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Flumetasone

Flumetasone structure

CAS No:
2135-17-3
Formula:
C22H28F2O5
Chemical Name:
Flumetasone
Synonyms:
Pregna-1,4-diene-3,20-dione,6,9-difluoro-11,17,21-trihydroxy-16-methyl-,(6α,11β,16α)-;Pregna-1,4-diene-3,20-dione,6α,9-difluoro-11β,17,21-trihydroxy-16α-methyl-;(6α,11β,16α)-6,9-Difluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione;U 10974;6α,9α-Difluoro-16α-methylprednisolone;6α,9-Difluoro-11β,17,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione;Flumethasone;6α-Fluorodexamethasone;6α,9α-Difluoro-16α-methyl-1,4-pregnadiene-11β,17α,21-triol-3,20-dione;Flumethason;Aniprime;Flucort;Methagon;Anaprime;Flucorticin;Fluvet;RS 2177;Cortexillar;Flumetasone;Vecort;6α-Fluorodexamethazone;Aniprome;NSC 5402;NSC 54702;Flutamethasone
Categories:
Biochemical Engineering > Inhibitors

Description

Flumethasone is a corticosteroid for topical use, in combination with Clioquinol for the treatment of otitis externa and otomycosis. Flumethasone shows fully 420 times the potency of cortisone in an animal model for anti-inflammatory activity.

Flumethasone is a fluorinated steroid, a glucocorticoid, an 11beta-hydroxy steroid, a 17alpha-hydroxy steroid, a 21-hydroxy steroid, a 20-oxo steroid, a 3-oxo-Delta(1),Delta(4)-steroid, a primary alpha-hydroxy ketone and a tertiary alpha-hydroxy ketone. It has a role as an anti-inflammatory drug. It derives from a hydride of a pregnane.|Flumethasone 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.|An anti-inflammatory glucocorticoid used in veterinary practice.

Flumetasone Basic Attributes

Molecular Weight：

410.45200

Exact Mass：

410.45

EC Number：

218-370-9

UNII：

LR3CD8SX89

DSSTox ID：

DTXSID2045365

ATC Code：

D - Dermatologicals

HScode：

2937229000

Characteristics

PSA：

94.83000

XLogP3：

1.84370

Appearance：

White crystalline powder

Density：

1.36 g/cm3

Melting Point：

202-204 °C

Boiling Point：

569.8ºC at 760 mmHg

Flash Point：

298.4ºC

Refractive Index：

1.579

Water Solubility：

1mg/L(20 ºC)

Storage Conditions：

2-8ºC

Vapor Pressure：

2.33E-15mmHg at 25°C

Collision Cross Section：

189.2 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]|193.2 Å² [M+H]+ [CCS Type: TW]|195.21 Å² [M-H]-

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

R40

safety instructions：

S22-S36

RTECS Number：

TU3832000

Marks：

Precautionary statement(s)：

P281

Hazard Statements：

H351

GHS Classification：

|Danger|H351 (80%): Suspected of causing cancer [Warning Carcinogenicity]|P201, P202, P281, P308+P313, P405, and P501|Aggregated GHS information provided by 50 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity Summary：

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

Drug Information

Drug Indication：

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

Pharmacology：

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.

MeSH：

A group of CORTICOSTEROIDS that affect carbohydrate metabolism (GLUCONEOGENESIS, liver glycogen deposition, elevation of BLOOD SUGAR), inhibit ADRENOCORTICOTROPIC HORMONE secretion, and possess pronounced anti-inflammatory activity. They also play a role in fat and protein metabolism, maintenance of arterial blood pressure, alteration of the connective tissue response to injury, reduction in the number of circulating lymphocytes, and functioning of the central nervous system. (See all compounds classified as Glucocorticoids.)|Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)

Absorption：

Minimal if applied topically

Metabolism/Metabolites：

Primarily hepatic

Mechanism of Action：

Flumethasone is a glucocorticoid receptor agonist. This complex binds to the nucleus causing a variety of genetic activation and repressions. The antiinflammatory actions of corticosteroids are thought to involve lipocortins, phospholipase A2 inhibitory proteins which, through inhibition arachidonic acid, control the biosynthesis of prostaglandins and leukotrienes. The immune system is suppressed by corticosteroids 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 binds to plasma transcortin, and it becomes active when it is not bound to transcortin.

MeSH Entry Terms：

Flumethasone

Flumetasone Use and Manufacturing

Uses

1. Topical anti-inflammatory corticosteroid
2. A glucocorticoid. An anti-inflammatory

Use Classification：

Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients|Pharmaceuticals

Computed Properties

Molecular Weight:410.5
XLogP3:1.9
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:2
Exact Mass:410.19048031
Monoisotopic Mass:410.19048031
Topological Polar Surface Area:94.8
Heavy Atom Count:29
Complexity:839
Defined Atom Stereocenter Count:9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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