chlorpromazine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

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

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.30 g O
0.10 g P
0.30 g R

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 400 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.50 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 52.37 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 25 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 10 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 16 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.06 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 11 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Sept. 18, 1957 FDA GLAXOSMITHKLINE

FDA Adverse Event Reporting System (Female)

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 276.07 56.17 50 581 2030 2355424
Toxicity to various agents 248.86 56.17 77 554 32677 2324777
Completed suicide 186.89 56.17 56 575 20978 2336476
Overdose 163.74 56.17 50 581 19857 2337597
Electrocardiogram QT prolonged 134.23 56.17 35 596 7779 2349675
Catatonia 129.20 56.17 23 608 827 2356627
Drug abuse 106.15 56.17 32 599 11994 2345460
Cardiac arrest 103.46 56.17 33 598 14897 2342557
Suicide attempt 82.44 56.17 26 605 11256 2346198
Maternal exposure during pregnancy 71.52 56.17 25 606 14838 2342616
Exposure during pregnancy 68.84 56.17 28 603 25191 2332263
Coma 66.63 56.17 21 610 9035 2348419
Cardio-respiratory arrest 62.29 56.17 20 611 9126 2348328
Drug hypersensitivity 61.04 56.17 31 600 46612 2310842
Sopor 59.34 56.17 16 615 3979 2353475
Eosinophilic myocarditis 59.11 56.17 9 622 118 2357336
Agitation 58.57 56.17 20 611 11031 2346423
Parkinsonism 58.11 56.17 13 618 1492 2355962

FDA Adverse Event Reporting System (Male)

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 462.67 51.08 92 684 3056 1742949
Completed suicide 189.05 51.08 63 713 16249 1729756
Aggression 177.12 51.08 51 725 8064 1737941
Drug withdrawal syndrome neonatal 155.20 51.08 29 747 659 1745346
Catatonia 141.82 51.08 28 748 857 1745148
Foetal exposure during pregnancy 120.95 51.08 36 740 6323 1739682
Toxicity to various agents 116.62 51.08 52 724 29089 1716916
Decreased eye contact 107.33 51.08 15 761 43 1745962
Oppositional defiant disorder 104.51 51.08 15 761 55 1745950
Dyskinesia 101.09 51.08 28 748 3791 1742214
Insomnia 98.25 51.08 39 737 16237 1729768
Homicidal ideation 95.18 51.08 19 757 612 1745393
Agitation 93.89 51.08 34 742 10992 1735013
Sydenham's chorea 82.42 51.08 10 766 3 1746002
Bruxism 81.87 51.08 15 761 302 1745703
Blood creatine phosphokinase increased 81.70 51.08 29 747 8827 1737178
Drug ineffective 78.31 51.08 52 724 63749 1682256
Irritability 78.27 51.08 25 751 5507 1740498
Psychotic disorder 76.28 51.08 24 752 5032 1740973
Psychomotor hyperactivity 74.40 51.08 19 757 1874 1744131
Sleep disorder 72.75 51.08 22 754 4041 1741964
Tachycardia 71.68 51.08 29 747 12599 1733406
Suicidal ideation 71.41 51.08 26 750 8492 1737513
Suicide attempt 71.19 51.08 25 751 7356 1738649
Speech disorder 70.31 51.08 22 754 4526 1741479
Coordination abnormal 63.62 51.08 16 760 1481 1744524
Anxiety 62.66 51.08 28 748 15499 1730506
Tardive dyskinesia 62.58 51.08 15 761 1137 1744868
Premature baby 61.65 51.08 18 758 2924 1743081
Overdose 60.71 51.08 28 748 16673 1729332
Parkinsonism 60.01 51.08 15 761 1354 1744651
Foetal alcohol syndrome 59.58 51.08 8 768 15 1745990
Sedation 58.99 51.08 18 758 3399 1742606
Crying 58.89 51.08 15 761 1460 1744545
Dextrocardia 56.45 51.08 8 768 26 1745979
Poor feeding infant 56.44 51.08 9 767 75 1745930
Somnolence 54.44 51.08 26 750 16713 1729292
Drug interaction 52.42 51.08 30 746 27928 1718077

Pharmacologic Action:

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 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)

DiseaseRelationSNOMED_IDDOID
Nausea and vomiting indication 16932000
Disruptive behavior disorder indication 54319003
Schizophrenia indication 58214004 DOID:5419
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
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
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

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:

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
5-hydroxytryptamine receptor 2C GPCR Ki 7.40 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
D(3) dopamine receptor GPCR ANTAGONIST Ki 8.54 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:

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

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
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 0904-6892 TABLET, FILM COATED 10 mg ORAL ANDA 13 sections
CHLORPROMAZINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0904-6893 TABLET, FILM COATED 25 mg ORAL ANDA 13 sections
CHLORPROMAZINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0904-6894 TABLET, FILM COATED 50 mg ORAL ANDA 13 sections
CHLORPROMAZINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0904-6895 TABLET, FILM COATED 100 mg ORAL ANDA 13 sections
CHLORPROMAZINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0904-6896 TABLET, FILM COATED 200 mg ORAL ANDA 13 sections
CHLORPROMAZINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 50268-162 TABLET, FILM COATED 10 mg ORAL ANDA 13 sections
CHLORPROMAZINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 50268-163 TABLET, FILM COATED 25 mg ORAL ANDA 13 sections
CHLORPROMAZINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 50268-164 TABLET, FILM COATED 50 mg ORAL ANDA 13 sections
CHLORPROMAZINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 50268-165 TABLET, FILM COATED 100 mg ORAL ANDA 13 sections
CHLORPROMAZINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 50268-166 TABLET, FILM COATED 200 mg ORAL ANDA 13 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