Chemical Component Summary

Name3-(2-chloro-10H-phenothiazin-10-yl)-N,N-dimethylpropan-1-amine
SynonymsChlorpromazine
Identifiers3-(2-chlorophenothiazin-10-yl)-N,N-dimethyl-propan-1-amine
FormulaC17 H19 Cl N2 S
Molecular Weight318.864
TypeNON-POLYMER
Isomeric SMILESCN(C)CCCN1c2ccccc2Sc3c1cc(cc3)Cl
InChIInChI=1S/C17H19ClN2S/c1-19(2)10-5-11-20-14-6-3-4-7-16(14)21-17-9-8-13(18)12-15(17)20/h3-4,6-9,12H,5,10-11H2,1-2H3
InChIKeyZPEIMTDSQAKGNT-UHFFFAOYSA-N

Chemical Details

Formal Charge0
Atom Count40
Chiral Atom Count0
Bond Count42
Aromatic Bond Count12

Drug Info: DrugBank

DrugBank IDDB00477 
NameChlorpromazine
Groups
  • investigational
  • vet_approved
  • approved
DescriptionThe prototypical phenothiazine antipsychotic drug. Like the other drugs in this class, chlorpromazine's antipsychotic actions are thought to be due to long-term adaptation by the brain to blocking dopamine receptors. Chlorpromazine has several other actions and therapeutic uses, including as an antiemetic and in the treatment of intractable hiccup.
Synonyms
  • Clorpromazina
  • 3-(2-chlorophenothiazin-10-yl)-N,N-dimethyl-propan-1-amine
  • Chlorpromazinum
  • N-(3-dimethylaminopropyl)-3-chlorophenothiazine
  • 3-(2-chloro-10H-phenothiazin-10-yl)-N,N-dimethyl-1-propanamine
Brand Names
  • Chlorpromazine Tablets B.P. 25mg
  • Chlorpromazine
  • Chlorpromanyl 40 Drops Syr 44.5mg/ml
  • Largactil Sup 100mg
  • Apo Chlorpromazine
IndicationFor the treatment of schizophrenia; to control nausea and vomiting; for relief of restlessness and apprehension before surgery; for acute intermittent porphyria; as an adjunct in the treatment of tetanus; to control the manifestations of the manic type of manic-depressive illness; for relief of intractable hiccups; for the treatment of severe behavioral problems in children (1 to 12 years of age) marked by combativeness and/or explosive hyperexcitable behavior (out of proportion to immediate provocations), and in the short-term treatment of hyperactive children who show excessive motor activity with accompanying conduct disorders consisting of some or all of the following symptoms: impulsivity, difficulty sustaining attention, aggressivity, mood lability, and poor frustration tolerance.
Categories
  • Adrenergic alpha-1 Receptor Antagonists
  • Adrenergic alpha-Antagonists
  • Adrenergic Antagonists
  • Agents producing tachycardia
  • Agents that produce hypertension
ATC-CodeN05AA01
CAS number50-53-3

Drug Targets

NameTarget SequencePharmacological ActionActions
Dopamine D2 receptorMDPLNLSWYDDDLERQNWSRPFNGSDGKADRPHYNYYATLLTLLIAVIVF...unknownantagonist
Dopamine D1 receptorMRTLNTSAMDGTGLVVERDFSVRILTACFLSLLILSTLLGNTLVCAAVIR...unknownantagonist
5-hydroxytryptamine receptor 1AMDVLSPGQGNNTTSPPAPFETGGNTTGISDVTVSYQVITSLLLGTLIFCA...unknownantagonist
5-hydroxytryptamine receptor 2AMDILCEENTSLSSTTNSLMQLNDDTRLYSNDFNSGEANTSDAFNWTVDSE...unknownantagonist
Alpha-1A adrenergic receptorMVFLSGNASDSSNCTQPPAPVNISKAILLGVILGGLILFGVLGNILVILS...unknownantagonist
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL71
PubChem 2726
ChEMBL CHEMBL71
ChEBI CHEBI:3647
CCDC/CSD DUKTOS, VICXAH
COD 2212995