2-(4-{1-hydroxy-4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]butyl}phenyl)-2-methylpropanoic acid

• ChemBase编号: 826
• 分子式: C32H39NO4
• 平均质量: 501.65636
• 单一同位素质量: 501.28790873
• SMILES: OC(C1CCN(CC1)CCCC(O)c1ccc(C(C)(C)C(=O)O)cc1)(c1ccccc1)c1ccccc1
• Canonical SMILES: OC(=O)C(c1ccc(cc1)C(CCCN1CCC(CC1)C(c1ccccc1)(c1ccccc1)O)O)(C)C
• InChI: InChI=1S/C32H39NO4/c1-31(2,30(35)36)25-17-15-24(16-18-25)29(34)14-9-21-33-22-19-28(20-23-33)32(37,26-10-5-3-6-11-26)27-12-7-4-8-13-27/h3-8,10-13,15-18,28-29,34,37H,9,14,19-23H2,1-2H3,(H,35,36)
• InChIKey: RWTNPBWLLIMQHL-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-(4-{1-hydroxy-4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]butyl}phenyl)-2-methylpropanoic acid
• IUPAC传统名: fexofenadine; telfast
• 商标名: Allegra; Allegra-D 12 Hour; Allegra-D 24 Hour
• 别名: 4-[1-Hydroxy-4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]butyl]-α,α-dimethyl-benzene-acetic Acid; 4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-α,α-dimethylphenylacetic Acid; MDL 16455; Terfenadine-COOH; Terfenadine carboxylate; Terfenadine acid metabolite; Fexofenadine hydrochloride; Fexofendine; Carboxyterfenadine; Fexofenadine

登记号

• CAS号: 83799-24-0
• PubChem SID: 160964289; 46504676
• PubChem CID: 3348
• CHEBI ID: 5050
• ATC码: R06AX26
• CHEMBL: 914
• Chemspider ID: 3231
• DrugBank ID: DB00950
• KEGG ID: D07958
• 美国药典/FDA物质标识码: E6582LOH6V
• 维基百科标题: Fexofenadine
• Medline Plus: a697035

理论计算性质

JChem

• Acid pKa: 4.040438
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): 2.9300497
• LogD (pH = 7.4): 2.9334483
• Log P: 2.938501
• 摩尔折射率: 147.9846 cm^3
• 极化性: 57.84285 Å^3
• 极化表面积: 81.0 Å^2
• 可自由旋转的化学键: 10
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 5.02
• LOG S: -5.28
• 溶解度: 2.66e-03 g/l

分子性质

理化性质

• 溶解度: Methanol; Slightly soluble
• 外观: White Solid
• 熔点: 218-220°C
• 疏水性(logP): 5.6

安全信息

• 保存条件: -20°C Freezer

药理学性质

• 给药途径: Oral
• 生物利用度: 30-41%
• 排泄: Feces (~80%) and urine (~11%) as unchanged drug
• 半衰期: 14.4 hours
• 代谢: Hepatic (5% of dose)
• 蛋白结合率: 60-70%
• 法定药品分级: OTC (Canada); OTC (US); POM (UK); Unscheduled (Australia)
• 妊娠期药物分类: B2 (Australia); C (US)
• 美国（FDA）药品许可证: Fexofenadine

详细说明

DrugBank - DB00950

• Drug Groups: approved
• Description: Fexofenadine hydrochloride (Allegra) is an antihistamine drug used in the treatment of hayfever and similar allergy symptoms. It was developed as a successor of and alternative to terfenadine. Fexofenadine, like other second and third-generation antihistamines, does not readily pass through the blood-brain barrier, and so causes less drowsiness than first-generation histamine-receptor antagonists.
• Indication: For management of Seasonal allergic rhinitis
• Pharmacology: Fexofenadine is a second-generation, long lasting H1-receptor antagonist (antihistamine) which has a selective and peripheral H1-antagonist action. Histamine is a chemical that causes many of the signs that are part of allergic reactions, such as the swelling of tissues. Histamine is released from histamine-storing cells (mast cells) and attaches to other cells that have receptors for histamine. The attachment of the histamine to the receptors causes the cell to be "activated," releasing other chemicals which produce the effects that we associate with allergy. Fexofenadine blocks one type of receptor for histamine (the H1 receptor) and thus prevents activation of cells by histamine. Unlike most other antihistamines, Fexofenadine does not enter the brain from the blood and, therefore, does not cause drowsiness. Fexofenadine lacks the cardiotoxic potential of terfenadine, since it does not block the potassium channel involved in repolarization of cardiac cells.
• Toxicity: Side effects include dizziness, drowsiness, and dry mouth.
• Affected Organisms: Humans and other mammals
• Biotransformation: Approximately 5% of the total dose is metabolized, by cytochrome P450 3A4 and by intestinal microflora.
• Absorption: 33%
• Half Life: 14.4 hours
• Protein Binding: 60%-70%
• References: Smith SM, Gums JG: Fexofenadine: biochemical, pharmacokinetic and pharmacodynamic properties and its unique role in allergic disorders. Expert Opin Drug Metab Toxicol. 2009 Jul;5(7):813-22. [Pubmed] ; Bachert C: A review of the efficacy of desloratadine, fexofenadine, and levocetirizine in the treatment of nasal congestion in patients with allergic rhinitis. Clin Ther. 2009 May;31(5):921-44. [Pubmed] ; Markham A, Wagstaff AJ: Fexofenadine. Drugs. 1998 Feb;55(2):269-74; discussion 275-6. [Pubmed] ; Golightly LK, Greos LS: Second-generation antihistamines: actions and efficacy in the management of allergic disorders. Drugs. 2005;65(3):341-84. [Pubmed] ; Molimard M, Diquet B, Benedetti MS: Comparison of pharmacokinetics and metabolism of desloratadine, fexofenadine, levocetirizine and mizolastine in humans. Fundam Clin Pharmacol. 2004 Aug;18(4):399-411. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - F322470

The active metabolite of Terfenadine (T114500), a H1-histamine receptor antagonist.

参考文献

• Smith SM, Gums JG: Fexofenadine: biochemical, pharmacokinetic and pharmacodynamic properties and its unique role in allergic disorders. Expert Opin Drug Metab Toxicol. 2009 Jul;5(7):813-22. Pubmed
• Bachert C: A review of the efficacy of desloratadine, fexofenadine, and levocetirizine in the treatment of nasal congestion in patients with allergic rhinitis. Clin Ther. 2009 May;31(5):921-44. Pubmed
• Golightly LK, Greos LS: Second-generation antihistamines: actions and efficacy in the management of allergic disorders. Drugs. 2005;65(3):341-84. Pubmed
• Molimard M, Diquet B, Benedetti MS: Comparison of pharmacokinetics and metabolism of desloratadine, fexofenadine, levocetirizine and mizolastine in humans. Fundam Clin Pharmacol. 2004 Aug;18(4):399-411. Pubmed
• Markham A, Wagstaff AJ: Fexofenadine. Drugs. 1998 Feb;55(2):269-74; discussion 275-6. Pubmed
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