2-chloro-10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine

• ChemBase编号: 316
• 分子式: C20H24ClN3S
• 平均质量: 373.94266
• 单一同位素质量: 373.13794646
• SMILES: Clc1cc2N(CCCN3CCN(CC3)C)c3c(Sc2cc1)cccc3
• Canonical SMILES: CN1CCN(CC1)CCCN1c2ccccc2Sc2c1cc(Cl)cc2
• InChI: InChI=1S/C20H24ClN3S/c1-22-11-13-23(14-12-22)9-4-10-24-17-5-2-3-6-19(17)25-20-8-7-16(21)15-18(20)24/h2-3,5-8,15H,4,9-14H2,1H3
• InChIKey: WIKYUJGCLQQFNW-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-chloro-10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine
• IUPAC传统名: prochlorperazine; compro
• 商标名: Bayer A 173; Buccastem; Compazine; Capazine; Combid; Compro; Emelent; Emetiral; Eskatrol; Kronocin; Meterazin; Meterazin Maleate; Meterazine; Nipodal; Novamin; Pasotomin; Stemetil; Tementil; Temetid; Vertigon
• 别名: Prochloroperazine; Prochlorpromazine; Prochlorperazine maleate; Prochlorperazine edisylate; Prochlorperazin; Prochlorpemazine; Proclorperazine; Procloperazine; Chlorperazine; Chlormeprazine; Prochlorperazine; Prochlorperazine edisylate salt; Novamin; Tementil; Prochlorperazine DimesylateAlso See: P755805; Buccastem; Emetiral; Meterazin Maleate; Pasotomin; Prochlorperazine Hydrogen Maleate; Prochloroperazine Dimaleate; Stemetil; Stemetil Dimaleate; Vertigon; Prochlorperazine DimaleateAlso See: P755800; 2-Chloro-10-[3-(4-methyl-1-piperazinyl)propyl]-10H-phenothiazine Dimethanesulfonate; 3-Chloro-10-[3-(4-methyl-1-piperazinyl)propyl]phenothiazine Dimesylate; 2-Chloro-10-[3-(4-methyl-1-piper-azinyl)propyl]-10H-pheno-thiazine dimaleate; Compazine

登记号

• CAS号: 58-38-8; 84-02-6; 51888-09-6; 1257-78-9
• EC号: 215-019-1; 200-379-4
• MDL号: MFCD00056797
• PubChem SID: 160963779; 46509018
• PubChem CID: 4917
• CHEBI ID: 8435
• ATC码: N05AB04
• CHEMBL: 728
• Chemspider ID: 4748
• DrugBank ID: DB00433
• KEGG ID: D00493
• 美国药典/FDA物质标识码: YHP6YLT61T
• 维基百科标题: Prochlorperazine
• Medline Plus: a682116

理论计算性质

JChem

• 质子受体: 3
• 质子供体: 0
• LogD (pH = 5.5): 1.5868546
• LogD (pH = 7.4): 3.352362
• Log P: 4.3821197
• 摩尔折射率: 109.8064 cm^3
• 极化性: 42.294575 Å^3
• 极化表面积: 9.72 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 4.67
• LOG S: -4.53
• 溶解度: 1.10e-02 g/l

分子性质

理化性质

• 溶解度: DMSO; Methanol; Methanol (sparingly); Very slightly soluble
• 外观: Off-White Solid; Off-White to Pale Yellow Solid
• 熔点: 196-198°C; 238-240°C
• 疏水性(logP): 4.6

安全信息

• 保存条件: Refrigerator; Room Temperature (15-30°C), Protect from light
• RTECS编号: SO2700000; SO2975000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22; R:22
• 安全公开号: 22; S:36/37/39
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

药理学性质

• 给药途径: Oral, buccal, rectal, IM
• 生物利用度: not exactly known, but substantial
• 排泄: Biliary, (colored) inactive metabolites in urine
• 半衰期: 4–8 hoursS, differs with the method of administration
• 代谢: Mainly hepatic (CYP2D6 and/or CYP3A4)
• 蛋白结合率: 91–99%
• 法定药品分级: OTC/POM (UK); Rx-only (US)
• 妊娠期药物分类: C (Au, U.S.)

详细说明

MP Biomedicals - 02153565

Dimaleate

DrugBank - DB00433

• Drug Groups: approved
• Description: A phenothiazine antipsychotic used principally in the treatment of nausea; vomiting; and vertigo. It is more likely than chlorpromazine to cause extrapyramidal disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p612)
• Indication: For the symptomatic management of psychotic disorders, short term management of nonpsychotic anxiety in patients with generalized anxiety disorder, and for the control of severe nausea and vomiting of various causes.
• Pharmacology: Prochlorperazine is a piperazine phenothiazine related to high-potency neuroleptics such as perphenazine. It shares many of the actions and adverse effects of the antipsychotics.
• Toxicity: Symptoms of central nervous system depression to the point of somnolence or coma. Agitation and restlessness may also occur. Other possible manifestations include convulsions, EKG changes and cardiac arrhythmias, fever and autonomic reactions such as hypotension, dry mouth and ileus; LD₅₀=400mg/kg (orally in mice)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Undergoes metabolism in the gastric mucosa and on first pass through the liver, CYP2D6 and/or CYP3A4.
• Absorption: Rapidly absorbed following oral administration
• Half Life: 6 to 8 hours
• Protein Binding: 91-99%
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - P7152

Biochem/physiol Actions
Phenothiazine antipsychotic; D2 antagonist; antispasmodic

Toronto Research Chemicals - P755800

Antiemetic, antipsychotic; used in treatment of vertigo.

Toronto Research Chemicals - P755805

Antiemetic.

参考文献

• Taylor, W.B., et al.: Br. J. Clin. Pharmacol., 23, 137 (1987)
• Ward, A.E., Br. J. Clin. Pract., 42, 228 (1987)
• Taylor, W.B., et al.: Br. J. Clin. Pharmacol., 23, 137 (1987)
• Ward, A.E., Br. J. Clin. Pract., 42, 228 (1988).