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

• ChemBase编号: 385
• 分子式: C21H23ClFNO2
• 平均质量: 375.8642232
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-1-(4-fluorophenyl)butan-1-one
• IUPAC传统名: haloperidol; 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-1-(4-fluorophenyl)butan-1-one
• 商标名: 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
• 别名: 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

登记号

• CAS号: 52-86-8
• EC号: 200-155-6
• MDL号: MFCD00051423
• PubChem SID: 46508794; 160963848; 24277917
• PubChem CID: 3559
• CHEBI ID: 5613
• ATC码: N05AD01
• CHEMBL: 54
• Chemspider ID: 3438
• DrugBank ID: DB00502
• IUPHAR配体索引: 86
• KEGG ID: D00136
• 美国药典/FDA物质标识码: J6292F8L3D
• 维基百科标题: Haloperidol
• Medline Plus: a682180

理论计算性质

JChem

• LogD (pH = 7.4): 2.9278276
• Log P: 3.6611137
• 摩尔折射率: 102.5919 cm^3
• 极化性: 39.481518 Å^3
• 极化表面积: 40.54 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true
• Acid pKa: 13.963255
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 1.160161

ALOGPS 2.1

• Log P: 3.7
• LOG S: -4.93
• 溶解度: 4.46e-03 g/l

分子性质

理化性质

• 溶解度: 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
• 外观: white powder
• 熔点: 148.0-149.4 °C
• 蒸汽压: 2.48 x 10-10 mm Hg at 25 °C (estimated).
• 疏水性(logP): 4

安全信息

• 保存条件: -20°C; Room Temperature (15-30°C)
• RTECS编号: EU1575000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3; III
• 澳大利亚Hazchem: 2X
• 危险公开号: 60-61-25-36/37/38-43; R:25
• 安全公开号: 53-26-36/37/39-45; S:28-29-36/37/39-45
• 欧盟危险货物分类: T2
• 欧盟危险识别号(EUHIN): 6.1B
• 美国ERG指导号: 154
• GHS危险品标识: GHS06; GHS08
• GHS警示词: Danger
• GHS危险声明: H301-H315-H317-H319-H335-H361
• GHS警示性声明: P261-P280-P301 + P310-P305 + P351 + P338
• RID/ADR: UN 2811 6.1/PG 3

药理学性质

• 给药途径: Oral, IM, IV, depot (as decanoate ester)
• 生物利用度: Approx. 50–60% (tablets and liquid)
• 排泄: Biliary and renal
• 半衰期: 10–30 hours
• 代谢: hepatic
• 法定药品分级: Rx-only
• 妊娠期药物分类: C
• 相关基因信息: 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)
• 生物活性机理: Dopaminergic antagonist with activity at sigma and NMDA receptors.Also reported to be a potassium channel (IK Ca ) blocker

产品相关信息

• 成盐信息: Free Base
• 应用领域: Antipsychotic; Tranquilliser

详细说明

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.

参考文献

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