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

Stem definitionDrug idCAS RN
2172 2062-78-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • pimozide
  • primozide
  • R6238
  • R-6238
A diphenylbutylpiperidine that is effective as an antipsychotic agent and as an alternative to HALOPERIDOL for the suppression of vocal and motor tics in patients with Tourette syndrome. Although the precise mechanism of action is unknown, blockade of postsynaptic dopamine receptors has been postulated. (From AMA Drug Evaluations Annual, 1994, p403)
  • Molecular weight: 461.56
  • Formula: C28H29F2N3O
  • CLOGP: 6.40
  • LIPINSKI: 1
  • HAC: 4
  • HDO: 1
  • TPSA: 35.58
  • ALOGS: -5.43
  • ROTB: 7

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
4 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.01 mg/mL Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.31 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 40 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
July 31, 1984 FDA TEVA

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

SourceCodeDescription
ATC N05AG02 NERVOUS SYSTEM
PSYCHOLEPTICS
ANTIPSYCHOTICS
Diphenylbutylpiperidine derivatives
FDA EPC N0000180182 Typical Antipsychotic
MeSH PA D018726 Anti-Dyskinesia Agents
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 D018377 Neurotransmitter Agents
MeSH PA D011619 Psychotropic Drugs
CHEBI has role CHEBI:37955 H1-receptor antagonist
CHEBI has role CHEBI:48279 serotonergic antagonist
CHEBI has role CHEBI:66956 antidyskinesia agent
CHEBI has role CHEBI:48561 dopaminergic antagonist
CHEBI has role CHEBI:65190 first generation antipsychotic
MeSH PA D014149 Tranquilizing Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Gilles de la Tourette's syndrome indication 5158005 DOID:11119
Neuroleptic malignant syndrome contraindication 15244003 DOID:14464
Senile dementia contraindication 15662003
Agranulocytosis contraindication 17182001 DOID:12987
Glaucoma contraindication 23986001 DOID:1686
Torsades de pointes contraindication 31722008
Parkinsonism contraindication 32798002
Hypokalemia contraindication 43339004
Conduction disorder of the heart contraindication 44808001
Leukopenia contraindication 84828003 DOID:615
Kidney disease contraindication 90708001 DOID:557
Tardive dyskinesia contraindication 102449007
Prolonged QT interval contraindication 111975006
Seizure disorder contraindication 128613002
Hypomagnesemia contraindication 190855004
Motor tic disorder contraindication 230337001
Disease of liver contraindication 235856003 DOID:409
Hyperprolactinemia contraindication 237662005 DOID:12700
Benign prostatic hyperplasia contraindication 266569009
Retention of urine contraindication 267064002
Neutropenic disorder contraindication 303011007 DOID:1227
Coma contraindication 371632003
Congenital long QT syndrome contraindication 442917000
Carcinoma of female breast contraindication 447782002
Drug Induced CNS Depression contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.93 acidic
pKa2 8.42 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 8.86 WOMBAT-PK CHEMBL
D(4) dopamine receptor GPCR ANTAGONIST Ki 8.74 WOMBAT-PK
5-hydroxytryptamine receptor 2C GPCR Ki 6.06 PDSP
5-hydroxytryptamine receptor 1D GPCR Ki 5.51 PDSP
Muscarinic acetylcholine receptor M3 GPCR Ki 5.71 PDSP
Alpha-2A adrenergic receptor GPCR Ki 5.80 PDSP
Voltage-dependent T-type calcium channel subunit alpha-1I Ion channel BLOCKER IC50 7.50 IUPHAR
Potassium voltage-gated channel subfamily A member 10 Ion channel BLOCKER IC50 6.50 IUPHAR
D(3) dopamine receptor GPCR ANTAGONIST Ki 9.05 WOMBAT-PK
5-hydroxytryptamine receptor 2A GPCR ANTAGONIST Ki 7.56 WOMBAT-PK
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 6.84 WOMBAT-PK
Calmodulin Cytosolic other IC50 5.22 WOMBAT-PK
Multidrug resistance-associated protein 1 Transporter IC50 6 WOMBAT-PK
Alpha-2C adrenergic receptor GPCR Ki 6.42 WOMBAT-PK
Histamine H1 receptor GPCR Ki 6.71 WOMBAT-PK
Alpha-2B adrenergic receptor GPCR Ki 6.09 WOMBAT-PK
Alpha-1A adrenergic receptor GPCR Ki 6.70 WOMBAT-PK
5-hydroxytryptamine receptor 7 GPCR Ki 9.30 WOMBAT-PK
5-hydroxytryptamine receptor 6 GPCR Ki 7.15 WOMBAT-PK
5-hydroxytryptamine receptor 1A GPCR Ki 6.63 WOMBAT-PK
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 7.74 WOMBAT-PK
Multidrug resistance protein 1 Transporter IC50 5.54 WOMBAT-PK
Solute carrier family 22 member 2 Transporter IC50 4.47 CHEMBL
Voltage-dependent T-type calcium channel subunit alpha-1G Ion channel Kd 7.40 CHEMBL
Kappa-type opioid receptor GPCR IC50 6 CHEMBL
Delta-type opioid receptor GPCR IC50 5.42 CHEMBL
Mu-type opioid receptor GPCR IC50 6.43 CHEMBL
Glycine receptor subunit alpha-1 Ion channel EC50 5.77 CHEMBL
Ubiquitin carboxyl-terminal hydrolase 1 Enzyme IC50 5.70 CHEMBL
5-hydroxytryptamine receptor 7 GPCR Ki 9.30 CHEMBL
D(2) dopamine receptor GPCR Ki 9.22 CHEMBL
Dopamine receptor GPCR IC50 9.40 CHEMBL
Sodium channel protein type 2 subunit alpha Ion channel IC50 6.47 CHEMBL
Voltage-dependent T-type calcium channel subunit alpha-1G Ion channel BLOCKER IC50 7.50 IUPHAR
5-hydroxytryptamine receptor 6 GPCR ANTAGONIST Ki 7.20 IUPHAR
G protein-activated inward rectifier potassium channel 2 Ion channel GATING INHIBITOR EC50 5.50 IUPHAR
Voltage-dependent T-type calcium channel subunit alpha-1H Ion channel BLOCKER IC50 7.30 IUPHAR

External reference:

IDSource
4018479 VUID
N0000146801 NUI
C0031935 UMLSCUI
D00560 KEGG_DRUG
1HIZ4DL86F UNII
2330 INN_ID
108438008 SNOMEDCT_US
4018479 VANDF
8331 RXNORM
386848009 SNOMEDCT_US
5301 MMSL
d00898 MMSL
001492 NDDF
131104 MMSL
CHEMBL1423 ChEMBL_ID
DB01100 DRUGBANK_ID
CHEBI:8212 CHEBI
D010868 MESH_DESCRIPTOR_UI
16362 PUBCHEM_CID
90 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Pimozide HUMAN PRESCRIPTION DRUG LABEL 1 49884-347 TABLET 1 mg ORAL ANDA 12 sections
Pimozide HUMAN PRESCRIPTION DRUG LABEL 1 49884-348 TABLET 2 mg ORAL ANDA 12 sections