6-[3-(adamantan-1-yl)-4-methoxyphenyl]naphthalene-2-carboxylic acid

• ChemBase编号: 95
• 分子式: C28H28O3
• 平均质量: 412.52012
• 单一同位素质量: 412.20384476
• SMILES: O(c1c(C23CC4CC(C2)CC(C3)C4)cc(cc1)c1cc2c(cc1)cc(cc2)C(=O)O)C
• Canonical SMILES: COc1ccc(cc1C12CC3CC(C2)CC(C1)C3)c1ccc2c(c1)ccc(c2)C(=O)O
• InChI: InChI=1S/C28H28O3/c1-31-26-7-6-23(21-2-3-22-12-24(27(29)30)5-4-20(22)11-21)13-25(26)28-14-17-8-18(15-28)10-19(9-17)16-28/h2-7,11-13,17-19H,8-10,14-16H2,1H3,(H,29,30)
• InChIKey: LZCDAPDGXCYOEH-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 6-[3-(adamantan-1-yl)-4-methoxyphenyl]naphthalene-2-carboxylic acid
• IUPAC传统名: differin
• 商标名: Differin, Teva, Pimpal, Gallet, Adelene, Adeferin; Differin; Adaferin
• 别名: 6-(3-(Adamantan-1-yl)-4-methoxyphenyl)-2-naphthoic acid; Adapaleno [INN-Spanish]; Adapalenum [INN-Latin]; Adapalene; Differin; 6-(3-(1-adamantyl)-4-methoxy-phenyl)Naphthalene-2-carboxylic acid

登记号

• CAS号: 106685-40-9
• MDL号: MFCD03106112
• PubChem SID: 160963558; 46505019
• PubChem CID: 60164
• CHEBI ID: 31174
• ATC码: D10AD03
• CHEMBL: 1265
• Chemspider ID: 54244
• DrugBank ID: DB00210
• KEGG ID: D01112
• 美国药典/FDA物质标识码: 1L4806J2QF
• 维基百科标题: Adapalene
• Medline Plus: a604001

理论计算性质

JChem

• Acid pKa: 3.9892612
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 4.938707
• LogD (pH = 7.4): 3.2933044
• Log P: 6.4585013
• 摩尔折射率: 122.0719 cm^3
• 极化性: 49.86113 Å^3
• 极化表面积: 46.53 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 6.06
• LOG S: -8.01
• 溶解度: 4.01e-06 g/l

分子性质

理化性质

• 溶解度: Practically Insoluble
• 疏水性(logP): 8.6

安全信息

• 保存条件: -20°C
• 保存注意事项: IRRITANT
• TSCA收录: false

药理学性质

• 给药途径: Topical
• 生物利用度: Very low
• 排泄: Biliary
• 法定药品分级: POM (UK); Rx-only (US)
• 妊娠期药物分类: C

产品相关信息

• 纯度: 95+%; 97%
• 成盐信息: Free Base

详细说明

DrugBank - DB00210

• Drug Groups: approved
• Description: Adapalene is a topical retinoid primarily used in the treatment of acne and is also used (off-label) to treat keratosis pilaris as well as other skin conditions. It is currently marketed by Galderma under the trade names Differin in some countries, and Adaferin in India. [Wikipedia]
• Indication: For the topical treatment of comedo, papular and pustular acne (acne vulgaris) of the face, chest or back.
• Pharmacology: Adapalene is a chemically stable retinoid-like compound. Biochemical and pharmacological profile studies have demonstrated that adapalene is a modulator of cellular differentiation, keratinization, and inflammatory processes all of which represent important features in the pathology of acne vulgaris.
• Toxicity: The acute oral toxicity of adapalene in mice and rats is greater than 10 mL/kg. Chronic ingestion of the drug may lead to the same side effects as those associated with excessive oral intake of Vitamin A.
• Affected Organisms: Humans and other mammals
• Biotransformation: Metabolized mainly by O-demethylation, hydroxylation and conjugation, and excretion is primarily by the biliary route.
• Absorption: Absorption of adapalene through human skin is low. Only trace amounts (<0.25 ng/mL) of parent substance have been found in the plasma of acne patients following chronic topical application of adapalene in controlled clinical trials
• Elimination: Excretion appears to be primarily by the biliary route.
• References: Rolewski SL: Clinical review: topical retinoids. Dermatol Nurs. 2003 Oct;15(5):447-50, 459-65. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S1276

Research Area: Endocrinology
Biological Activity:
Adapalene is a third-generation topical retinoid primarily used in the treatment of mild-moderate acne and is also used (off-label) to treat keratosis pilaris as well as other skin conditions. Adapalene is possibly more effective than tretinoin 0.025% gel in the treatment of acne vulgaris. [1]

参考文献

• Rolewski SL: Clinical review: topical retinoids. Dermatol Nurs. 2003 Oct;15(5):447-50, 459-65. Pubmed
• http://en.wikipedia.org/wiki/Adapalene