CHEBI:8461 - promethazine

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ChEBI Name promethazine
ChEBI ID CHEBI:8461
Definition A tertiary amine that is a substituted phenothiazine in which the ring nitrogen at position 10 is attached to C-3 of an N,N-dimethylpropan-2-amine moiety.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C17H20N2S
Net Charge 0
Average Mass 284.42018
Monoisotopic Mass 284.13472
InChI InChI=1S/C17H20N2S/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
InChIKey PWWVAXIEGOYWEE-UHFFFAOYSA-N
SMILES CC(CN1c2ccccc2Sc2ccccc12)N(C)C
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): anticoronaviral agent
Any antiviral agent which inhibits the activity of coronaviruses.
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): sedative
A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
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.
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.
antipruritic drug
A drug, usually applied topically, that relieves pruritus (itching).
anti-allergic agent
A drug used to treat allergic reactions.
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 promethazine (CHEBI:8461) has role anti-allergic agent (CHEBI:50857)
promethazine (CHEBI:8461) has role anticoronaviral agent (CHEBI:149553)
promethazine (CHEBI:8461) has role antiemetic (CHEBI:50919)
promethazine (CHEBI:8461) has role antipruritic drug (CHEBI:59683)
promethazine (CHEBI:8461) has role H1-receptor antagonist (CHEBI:37955)
promethazine (CHEBI:8461) has role local anaesthetic (CHEBI:36333)
promethazine (CHEBI:8461) has role sedative (CHEBI:35717)
promethazine (CHEBI:8461) is a phenothiazines (CHEBI:38093)
promethazine (CHEBI:8461) is a tertiary amine (CHEBI:32876)
promethazine (CHEBI:8461) is conjugate base of promethazine(1+) (CHEBI:61214)
Incoming promethazine(1+) (CHEBI:61214) is conjugate acid of promethazine (CHEBI:8461)
IUPAC Name
N,N-dimethyl-1-(10H-phenothiazin-10-yl)propan-2-amine
INNs Sources
prometazina ChEBI
prométhazine ChEBI
promethazine ChEBI
promethazinum ChEBI
Synonyms Sources
(2-dimethylamino-2-methyl)ethyl-N-dibenzoparathiazine ChemIDplus
10-(2-Dimethylaminopropyl)phenothiazine KEGG COMPOUND
10-[2-(dimethylamino)propyl]phenothiazine NIST Chemistry WebBook
N,N,α-trimethyl-10H-phenothiazine-10-ethanamine NIST Chemistry WebBook
N-(2'-dimethylamino-2'-methyl)ethylphenothiazine ChemIDplus
proazamine ChemIDplus
Promethazine KEGG COMPOUND
Manual Xrefs Databases
2286 DrugCentral
C07404 KEGG COMPOUND
D00494 KEGG DRUG
DB01069 DrugBank
HMDB0015202 HMDB
LSM-4440 LINCS
Promethazine Wikipedia
US2530451 Patent
US2607773 Patent
View more database links
Registry Numbers Types Sources
337077 Gmelin Registry Number Gmelin
60-87-7 CAS Registry Number KEGG COMPOUND
60-87-7 CAS Registry Number NIST Chemistry WebBook
60-87-7 CAS Registry Number ChemIDplus
88554 Reaxys Registry Number Reaxys
88554 Beilstein Registry Number Beilstein
Last Modified
23 April 2020
General Comments
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.
2014-07-15 Promethazine can be found in blood and urine samples of individuals who have taken this drug.