CHLORPROMAZINE

Search structure
Trade Names:
Synonyms:
Status: Approved (1957)
Entry Type: Small molecule
Molecule Category: Parent
ATC: N05AA01
UNII: U42B7VYA4P

Structure
InChI Key ZPEIMTDSQAKGNT-UHFFFAOYSA-N
Smile CN(C)CCCN1c2ccccc2Sc2ccc(Cl)cc21
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C17H19ClN2S
Molecular Weight 318.87
AlogP 4.89
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 4.0
Polar Surface Area 6.48
Molecular species BASE
Aromatic Rings 2.0
Heavy Atoms 21.0

Pharmacology

Action Mechanism of Action Reference
ANTAGONIST D2-like dopamine receptor antagonist ISBN PubMed Wikipedia
Primary Target
5-HT2A receptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 1 Cytochrome P450 family 1A Cytochrome P450 1A2
- 4140 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C19
- 34100 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2D Cytochrome P450 2D6
- 1490 - 7000 -
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- 23300 - - -
Enzyme Hydrolase
- 23000 - - -
Enzyme Lyase
- 1300 - 118 -
Enzyme Oxidoreductase
- 5800-35400 - 3200-10800 70
Enzyme Phosphodiesterase
- 11000 - - -
Enzyme
- 5800-35400 - 3200-10800 70
Ion channel Ligand-gated ion channel Ionotropic glutamate receptor NMDA receptor
- 1300-21000 - - 25
Ion channel Ligand-gated ion channel Nicotinic acetylcholine receptor Nicotinic acetylcholine receptor alpha subunit
- 1280-16400 - - 7
Ion channel Voltage-gated ion channel Potassium channels Two-pore domain potassium channel
- 2700 - - -
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 1470-1479 - - -
Ion channel Voltage-gated ion channel Transient receptor potential channel
- - - 520-1300 -
Ion channel Voltage-gated ion channel Voltage-gated calcium channel
- 3400 - - -
Ion channel Voltage-gated ion channel Voltage-gated sodium channel
- 4300 - - 72
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Acetylcholine receptor
- - - 60-61 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Adrenergic receptor
- 31-31 - 2-6 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Dopamine receptor
- 10-112 - 1-50 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Histamine receptor
- 12 - 4 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Serotonin receptor
- 3 - 11-120 -
Secreted protein
- - 11700 - -
Surface antigen
2000 - - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC06 neurotransmitter transporter family
- 120 - 63 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 23-98
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- 27000 - - 85
Transporter Electrochemical transporter
- 120 - 63 23-98
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 90970 - 600-12200 -
Transporter Primary active transporter P-type ATPase Calcium ATPase
- 23000 - - -
Transporter
- 120 - 600-12200 23-98
Unclassified protein
- 7260-10300 1240 19280 -

Metabolites

visNetwork

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Schizophrenia 4 D012559 ClinicalTrials
Neonatal Abstinence Syndrome 3 D009357 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Delirium 2 D003693 ClinicalTrials
Glioblastoma 2 D005909 ClinicalTrials

Related Entries

MCS

Scaffolds

Salt

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Blood and lymphatic system disorders
37.5
Endocrine disorders
12.5
General disorders and administration site conditions
12.5
Investigations
12.5
Metabolism and nutrition disorders
12.5
Nervous system disorders
12.5

Cross References

Resources Reference
CAS NUMBER 50-53-3
ChEBI 3647
ChEMBL CHEMBL71
DrugBank DB00477
DrugCentral 621
EPA CompTox DTXSID0022808
FDA SRS U42B7VYA4P
Human Metabolome Database HMDB0014620
Guide to Pharmacology 83
KEGG C06906
PDB Z80
PharmGKB PA448964
PubChem 2726
SureChEMBL SCHEMBL8321
ZINC ZINC000000044027
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