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50-53-3 molecular structure
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[3-(2-chloro-10H-phenothiazin-10-yl)propyl]dimethylamine

ChemBase ID: 360
Molecular Formular: C17H19ClN2S
Molecular Mass: 318.86416
Monoisotopic Mass: 318.0957473
SMILES and InChIs

SMILES:
Clc1cc2N(CCCN(C)C)c3c(Sc2cc1)cccc3
Canonical SMILES:
CN(CCCN1c2ccccc2Sc2c1cc(Cl)cc2)C
InChI:
InChI=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
InChIKey:
ZPEIMTDSQAKGNT-UHFFFAOYSA-N

Cite this record

CBID:360 http://www.chembase.cn/molecule-360.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
[3-(2-chloro-10H-phenothiazin-10-yl)propyl]dimethylamine
IUPAC Traditional name
chlorpromazine
Brand Name
Chlorpromanyl (discontinued)
Intensol
Largactil Liquid
Largactil Oral Drops
Novo-Chlorpromazine
Thorazine Spansule
Synonyms
Chlorpromazine hydrochloride
Chlorpromazine
CAS Number
50-53-3
PubChem SID
160963823
46508395
PubChem CID
2726
CHEBI ID
3647
ATC CODE
N05AA01
CHEMBL
71
Chemspider ID
2625
DrugBank ID
DB00477
IUPHAR ligand ID
83
KEGG ID
D00270
Unique Ingredient Identifier
U42B7VYA4P
Wikipedia Title
Chlorpromazine
Medline Plus
a682040

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 1.2476761  LogD (pH = 7.4) 2.739641 
Log P 4.5350003  Molar Refractivity 93.7563 cm3
Polarizability 35.9708 Å3 Polar Surface Area 6.48 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 5.18  LOG S -4.88 
Solubility (Water) 4.17e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Pharmacology Properties Bioassay(PubChem)
Solubility
2.55 mg/L expand Show data source
Hydrophobicity(logP)
4.9 expand Show data source
Admin Routes
Oral, rectal (suppository), IM, IV infusion expand Show data source
Bioavailability
Oral, 30 to 50% (interindividual variations 10–70%) expand Show data source
Excretion
Biliary and renal, as metabolites (only traces of unchanged drug) expand Show data source
Half Life
16 to 30 hours. In long term treatment, CPZ induces its own metabolism expand Show data source
Metabolism
Hepatic, mostly CYP2D6-mediated expand Show data source
Legal Status
Rx-only expand Show data source
Pregnancy Category
C—only when benefit for the mother exceeds risk to unborn child expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia
DrugBank - DB00477 external link
Item Information
Drug Groups approved
Description The 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. [PubChem]
Indication For the treatment of schizophrenia, control nausea and vomiting, For relief of restlessness and apprehension before surgery, adjunct in the treatment of tetanus, control the manifestations of the manic type of manic-depressive illness.
Pharmacology Chlorpromazine is a psychotropic agent indicated for the treatment of schizophrenia. It also exerts sedative and antiemetic activity. Chlorpromazine has actions at all levels of the central nervous system-primarily at subcortical levels-as well as on multiple organ systems. Chlorpromazine has strong antiadrenergic and weaker peripheral anticholinergic activity; ganglionic blocking action is relatively slight. It also possesses slight antihistaminic and antiserotonin activity.
Toxicity Agitation, coma, convulsions, difficulty breathing, difficulty swallowing, dry mouth, extreme sleepiness, fever, intestinal blockage, irregular heart rate, low blood pressure, restlessness
Affected Organisms
Humans and other mammals
Biotransformation Extensively metabolized in the liver and kidneys. It is extensively metabolized by cytochrome P450 isozymes CYP2D6 (major pathway), CYP1A2 and CYP3A4. Approximately 10 to 12 major metabolite have been identified. Hydroxylation at positions 3 and 7 of the phenothiazine nucleus and the N-dimethylaminopropyl side chain undergoes demethylation and is also metabolized to an N-oxide. In urine, 20% of chlopromazine and its metabolites are excreted unconjugated in the urine as unchanged drug, demonomethylchlorpromazine, dedimethylchlorpromazine, their sulfoxide metabolites, and chlorpromazine-N-oxide. The remaining 80% consists of conjugated metabolites, principally O-glucuronides and small amounts of ethereal sulfates of the mono- and dihydroxy-derivatives of chlorpromazine and their sulfoxide metabolites. The major metabolites are the monoglucuronide of N-dedimethylchlorpromazine and 7-hydroxychlorpromazine. Approximately 37% of the administered dose of chlorpromazine is excreted in urine.
Absorption Readily absorbed from the GI tract. Bioavailability varies due to first-pass metabolism by the liver.
Half Life ~ 30 hours
Protein Binding > 90% to plasma proteins, primarily albumin
Elimination Kidneys, ~ 37% excreted in urine
Distribution * 20 L/kg
References
Leucht S, Wahlbeck K, Hamann J, Kissling W: New generation antipsychotics versus low-potency conventional antipsychotics: a systematic review and meta-analysis. Lancet. 2003 May 10;361(9369):1581-9. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com

REFERENCES

REFERENCES

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  • • Leucht S, Wahlbeck K, Hamann J, Kissling W: New generation antipsychotics versus low-potency conventional antipsychotics: a systematic review and meta-analysis. Lancet. 2003 May 10;361(9369):1581-9. Pubmed
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PATENTS

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