CHEBI:8435 - prochlorperazine

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ChEBI Name prochlorperazine
ChEBI ID CHEBI:8435
Definition A member of the class of phenothiazines that is 10H-phenothiazine having a chloro substituent at the 2-position and a 3-(4-methylpiperazin-1-yl)propyl group at the N-10 position.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:59073
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Formula C20H24ClN3S
Net Charge 0
Average Mass 373.94300
Monoisotopic Mass 373.13795
InChI InChI=1S/C20H24ClN3S/c1-22-11-13-23(14-12-22)9-4-10-24-17-5-2-3-6-19(17)25-20-8-7-16(21)15-18(20)24/h2-3,5-8,15H,4,9-14H2,1H3
InChIKey WIKYUJGCLQQFNW-UHFFFAOYSA-N
SMILES CN1CCN(CCCN2c3ccccc3Sc3ccc(Cl)cc23)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): dopaminergic antagonist
A drug that binds to but does not activate dopamine receptors, thereby blocking the actions of dopamine or exogenous agonists.
alpha-adrenergic antagonist
An agent that binds to but does not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous alpha-adrenergic agonists. alpha-Adrenergic antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma.
cholinergic antagonist
Any drug that binds to but does not activate cholinergic receptors, thereby blocking the actions of acetylcholine or cholinergic 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).
dopamine receptor D2 antagonist
An antagonist that binds to and deactivates the dopamine receptor D2, the main receptor for all antipsychotic drugs.
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.
dopaminergic antagonist
A drug that binds to but does not activate dopamine receptors, thereby blocking the actions of dopamine or exogenous agonists.
alpha-adrenergic antagonist
An agent that binds to but does not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous alpha-adrenergic agonists. alpha-Adrenergic antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma.
cholinergic antagonist
Any drug that binds to but does not activate cholinergic receptors, thereby blocking the actions of acetylcholine or cholinergic agonists.
first generation antipsychotic
Antipsychotic drugs which can have different modes of action but which tend to be more likely than second generation antipsychotics to cause extrapyramidal motor control disabilities such as body rigidity or Parkinson's disease-type movements; such body movements can become permanent even after treatment has ceased.
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ChEBI Ontology
Outgoing prochlorperazine (CHEBI:8435) has parent hydride 10H-phenothiazine (CHEBI:37931)
prochlorperazine (CHEBI:8435) has role α-adrenergic antagonist (CHEBI:37890)
prochlorperazine (CHEBI:8435) has role antiemetic (CHEBI:50919)
prochlorperazine (CHEBI:8435) has role cholinergic antagonist (CHEBI:48873)
prochlorperazine (CHEBI:8435) has role dopamine receptor D2 antagonist (CHEBI:131787)
prochlorperazine (CHEBI:8435) has role dopaminergic antagonist (CHEBI:48561)
prochlorperazine (CHEBI:8435) has role EC 3.4.21.26 (prolyl oligopeptidase) inhibitor (CHEBI:76779)
prochlorperazine (CHEBI:8435) has role first generation antipsychotic (CHEBI:65190)
prochlorperazine (CHEBI:8435) is a N-alkylpiperazine (CHEBI:46845)
prochlorperazine (CHEBI:8435) is a N-methylpiperazine (CHEBI:46920)
prochlorperazine (CHEBI:8435) is a organochlorine compound (CHEBI:36683)
prochlorperazine (CHEBI:8435) is a phenothiazines (CHEBI:38093)
Incoming prochlorperazine maleate (CHEBI:8436) has part prochlorperazine (CHEBI:8435)
prochlorperazine methanesulfonate (CHEBI:34932) has part prochlorperazine (CHEBI:8435)
IUPAC Name
2-chloro-10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine
INNs Sources
prochlorpérazine ChEBI
prochlorperazine ChEBI
prochlorperazinum ChEBI
proclorperazina ChEBI
Synonyms Sources
2-Chloro-10-(3-(1-methyl-4-piperazinyl)propyl)-phenothiazine ChemIDplus
2-Chloro-10-(3-(4-methyl-1-piperazinyl)propyl)phenothiazine ChemIDplus
3-Chloro-10-(3-(1-methyl-4-piperazinyl)propyl)phenothiazine ChemIDplus
3-Chloro-10-(3-(4-methyl-1-piperazinyl)propyl)phenothiazine ChemIDplus
Chloro-3 (N-methylpiperazinyl-3 propyl)-10 phenothiazine ChemIDplus
N-(gamma-(4'-Methylpiperazinyl-1')propyl)-3-chlorophenothiazine ChemIDplus
Prochlorperazin ChemIDplus
Prochlorperazine KEGG COMPOUND
Prochlorpermazine ChemIDplus
Prochlorpromazine ChemIDplus
Procloperazine ChemIDplus
Manual Xrefs Databases
2274 DrugCentral
C07403 KEGG COMPOUND
D00493 KEGG DRUG
DB00433 DrugBank
FR1167627 Patent
GB780193 Patent
HMDB0014577 HMDB
LSM-2436 LINCS
Prochlorperazine Wikipedia
US2902484 Patent
View more database links
Registry Numbers Types Sources
48537 Reaxys Registry Number Reaxys
48537 Beilstein Registry Number Beilstein
58-38-8 CAS Registry Number NIST Chemistry WebBook
58-38-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
13808146 PubMed citation Europe PMC
1650428 PubMed citation Europe PMC
20825390 PubMed citation Europe PMC
4891872 PubMed citation Europe PMC
Last Modified
22 February 2017