Basic information
- CAS
2062-78-4- Standard SMILES
O=c1[nH]c2ccccc2n1C1CCN(CCCC(c2ccc(F)cc2)c2ccc(F)cc2)CC1- InChIKey
YVUQSNJEYSNKRX-UHFFFAOYSA-N- Molecular formula
- C28H29F2N3O
- Average molar mass
- 461.5 g/mol
- Monoisotopic mass
- 461.22786888
Overview
Pimozide can cause developmental toxicity and female reproductive toxicity according to state or federal government labeling requirements.
Names & identifiers
- Preferred name
- Pimozide
- IUPAC
- 3-[1-[4,4-bis(4-fluorophenyl)butyl]piperidin-4-yl]-1H-benzimidazol-2-one
- English name
- Pimozide
- Molecular formula
- C28H29F2N3O
- Molecular weight
- 461.55
Names & synonyms
pimozide2062-78-4OrapOpiranPimozidumMcN-JR-6238pimozidaR-6238R 6238DTXSID8023474R62381HIZ4DL86F
Show more names
PimochiPriMozideNSC 170984Pimozide CRSPIMOZIDE USP
3-[1-[4,4-bis(4-fluorophenyl)butyl]piperidin-4-yl]-1H-benzimidazol-2-oneNSC-170984NSC1709841-{1-[4,4-bis(4-fluorophenyl)butyl]piperidin-4-yl}-2,3-dihydro-1H-1,3-benzodiazol-2-oneCHEBI:8212DTXCID803474R 623R-623
Database identifiers
- CAS
2062-78-4- PubChem CID
- 16362
- DTXSID
DTXSID8023474- ChEMBL
CHEMBL1423- ChEBI
CHEBI:8212- UNII
- 1HIZ4DL86F
- EC Number
- 218-171-7
- Nikkaji
- J3.698F
Properties
Computed structural properties
- XLogP
- 6.3
- Topological polar surface area
- 35.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 7
- Heavy atoms
- 34
- Formal charge
- 0
- Complexity
- 632
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Nervous system -> Antipsychotics
Pharmaceuticals -> Antipsychotics
Pharmaceuticals -> Listed in ZINC15
LogP
5.6
6.06
Solubility1.73e-03 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antipsychotic Agents
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Pharmaceuticals
Melting Point
214-218 °C
214 - 218 °C
Physical DescriptionSolid
Dissociation Constants
7.32
7.45
8.63
Collision Cross Section
211.8 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID8023474]
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 45 reports by companies from 5 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Hazard Traits - Bioaccumulation; Developmental Toxicity; Environmental Persistence; Environmental tox; Reproductive Toxicity
2H-Benzimidazol-2-one, 1-1-4,4-bis(4-fluorophenyl)butyl-4-piperidinyl-1,3-dihydro-: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 2H-Benzimidazol-2-one, 1-[1-[4,4-bis(4-fluorophenyl)butyl]-4-piperidinyl]-1,3-dihydro-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
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. (L1712)
Chemistry & industry
Pharmacology
ATC Code
N05AG02
N - Nervous system
QN - Nervous system
Pharmacodynamics
Pimozide is an orally active antipsychotic drug product which shares with other antipsychotics the ability to blockade dopaminergic receptors on neurons in the central nervous system. However, receptor blockade is often accompanied by a series of secondary alterations in central dopamine metabolism and function which may contribute to both pimozide's therapeutic and untoward effects. In addition, pimozide, in common with other antipsychotic drugs, has various effects on other central nervous system receptor systems which are not fully characterized. Pimozide also has less potential for inducing sedation and hypotension as it has more specific dopamine receptor blocking activity than other neuroleptic agents (and is therefore a suitable alternative to haloperidol).
Mechanism of ActionThe 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.
Biological Half-Life29 ± 10 hours (single-dose study of healthy volunteers).
Metabolism/Metabolites
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.
Pimozide has known human metabolites that include 1,3- dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one (DHPBI).
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).
FDA Pharmacological Classification
1HIZ4DL86F
PIMOZIDE
Established Pharmacologic Class [EPC] - Typical Antipsychotic
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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