4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-1-(4-fluorophenyl)butan-1-one

• ChemBase ID: 385
• Molecular Formular: C21H23ClFNO2
• Molecular Mass: 375.8642232
• Monoisotopic Mass: 375.14013488
• SMILES: Clc1ccc(C2(O)CCN(CC2)CCCC(=O)c2ccc(F)cc2)cc1
• Canonical SMILES: Fc1ccc(cc1)C(=O)CCCN1CCC(CC1)(O)c1ccc(cc1)Cl
• InChI: InChI=1S/C21H23ClFNO2/c22-18-7-5-17(6-8-18)21(26)11-14-24(15-12-21)13-1-2-20(25)16-3-9-19(23)10-4-16/h3-10,26H,1-2,11-15H2
• InChIKey: LNEPOXFFQSENCJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-1-(4-fluorophenyl)butan-1-one
• IUPAC Traditional name: haloperidol; 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-1-(4-fluorophenyl)butan-1-one
• Brand Name: Serenase; Serenelfi; Sernas; Sernel; Sigaperidol; Ulcolind; Uliolind; Vesalium; ALDO; Aloperidin; Aloperidol; Aloperidolo; Aloperidon; Apo-Haloperidol; Bioperidolo; Brotopon; Dozic; Dozix; Einalon S; Eukystol; Galoperidol; Haldol; Haldol Decanoate; Haldol La; Haldol Solutab; Halidol; Halojust; Halol; Halopal; Haloperido; Haloperidol Decanoate; Haloperidol Intensol; Haloperidol Lactate; Halopidol; Halopoidol; Halosten; Keselan; Lealgin Compositum; Linton; Mixidol; Novo-Peridol; Pekuces; Peluces; Peridol; Pernox; Pms Haloperidol; Serenace
• Synonyms: Haloperidol; Aloperidin; Bioperidolo; Brotopon; Dozic; 4-[4-(4-Chlorophenyl)-4-hydroxypiperidino]-4′-fluorobutyrophenone; 4-[4-(p-Chlorophenyl)-4-hydroxypiperidino]-4′-fluorobutyrophenone; Haloperidol; Fortunan; Haldol; Serenace; 4-[4-(4-Chlorophenyl)-4-hydroxy-1-piperidinyl]-1-(4-fluorophenyl)-1-butanone; 4-[4-(4-Chlorophenyl)-4-hydroxypiperidino]-4'-fluorobutyrophenone; 4-[4-(p-Chlorophenyl)-4-hydroxypiperidino]-4'-fluorobutyrophenone

Database IDs

• CAS Number: 52-86-8
• EC Number: 200-155-6
• MDL Number: MFCD00051423
• PubChem SID: 24277917; 46508794; 160963848
• PubChem CID: 3559
• CHEBI ID: 5613
• ATC CODE: N05AD01
• CHEMBL: 54
• Chemspider ID: 3438
• DrugBank ID: DB00502
• IUPHAR ligand ID: 86
• KEGG ID: D00136
• Unique Ingredient Identifier: J6292F8L3D
• Wikipedia Title: Haloperidol
• Medline Plus: a682180

CALCULATED PROPERTIES

JChem

• LogD (pH = 7.4): 2.9278276
• Log P: 3.6611137
• Molar Refractivity: 102.5919 cm^3
• Polarizability: 39.481518 Å^3
• Polar Surface Area: 40.54 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true
• Acid pKa: 13.963255
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.160161

ALOGPS 2.1

• Log P: 3.7
• LOG S: -4.93
• Solubility (Water): 4.46e-03 g/l

PROPERTIES

Physical Property

• Solubility: 0.1 M HCl: soluble3 mg/mL; 14 mg/L; 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble0.39 mg/mL; DMSO: soluble; ethanol: soluble; H2O: insoluble
• Apperance: white powder
• Melting Point: 148.0-149.4 °C
• Vapor Pressure: 2.48 x 10-10 mm Hg at 25 °C (estimated).
• Hydrophobicity(logP): 4

Safety Information

• Storage Condition: -20°C; Room Temperature (15-30°C)
• RTECS: EU1575000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Australian Hazchem: 2X
• Risk Statements: 60-61-25-36/37/38-43; R:25
• Safety Statements: 53-26-36/37/39-45; S:28-29-36/37/39-45
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H317-H319-H335-H361
• GHS Precautionary statements: P261-P280-P301 + P310-P305 + P351 + P338
• RID/ADR: UN 2811 6.1/PG 3

Pharmacology Properties

• Admin Routes: Oral, IM, IV, depot (as decanoate ester)
• Bioavailability: Approx. 50–60% (tablets and liquid)
• Excretion: Biliary and renal
• Half Life: 10–30 hours
• Metabolism: hepatic
• Legal Status: Rx-only
• Pregnancy Category: C
• Gene Information: human ... ABCB1(5243), ADRA1A(148), ADRA2A(150), ADRA2C(152), CHRM1(1128), DRD2(1813), DRD3(1814), DRD4(1815), EBP(10682), HRH1(3269), HTR2A(3356), HTR2C(3358), HTR7(3363), KCNH1(3756), KCNH2(3757), PRNP(5621)rat ... Adra1a(29412), Adra2a(25083), Chrm1(25229), Chrm2(81645), Drd1a(24316), Drd2(24318), Drd3(29238), Drd4(25432), Hrh1(24448), Htr1a(24473), Htr1b(25075), Htr2a(29595), Htr2c(25187), Oprs1(29336), Slc6a3(24898), Slc6a4(25553)
• Mechanism of Action: Dopaminergic antagonist with activity at sigma and NMDA receptors.Also reported to be a potassium channel (IK Ca ) blocker

Product Information

• Salt Data: Free Base
• Application(s): Antipsychotic; Tranquilliser

DETAILS

MP Biomedicals - 02153696

Dopamine antagonist

DrugBank - DB00502

• Drug Groups: approved
• Description: A phenyl-piperidinyl-butyrophenone that is used primarily to treat schizophrenia and other psychoses. It is also used in schizoaffective disorder, delusional disorders, ballism, and tourette syndrome (a drug of choice) and occasionally as adjunctive therapy in mental retardation and the chorea of huntington disease. It is a potent antiemetic and is used in the treatment of intractable hiccups. (From AMA Drug Evaluations Annual, 1994, p279)
• Indication: For the management of psychotic disorders (eg. schizophrenia) and delirium, as well as to control tics and vocal utterances of Tourette's syndrome (Gilles de la Tourette's syndrome). Also used for the treatment of severe behavioural problems in children with disrubtive behaviour disorder or ADHD (attention-deficit hyperactivity disorder). Haloperidol has been used in the prevention and control of severe nausea and vomiting.
• Pharmacology: Haloperidol is a psychotropic agent indicated for the treatment of schizophrenia. It also exerts sedative and antiemetic activity. Haloperidol principal pharmacological effects are similar to those of piperazine-derivative phenothiazines. The drug has action at all levels of the central nervous system-primarily at subcortical levels-as well as on multiple organ systems. Haloperidol has strong antiadrenergic and weaker peripheral anticholinergic activity; ganglionic blocking action is relatively slight. It also possesses slight antihistaminic and antiserotonin activity.
• Toxicity: LD₅₀=165 mg/kg (rats, oral)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Oral-60%
• Half Life: 3 weeks
• Protein Binding: 92%
• References: Niemegeers CJ, Laduron PM: Pharmacology and biochemistry of haloperidol. Proc R Soc Med. 1976;69 suppl 1:3-8. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1920

Research Area: Neurological Disease
Biological Activity:
Haloperidol (Haldol) is an antipsychotic and butyrophenone. It is in the butyrophenone class of antipsychotic medications and has pharmacological effects similar to the phenothiazines. Haloperidol is an older antipsychotic used in the treatment of schizophrenia and, more acutely, in the treatment of acute psychotic states and delirium. A long-acting decanoate ester is used as a long acting injection given every 4 weeks to people with schizophrenia or related illnesses who have a poor compliance with medication and suffer frequent relapses of illness, or to overcome the drawbacks inherent to its orally administered counterpart that burst dosage increases risk or intensity of side effects. [1]

Sigma Aldrich - H1512

Biochem/physiol Actions
Butyrophenone antipsychotic; D2, D3, and D4 dopamine receptor antagonist.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. H1512.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

REFERENCES

• Niemegeers CJ, Laduron PM: Pharmacology and biochemistry of haloperidol. Proc R Soc Med. 1976;69 suppl 1:3-8. Pubmed
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 868B, (nmr)
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• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CLY500; HAG300