2-(2-{4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)ethan-1-ol

• ChemBase编号: 439
• 分子式: C21H27ClN2O2
• 平均质量: 374.90428
• 单一同位素质量: 374.17610579
• SMILES: Clc1ccc(C(N2CCN(CC2)CCOCCO)c2ccccc2)cc1
• Canonical SMILES: OCCOCCN1CCN(CC1)C(c1ccc(cc1)Cl)c1ccccc1
• InChI: InChI=1S/C21H27ClN2O2/c22-20-8-6-19(7-9-20)21(18-4-2-1-3-5-18)24-12-10-23(11-13-24)14-16-26-17-15-25/h1-9,21,25H,10-17H2
• InChIKey: ZQDWXGKKHFNSQK-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-(2-{4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)ethan-1-ol
• IUPAC传统名: hydroxyzine
• 商标名: Alamon; Atara; Atarax; Ataraxoid; Atarazoid; Atarox; Atazina; Aterax; Deinait; Durrax; Equipoise; Equipose; Fenarol; Hy-Pam 25; Hychotine; Masmoran; Neo-Calma; Neurozina; Nevrolaks; Orgatrax; Pamazone; Paxistil; Placidol; Plaxidol; Quiess; Tran-Q; Tranquizine; Traquizine; Vesparaz-Wirkstoff; Vistaril; Vistaril Pamoate; Vistazine
• 别名: Hidroxizina [INN-Spanish]; Hydroksyzyny [Polish]; Hydroxizinum; Hydroxyzinum [INN-Latin]; Hydroxyzine Pamoate; Hydroxyzine Hcl; Hydroxyzine Base; Hydroxyzyne; Hydroxyzin; Hydroxycine; Idrossizina [Dcit]; Hydroxizine; Hydroxine; Hydroxyzine; 2-[2-[4-[(4-Chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]ethanol; 1-(p-Chloro-α-phenylbenzyl)-4-[2-(2-hydroxyethoxy)ethyl)]piperazine; Tran-Q; Tranquizine; NSC 169188; U.C.B 4492; HydroxyzineSee: H996500; 2-[2-[4-[(4-Chlorophenyl)-phenylmethyl]-1-piperazinyl]ethoxy]ethanol Dihydrochloride; Alamon; Atarax; Aterax; Durrax; Orgatrax; Quiess; Hydroxyzine Dihydrochloride

登记号

• CAS号: 2192-20-3; 68-88-2
• PubChem SID: 46508556; 160963902
• PubChem CID: 3658

理论计算性质

JChem

• Acid pKa: 15.121227
• 质子受体: 4
• 质子供体: 1
• LogD (pH = 5.5): 1.1205807
• LogD (pH = 7.4): 2.8550582
• Log P: 3.4129696
• 摩尔折射率: 107.0742 cm^3
• 极化性: 41.987366 Å^3
• 极化表面积: 35.94 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.43
• LOG S: -3.61
• 溶解度: 9.14e-02 g/l

分子性质

理化性质

• 溶解度: < 700 mg/mL; Chloroform; Methanol; Water
• 外观: White Solid; Yellow Oil
• 熔点: 202-205°C
• 疏水性(logP): 2.7

安全信息

• 保存条件: Refrigerator

详细说明

DrugBank - DB00557

• Drug Groups: approved
• Description: A histamine H1 receptor antagonist that is effective in the treatment of chronic urticaria, dermatitis, and histamine-mediated pruritus. Unlike its major metabolite cetirizine, it does cause drowsiness. It is also effective as an antiemetic, for relief of anxiety and tension, and as a sedative. [PubChem]
• Indication: For symptomatic relief of anxiety and tension associated with psychoneurosis and as an adjunct in organic disease states in which anxiety is manifested. Useful in the management of pruritus due to allergic conditions such as chronic urticaria.
• Pharmacology: Hydroxyzine, a piperazine antihistamine structurally related to buclizine, cyclizine, and meclizine, is used to treat histamine-mediated pruritus or pruritus due to allergy, nausea and vomiting, and, in combination with an opiate agonist, anxiolytic pain. Hydroxyzine is also used as a perioperative sedative and anxiolytic and to manage acute alcohol withdrawal. Hydroxyzine's active metabolite, cetirizine, is also used as an H₁-antagonist.
• Toxicity: Oral, rat LD₅₀: 950 mg/kg. Symptoms of overexposure include hypersedation.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Rapidly absorbed from the gastrointestinal tract
• Half Life: 20 to 25 hours
• Protein Binding: 93%
• References: HUTCHEON DE, MORRIS DL, SCRIABINE A: Cardiovascular action of hydroxyzine (atarax). J Pharmacol Exp Ther. 1956 Dec;118(4):451-60. [Pubmed] ; DOLAN CM: Management of emotional disturbances; use of hydroxyzine (atarax) in general practice. Calif Med. 1958 Jun;88(6):443-4. [Pubmed] ; Clark BG, Araki M, Brown HW: Hydroxyzine-associated tardive dyskinesia. Ann Neurol. 1982 Apr;11(4):435. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Toronto Research Chemicals - H996495

H1 receptor antagonist. Anxiolytic. Antihistaminic.

Toronto Research Chemicals - H996500

H1 receptor antagonist. Anxiolytic. Antihistaminic.

参考文献

• Clark BG, Araki M, Brown HW: Hydroxyzine-associated tardive dyskinesia. Ann Neurol. 1982 Apr;11(4):435. Pubmed
• HUTCHEON DE, MORRIS DL, SCRIABINE A: Cardiovascular action of hydroxyzine (atarax). J Pharmacol Exp Ther. 1956 Dec;118(4):451-60. Pubmed
• DOLAN CM: Management of emotional disturbances; use of hydroxyzine (atarax) in general practice. Calif Med. 1958 Jun;88(6):443-4. Pubmed
• Goldenthal, E.I., et al.: Toxicol. Appl. Pharmacol., 18, 185 (1971)
• Tsau, J., et al.: Anal. Profiles Drug Subs., 7, 319 (1978)
• Goldenthal, E.I., et al.: Toxicol. Appl. Pharmacol., 18, 185 (1971)
• Tsau, J., et al.: Anal. Profiles Drug Subs., 7, 319 (1978)