ContaminantDB: Pimozide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (21)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:28:22 UTC

Update Date

2026-05-14 16:57:49 UTC

Accession Number

CHEM002345

Identification

Common Name

Pimozide

Class

Small Molecule

Description

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)

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Anti-Dyskinesia Agent
Antidyskinetic
Antipsychotic Agent
Dopamine Antagonist
Drug
Human Neurotoxin
Metabolite
Organic Compound
Organofluoride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Halomonth	ChEBI
Neoperidole	ChEBI
Opiran	ChEBI
Orap	ChEBI
Pimozida	ChEBI
Pimozidum	ChEBI
Janssen brand OF pimozide	HMDB
Pharmascience brand OF pimozide	HMDB
Orap forte	HMDB
ASTA medica brand OF pimozide	HMDB
Antalon	HMDB

Chemical Formula

C₂₈H₂₉F₂N₃O

Average Molecular Mass

461.546 g/mol

Monoisotopic Mass

461.228 g/mol

CAS Registry Number

2062-78-4

IUPAC Name

1-{1-[4,4-bis(4-fluorophenyl)butyl]piperidin-4-yl}-2,3-dihydro-1H-1,3-benzodiazol-2-one

Traditional Name

pimozide

SMILES

FC1=CC=C(C=C1)C(CCCN1CCC(CC1)N1C(=O)NC2=CC=CC=C12)C1=CC=C(F)C=C1

InChI Identifier

InChI=1S/C28H29F2N3O/c29-22-11-7-20(8-12-22)25(21-9-13-23(30)14-10-21)4-3-17-32-18-15-24(16-19-32)33-27-6-2-1-5-26(27)31-28(33)34/h1-2,5-14,24-25H,3-4,15-19H2,(H,31,34)

InChI Key

YVUQSNJEYSNKRX-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Phenylbutylamine
Benzimidazole
Aralkylamine
Fluorobenzene
Halobenzene
Aryl fluoride
Aryl halide
Piperidine
N-substituted imidazole
Azole
Heteroaromatic compound
Imidazole
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Organooxygen compound
Amine
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organofluoride
Organohalogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organofluorine compound (CHEBI:8212 )
benzimidazoles (CHEBI:8212 )
heteroarylpiperidine (CHEBI:8212 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	214-218°C
Boiling Point	Not Available
Solubility	10 mg/L (at 25°C)

Predicted Properties

Property	Value	Source
Water Solubility	0.0017 g/L	ALOGPS
logP	6.36	ALOGPS
logP	5.83	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	12.9	ChemAxon
pKa (Strongest Basic)	8.38	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	35.58 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	132.21 m³·mol⁻¹	ChemAxon
Polarizability	50.04 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ugi-1391000000-81a5491e04c0772aa266	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-03fr-3945500000-63d831a19fe77286e9e1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-0a4i-2900000000-c5c24c6004ad63c44b7b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-0a4i-2900000000-4ec6383bd789926aace8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-001i-0900000000-f7e5bc8b3118f019d29a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-001i-0900000000-15ed37cc4150d726424f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0a4j-2900000000-4cb696b16013c21eaecc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-054k-3922000000-3dece675311cfc7dcecb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-03di-0000900000-a6c11637d319ae7e0d4b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-03di-0001900000-e11e7746c656531d49c3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-001i-0900000000-a10c36c7b309fd6a144a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0010900000-930a125974bd00e0c2eb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dj-0292700000-2985b790e5501b39bbd6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ks-2981100000-75644e2a4fa99f98d3bc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000900000-d214f454d376b4403edd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03e9-0410900000-0d1a6255c713f6209ad8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-2920000000-0b02fc753cd5d50662e6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000900000-1007eb55b47c59016fd5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0001900000-6016ca53ea77d615c57c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03yj-2790700000-5ee4d094cbf2edb564c4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000900000-d24101b35641ce78a840	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03xr-1000900000-a8261095a6ae4bd8e429	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-3911100000-2bfbcbf4417742b7624d	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001i-4890100000-ff909df45204eac82c46	Spectrum

Toxicity Profile

Route of Exposure

Greater than 50% absorption after oral administration. Serum peak appears 6-8 hours post ingestion.

Mechanism of Toxicity

The ability of pimozide to suppress motor and phonic tics in Tourette's Disorder is thought to be primarily a function of its dopaminergic blocking activity. Pimozide binds and inhibits the dopamine D2 receptor in the CNS. It also appears to block voltage-operated calcium channels and acts as an antagonist at opiate receptors (OP2).

Metabolism

Notable first-pass metabolism in the liver, primarily by N-dealkylation via the cytochrome P450 isoenzymes CYP3A and CYP1A2 (and possibly CYP2D6). The activity of the two major metabolites has not been determined. Half Life: 29 ± 10 hours (single-dose study of healthy volunteers).

Toxicity Values

LD50: 1100 mg/kg (Oral, Rat) (1) LD50: 228 mg/kg (Oral, Mouse) (1)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Used for the suppression of motor and phonic tics in patients with Tourette's Disorder who have failed to respond satisfactorily to standard treatment.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

In the event of overdosage, gastric lavage, establishment of a patent airway and, if necessary, mechanically-assisted respiration are advised. Electrocardiographic monitoring should commence immediately and continue until the ECG parameters are within the normal range. Hypotension and circulatory collapse may be counteracted by use of intravenous fluids, plasma, or concentrated albumin, and vasopressor agents such as metaraminol, phenylephrine and norepinephrine. Epinephrine should not be used. In case of severe extrapyramidal reactions, antiparkinson medication should be administered. Because of the long half-life of pimozide, patients who take an overdose should be observed for at least 4 days. (3)

Concentrations

Not Available

External Links

DrugBank ID

DB01100

HMDB ID

HMDB0015232

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID