CAS 52-86-8|Haloperidol Intensol|Dozic|Haloperidol Lactate|Keselan|Ulcolind|Aloperidin|Pernox|Haloperidol Decanoate|Serenelfi|Sernel|Aloperidon|Novo-Peridol|Halopal|Vesalium|Peridol|Lealgin Composit...

General Information

Structure

Molecular Formula

C₂₁H₂₃ClFNO₂

Molecular Mass

375.8642232

Exact Mass

375.14013488

Charge

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

Canonic Smiles

Fc1ccc(cc1)C(=O)CCCN1CCC(CC1)(O)c1ccc(cc1)Cl

Isomeric Smiles

Clc1ccc(C2(O)CCN(CC2)CCCC(=O)c2ccc(F)cc2)cc1

Calculated Properties

JChem

Acid pKa

13.963255

H Acceptors

H Donor

LogD (pH = 5.5)

1.160161

LogD (pH = 7.4)

2.9278276

Log P

3.6611137

Molar Refractivity

102.5919

Polarizability

39.481518

Polar Surface Area

40.54

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

3.7

LOG S

-4.93

Solubility (Water)

4.46e-03 g/l

Data Source

Names and Identifiers

Brand Name

Haloperidol IntensolDozicHaloperidol LactateKeselanUlcolindAloperidinPernoxHaloperidol DecanoateSerenelfiSernelAloperidonNovo-PeridolHalopalVesaliumPeridolLealgin CompositumBioperidoloHalopidolSigaperidolDozixHaloperidoSerenaseHalojustHalostenLintonMixidolALDOSerenaceHaldol DecanoateAloperidoloPekucesApo-HaloperidolHalolHaldol LaHaldolEinalon SHaldol SolutabHalidolUliolindPms HaloperidolGaloperidolAloperidolPelucesSernasHalopoidolBrotoponEukystol

IUPAC name

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

Synonyms

Haloperidol4-[4-(p-Chlorophenyl)-4-hydroxypiperidino]-4'-fluorobutyrophenone4-[4-(4-Chlorophenyl)-4-hydroxypiperidino]-4'-fluorobutyrophenone4-[4-(4-Chlorophenyl)-4-hydroxy-1-piperidinyl]-1-(4-fluorophenyl)-1-butanoneBrotoponDozicHaloperidolAloperidin4-[4-(4-Chlorophenyl)-4-hydroxypiperidino]-4′-fluorobutyrophenoneBioperidolo4-[4-(p-Chlorophenyl)-4-hydroxypiperidino]-4′-fluorobutyrophenoneFortunanSerenaceHaldol

IUPAC Traditional name

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

Names and Identifiers

Registration numbers

PubChem CID

3559

PubChem SID

1609638482427791746508794

CAS Number

52-86-8

IUPHAR ligand ID

DrugBank ID

KEGG ID

Chemspider ID

CHEBI ID

Medline Plus

Wikipedia Title

ATC CODE

Unique Ingredient Identifier

J6292F8L3D

CHEMBL

EC Number

200-155-6

MDL Number

MFCD00051423

Registration numbers

Properties

Product Information

Salt Data

Free Base

Certificate of Analysis

Download link

Application(s)

Tranquilliser

Antipsychotic

Pharmacology Properties

Admin Routes

Oral, IM, IV, depot (as decanoate ester)

Metabolism

hepatic

Legal Status

Rx-only

Bioavailability

Approx. 50–60% (tablets and liquid)

Excretion

Biliary and renal

Pregnancy Category

10–30 hours

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)

Dopaminergic antagonist with activity at sigma and NMDA receptors.Also reported to be a potassium channel (IK Ca ) blocker

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

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]

Dopamine antagonist

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.

Molecule Details

References

PubChem Literature

From Data Sources

• Niemegeers CJ, Laduron PM: Pharmacology and biochemistry of haloperidol. Proc R Soc Med. 1976;69 suppl 1:3-8. Pubmed

• Girant, Y. et al., Arch. Int. Pharmacodyn. Ther., 1973, 205, 317, (pharmacol, tox)

• Janssen, P.A.J. et al., Handb. Exp. Pharmacol., (Part 1), 1980, 55, 25-41, (pharmacol, rev)

• Hoja, H. et al., J. Chromatogr., B: Biomed. Appl., 1997, 688, 275, (hplc-ms)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 868B, (nmr)

• Settle, E.C. et al., J. Clin. Psychiatry, 1983, 44, 440, (rev, pharmacol)

• Froemming, J.S. et al., Clin. Pharmacokinet., 1989, 17, 396, (rev)

• Usuki, E. et al., Chem. Res. Technol., 1996, 9, 800, (metab)

• Harper, N.J. et al., J. Pharm. Pharmacol., 1966, 18, 150, (synth, pharmacol)

• Park, K.H. et al., J. Chromatogr., 1991, 572, 259, (hplc)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CLY500; HAG300

• Aravagiri, M. et al., J. Chromatogr., B: Biomed. Appl., 1994, 656, 373, (hplc)

• Janicki, C.A. et al., Anal. Profiles Drug Subst., 1980, 9, 341, (rev)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6089, (synonyms)

• Lynch, D.R. et al., J. Pharmacol. Exp. Ther., 1996, 279, 154, (pharmacol)

• Janssen, P.A.J. et al., J. Med. Chem., 1959, 1, 281, (synth, pharmacol)

• Blessington, B., Org. Mass Spectrom., 1971, 5, 1113, (ms)

• Haloperidol Update 1958-1980, (ed. Ayd, F.J.), Ayd Medical Communications, 1980, (book)

• Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 714

• Ulrich, S. et al., J. Chromatogr., B: Biomed. Appl., 1995, 663, 289, (gc)

• Fang, J. et al., Psychopharmacology, 1995, 121, 373, (tox)

• Azibi, M. et al., J. Pharm. Sci., 1984, 73, 512, (cryst struct, ir)

References

Bioactivity

PubChem BioAssay

Bioactivity