1-(4-tert-butylphenyl)-4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]butan-1-ol

• ChemBase编号: 226
• 分子式: C32H41NO2
• 平均质量: 471.67344
• 单一同位素质量: 471.31372956
• SMILES: OC(C1CCN(CC1)CCCC(O)c1ccc(C(C)(C)C)cc1)(c1ccccc1)c1ccccc1
• Canonical SMILES: OC(c1ccc(cc1)C(C)(C)C)CCCN1CCC(CC1)C(c1ccccc1)(c1ccccc1)O
• InChI: InChI=1S/C32H41NO2/c1-31(2,3)26-18-16-25(17-19-26)30(34)15-10-22-33-23-20-29(21-24-33)32(35,27-11-6-4-7-12-27)28-13-8-5-9-14-28/h4-9,11-14,16-19,29-30,34-35H,10,15,20-24H2,1-3H3
• InChIKey: GUGOEEXESWIERI-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1-(4-tert-butylphenyl)-4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]butan-1-ol
• IUPAC传统名: terfenadine
• 商标名: Aldaban; Allerplus; Cyater; Seldane; Teldane; Teldanex; Terdin; Terfex; Triludan
• 别名: α-[4-(1,1-Dimethylethyl)phenyl]-4-(hydroxydiphenylmethyl)-1-piperidinebutanol; Terfenadine; α-[4-(1,1-Dmethylethyl)phenyl]-4-(hydroxydiphenylmethyl)-1-piperidinebutanol; α-(p-tert-Butylphenyl)-4-(α-hydroxy-α-phenylbenzyl)-1-piperidinebutanol; Allerplus; Cyater; Histadin; MDL 9918; NSC 665802; (±)-Terfenadine; Ternadin; Terfenadine

登记号

• CAS号: 50679-08-8
• EC号: 256-710-8
• MDL号: MFCD00079622
• PubChem SID: 24277779; 46507007; 160963689
• PubChem CID: 5405

理论计算性质

JChem

• Acid pKa: 13.197068
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 3.2679386
• LogD (pH = 7.4): 4.8515763
• Log P: 6.4791093
• 摩尔折射率: 146.2674 cm^3
• 极化性: 57.32755 Å^3
• 极化表面积: 43.7 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 5.89
• LOG S: -6.01
• 溶解度: 4.58e-04 g/l

分子性质

理化性质

• 溶解度: 10 mg/L; Chloroform
• 外观: White Solid
• 熔点: 130-140°C
• 疏水性(logP): 7.1

安全信息

• 保存条件: Refrigerator
• RTECS编号: TM4969000
• 德国WGK号: 2
• 保存温度: 2-8°C

药理学性质

• 作用靶点: Others
• 相关基因信息: human ... ABCB1(5243), CYP2C8(1558), CYP3A4(1576), HRH1(3269), IL4(3565), IL5(3567), KCNH1(3756), KCNH2(3757)mouse ... Abcb1a(18671), Abcb1b(18669)rat ... Hrh1(24448)

产品相关信息

• 成盐信息: Free Base

详细说明

DrugBank - DB00342

• Drug Groups: approved; withdrawn
• Description: In the U.S., Terfenadine was superseded by fexofenadine in the 1990s due to the risk of cardiac arrhythmia caused by QT interval prolongation.
• Indication: For the treatment of allergic rhinitis, hay fever, and allergic skin disorders.
• Pharmacology: Terfenadine, an H1-receptor antagonist antihistamine, is similar in structure to astemizole and haloperidol, a butyrophenone antipsychotic. The active metabolite of terfenadine is fexofenadine.
• Toxicity: Mild (e.g., headache, nausea, confusion), but adverse cardiac events including cardiac arrest, ventricular arrhythmias including torsades de pointes and QT prolongation have been reported. LD₅₀=mg/kg (orally in mice)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: On the basis of a mass balance study using 14C labeled terfenadine the oral absorption of terfenadine was estimated to be at least 70%
• Half Life: 3.5 hours
• Protein Binding: 70%
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - T9652

Biochem/physiol Actions
Non-sedating second generation H1 histamine receptor antagonist. Mainly metabolized by Cyp3A4, 5, 7. Inhibits CYP2C8.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. T9652.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - T114500

Nonsedating-type histamine H1-receptor antagonist. Antihistaminic.

参考文献

• Carr, A.A., et al.: Arzneim. Forsch., 32, 1157 (1982)
• Badwan, A.A., et al.: Anal. Profiles Drug Subs., 19, 627 (1982)
• Masheter, H.C., et al.: Clin. Rev. Allergy, 11, 5 (1982)
• Jurima-Romet, M., et al.: Drug Metab. Dispos., 22, 849 (1982)