CHEBI:8462 - promethazine hydrochloride

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ChEBI Name promethazine hydrochloride
ChEBI ID CHEBI:8462
Definition The hydrochloride salt of promethazine.
Stars This entity has been manually annotated by the ChEBI Team.
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Formulae C17H20N2S.HCl
C17H21ClN2S
Net Charge 0
Average Mass 320.88000
Monoisotopic Mass 320.11140
InChI InChI=1S/C17H20N2S.ClH/c1-13(18(2)3)12-19-14-8-4-6-10-16(14)20-17-11-7-5-9-15(17)19;/h4-11,13H,12H2,1-3H3;1H
InChIKey XXPDBLUZJRXNNZ-UHFFFAOYSA-N
SMILES Cl.CC(CN1c2ccccc2Sc2ccccc12)N(C)C
Roles Classification
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.
Application(s): antipruritic drug
A drug, usually applied topically, that relieves pruritus (itching).
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.
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.
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.
sedative
A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
anti-allergic agent
A drug used to treat allergic reactions.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing promethazine hydrochloride (CHEBI:8462) has part promethazine(1+) (CHEBI:61214)
promethazine hydrochloride (CHEBI:8462) has role anti-allergic agent (CHEBI:50857)
promethazine hydrochloride (CHEBI:8462) has role antiemetic (CHEBI:50919)
promethazine hydrochloride (CHEBI:8462) has role antipruritic drug (CHEBI:59683)
promethazine hydrochloride (CHEBI:8462) has role H1-receptor antagonist (CHEBI:37955)
promethazine hydrochloride (CHEBI:8462) has role local anaesthetic (CHEBI:36333)
promethazine hydrochloride (CHEBI:8462) has role sedative (CHEBI:35717)
promethazine hydrochloride (CHEBI:8462) is a hydrochloride (CHEBI:36807)
IUPAC Name
N,N-dimethyl-1-(10H-phenothiazin-10-yl)propan-2-amine hydrochloride
Synonyms Sources
(+-)-10-(2-(Dimethylamino)propyl)phenothiazine monohydrochloride ChemIDplus
10-(2-Dimethylamino-1-propyl)phenothiazine hydrochloride ChemIDplus
10-(3-Dimethylaminoisopropyl)phenothiazine hydrochloride ChemIDplus
N-(2'-dimethylamino-2'-methyl)ethylphenothiazine hydrochloride ChemIDplus
N-(2-dimethylaminopropyl-1)phenothiazine hydrochloride ChemIDplus
promethazine HCl ChemIDplus
Brand Names Sources
Fenergan DrugBank
Phenergan DrugBank
Manual Xrefs Databases
D00480 KEGG DRUG
DB01069 DrugBank
View more database links
Registry Numbers Types Sources
4166397 Reaxys Registry Number Reaxys
4166397 Beilstein Registry Number Beilstein
58-33-3 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
20541454 PubMed citation Europe PMC
21125640 PubMed citation Europe PMC
21134682 PubMed citation Europe PMC
21788155 PubMed citation Europe PMC
21871787 PubMed citation Europe PMC
22119804 PubMed citation Europe PMC
22346617 PubMed citation Europe PMC
6196640 PubMed citation Europe PMC
Last Modified
24 September 2014
General Comment
2011-02-04 A sedating antihistamine with antimuscarinic properties, promethazine is used as the monohydrochloride salt for the symptomatic relief of a variety of allergic conditions including conjunctivitis, rhinitis, and urticaria, as well as pruritic skin disorders. The anti-emetic action of both the hydrochloride and the teoclate (8-chlorotheophylline) salts is used for the prevention of nausea in cases of motion sickness and post-operative vomiting.