINCS
1878DrugCentral
Registry NumbersSources
Reaxys:1089071Reaxys
CAS:465-65-6KEGG COMPOUND
CAS:465-65-6ChemIDplus
CAS:465-65-6NIST Chemistry WebBook
Citations