(2Z,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid

• ChemBase编号: 342
• 分子式: C21H26O3
• 平均质量: 326.42934
• 单一同位素质量: 326.18819469
• SMILES: O(c1c(c(c(c(c1)C)/C=C/C(=C/C=C/C(=C\C(=O)O)/C)/C)C)C)C
• Canonical SMILES: COc1cc(C)c(c(c1C)C)/C=C/C(=C/C=C/C(=C\C(=O)O)/C)/C
• InChI: InChI=1S/C21H26O3/c1-14(8-7-9-15(2)12-21(22)23)10-11-19-16(3)13-20(24-6)18(5)17(19)4/h7-13H,1-6H3,(H,22,23)/b9-7+,11-10+,14-8+,15-12-
• InChIKey: IHUNBGSDBOWDMA-UGOGCBOOSA-N

名称和登记号

名称

• IUPAC标准名: (2Z,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
• IUPAC传统名: acetretin
• 商标名: Acetretin; Soriatane
• 别名: Acitretin; 9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic Acid, 13-cis-Etretin, Isoacitretin, Isoetretin, Ro 13-7652; 13-cis Acitretin

登记号

• CAS号: 69427-46-9; 55079-83-9
• PubChem SID: 160963805
• PubChem CID: 6437841

理论计算性质

JChem

• Acid pKa: 5.011076
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 4.976502
• LogD (pH = 7.4): 3.2266924
• Log P: 5.5870485
• 摩尔折射率: 104.1665 cm^3
• 极化性: 38.030373 Å^3
• 极化表面积: 46.53 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 5.2
• LOG S: -5.83
• 溶解度: 4.78e-04 g/l

分子性质

理化性质

• 溶解度: 0.0729 mg/L; Acetone; Chloroform; Dichloromethane; Ethyl Acetate,
• 外观: Yellow Solid
• 熔点: 190-193°C
• 疏水性(logP): 5.7

安全信息

• 保存条件: Amber Vial, -80°C Freezer

详细说明

DrugBank - DB00459

• Drug Groups: approved
• Description: An oral retinoid effective in the treatment of psoriasis. It is the major metabolite of etretinate with the advantage of a much shorter half-life when compared with etretinate. [PubChem]
• Indication: For the treatment of severe psoriasis in adults.
• Pharmacology: Acitretin is a retinoid. Retinoids have a structure similar to vitamin A and are involved in the normal growth of skin cells. Acitretin works by inhibiting the excessive cell growth and keratinisation (process by which skin cells become thickened due to the deposition of a protein within them) seen in psoriasis. It therefore reduces the thickening of the skin, plaque formation and scaling.
• Toxicity: Oral, rat: LD₅₀ = >4000 mg/kg. Symptoms of overdose include headache and vertigo.
• Affected Organisms: Humans and other mammals
• Biotransformation: Following oral absorption, acitretin undergoes extensive metabolism and interconversion by simple isomerization to its 13-cis form (cis-acitretin). Both parent compound and isomer are further metabolized into chain-shortened breakdown products and conjugates, which are excreted.
• Absorption: Oral absorption of acitretin is optimal when given with food, and is linear and proportional with increasing doses from 25 to 100 mg. Approximately 72% (range 47% to 109%) of the administered dose was absorbed after a single 50 mg dose of acitretin was given to 12 healthy subjects.
• Half Life: 49 hours (range 33 to 96 hours)
• Protein Binding: Over 99.9% bound to plasma proteins, primarily albumin.
• Elimination: Both parent compound and isomer are further metabolized into chain-shortened breakdown products and conjugates, which are excreted. The chain-shortened metabolites and conjugates of acitretin and cis-acitretin are ultimately excreted in the feces (34% to 54%) and urine (16% to 53%).
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Toronto Research Chemicals - A189925

A synthetic retinoid which is the major metabolite of etretinate (E938000).

参考文献

• Sato, T., et al.: J. Med. Chem., 51, 7705 (2008)
• Liu, X., et al.: Cancer Chemother. Pharmacol., 63, 167 (2008)