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

Stem definitionDrug idCAS RN
2274 58-38-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • prochlorperazine mesylate
  • prochlorperazine
  • capazine
  • chlormeprazine
  • chlorperazine
  • meterazin
  • meterazine
  • proazine
  • prochlorpemazine
  • prochlorperazin
  • prochlorpromazine
  • prochlorperazine maleate
  • prochlorperazine edisylate
  • prochlorperazine dimaleate
  • prochlorperzine
A phenothiazine antipsychotic used principally in the treatment of NAUSEA; VOMITING; and VERTIGO. It is more likely than CHLORPROMAZINE to cause EXTRAPYRAMIDAL DISORDERS. (From Martindale, The Extra Pharmacopoeia, 30th ed, p612)
  • Molecular weight: 373.94
  • Formula: C20H24ClN3S
  • CLOGP: 4.58
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 0
  • TPSA: 9.72
  • ALOGS: -4.53
  • ROTB: 4

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
0.10 g O
50 mg P
0.10 g R

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.10 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.10 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 3.83 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 15 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 22 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 16 mL/min/kg Lombardo F, Berellini G, Obach RS
t_half (Half-life) 9 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Oct. 23, 1956 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
Drug hypersensitivity 259.88 40.83 72 230 46571 2311212
Akathisia 214.82 40.83 35 267 1639 2356144
Gastrointestinal disorder 108.07 40.83 26 276 8891 2348892
Completed suicide 103.62 40.83 30 272 21004 2336779
Suicidal ideation 97.49 40.83 25 277 11062 2346721
Vomiting 67.68 40.83 30 272 71572 2286211
Nausea 66.41 40.83 34 268 112155 2245628
Neutropenic sepsis 62.13 40.83 12 290 1430 2356353
Oral herpes 57.06 40.83 12 290 2190 2355593
Mucosal inflammation 46.75 40.83 12 290 5212 2352571
Serotonin syndrome 46.14 40.83 11 291 3529 2354254
Exposure during pregnancy 45.82 40.83 17 285 25202 2332581
Dystonia 45.74 40.83 10 292 2184 2355599

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
Completed suicide 56.30 56.02 17 138 16295 1730331

Pharmacologic Action:

SourceCodeDescription
ATC N05AB04 NERVOUS SYSTEM
PSYCHOLEPTICS
ANTIPSYCHOTICS
Phenothiazines with piperazine structure
FDA EPC N0000175746 Phenothiazine
FDA Chemical/Ingredient N0000007544 Phenothiazines
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
CHEBI has role CHEBI:50919 antiemetic
CHEBI has role CHEBI:48561 dopaminergic antagonist
CHEBI has role CHEBI:37890 alpha-adrenergic antagonist
CHEBI has role CHEBI:48873 cholinergic antagonist
CHEBI has role CHEBI:65190 first generation antipsychotic
MeSH PA D014149 Tranquilizing Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Nausea and vomiting indication 16932000
Schizophrenia indication 58214004 DOID:5419
Nonpsychotic Anxiety indication
Prolonged-Severe Nausea and Vomiting indication
Chemotherapy-induced nausea and vomiting off-label use 236084000
Brain damage contraindication 2470005
Tachyarrhythmia contraindication 6285003
Urinary tract obstruction contraindication 7163005 DOID:5200
Alcoholism contraindication 7200002
Organophosphate poisoning contraindication 8260003
Weight gain finding contraindication 8943002
Severe chronic ulcerative colitis contraindication 14311001
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
Toxic megacolon contraindication 28536002 DOID:1770
Orthostatic hypotension contraindication 28651003
Atony of colon contraindication 29479008
Torsades de pointes contraindication 31722008
Parkinsonism contraindication 32798002
Hyperthyroidism contraindication 34486009 DOID:7998
Hypertensive disorder contraindication 38341003 DOID:10763
Complete trisomy 21 syndrome contraindication 41040004 DOID:14250
Conduction disorder of the heart contraindication 44808001
Achalasia of esophagus contraindication 45564002 DOID:9164
Chronic heart failure contraindication 48447003
Bradycardia contraindication 48867003
Paralytic ileus contraindication 55525008 DOID:8442
Peptic reflux disease contraindication 57643001
Ulcerative colitis contraindication 64766004 DOID:8577
Drug AND/OR toxin-induced diarrhea contraindication 65979008
Extrapyramidal disease contraindication 76349003
Spastic paralysis contraindication 78403003
Disturbance of salivary secretion contraindication 78948009
Hyperglycemia contraindication 80394007 DOID:4195
Hiatal hernia contraindication 84089009 DOID:12642
Epilepsy contraindication 84757009 DOID:1826
Leukopenia contraindication 84828003 DOID:615
Stupor contraindication 89458003
Kidney disease contraindication 90708001 DOID:557
Myasthenia gravis contraindication 91637004 DOID:437
Tardive dyskinesia contraindication 102449007
Prolonged QT interval contraindication 111975006
Gastrointestinal obstruction contraindication 126765001
Acute disease of cardiovascular system contraindication 128487001
Autonomic dysreflexia contraindication 129618003
Bleeding contraindication 131148009
Angina pectoris contraindication 194828000
Myocardial dysfunction contraindication 233928007
Disease of liver contraindication 235856003 DOID:409
Bladder outflow obstruction contraindication 236645006
Metabolic syndrome X contraindication 237602007 DOID:14221
Hyperprolactinemia contraindication 237662005 DOID:12700
Pyloric obstruction contraindication 244815007
Benign prostatic hyperplasia contraindication 266569009
Retention of urine contraindication 267064002
Anemia contraindication 271737000 DOID:2355
Drowsy contraindication 271782001
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Neutropenic disorder contraindication 303011007 DOID:1227
Coma contraindication 371632003
At risk for aspiration contraindication 371736008
Angle-closure glaucoma contraindication 392291006 DOID:13550
Visual impairment contraindication 397540003
Gastric ulcer contraindication 397825006 DOID:10808
Breastfeeding (mother) contraindication 413712001
Chronic lung disease contraindication 413839001
Disorder of coronary artery contraindication 414024009
Myocardial ischemia contraindication 414795007 DOID:3393
Obesity contraindication 414916001 DOID:9970
Congenital long QT syndrome contraindication 442917000
Carcinoma of female breast contraindication 447782002

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.74 Basic
pKa2 4.74 Basic
pKa3 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(3) dopamine receptor GPCR ANTAGONIST Ki 8.61 WOMBAT-PK IUPHAR
D(2) dopamine receptor GPCR ANTAGONIST Ki 8.76 WOMBAT-PK CHEMBL
Alpha-2A adrenergic receptor GPCR Ki 7.20 DRUG MATRIX
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 7.64 DRUG MATRIX
Potassium voltage-gated channel subfamily H member 2 Ion channel Ki 5.82 DRUG MATRIX
Sodium-dependent serotonin transporter Transporter Ki 6.21 DRUG MATRIX
Sodium-dependent noradrenaline transporter Transporter Ki 6.40 DRUG MATRIX
5-hydroxytryptamine receptor 2B GPCR Ki 7.19 DRUG MATRIX
5-hydroxytryptamine receptor 6 GPCR Ki 6.91 DRUG MATRIX
Alpha-2B adrenergic receptor GPCR Ki 8.32 DRUG MATRIX
Muscarinic acetylcholine receptor M1 GPCR Ki 6.61 DRUG MATRIX
Muscarinic acetylcholine receptor M2 GPCR Ki 5.96 DRUG MATRIX
Muscarinic acetylcholine receptor M3 GPCR Ki 6.49 DRUG MATRIX
Muscarinic acetylcholine receptor M4 GPCR Ki 6.72 DRUG MATRIX
Muscarinic acetylcholine receptor M5 GPCR Ki 6.80 DRUG MATRIX
Alpha-2C adrenergic receptor GPCR Ki 7.92 DRUG MATRIX
Sodium-dependent dopamine transporter Transporter Ki 5.86 DRUG MATRIX
Cytochrome P450 2D6 Enzyme IC50 6.52 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR Ki 7.89 DRUG MATRIX
Cytochrome P450 1A2 Enzyme IC50 5.70 DRUG MATRIX
Tyrosine-protein kinase Fyn Kinase IC50 5.25 DRUG MATRIX
D(4) dopamine receptor GPCR Ki 7.17 WOMBAT-PK
Histamine H1 receptor GPCR Ki 7.72 WOMBAT-PK
Alpha-1A adrenergic receptor GPCR Ki 7.62 WOMBAT-PK
5-hydroxytryptamine receptor 2C GPCR Ki 6.91 WOMBAT-PK
5-hydroxytryptamine receptor 2A GPCR Ki 7.82 WOMBAT-PK
Solute carrier family 22 member 1 Transporter IC50 4.30 CHEMBL
5-hydroxytryptamine receptor 1A GPCR Ki 5.23 PDSP
D(1A) dopamine receptor GPCR Ki 7.11 DRUG MATRIX
5-hydroxytryptamine receptor 4 GPCR Ki 6.71 DRUG MATRIX
Alpha-1B adrenergic receptor GPCR Ki 7.31 DRUG MATRIX
5-hydroxytryptamine receptor 1B GPCR Ki 5.92 DRUG MATRIX
Membrane-associated progesterone receptor component 1 Membrane receptor Ki 6.38 DRUG MATRIX
Pleiotropic ABC efflux transporter of multiple drugs Transporter IC50 5.77 CHEMBL
5-hydroxytryptamine receptor 1A GPCR IC50 6.02 CHEMBL
Alpha-1A adrenergic receptor GPCR IC50 7.49 CHEMBL

External reference:

IDSource
4018001 VUID
N0000146346 NUI
C0033229 UMLSCUI
D00479 KEGG_DRUG
79129001 SNOMEDCT_US
2073 MMSL
8704 RXNORM
372853006 SNOMEDCT_US
5361 MMSL
d00355 MMSL
4018001 VANDF
001478 NDDF
CHEMBL728 ChEMBL_ID
DB00433 DRUGBANK_ID
CHEMBL1200587 ChEMBL_ID
I1T8O1JTL6 UNII
84-02-6 SECONDARY_CAS_RN
CHEBI:8435 CHEBI
699 INN_ID
CHEMBL1201154 ChEMBL_ID
CHEMBL1314751 ChEMBL_ID
D011346 MESH_DESCRIPTOR_UI
4917 PUBCHEM_CID
7279 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Prochlorperazine Maleate HUMAN PRESCRIPTION DRUG LABEL 1 0378-5105 TABLET, FILM COATED 5 mg ORAL ANDA 12 sections
Prochlorperazine Maleate HUMAN PRESCRIPTION DRUG LABEL 1 0378-5110 TABLET, FILM COATED 10 mg ORAL ANDA 12 sections
PROCHLORPERAZINE MALEATE HUMAN PRESCRIPTION DRUG LABEL 1 0440-8190 TABLET 5 mg ORAL ANDA 12 sections
Compro HUMAN PRESCRIPTION DRUG LABEL 1 0574-7226 SUPPOSITORY 25 mg RECTAL ANDA 13 sections
Prochlorperazine Maleate HUMAN PRESCRIPTION DRUG LABEL 1 0615-2519 TABLET, FILM COATED 5 mg ORAL ANDA 12 sections
Prochlorperazine Maleate HUMAN PRESCRIPTION DRUG LABEL 1 0615-2520 TABLET, FILM COATED 10 mg ORAL ANDA 12 sections
Prochlorperazine Edisylate HUMAN PRESCRIPTION DRUG LABEL 1 0641-0491 INJECTION 5 mg INTRAVENOUS ANDA 12 sections
Prochlorperazine Edisylate HUMAN PRESCRIPTION DRUG LABEL 1 0641-6135 INJECTION 5 mg INTRAMUSCULAR ANDA 13 sections
Prochlorperazine HUMAN PRESCRIPTION DRUG LABEL 1 0713-0135 SUPPOSITORY 25 mg RECTAL ANDA 12 sections
Prochlorperazine Maleate HUMAN PRESCRIPTION DRUG LABEL 1 0781-5020 TABLET, FILM COATED 5 mg ORAL ANDA 13 sections
Prochlorperazine Maleate HUMAN PRESCRIPTION DRUG LABEL 1 0781-5021 TABLET, FILM COATED 10 mg ORAL ANDA 13 sections
PROCHLORPERAZINE MALEATE HUMAN PRESCRIPTION DRUG LABEL 1 10544-281 TABLET 10 mg ORAL ANDA 12 sections
PROCHLORPERAZINE MALEATE HUMAN PRESCRIPTION DRUG LABEL 1 10544-511 TABLET 5 mg ORAL ANDA 12 sections
Prochlorperazine Edisylate HUMAN PRESCRIPTION DRUG LABEL 1 14789-700 INJECTION 5 mg INTRAMUSCULAR ANDA 12 sections
PROCHLORPERAZINE HUMAN PRESCRIPTION DRUG LABEL 1 16590-327 TABLET 10 mg ORAL ANDA 10 sections
PROCHLORPERAZINE MALEATE HUMAN PRESCRIPTION DRUG LABEL 1 21695-571 TABLET 5 mg ORAL ANDA 12 sections
PROCHLORPERAZINE MALEATE HUMAN PRESCRIPTION DRUG LABEL 1 21695-572 TABLET 10 mg ORAL ANDA 12 sections
Prochlorperazine Edisylate HUMAN PRESCRIPTION DRUG LABEL 1 23155-294 INJECTION 5 mg INTRAMUSCULAR ANDA 12 sections
PROCHLORPERAZINE EDISYLATE HUMAN PRESCRIPTION DRUG LABEL 1 23155-497 INJECTION 5 mg INTRAMUSCULAR ANDA 12 sections
Prochlorperazine Edisylate HUMAN PRESCRIPTION DRUG LABEL 1 23155-523 INJECTION 5 mg INTRAMUSCULAR ANDA 12 sections
PROCHLORPERAZINE MALEATE HUMAN PRESCRIPTION DRUG LABEL 1 33261-141 TABLET 5 mg ORAL ANDA 12 sections
PROCHLORPERAZINE MALEATE HUMAN PRESCRIPTION DRUG LABEL 1 33261-550 TABLET 10 mg ORAL ANDA 12 sections
PROCHLORPERAZINE MALEATE HUMAN PRESCRIPTION DRUG LABEL 1 42291-728 TABLET 5 mg ORAL ANDA 12 sections
PROCHLORPERAZINE MALEATE HUMAN PRESCRIPTION DRUG LABEL 1 42291-729 TABLET 10 mg ORAL ANDA 12 sections
Prochlorperazine Maleate HUMAN PRESCRIPTION DRUG LABEL 1 42708-048 TABLET, FILM COATED 10 mg ORAL ANDA 11 sections
Prochlorperazine maleate HUMAN PRESCRIPTION DRUG LABEL 1 42708-103 TABLET 10 mg ORAL ANDA 12 sections
Prochlorperazine Maleate HUMAN PRESCRIPTION DRUG LABEL 1 43063-353 TABLET, FILM COATED 5 mg ORAL ANDA 12 sections
PROCHLORPERAZINE MALEATE HUMAN PRESCRIPTION DRUG LABEL 1 43063-742 TABLET 10 mg ORAL ANDA 12 sections
Prochlorperazine Maleate HUMAN PRESCRIPTION DRUG LABEL 1 50090-0109 TABLET, FILM COATED 5 mg ORAL ANDA 11 sections
Prochlorperazine Maleate HUMAN PRESCRIPTION DRUG LABEL 1 50090-0110 TABLET, FILM COATED 5 mg ORAL ANDA 13 sections