CHEBI:7459 - naloxone

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name naloxone
ChEBI ID CHEBI:7459
Definition A 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that is morphinone in which the enone double bond has been reduced to a single bond, the hydrogen at position 14 has been replaced by a hydroxy group, and the methyl group attached to the nitrogen has been replaced by an allyl group.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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C19H21NO4
Net Charge 0
Average Mass 327.37430
Monoisotopic Mass 327.147
InChI InChI=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
InChIKey UZHSEJADLWPNLE-GRGSLBFTSA-N
SMILES Oc1ccc2C[C@H]3N(CC[C@@]45[C@@H](Oc1c24)C(=O)CC[C@@]35O)CC=C
Roles Classification
Biological Role(s): mu-opioid receptor antagonist

metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): mu-opioid receptor antagonist

central nervous system depressant
A loosely defined group of drugs that tend to reduce the activity of the central nervous system.
antidote to opioid poisoning
A role borne by a molecule that acts to counteract or neutralise the deleterious effects of opioids.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing naloxone (CHEBI:7459) has parent hydride morphinan (CHEBI:35649)
naloxone (CHEBI:7459) has role μ-opioid receptor antagonist (CHEBI:50137)
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) 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 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 Sources
naloxona DrugBank
naloxone WHO MedNet
naloxone ChemIDplus
naloxonum DrugBank
Synonyms Sources
(−)-naloxone ChEBI
1-N-Allyl-14-hydroxynordihydromorphinone ChemIDplus
17-allyl-3,14-dihydroxy-4,5α-epoxymorphinan-6-one ChEBI
Database Links Databases
1878 DrugCentral
C07252 KEGG COMPOUND
D08249 KEGG DRUG
DB01183 DrugBank
GB939287 Patent
HMDB0015314 HMDB
LSM-3504 LINCS
Naloxone Wikipedia
US3254088 Patent
View more database links
Registry Numbers Types Sources
1089071 Reaxys Registry Number Reaxys
1089071 Beilstein Registry Number Beilstein
465-65-6 CAS Registry Number KEGG COMPOUND
465-65-6 CAS Registry Number ChemIDplus
465-65-6 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
17023477 PubMed citation Europe PMC
24868924 PubMed citation Europe PMC
25468814 PubMed citation Europe PMC
26469689 PubMed citation Europe PMC
26604818 PubMed citation Europe PMC
26634308 PubMed citation Europe PMC
Last Modified
22 February 2017