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    Chemistry

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    Also known as: 2062-78-4, Orap, Opiran, Pimozidum, Mcn-jr-6238, Pimozidum [inn-latin]
    Molecular Formula
    C28H29F2N3O
    Molecular Weight
    461.5  g/mol
    InChI Key
    YVUQSNJEYSNKRX-UHFFFAOYSA-N
    FDA UNII
    1HIZ4DL86F
    Pimozide
    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)
    Pimozide is a Typical Antipsychotic.
    1 2D Structure

    Pimozide

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    3-[1-[4,4-bis(4-fluorophenyl)butyl]piperidin-4-yl]-1H-benzimidazol-2-one
    2.1.2 InChI
    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)
    2.1.3 InChI Key
    YVUQSNJEYSNKRX-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1CN(CCC1N2C3=CC=CC=C3NC2=O)CCCC(C4=CC=C(C=C4)F)C5=CC=C(C=C5)F
    2.2 Other Identifiers
    2.2.1 UNII
    1HIZ4DL86F
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Antalon

    2. Orap

    3. Orap Forte

    4. R-6238

    5. R6238

    2.3.2 Depositor-Supplied Synonyms

    1. 2062-78-4

    2. Orap

    3. Opiran

    4. Pimozidum

    5. Mcn-jr-6238

    6. Pimozidum [inn-latin]

    7. R-6238

    8. R 6238

    9. R6238

    10. Nsc 170984

    11. Mcn-jr 6238

    12. 3-[1-[4,4-bis(4-fluorophenyl)butyl]piperidin-4-yl]-1h-benzimidazol-2-one

    13. 1-[1-[4,4-bis(4-fluorophenyl)butyl]-4-piperidinyl]-1,3-dihydro-2h-benzimidazol-2-one

    14. 2h-benzimidazol-2-one, 1-[1-[4,4-bis(4-fluorophenyl)butyl]-4-piperidinyl]-1,3-dihydro-

    15. Nsc-170984

    16. 1-(1-(4,4-bis(p-fluorophenyl)butyl)-4-piperidyl)-2-benzimidazolinone

    17. 1-[1-[4,4-bis(p-fluorophenyl)butyl]-4-piperidyl]-2-benzimidazolinone

    18. 1hiz4dl86f

    19. Chembl1423

    20. 1-(4,4-bis(p-fluorophenyl)butyl)-4-(2-oxo-1-benzimidazolinyl)piperidine

    21. Mls000028410

    22. Mls002702058

    23. Chebi:8212

    24. Nsc170984

    25. 1-{1-[4,4-bis(4-fluorophenyl)butyl]piperidin-4-yl}-1,3-dihydro-2h-benzimidazol-2-one

    26. 1-{1-[4,4-bis(4-fluorophenyl)butyl]piperidin-4-yl}-2,3-dihydro-1h-1,3-benzodiazol-2-one

    27. 2h-benzimidazol-2-one, 1-(1-(4,4-bis(4-fluorophenyl)butyl)-4-piperidinyl)-1,3-dihydro-

    28. Pimozida

    29. Ncgc00015802-08

    30. Ncgc00015802-18

    31. Primozida

    32. Smr000058385

    33. Cas-2062-78-4

    34. R 623

    35. R-623

    36. Dsstox_cid_3474

    37. 1-(1-(4,4-bis(4-fluorophenyl)butyl)piperidin-4-yl)-1h-benzo[d]imidazol-2(3h)-one

    38. Dsstox_rid_77042

    39. Dsstox_gsid_23474

    40. Primozida [inn-spanish]

    41. Primozide

    42. Pimozida [inn-spanish]

    43. 1-[4,4-bis(p-fluorophenyl)butyl]-4-(2-oxo-1-benzimidazolinyl)piperidine

    44. Ccris 9172

    45. Orap (tn)

    46. Sr-01000075392

    47. Einecs 218-171-7

    48. Unii-1hiz4dl86f

    49. Brn 0729089

    50. 1-(1-(4,4-bis(4-fluorophenyl)butyl)-4-piperidinyl)-1,3-dihydro-2h-benzimidazol-2-one

    51. Prestwick_395

    52. Mfcd00055081

    53. Pimozide [usan:usp:inn:ban:jan]

    54. Spectrum_000445

    55. Tocris-0937

    56. Pimozide [usan]

    57. Pimozide [inn]

    58. Pimozide [jan]

    59. Pimozide [mi]

    60. Pimozide [vandf]

    61. Opera_id_1580

    62. Prestwick0_000308

    63. Prestwick1_000308

    64. Prestwick2_000308

    65. Prestwick3_000308

    66. Spectrum2_001026

    67. Spectrum3_001451

    68. Spectrum4_000420

    69. Spectrum5_001308

    70. Lopac-p-1793

    71. Pimozide [mart.]

    72. Gtpl90

    73. Pimozide [usp-rs]

    74. Pimozide [who-dd]

    75. Ncimech_000356

    76. P 1793

    77. Lopac0_000946

    78. Schembl41584

    79. Bspbio_000276

    80. Bspbio_001439

    81. Bspbio_002941

    82. Kbiogr_000720

    83. Kbioss_000925

    84. 5-24-02-00367 (beilstein Handbook Reference)

    85. Mls001077311

    86. Bidd:gt0435

    87. Divk1c_000386

    88. Methyl-(2-m-tolylethyl)amine

    89. Spectrum1501134

    90. Pimozide (jp17/usp/inn)

    91. Spbio_001211

    92. Spbio_002495

    93. Pimozide [orange Book]

    94. Bpbio1_000304

    95. Schembl7519553

    96. Pimozide [ep Monograph]

    97. Dtxsid8023474

    98. Pimozide [usp Monograph]

    99. Bcbcmap01_000043

    100. Hms501d08

    101. Kbio1_000386

    102. Kbio2_000925

    103. Kbio2_003493

    104. Kbio2_006061

    105. Kbio3_002441

    106. Ninds_000386

    107. Hms1568n18

    108. Hms1791h21

    109. Hms1921h19

    110. Hms1989h21

    111. Hms2089c11

    112. Hms2092f09

    113. Hms2095n18

    114. Hms2231p23

    115. Hms3262n14

    116. Hms3267e19

    117. Hms3370n13

    118. Hms3402h21

    119. Hms3411j16

    120. Hms3675j16

    121. Hms3712n18

    122. Pharmakon1600-01501134

    123. Zinc4175630

    124. Tox21_110224

    125. Tox21_301586

    126. Tox21_500946

    127. Bdbm50334150

    128. Ccg-35918

    129. Ccg-36461

    130. Ccg-39728

    131. Nsc757854

    132. S4358

    133. 2-benzimidazolinone, 1-[1-[4,4-bis(p-fluorophenyl)butyl]-4-piperidyl]-

    134. 3-[1-[4,4-bis(4-fluorophenyl)butyl]-4-piperidyl]-1h-benzimidazol-2-one

    135. Akos024458706

    136. Tox21_110224_1

    137. Db01100

    138. Lp00946

    139. Nsc-757854

    140. Sdccgsbi-0050920.p004

    141. Idi1_000386

    142. Smp1_000241

    143. Ncgc00015802-01

    144. Ncgc00015802-02

    145. Ncgc00015802-03

    146. Ncgc00015802-04

    147. Ncgc00015802-05

    148. Ncgc00015802-06

    149. Ncgc00015802-07

    150. Ncgc00015802-09

    151. Ncgc00015802-10

    152. Ncgc00015802-11

    153. Ncgc00015802-12

    154. Ncgc00015802-13

    155. Ncgc00015802-14

    156. Ncgc00015802-15

    157. Ncgc00015802-16

    158. Ncgc00015802-26

    159. Ncgc00015802-29

    160. Ncgc00016601-01

    161. Ncgc00022282-03

    162. Ncgc00024888-01

    163. Ncgc00024888-02

    164. Ncgc00024888-03

    165. Ncgc00024888-04

    166. Ncgc00024888-05

    167. Ncgc00024888-06

    168. Ncgc00024888-07

    169. Ncgc00255294-01

    170. Ncgc00261631-01

    171. As-13916

    172. Hy-12987

    173. Sbi-0050920.p003

    174. Ab00052215

    175. Cs-0012921

    176. Eu-0100946

    177. Ft-0673903

    178. Sw196639-3

    179. C07566

    180. D00560

    181. F70142

    182. Ab00052215-06

    183. Ab00052215_07

    184. Ab00052215_08

    185. 062p784

    186. L000494

    187. Q144085

    188. Wln: T56 Bmvnj D- Dt6ntj A3yr Df&r Df

    189. J-013477

    190. Sr-01000075392-1

    191. Sr-01000075392-3

    192. Sr-01000075392-4

    193. Sr-01000075392-6

    194. Brd-k01292756-001-06-0

    195. Brd-k01292756-001-13-6

    196. Pimozide, European Pharmacopoeia (ep) Reference Standard

    197. Z241910386

    198. 2-benzimidazolinone,4-bis(p-fluorophenyl)butyl]-4-piperidyl]-

    199. N-benzyl-n-(3-isobutoxy-2-(pyrrolidin-1-yl)propyl)benzenamine

    200. Pimozide, United States Pharmacopeia (usp) Reference Standard

    201. 1-[1-[4,4-bis(p-flurophenyl)butyl]-4-piperidyl]-2-benzimidazolinone

    202. 1-(1-(4,4-bis(4-fluorophenyl)butyl)-4-piperidyl)-2-benzimidazolinone

    203. 1-(1-(4,4-bis(4-fluorophenyl)butyl)piperidin-4-yl)-1,3-dihydro-2h-benzo[d]imidazol-2-one

    204. 1-{1-[4,4-bis-(4-fluoro-phenyl)-butyl]-piperidin-4-yl}-1,3-dihydro-benzoimidazol-2-one

    205. 2h-benzimidazol-2-one,4-bis(4-fluorophenyl)butyl]-4-piperidinyl]-1,3-dihydro-

    206. 1-{1-[4,4-bis-(4-fluoro-phenyl)-butyl]-piperidin-4-yl}-1,3-dihydro-benzoimidazol-2-one(pimozide)

    207. 2h-benzimidazol-2-one, 1-(1-(4,4-bis(4-fluorophenyl)butyl)-4-piperidinyl)-1,3-dihydro

    208. Pimozide (1-[1-[4,4-bis(4-fluorophenyl)butyl]-4-piperidinyl]-1,3-dihydro-2h-benzimidaol-2-one)

    209. Pimozide1-{1-[4,4-bis-(4-fluoro-phenyl)-butyl]-piperidin-4-yl}-1,3-dihydro-benzoimidazol-2-one

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 461.5 g/mol
    Molecular Formula C28H29F2N3O
    XLogP36.3
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count7
    Exact Mass461.22786888 g/mol
    Monoisotopic Mass461.22786888 g/mol
    Topological Polar Surface Area35.6 Ų
    Heavy Atom Count34
    Formal Charge0
    Complexity632
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameOrap
    PubMed HealthPimozide (By mouth)
    Drug ClassesAntipsychotic
    Drug LabelORAP (pimozide) is an orally active antipsychotic agent of the diphenyl-butylpiperidine series. The structural formula of pimozide, 1-[1-[4,4-bis(4-fluorophenyl)butyl]-4-piperidinyl]-1,3-dihydro-2H-benzimidazole-2-one is:The solubility of pimozide...
    Active IngredientPimozide
    Dosage FormTablet
    RouteOral
    Strength1mg; 2mg
    Market StatusPrescription
    CompanyTeva

    2 of 2  
    Drug NameOrap
    PubMed HealthPimozide (By mouth)
    Drug ClassesAntipsychotic
    Drug LabelORAP (pimozide) is an orally active antipsychotic agent of the diphenyl-butylpiperidine series. The structural formula of pimozide, 1-[1-[4,4-bis(4-fluorophenyl)butyl]-4-piperidinyl]-1,3-dihydro-2H-benzimidazole-2-one is:The solubility of pimozide...
    Active IngredientPimozide
    Dosage FormTablet
    RouteOral
    Strength1mg; 2mg
    Market StatusPrescription
    CompanyTeva

    4.2 Drug Indication

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

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    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).

    5.2 MeSH Pharmacological Classification

    Dopamine Antagonists

    Drugs that bind to but do not activate DOPAMINE RECEPTORS, thereby blocking the actions of dopamine or exogenous agonists. Many drugs used in the treatment of psychotic disorders (ANTIPSYCHOTIC AGENTS) are dopamine antagonists, although their therapeutic effects may be due to long-term adjustments of the brain rather than to the acute effects of blocking dopamine receptors. Dopamine antagonists have been used for several other clinical purposes including as ANTIEMETICS, in the treatment of Tourette syndrome, and for hiccup. Dopamine receptor blockade is associated with NEUROLEPTIC MALIGNANT SYNDROME. (See all compounds classified as Dopamine Antagonists.)

    Antipsychotic Agents

    Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus. (See all compounds classified as Antipsychotic Agents.)

    Anti-Dyskinesia Agents

    Drugs used in the treatment of movement disorders. Most of these act centrally on dopaminergic or cholinergic systems. Among the most important clinically are those used for the treatment of Parkinson disease (ANTIPARKINSON AGENTS) and those for the tardive dyskinesias. (See all compounds classified as Anti-Dyskinesia Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    PIMOZIDE
    5.3.2 FDA UNII
    1HIZ4DL86F
    5.3.3 Pharmacological Classes
    Typical Antipsychotic [EPC]
    5.4 ATC Code

    N05AG02

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    N - Nervous system

    N05 - Psycholeptics

    N05A - Antipsychotics

    N05AG - Diphenylbutylpiperidine derivatives

    N05AG02 - Pimozide

    5.5 Absorption, Distribution and Excretion

    Absorption

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

    5.6 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).

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.7 Biological Half-Life

    29 ± 10 hours (single-dose study of healthy volunteers).

    5.8 Mechanism of Action

    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.

    API Reference Price

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    23-Feb-2023
    01-Mar-2024
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    Average Price (USD/KGS)

    Number of Transactions

    Total Quantity (KGS)

    Total Value (USD)

    Quantity (KGS) & Unit rate (USD/KGS) over time

    API Imports and Exports

    Importing Country Total Quantity
    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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    DRUG PRODUCT COMPOSITIONS

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    DOSAGE - TABLET;ORAL - 1MG **Federal Register...DOSAGE - TABLET;ORAL - 1MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 17473

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    DOSAGE - TABLET;ORAL - 2MG **Federal Register...DOSAGE - TABLET;ORAL - 2MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 17473

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