(2Z)-but-2-enedioic acid; [3-(4-chlorophenyl)-3-(pyridin-2-yl)propyl]dimethylamine

• ChemBase编号: 72808
• 分子式: C20H23ClN2O4
• 平均质量: 390.86062
• 单一同位素质量: 390.13463491
• SMILES: c1cccc(n1)C(CCN(C)C)c1ccc(cc1)Cl.C(=O)(/C=C\C(=O)O)O
• Canonical SMILES: CN(CCC(c1ccccn1)c1ccc(cc1)Cl)C.OC(=O)/C=C\C(=O)O
• InChI: InChI=1S/C16H19ClN2.C4H4O4/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13;5-3(6)1-2-4(7)8/h3-9,11,15H,10,12H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1-
• InChIKey: DBAKFASWICGISY-BTJKTKAUSA-N

名称和登记号

名称

• IUPAC标准名: (2Z)-but-2-enedioic acid; [3-(4-chlorophenyl)-3-(pyridin-2-yl)propyl]dimethylamine
• IUPAC传统名: chlorpheniramine; maleic acid; hayon; maleic acid
• 别名: 马来酸氯苯那敏; 2-[p-Chloro-α-(2-dimethyl-aminoethyl)benzyl]pyridine Maleate Salt; 1-(p-Chlorophenyl)-1-(2-pyridil)-3-dimethylaminopropane Maleate Salt; Chlorpheniramine Maleate Salt; Chlorpheniramine maleate; 3-(4-chlorophenyl)-N,N-dimethyl-3-(pyridin-2-yl)propan-1-amine maleate; Chlor-Trimeton; Allergisan; Piriton; Teldrin; Chlorpheniramine maleate; (±)-Chlorpheniramine maleate salt

登记号

• CAS号: 113-92-8
• EC号: 204-037-5
• MDL号: MFCD00069225
• PubChem SID: 24277767; 162037729; 24892764
• PubChem CID: 5281068

理论计算性质

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 0.20455076
• LogD (pH = 7.4): 1.5225012
• Log P: 3.584951
• 摩尔折射率: 80.8503 cm^3
• 极化性: 31.551079 Å^3
• 极化表面积: 16.13 Å^2
• 可自由旋转的化学键: 7
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Methanol; Water
• 外观: White Solid
• 熔点: 130-135 °C(lit.); 130-135°C; 131-133°C

安全信息

• 保存条件: -20°C; -20°C Freezer
• RTECS编号: US6503000; US6504000
• 欧盟危险性物质标志: 有毒(Toxic) (T); X
• 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
• 危险公开号: 22; 25
• 安全公开号: 36; 36/37/39-45
• TSCA收录: 是
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H301
• GHS警示性声明: P264-P270-P301+P310-P321-P405-P501A; P301 + P310
• 个人保护装置: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

药理学性质

• 相关基因信息: human ... HRH1(3269)

产品相关信息

• 纯度: ≥99% (perchloric acid titration); 99%
• 级别: Sigma Reference Standard
• 成盐信息: Maleate
• 包装: vial of 250 mg

详细说明

Selleck Chemicals - S1816

Research Area

• Description: Neurological Disease

Biological Activity

• Description: Chlorpheniramine (Chlorpheniramine maleate, Chlorphenamine) is a histamine H1 receptor antagonist with IC50 of 12 nM.
• Targets: Histamine H1 receptor
• IC50: 12 nM ^[1]
• In Vitro: Chlorpheniramine inhibits the [^3H]mepyramine binding to the histamine H1 receptor in guinea pig cortex with IC50 of 8.8 nM. ^[2] Chlorpheniramine inhibits the proliferation of MCF-7, MDA-MB 231, and Ehrlich cells in a dose-response manner, and significantly reduces the ornithine decarboxylase mRNA translation by 50%-70% at the 250 μM. ^[3] Chlorpheniramine displaces of [^3H]pyrilamine from human histamine receptor subtype 1 expressed in CHO cells with IC50 of 66 nM. Chlorpheniramine displays antimalarial activity against CQS strain (D6) and MDR strain (Dd2) of P. falciparum with IC50 of 61.2 uM and 3.9 uM, respectively. Chlorpheniramine displays cytotoxicity against the proliferation of concanavalin A-induced murine splenic lymphocytes with IC50 of 33.4 μM. ^[4] Chlorpheniramine treatment in human salivary gland cells more significantly inhibits the histamine-induced [Ca^2+]_i increase in a concentration-dependent manner with IC50 of 128 nM than that of carbachol-induced [Ca^2+]_i increase with an IC50 of 43.9 μM. ^[5]
• In Vivo: Oral administration of Chlorpheniramine inhibits histamine-induced mortality in guinea pigs with an ED50 of 0.17 mg/kg. ^[1] Oral administration of Chlorpheniramine (10 mg/kg) significantly inhibits short-duration scratching in BALB/c mice stimulated by ovalbumin active cutaneous anaphylaxis and in ICR mice subcutaneously injected with histamine, but not long-duration scratching seen in NC/Nga mice, in contrast to that of dexamethasone or tacrolimus. ^[6] Administration of Chlorpheniramine (20 mg/kg) significantly abolishes the increase in REM sleep in rats induced by immobilization stress due to the blockage of the histaminergic and cholinergic mechanisms generating REM sleep. ^[7]
• Clinical Trials: A Phase III study to evaluate the efficacy and safety of a fixed combination of paracetamol, phenylephrine and Chlorpheniramine in symptomatic treatment of common cold and flu-like illness in adults has been completed.

Protocol

• Protocol: Kinase Assay ^[1]
• H1-Antihistaminic Activity: The segments (1 cm) of isolated ileum from guinea pigs are suspended in an organ bath containing Tyrode solution (ventilation, 32 °C). The contractile responses to histamine (0.54 μM) are measured with an isotonic transducer. A set concentration of Chlorpheniramine is added in the organ bath 5 minutes before the addition of histamine. IC50 value of Chlorpheniramine is calculated by the probit methond.
• Protocol: Cell Assay ^[3]
• Cell Lines: MCF-7, MDA-MB 231, and Ehrlich
• Concentrations: Dissolved in water, final concentrations ~500 μM
• Incubation Time: 48 hours
• Methods: Cells are exposed to various concentrations of Chlorpheniramine for 48 hours. Cells are washed, detached, and counted with a Coulter counter for the determination of cell growth.
• Protocol: Animal Study ^[6]
• Animal Models: Male NC/Nga mice, male ICR mice and female BALB/c mice with atopic dermatitis
• Formulation: Suspended in 1% (v/v) Tween 80
• Doses: 10 mg/kg
• Administration: Orally

References

• References: [1] Iemura R, et al. J Med Chem, 1986, 29(7), 1178-1183.
• References: [2] Sleevi MC, et al. J Med Chem, 1991, 34(4), 1314-1328.
• References: [3] Medina MA, et al. Breast Cancer Res Treat, 1995, 35(2), 187-194.
• References: [4] Kelly JX, et al. Antimicrob Agents Chemother, 2007, 51(11), 4133-4140.
• References: [5] Kim JH, et al. J Pharmacol Exp Ther, 2009, 330(2), 403-412.
• References: [6] Takano N, et al. Eur J Pharmacol, 2003, 471(3), 223-228.

Sigma Aldrich - C5172

Biochem/physiol Actions
H1 Histamine receptor antagonist.
包装
Supplied in amber screw-cap vials

Sigma Aldrich - C3025

Biochem/physiol Actions
H1 Histamine receptor antagonist.

Toronto Research Chemicals - C424300

Antihistaminic.

参考文献

• Iemura R, et al. J Med Chem, 1986, 29(7), 1178-1183.
• Sleevi MC, et al. J Med Chem, 1991, 34(4), 1314-1328.
• Medina MA, et al. Breast Cancer Res Treat, 1995, 35(2), 187-194.
• Kelly JX, et al. Antimicrob Agents Chemother, 2007, 51(11), 4133-4140.
• Kim JH, et al. J Pharmacol Exp Ther, 2009, 330(2), 403-412.
• Takano N, et al. Eur J Pharmacol, 2003, 471(3), 223-228.
• Roth, F.E., et al.: J. Pharmacol. Exp. Ther., 124, 347 (1958)
• Smith, R.B., et al.: Toxicol. Appl. Pharmacol., 28, 240 (1958)
• Eckhart, C.G., et al.: Anal. Profiles Drug Subs., 7, 43 (1978)