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...

基本信息

化学结构

分子式

C₂₁H₂₃ClFNO₂

分子量

375.8642232

精确质量

375.14013488

电荷

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

计算属性

JChem

Acid pKa

13.963255

质子受体

质子供体

LogD (pH = 5.5)

1.160161

LogD (pH = 7.4)

2.9278276

Log P

3.6611137

摩尔折射率

102.5919

极化性

39.481518

极化表面积

40.54

可自由旋转的化学键

里宾斯基五规则

true

ALOGPS 2.1

Log P

3.7

LOG S

-4.93

溶解度

4.46e-03 g/l

数据来源

名称和标识

商标名

PekucesDozicSigaperidolHaloperidol DecanoateUliolindAloperidonHalostenMixidolHaldol LaAloperidolHaldolHalolGaloperidolBioperidoloHaldol SolutabHalidolSerenaceSerenaseHalopalALDOHalopidolHaldol DecanoateVesaliumHaloperidol IntensolKeselanBrotoponUlcolindPms HaloperidolDozixHaloperidoEinalon SHalopoidolPelucesHaloperidol LactateLintonPeridolEukystolLealgin CompositumAloperidoloApo-HaloperidolHalojustNovo-PeridolSernasAloperidinPernoxSerenelfiSernel

IUPAC传统名

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

IUPAC标准名

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

别名

Haloperidol4-[4-(4-Chlorophenyl)-4-hydroxy-1-piperidinyl]-1-(4-fluorophenyl)-1-butanone4-[4-(p-Chlorophenyl)-4-hydroxypiperidino]-4'-fluorobutyrophenone4-[4-(4-Chlorophenyl)-4-hydroxypiperidino]-4'-fluorobutyrophenoneBrotoponDozicHaloperidolAloperidin4-[4-(4-Chlorophenyl)-4-hydroxypiperidino]-4′-fluorobutyrophenone4-[4-(p-Chlorophenyl)-4-hydroxypiperidino]-4′-fluorobutyrophenoneBioperidoloHaldolFortunanSerenace

名称和标识

数据登录号

PubChem CID

3559

PubChem SID

1609638484650879424277917

CAS号

52-86-8

IUPHAR配体索引

DrugBank ID

CHEBI ID

KEGG ID

Chemspider ID

Medline Plus

维基百科标题

CHEMBL

美国药典/FDA物质标识码

ATC码

EC号

MDL号

数据登录号

化合物性质

产品相关信息

Free Base

下载链接

Tranquilliser

Antipsychotic

药理学性质

化合物性质

分子相关蛋白质

暂无数据

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分子图谱

描述信息

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.

描述信息

参考文献

PubChem文献

数据源提供

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

参考文献

生物活性

PubChem BioAssay

生物活性