CHEBI:3738 - clemastine

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ChEBI Name clemastine
ChEBI ID CHEBI:3738
Definition 2-[(2R)-1-Methylpyrrolidin-2-yl]ethanol in which the hydrogen of the hydroxy group is substituted by a 1-(4-chlorophenyl)-1-phenylethyl group (R configuration). An antihistamine with antimuscarinic and moderate sedative properties, it is used as its fumarate salt for the symptomatic relief of allergic conditions such as rhinitis, urticaria, conjunctivitis and in pruritic (severe itching) skin conditions.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:569763
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Formula C21H26ClNO
Net Charge 0
Average Mass 343.89000
Monoisotopic Mass 343.17029
InChI InChI=1S/C21H26ClNO/c1-21(17-7-4-3-5-8-17,18-10-12-19(22)13-11-18)24-16-14-20-9-6-15-23(20)2/h3-5,7-8,10-13,20H,6,9,14-16H2,1-2H3/t20-,21-/m1/s1
InChIKey YNNUSGIPVFPVBX-NHCUHLMSSA-N
SMILES [H][C@@]1(CCCN1C)CCO[C@](C)(c1ccccc1)c1ccc(Cl)cc1
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): 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.
muscarinic antagonist
A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
Application(s): 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.
anti-allergic agent
A drug used to treat allergic reactions.
muscarinic antagonist
A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
antipruritic drug
A drug, usually applied topically, that relieves pruritus (itching).
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ChEBI Ontology
Outgoing clemastine (CHEBI:3738) has role anti-allergic agent (CHEBI:50857)
clemastine (CHEBI:3738) has role antipruritic drug (CHEBI:59683)
clemastine (CHEBI:3738) has role H1-receptor antagonist (CHEBI:37955)
clemastine (CHEBI:3738) has role muscarinic antagonist (CHEBI:48876)
clemastine (CHEBI:3738) is a N-alkylpyrrolidine (CHEBI:46775)
clemastine (CHEBI:3738) is a monochlorobenzenes (CHEBI:83403)
Incoming clemastine fumarate (CHEBI:3739) has part clemastine (CHEBI:3738)
IUPAC Name
(2R)-2-{2-[(1R)-1-(4-chlorophenyl)-1-phenylethoxy]ethyl}-1-methylpyrrolidine
INNs Sources
clemastina ChemIDplus
clemastine ChemIDplus
clemastinum ChemIDplus
Synonyms Sources
(+)-(2R)-2-(2-(((R)-p-chloro-α-methyl-α-phenylbenzyl)oxy)ethyl)-1-methylpyrrolidine ChemIDplus
(+)-(2R)-2-[2-[[(R)-p-chloro-α-methyl-α-phenylbenzyl]oxy]ethyl]-1-methylpyrrolidine NIST Chemistry WebBook
Clemastine KEGG COMPOUND
Manual Xrefs Databases
671 DrugCentral
C06913 KEGG COMPOUND
Clemastine Wikipedia
D03535 KEGG DRUG
DB00283 DrugBank
GB942152 Patent
LSM-2655 LINCS
View more database links
Registry Numbers Types Sources
15686-51-8 CAS Registry Number KEGG COMPOUND
15686-51-8 CAS Registry Number NIST Chemistry WebBook
15686-51-8 CAS Registry Number ChemIDplus
6486432 Beilstein Registry Number Beilstein
Citation Waiting for Citations Type Source
18788725 PubMed citation ChEMBL
Last Modified
22 February 2017