chlorpromazine indications/contra

Stem definitionDrug idCAS RN
621 50-53-3

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • chlorpromazine
  • 2-Chloropromazine
  • chlordelazin
  • chlorderazin
  • thorazine
  • contomin
  • chlorpromazine hydrochloride
  • chlorpromazine HCl
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.
  • Molecular weight: 318.86
  • Formula: C17H19ClN2S
  • CLOGP: 5.50
  • LIPINSKI: 1
  • HAC: 2
  • HDO: 0
  • TPSA: 6.48
  • ALOGS: -4.88
  • ROTB: 4

Drug dosage:

DoseUnitRoute
0.30 g O
0.10 g P
0.30 g R

Approvals:

DateAgencyCompanyOrphan
Sept. 18, 1957 FDA GLAXOSMITHKLINE

FDA Adverse Event Reporting System

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MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Neuroleptic malignant syndrome 698.09 46.01 131 1133 4310 3380285
Completed suicide 435.54 46.01 129 1135 30985 3353610
Toxicity to various agents 427.52 46.01 140 1124 46914 3337681
Catatonia 307.09 46.01 55 1209 1345 3383250
Overdose 266.68 46.01 91 1173 33887 3350708
Drug withdrawal syndrome neonatal 168.46 46.01 36 1228 2214 3382381
Aggression 161.28 46.01 48 1216 11337 3373258
Drug abuse 134.92 46.01 47 1217 18283 3366312
Agitation 127.80 46.01 46 1218 19660 3364935
Foetal exposure during pregnancy 118.71 46.01 41 1223 15510 3369085
Psychotic disorder 102.89 46.01 32 1232 8702 3375893
Suicide attempt 91.51 46.01 34 1230 15813 3368782
Sedation 87.41 46.01 26 1238 6075 3378520
Muscle rigidity 85.51 46.01 22 1242 3012 3381583
Dystonia 85.48 46.01 23 1241 3744 3380851
Intentional overdose 85.46 46.01 32 1232 15193 3369402
Insomnia 82.47 46.01 40 1224 35858 3348737
Cardio-respiratory arrest 81.39 46.01 31 1233 15409 3369186
Parkinsonism 80.66 46.01 20 1244 2358 3382237
Somnolence 80.39 46.01 38 1226 32166 3352429
Blood creatine phosphokinase increased 79.07 46.01 29 1235 12984 3371611
Drug ineffective 76.85 46.01 58 1206 116032 3268563
Exposure during pregnancy 76.46 46.01 35 1229 27528 3357067
Respiratory depression 75.77 46.01 21 1243 3813 3380782
Tardive dyskinesia 74.63 46.01 19 1245 2492 3382103
Electrocardiogram QT prolonged 72.83 46.01 26 1238 10769 3373826
Tachycardia 72.19 46.01 32 1232 23339 3361256
Rhabdomyolysis 70.21 46.01 28 1236 15701 3368894
Drug interaction 69.69 46.01 39 1225 46773 3337822
Dyskinesia 66.47 46.01 22 1242 7263 3377332

Pharmacologic Action:

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SourceCodeDescription
ATC N05AA01 NERVOUS SYSTEM
PSYCHOLEPTICS
ANTIPSYCHOTICS
Phenothiazines with aliphatic side-chain
FDA EPC N0000175746 Phenothiazine
FDA Chemical/Ingredient N0000007544 Phenothiazines
CHEBI has role CHEBI:50919 antiemetic
CHEBI has role CHEBI:48561 dopaminergic antagonist
CHEBI has role CHEBI:37930 phenothiazine antipsychotic drug
MeSH PA D000932 Antiemetics
MeSH PA D014150 Antipsychotic Agents
MeSH PA D001337 Autonomic Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D015259 Dopamine Agents
MeSH PA D018492 Dopamine Antagonists
MeSH PA D005765 Gastrointestinal Agents
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D011619 Psychotropic Drugs
MeSH PA D014149 Tranquilizing Agents

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Nausea and vomiting indication 16932000
Disruptive behavior disorder indication 54319003
Schizophrenia indication 58214004
Psychotic disorder indication 69322001
Bipolar affective disorder, current episode manic indication 191618007
Acute intermittent porphyria indication 234422006 DOID:3890
Pre-Op Apprehension indication
Tetanus Adjunct Treatment indication
Intractable Hiccups indication
Alcoholism contraindication 7200002
Organophosphate poisoning contraindication 8260003
Weight gain finding contraindication 8943002
Neuroleptic malignant syndrome contraindication 15244003 DOID:14464
Senile dementia contraindication 15662003
Chronic disease of respiratory system contraindication 17097001
Myocardial infarction contraindication 22298006 DOID:5844
Glaucoma contraindication 23986001 DOID:1686
Orthostatic hypotension contraindication 28651003
Torsades de pointes contraindication 31722008
Parkinsonism contraindication 32798002 DOID:13548
Conduction disorder of the heart contraindication 44808001
Chronic heart failure contraindication 48447003
Bradycardia contraindication 48867003
Extrapyramidal disease contraindication 76349003
Hyperglycemia contraindication 80394007 DOID:4195
Epilepsy contraindication 84757009 DOID:1826
Leukopenia contraindication 84828003 DOID:615
Stupor contraindication 89458003
Tardive dyskinesia contraindication 102449007
Prolonged QT interval contraindication 111975006
Acute disease of cardiovascular system contraindication 128487001
Angina pectoris contraindication 194828000
Disease of liver contraindication 235856003 DOID:409
Metabolic syndrome X contraindication 237602007 DOID:14221
Hyperprolactinemia contraindication 237662005 DOID:12700
Benign prostatic hyperplasia contraindication 266569009 DOID:2883
Retention of urine contraindication 267064002
Anemia contraindication 271737000 DOID:2355
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Neutropenic disorder contraindication 303011007 DOID:1227
Coma contraindication 371632003
At risk for aspiration contraindication 371736008
Visual impairment contraindication 397540003
Breastfeeding (mother) contraindication 413712001
Myocardial ischemia contraindication 414795007 DOID:3393
Obesity contraindication 414916001 DOID:9970
Congenital long QT syndrome contraindication 442917000
Carcinoma of female breast contraindication 447782002
Smokes tobacco daily contraindication 449868002

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.04 Basic
pKa2 2.21 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
D(2) dopamine receptor GPCR ANTAGONIST Ki 8.15 WOMBAT-PK CHEMBL
D(4) dopamine receptor GPCR ANTAGONIST Ki 7.69 WOMBAT-PK
Histamine H4 receptor GPCR Ki 6.87 WOMBAT-PK
Histamine H1 receptor GPCR Ki 8.20 WOMBAT-PK
5-hydroxytryptamine receptor 5A GPCR Ki 6.93 PDSP
5-hydroxytryptamine receptor 3A Ion channel Ki 6.01 PDSP
Alpha-1B adrenergic receptor GPCR Ki 9.09 PDSP
5-hydroxytryptamine receptor 1E GPCR Ki 6.46 PDSP
5-hydroxytryptamine receptor 1B GPCR Ki 5.83 PDSP
5-hydroxytryptamine receptor 1D GPCR Ki 6.34 PDSP
Histamine H2 receptor GPCR Ki 6.76 PDSP
Muscarinic acetylcholine receptor M3 GPCR Ki 7.25 PDSP
Muscarinic acetylcholine receptor M1 GPCR Ki 7.60 PDSP
Muscarinic acetylcholine receptor M5 GPCR Ki 7.38 PDSP
Muscarinic acetylcholine receptor M4 GPCR Ki 7.40 PDSP
Muscarinic acetylcholine receptor M2 GPCR Ki 6.75 PDSP
Mu-type opioid receptor GPCR Ki 5.23 DRUG MATRIX
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 6.72 DRUG MATRIX
Sodium-dependent noradrenaline transporter Transporter Ki 7.72 DRUG MATRIX
Sodium-dependent dopamine transporter Transporter Ki 5.68 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR Ki 8.71 DRUG MATRIX
Kappa-type opioid receptor GPCR Ki 5.35 DRUG MATRIX
Delta-type opioid receptor GPCR Ki 5.13 DRUG MATRIX
Epidermal growth factor receptor Kinase IC50 4.54 DRUG MATRIX
Tyrosine-protein kinase Fyn Kinase IC50 5.06 DRUG MATRIX
Receptor tyrosine-protein kinase erbB-2 Kinase IC50 4.71 DRUG MATRIX
Substance-K receptor GPCR Ki 5.04 DRUG MATRIX
Melanocortin receptor 4 GPCR Ki 4.84 DRUG MATRIX
Melanocortin receptor 5 GPCR Ki 5.15 DRUG MATRIX
Melanocortin receptor 3 GPCR Ki 4.67 DRUG MATRIX
D(3) dopamine receptor GPCR ANTAGONIST Ki 8.54 WOMBAT-PK
Multidrug resistance protein 1 Transporter Ki 6.22 CHEMBL
Solute carrier family 22 member 1 Transporter IC50 4.57 CHEMBL
5-hydroxytryptamine receptor 1A GPCR Ki 6.17 CHEMBL
Sodium channel alpha subunits; brain (Types I, II, III) Ion channel IC50 5.37 CHEMBL
Major prion protein Surface antigen EC50 5.70 CHEMBL
Sodium-dependent serotonin transporter Transporter IC50 6.92 CHEMBL
Calmodulin Cytosolic other Kd 5.91 CHEMBL
Glutamate [NMDA] receptor Ion channel IC50 6.22 CHEMBL
5-hydroxytryptamine receptor 2B GPCR Ki 7.28 CHEMBL
5-hydroxytryptamine receptor 2C GPCR Ki 7.40 WOMBAT-PK
5-hydroxytryptamine receptor 2A GPCR ANTAGONIST Ki 8.10 WOMBAT-PK
5-hydroxytryptamine receptor 6 GPCR Ki 7.44 WOMBAT-PK
D(1A) dopamine receptor GPCR Ki 7.19 WOMBAT-PK
Alpha-2C adrenergic receptor GPCR Ki 7.10 WOMBAT-PK
D(1B) dopamine receptor GPCR Ki 6.93 WOMBAT-PK
Alpha-2B adrenergic receptor GPCR Ki 7.60 WOMBAT-PK
5-hydroxytryptamine receptor 7 GPCR Ki 7.41 WOMBAT-PK
Solute carrier family 22 member 2 Transporter IC50 4.85 WOMBAT-PK
Cytochrome P450 2D6 Enzyme Ki 5.15 WOMBAT-PK
Aldehyde oxidase Enzyme IC50 6.24 WOMBAT-PK
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 5.83 WOMBAT-PK
Alpha-2A adrenergic receptor GPCR Ki 6.20 WOMBAT-PK
Ryanodine receptor 1 Ion channel IC50 3.57 WOMBAT-PK
FAD-linked sulfhydryl oxidase ALR Enzyme AC50 5.99 CHEMBL
Alpha-1A adrenergic receptor GPCR Ki 9.55 PDSP
Arachidonate 15-lipoxygenase Enzyme IC50 4.80 DRUG MATRIX
Alpha-1B adrenergic receptor GPCR Ki 8.30 DRUG MATRIX
5-hydroxytryptamine receptor 1B GPCR Ki 5.74 DRUG MATRIX
Membrane-associated progesterone receptor component 1 Membrane receptor Ki 5.78 DRUG MATRIX
Trypanothione reductase Enzyme Ki 5.49 CHEMBL
Dopamine receptor GPCR IC50 7.60 CHEMBL
5-hydroxytryptamine receptor 7 GPCR Ki 7.68 CHEMBL
Glutamate NMDA receptor Ion channel IC50 5.89 CHEMBL
Muscarinic acetylcholine receptor GPCR Ki 7.22 CHEMBL
D(2) dopamine receptor GPCR IC50 7.10 CHEMBL
Serotonin 2 (5-HT2) receptor GPCR Ki 9.15 CHEMBL
Dopamine receptor GPCR Ki 7.85 CHEMBL
Pleiotropic ABC efflux transporter of multiple drugs Transporter IC50 5.35 CHEMBL
Transient receptor potential cation channel subfamily V member 1 Ion channel Ki 5.89 CHEMBL
Adenylate cyclase Enzyme Ki 6.93 CHEMBL
5-hydroxytryptamine receptor 1A GPCR Ki 6.75 CHEMBL
D(1A) dopamine receptor GPCR Ki 7.46 CHEMBL
Acetylcholine receptor subunit alpha Ion channel IC50 5.89 CHEMBL
D(2) dopamine receptor GPCR Ki 8.92 CHEMBL
Histamine H1 receptor GPCR Ki 7.30 CHEMBL
Alpha-1A adrenergic receptor GPCR IC50 8.07 CHEMBL
5-hydroxytryptamine receptor 6 GPCR ANTAGONIST Ki 8.40 IUPHAR
5-hydroxytryptamine receptor 7 GPCR ANTAGONIST Ki 5.30 IUPHAR

External reference:

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IDSource
DB00477 DRUGBANK_ID
83 IUPHAR_LIGAND_ID
4017861 VUID
N0000146214 NUI
C0008286 UMLSCUI
D00270 KEGG_DRUG
CHEMBL71 ChEMBL_ID
4017861 VANDF
N0000006947 NDFRT
N0000146214 NDFRT
004587 NDDF
2403 RXNORM
387258005 SNOMEDCT_US
47331002 SNOMEDCT_US
4428 MMSL
d00064 MMSL
9WP59609J6 UNII
69-09-0 SECONDARY_CAS_RN
2726 PUBCHEM_CID
CHEMBL1713 ChEMBL_ID
D002746 MESH_DESCRIPTOR_UI
183 INN_ID
CHEBI:3647 CHEBI
Z80 PDB_CHEM_ID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Chlorpromazine HUMAN PRESCRIPTION DRUG LABEL 1 0615-1546 TABLET, FILM COATED 25 mg ORAL ANDA 13 sections
Chlorpromazine HUMAN PRESCRIPTION DRUG LABEL 1 0615-1547 TABLET, FILM COATED 50 mg ORAL ANDA 13 sections
Chlorpromazine HUMAN PRESCRIPTION DRUG LABEL 1 0615-1548 TABLET, FILM COATED 100 mg ORAL ANDA 13 sections
Chlorpromazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-7683 TABLET, SUGAR COATED 50 mg ORAL ANDA 13 sections
Chlorpromazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-7717 TABLET, SUGAR COATED 100 mg ORAL ANDA 13 sections
Chlorpromazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-7737 TABLET, SUGAR COATED 25 mg ORAL ANDA 13 sections
Chlorpromazine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0641-1397 INJECTION 25 mg INTRAMUSCULAR ANDA 13 sections
Chlorpromazine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0641-1398 INJECTION 25 mg INTRAMUSCULAR ANDA 13 sections
Chlorpromazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-5913 TABLET, SUGAR COATED 10 mg ORAL ANDA 13 sections
Chlorpromazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-5914 TABLET, SUGAR COATED 25 mg ORAL ANDA 13 sections
Chlorpromazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-5915 TABLET, SUGAR COATED 50 mg ORAL ANDA 13 sections
Chlorpromazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-5916 TABLET, SUGAR COATED 100 mg ORAL ANDA 13 sections
Chlorpromazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-5917 TABLET, SUGAR COATED 200 mg ORAL ANDA 13 sections
Chlorpromazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0832-0300 TABLET, SUGAR COATED 10 mg ORAL ANDA 12 sections
Chlorpromazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0832-0301 TABLET, SUGAR COATED 25 mg ORAL ANDA 12 sections
Chlorpromazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0832-0302 TABLET, SUGAR COATED 50 mg ORAL ANDA 12 sections
Chlorpromazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0832-0303 TABLET, SUGAR COATED 100 mg ORAL ANDA 12 sections
Chlorpromazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0832-0304 TABLET, SUGAR COATED 200 mg ORAL ANDA 12 sections
Chlorpromazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 24236-027 TABLET, SUGAR COATED 100 mg ORAL ANDA 12 sections
Chlorpromazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 24236-029 TABLET, SUGAR COATED 50 mg ORAL ANDA 12 sections
Chlorpromazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 24236-181 TABLET, SUGAR COATED 25 mg ORAL ANDA 12 sections
Chlorpromazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 24236-258 TABLET, SUGAR COATED 100 mg ORAL ANDA 12 sections
Chlorpromazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 24236-323 TABLET, SUGAR COATED 25 mg ORAL ANDA 12 sections
Chlorpromazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51079-130 TABLET, SUGAR COATED 50 mg ORAL ANDA 12 sections
Chlorpromazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51079-516 TABLET, SUGAR COATED 100 mg ORAL ANDA 12 sections
Chlorpromazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51079-517 TABLET, SUGAR COATED 200 mg ORAL ANDA 12 sections
Chlorpromazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51079-518 TABLET, SUGAR COATED 10 mg ORAL ANDA 12 sections
Chlorpromazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51079-519 TABLET, SUGAR COATED 25 mg ORAL ANDA 12 sections
Chlorpromazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 52125-062 TABLET, SUGAR COATED 50 mg ORAL ANDA 13 sections
Chlorpromazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 52125-138 TABLET, SUGAR COATED 100 mg ORAL ANDA 13 sections