CHEBI:8459 - promazine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name promazine
ChEBI ID CHEBI:8459
Definition A phenothiazine deriative in which the phenothiazine tricycle has a 3-(dimethylaminopropyl) group at the N-10 position.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB5875452, ZINC000000010402
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Promazine (brand name Sparine among others), is used as a short-term add-on treatment for psychomotor agitation. Its approved uses in people is limited, but is used as a tranquilizer in veterinary medicine. It has weak antipsychotic effects but is generally not used to treat psychoses. It acts similar to chlorpromazine and causes sedation. It has predominantly anticholinergic side effects, though extrapyramidal side effects are not uncommon. It belongs to the typical antipsychotic and phenothiazine class of drugs. Promazine was approved for medical use in the United States in the 1950s, although it is no longer commercially available there.
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Formula C17H20N2S
Net Charge 0
Average Mass 284.42018
Monoisotopic Mass 284.13472
InChI InChI=1S/C17H20N2S/c1-18(2)12-7-13-19-14-8-3-5-10-16(14)20-17-11-6-4-9-15(17)19/h3-6,8-11H,7,12-13H2,1-2H3
InChIKey ZGUGWUXLJSTTMA-UHFFFAOYSA-N
SMILES CN(C)CCCN1c2ccccc2Sc2ccccc12
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): dopaminergic antagonist
A drug that binds to but does not activate dopamine receptors, thereby blocking the actions of dopamine or exogenous 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.
muscarinic antagonist
A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
serotonergic antagonist
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
Any EC 3.4.21.* (serine endopeptidase) inhibitor that interferes with the action of prolyl oligopeptidase (EC 3.4.21.26).
Application(s): dopaminergic antagonist
A drug that binds to but does not activate dopamine receptors, thereby blocking the actions of dopamine or exogenous 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.
muscarinic antagonist
A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
serotonergic antagonist
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
phenothiazine antipsychotic drug

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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing promazine (CHEBI:8459) has role antiemetic (CHEBI:50919)
promazine (CHEBI:8459) has role dopaminergic antagonist (CHEBI:48561)
promazine (CHEBI:8459) has role EC 3.4.21.26 (prolyl oligopeptidase) inhibitor (CHEBI:76779)
promazine (CHEBI:8459) has role H1-receptor antagonist (CHEBI:37955)
promazine (CHEBI:8459) has role muscarinic antagonist (CHEBI:48876)
promazine (CHEBI:8459) has role phenothiazine antipsychotic drug (CHEBI:37930)
promazine (CHEBI:8459) has role serotonergic antagonist (CHEBI:48279)
promazine (CHEBI:8459) is a phenothiazines (CHEBI:38093)
promazine (CHEBI:8459) is a tertiary amine (CHEBI:32876)
Incoming promazine sulfoxide (CHEBI:145225) has functional parent promazine (CHEBI:8459)
promazine hydrochloride (CHEBI:8460) has part promazine (CHEBI:8459)
IUPAC Name
N,N-dimethyl-3-(10H-phenothiazin-10-yl)propan-1-amine
INNs Sources
promazina ChemIDplus
promazine ChEBI
promazinum ChemIDplus
Synonyms Sources
10-(3-(Dimethylamino)propyl)phenothiazine ChemIDplus
N-(3-Dimethylaminopropyl)phenothiazine ChemIDplus
N-Dimethylamino-1-methylethyl thiodiphenylamine ChemIDplus
Promazine KEGG COMPOUND
Manual Xrefs Databases
2284 DrugCentral
C07379 KEGG COMPOUND
D08430 KEGG DRUG
DB00420 DrugBank
HMDB0014564 HMDB
LSM-2137 LINCS
Promazine Wikipedia
US2519886 Patent
View more database links
Registry Numbers Types Sources
244925 Reaxys Registry Number Reaxys
58-40-2 CAS Registry Number ChemIDplus
Citations
Peltonen I, Männistö PT (2011)
Effects of diverse psychopharmacological substances on the activity of brain prolyl oligopeptidase.
Basic & clinical pharmacology & toxicology 108, 46-54 [PubMed:20825390]
[show Abstract]
Rossi R, De Giorgio F, Benucci G, Oliva A, Fucci N (2009)
Acute intoxication by triazolam and promazine: a case report.
Medicine, science, and the law 49, 65-68 [PubMed:19306624]
[show Abstract]
Barnard DL, Day CW, Bailey K, Heiner M, Montgomery R, Lauridsen L, Jung KH, Li JK, Chan PK, Sidwell RW (2008)
Is the anti-psychotic, 10-(3-(dimethylamino)propyl)phenothiazine (promazine), a potential drug with which to treat SARS infections? Lack of efficacy of promazine on SARS-CoV replication in a mouse model.
Antiviral research 79, 105-113 [PubMed:18423639]
[show Abstract]
Varga JM, Kalchschmid G, Klein GF, Fritsch P (1991)
Mechanism of allergic cross-reactions--I. Multispecific binding of ligands to a mouse monoclonal anti-DNP IgE antibody.
Molecular immunology 28, 641-654 [PubMed:1650428]
[show Abstract]
Last Modified
07 November 2019