CHEBI:7862 - oxymetazoline

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ChEBI Name oxymetazoline
ChEBI ID CHEBI:7862
Definition A member of the class of phenols that is 2,4-dimethylphenol which is substituted at positions 3 and 6 by 4,5-dihydro-1H-imidazol-2-ylmethyl and tert-butyl groups, respectively. A direct-acting sympathomimetic with marked α-adrenergic activity, it is a vasoconstrictor that is used (generally as the hydrochloride salt) to relieve nasal congestion.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C16H24N2O
Net Charge 0
Average Mass 260.37460
Monoisotopic Mass 260.189
InChI InChI=1S/C16H24N2O/c1-10-8-13(16(3,4)5)15(19)11(2)12(10)9-14-17-6-7-18-14/h8,19H,6-7,9H2,1-5H3,(H,17,18)
InChIKey WYWIFABBXFUGLM-UHFFFAOYSA-N
SMILES Cc1cc(c(O)c(C)c1CC1=NCCN1)C(C)(C)C
Roles Classification
Biological Role(s): alpha-adrenergic agonist
An agent that selectively binds to and activates alpha-adrenergic receptors.
sympathomimetic agent
A drug that mimics the effects of stimulating postganglionic adrenergic sympathetic nerves. Included in this class are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.
Application(s): alpha-adrenergic agonist
An agent that selectively binds to and activates alpha-adrenergic receptors.
sympathomimetic agent
A drug that mimics the effects of stimulating postganglionic adrenergic sympathetic nerves. Included in this class are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.
nasal decongestant
A drug used to relieve nasal congestion in the upper respiratory tract.
vasoconstrictor agent
Drug used to cause constriction of the blood vessels.
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ChEBI Ontology
Outgoing oxymetazoline (CHEBI:7862) has role α-adrenergic agonist (CHEBI:35569)
oxymetazoline (CHEBI:7862) has role nasal decongestant (CHEBI:77715)
oxymetazoline (CHEBI:7862) has role sympathomimetic agent (CHEBI:35524)
oxymetazoline (CHEBI:7862) has role vasoconstrictor agent (CHEBI:50514)
oxymetazoline (CHEBI:7862) is a carboxamidine (CHEBI:35359)
oxymetazoline (CHEBI:7862) is a imidazolines (CHEBI:53095)
oxymetazoline (CHEBI:7862) is a phenols (CHEBI:33853)
oxymetazoline (CHEBI:7862) is conjugate base of oxymetazoline(1+) (CHEBI:77716)
Incoming oxymetazoline(1+) (CHEBI:77716) is conjugate acid of oxymetazoline (CHEBI:7862)
IUPAC Name
6-tert-butyl-3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethylphenol
INNs Sources
oxymetazolina WHO MedNet
oxymetazoline WHO MedNet
oxymétazoline WHO MedNet
oxymetazolinum WHO MedNet
Synonyms Sources
2-(4-tert-butyl-2,6-dimethyl-3-hydroxybenzyl)-2-imidazoline NIST Chemistry WebBook
3-[(4,5-dihydro-1H-imidazol-2-yl)methyl]-6-(1,1-dimethylethyl)-2,4-dimethylphenol NIST Chemistry WebBook
6-t-butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenol NIST Chemistry WebBook
6-tert-butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenol NIST Chemistry WebBook
Database Links Databases
C07363 KEGG COMPOUND
D08322 KEGG DRUG
DB00935 DrugBank
DE1117588 Patent
HMDB15070 HMDB
LSM-2353 LINCS
Oxymetazoline Wikipedia
View more database links
Registry Numbers Types Sources
1491-59-4 CAS Registry Number KEGG COMPOUND
1491-59-4 CAS Registry Number NIST Chemistry WebBook
886303 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10487000 PubMed citation Europe PMC
21177487 PubMed citation Europe PMC
23679077 PubMed citation Europe PMC
23988443 PubMed citation Europe PMC
4003266 PubMed citation Europe PMC
Last Modified
24 February 2016