CHEBI:3994 - cyclizine

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ChEBI Name cyclizine
ChEBI ID CHEBI:3994
Definition An N-alkylpiperazine in which one nitrogen of the piperazine ring is substituted by a methyl group, while the other is substituted by a diphenylmethyl group.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:127546
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Formula C18H22N2
Net Charge 0
Average Mass 266.38076
Monoisotopic Mass 266.178
InChI InChI=1S/C18H22N2/c1-19-12-14-20(15-13-19)18(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18H,12-15H2,1H3
InChIKey UVKZSORBKUEBAZ-UHFFFAOYSA-N
SMILES CN1CCN(CC1)C(c1ccccc1)c1ccccc1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): cholinergic antagonist
Any drug that binds to but does not activate cholinergic receptors, thereby blocking the actions of acetylcholine or cholinergic agonists.
H1-receptor antagonist
H1-receptor antagonists are the drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine.
Application(s): antiemetic
A drug used to prevent nausea or vomiting. An antiemetic may act by a wide range of mechanisms: it might affect the medullary control centres (the vomiting centre and the chemoreceptive trigger zone) or affect the peripheral receptors.
cholinergic antagonist
Any drug that binds to but does not activate cholinergic receptors, thereby blocking the actions of acetylcholine or cholinergic agonists.
central nervous system depressant
A loosely defined group of drugs that tend to reduce the activity of the central nervous system.
local anaesthetic
Any member of a group of drugs that reversibly inhibit the propagation of signals along nerves. Wide variations in potency, stability, toxicity, water-solubility and duration of action determine the route used for administration, e.g. topical, intravenous, epidural or spinal block.
H1-receptor antagonist
H1-receptor antagonists are the drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine.
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ChEBI Ontology
Outgoing cyclizine (CHEBI:3994) has role antiemetic (CHEBI:50919)
cyclizine (CHEBI:3994) has role central nervous system depressant (CHEBI:35488)
cyclizine (CHEBI:3994) has role cholinergic antagonist (CHEBI:48873)
cyclizine (CHEBI:3994) has role H1-receptor antagonist (CHEBI:37955)
cyclizine (CHEBI:3994) has role local anaesthetic (CHEBI:36333)
cyclizine (CHEBI:3994) is a N-alkylpiperazine (CHEBI:46845)
Incoming cyclizine hydrochloride (CHEBI:51045) has part cyclizine (CHEBI:3994)
IUPAC Name
1-(diphenylmethyl)-4-methylpiperazine
INNs Sources
ciclizina ChEBI
cyclizine ChEBI
cyclizine ChemIDplus
cyclizinum ChEBI
Synonyms Sources
(±)-1-diphenylmethyl-4-methylpiperazine ChEBI
(N-Benzhydryl)(N'-methyl)diethylenediamine ChemIDplus
1-(Diphenylmethyl)-4-methylpiperazine ChemIDplus
1-Benzhydryl-4-methylpiperazin ChemIDplus
Cyclizine KEGG COMPOUND
N-Benzhydryl-N'-methylpiperazine ChemIDplus
N-methyl-N'-benzhydrylpiperazine NIST Chemistry WebBook
Manual Xrefs Databases
749 DrugCentral
C06930 KEGG COMPOUND
Cyclizine Wikipedia
D03621 KEGG DRUG
DB01176 DrugBank
HMDB0015307 HMDB
LSM-5857 LINCS
US2630435 Patent
View more database links
Registry Numbers Types Sources
230441 Beilstein Registry Number Beilstein
230441 Reaxys Registry Number Reaxys
82-92-8 CAS Registry Number NIST Chemistry WebBook
82-92-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
22209223 PubMed citation Europe PMC
24215049 PubMed citation Europe PMC
24324230 PubMed citation Europe PMC
Last Modified
22 February 2017
General Comments
2011-01-07 A sedating histamine H1 antagonist with antimuscarinic activity, cyclizine is given by mouth as the hydrochloride salt, or intramuscularly or intravenously as the lactate, for the control of management of postoperative nausea and vomiting, and for the management of motion sickness.
2014-05-29 Cyclizine can be found in blood and urine samples of individuals who have taken this drug.