CAS 2002-29-1|Locorten|2-[(1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl]-2-oxoethyl 2,2-dimethylp...

基本信息

化学结构

分子式

C₂₇H₃₆F₂O₆

分子量

494.5679464

精确质量

494.24799531

电荷

InChI

InChI=1S/C27H36F2O6/c1-14-9-16-17-11-19(28)18-10-15(30)7-8-24(18,5)26(17,29)20(31)12-25(16,6)27(14,34)21(32)13-35-22(33)23(2,3)4/h7-8,10,14,16-17,19-20,31,34H,9,11-13H2,1-6H3/t14-,16+,17+,19+,20+,24+,25+,26+,27+/m1/s1

InChIKey

JWRMHDSINXPDHB-OJAGFMMFSA-N

Canonic Smiles

O=C1C=C[C@]2(C(=C1)[C@@H](F)C[C@@H]1[C@]2(F)[C@@H](O)C[C@]2([C@H]1C[C@H]([C@]2(O)C(=O)COC(=O)C(C)(C)C)C)C)C

Isomeric Smiles

F[C@@]12[C@H]([C@H]3[C@@]([C@](O)([C@@H](C3)C)C(=O)COC(=O)C(C)(C)C)(C[C@@H]1O)C)C[C@H](F)C1=CC(=O)C=C[C@]21C

计算属性

JChem

Acid pKa

12.435035

质子受体

质子供体

LogD (pH = 5.5)

3.5825121

LogD (pH = 7.4)

3.5825083

Log P

3.5825121

摩尔折射率

125.1702

极化性

48.730103

极化表面积

100.9

可自由旋转的化学键

里宾斯基五规则

true

ALOGPS 2.1

Log P

3.21

LOG S

-4.67

溶解度

1.07e-02 g/l

数据来源

学术数据

产品目录

数据来源

名称和标识

IUPAC传统名

flumethasone pivalate

别名

Flumethasone Pivalate6α,9-Difluoro-11β,17,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione 21-(2,2-dimethylpropionate)Flumethasone pivalateLorindenLocacortenNSC 107680(6α,11β,16α)-21-(2,2-Dimethyl-1-oxopropoxy)-6,9-difluoro-11,17-dihydroxy-16-methyl-pregna-1,4-diene-3,20-dioneFlumetasone PivalateLocortenFlumethasone 21-PivalateLosalen

IUPAC标准名

2-[(1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl]-2-oxoethyl 2,2-dimethylpropanoate 2-[(1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-14-yl]-2-oxoethyl 2,2-dimethylpropanoate

商标名

Locorten

名称和标识

数据登录号

PubChem CID

443980

PubChem SID

4650512116096400824894735

CAS号

2002-29-1

MDL号

MFCD00079287

EC号

217-901-1

数据登录号

化合物性质

理化性质

溶解度

0.392 mg/L

疏水性(logP)

2.1

产品相关信息

质检报告

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化合物性质

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描述信息

DrugBank

DB00663

Drug Groups

approved

Description

Flumethasone pivalate is a moderately potent difluorinated corticosteroid ester with anti-inflammatory, antipruritic and vasoconstrictive properties. As it is a privalate salt, its anti-inflammatory action is concentrated at the site of application. This local effect on diseased areas results in a prompt decrease in inflammation, exudation and itching.

Indication

For the treatment of contact dermatitis, atopic dermatitis, exczema, psoriasis, diaper rash and other skin conditions

Pharmacology

Toxicity

Can lead to signs of irritation such as burning sensation, itching or skin rash at the site of application; hypersensitivity reactions.

Affected Organisms

Humans and other mammals

Biotransformation

Primarily hepatic

Absorption

Minimal if applied topically

Sigma Aldrich

F0891

Application
Flumethasone pivalate is a topical corticosteroid. Prompt decrease in inflammation, exudation and itching is experienced after application. It is a difluorinated corticosteroid ester with anti-inflammatory, antipruritic and vasoconstrictive properties. It is used to study adrenocortical suppression1, plasma transcortin binding, and cutaneous atrophy and telangiectasia2.
Biochem/physiol Actions
Flumethasone is a glucocorticoid receptor agonist. It binds to the nucleus causing a variety of genetic activation and repressions. The anti-inflammatory actions of flumethasone is thought to involve lipocortins and phospholipase A2 inhibitory proteins, which results in the inhibition of arachidonic acid and the control of prostaglandin and leukotriene biosynthesis. Flumethasone suppresses the immune system due to a decrease in the function of the lymphatic system, a reduction in immunoglobulin and complement concentrations, the precipitation of lymphocytopenia, and interference with antigen-antibody binding.
Flumethasone pivalate is a glucocorticoid receptor agonist used in studies on plasma transcortin binding.

TRC

F455015

An anti-inflammatory anti-itching corticosteroid found in topical creams.

描述信息

参考文献

PubChem文献

数据源提供

• Fliri, A., et al.: J. Med. Chem., 52, 8038 (2009)

• Hoeller, S., et al.: J. Pharm. Sci., 98, 2686 (2009)

• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2009)

参考文献

生物活性