(1R,2S,10S,11S,13S,14R,15S,17S)-14-(2-chloroacetyl)-1-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl propanoate

• ChemBase编号: 886
• 分子式: C25H32ClFO5
• 平均质量: 466.9699832
• 单一同位素质量: 466.19223002
• SMILES: ClCC(=O)[C@]1(OC(=O)CC)[C@@]2([C@H]([C@H]3[C@](F)([C@@H](O)C2)[C@@]2(C(=CC(=O)C=C2)CC3)C)C[C@@H]1C)C
• Canonical SMILES: CCC(=O)O[C@@]1([C@@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2CCC2=CC(=O)C=C[C@]12C)F)C(=O)CCl
• InChI: InChI=1S/C25H32ClFO5/c1-5-21(31)32-25(20(30)13-26)14(2)10-18-17-7-6-15-11-16(28)8-9-22(15,3)24(17,27)19(29)12-23(18,25)4/h8-9,11,14,17-19,29H,5-7,10,12-13H2,1-4H3/t14-,17-,18-,19-,22-,23-,24-,25-/m0/s1
• InChIKey: CBGUOGMQLZIXBE-XGQKBEPLSA-N

名称和登记号

名称

• IUPAC标准名: (1R,2S,10S,11S,13S,14R,15S,17S)-14-(2-chloroacetyl)-1-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl propanoate; (1R,2S,10S,11S,13S,14R,15S,17S)-14-(2-chloroacetyl)-1-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl propanoate
• IUPAC传统名: clobetasol; temovate
• 商标名: Clobesol; Clobetasol Propionate; Clobetasol propionate [USAN:JAN]; Clobetasole propionate; Clobetasolpropionat mikron.; Clobex; Dermovate; Embeline; Embeline E; Olux; Temovate; Temovate E
• 别名: 丙酸氯倍他索; Clobetasol propionate; Clobetasol; Clobetasol propionate; (11β,16β)-21-Chloro-9-fluoro-11-hydroxy-16-methyl-17-(1-oxopropoxy)pregna-1,4-diene-3,20-dione; 21-Chloro-21-deoxybetamethasone 17-Propionate; Clobederm; Clobesol; Clobex; Dermoval; Dermovate; Dermoxin; Dermoxinale; GR 2/925; Karison; Olux; Skin Cap; Temovate; Clobetasol 17-Propionate

登记号

• CAS号: 25122-46-7
• EC号: 246-634-3
• MDL号: MFCD00058499
• PubChem SID: 160964349; 24893013
• PubChem CID: 32798

理论计算性质

JChem

• Acid pKa: 13.626671
• 质子受体: 4
• 质子供体: 1
• LogD (pH = 5.5): 4.1778226
• LogD (pH = 7.4): 4.1778226
• Log P: 4.1778226
• 摩尔折射率: 119.3223 cm^3
• 极化性: 46.51583 Å^3
• 极化表面积: 80.67 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.49
• LOG S: -5.05
• 溶解度: 4.13e-03 g/l

分子性质

理化性质

• 溶解度: 3.86 mg/L; Dioxane; DMSO
• 外观: White Solid
• 熔点: 191-193°C
• 疏水性(logP): 3

安全信息

• 保存条件: -20°C; -20°C Freezer
• RTECS编号: TU3725000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 德国WGK号: 2
• 危险公开号: 61-48/20/21-53-62
• 安全公开号: 53-36/37-45
• GHS危险品标识: GHS08
• GHS警示词: Danger
• GHS危险声明: H360Df-H373-H413
• GHS警示性声明: P201-P308 + P313
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: rat ... Nr3c1(24413)
• 作用器官: Adrenal gland, Immune system

产品相关信息

• 纯度: ≥98%
• 级别: analytical standard
• 成盐信息: propionate

详细说明

DrugBank - DB01013

• Drug Groups: approved
• Description: A derivative of prednisolone with high glucocorticoid activity and low mineralocorticoid activity. Absorbed through the skin faster than fluocinonide, it is used topically in treatment of psoriasis but may cause marked adrenocortical suppression. [PubChem]
• Indication: For short-term topical treatment of the inflammatory and pruritic manifestations of moderate to severe corticosteroid-responsive dermatoses of the scalp.
• Pharmacology: Like other topical corticosteroids, clobetasol has anti-inflammatory, antipruritic, and vasoconstrictive properties. It is a very high potency topical corticosteroid that should not be used with occlusive dressings. It is recommended that treatment should be limited to 2 consecutive weeks and therapy should be discontinued when adequate results have been achieved.
• Toxicity: Oral LD₅₀ in rat and mouse is >3000 mg/kg. Topically applied clobetasol can be absorbed in sufficient amounts to produce systemic effects. Symptoms of overdose include thinning of skin and suppression of adrenal cortex (decreased ability to respond to stress).
• Affected Organisms: Humans and other mammals
• Biotransformation: Metabolized, primarily in the liver, and then excreted by the kidneys.
• Absorption: Topical corticosteroids can be absorbed from intact healthy skin. The extent of percutaneous absorption of topical corticosteroids is determined by many factors, including the vehicle and the integrity of the epidermal barrier. Occlusion, inflammation and/or other disease processes in the skin may also increase percutaneous absorption.
• Elimination: Corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys. Some of the topical corticosteroids, including clobetasol propionate and its metabolites, are also excreted into the bile.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S2584

Research Area: Inflammation
Biological Activity:
Clobetasol propionate is a anti-inflammatory corticosteroid used to treat various skin disorders including eczema and psoriasis. Clobetasol propionate is also highly effective for contact dermatitis caused by exposure to poison ivy/oak. Clobetasol belongs to US Class I (Europe: class IV) of the corticosteroids, making it one of the most potent available. Clobetasol propionate has very high potency and typically should not be used with occlusive dressings, or for extended continuous use (beyond two weeks). Clobetasol propionate is also used to treat several auto-immune diseases including alopecia areata, vitiligo and lichen planus. [1][2]References on Clobetasol propionate[1] http://en.wikipedia.org/wiki/Clobetasol_propionate, , [2] Forensic Sci Int. , 2011 Apr 5,

Sigma Aldrich - C8037

Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C8037.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - C583500

Topical corticosteroid. Glucocorticoid; anti-inflammatory.

参考文献

• Nam YS et al. Forensic Sci Int. 2011 Apr 5
• Olsen, E.A., et al.: J. Am. Acad. Dermatol., 15, 246 (1986)