DIFLUCORTOLONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H28F2O4
Molecular Weight	394.4521
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12C[C@@H](C)[C@H](C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]3(F)[C@@]2([H])C[C@H](F)C4=CC(=O)C=C[C@]34C

InChI

InChIKey=OGPWIDANBSLJPC-RFPWEZLHSA-N

InChI=1S/C22H28F2O4/c1-11-6-13-14-8-16(23)15-7-12(26)4-5-21(15,3)22(14,24)18(28)9-20(13,2)19(11)17(27)10-25/h4-5,7,11,13-14,16,18-19,25,28H,6,8-10H2,1-3H3/t11-,13+,14+,16+,18+,19-,20+,21+,22+/m1/s1

HIDE SMILES / InChI

Description
Sources: https://web.archive.org/web/20170630002752/http://ca.gsk.com/media/1187415/nerisone.pdf
Curator's Comment: description was created based on several sources, including, www.ncbi.nlm.nih.gov/pubmed/23213332

Diflucortolone (used in the form of valerate prodrug) is a corticosteroid developed for the treatment of inflammatory skin diseases. It is supposed that Diflucortolone acts by inducing Annexin A1, a phospholipase A2 inhibitory protein, and thus controls the biosynthesis of prostagladins and leukotrienes. The drug is marketed as a cream under the tradename Nerisone.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Annexin A1 17 Target ID: P04083 Gene ID: 301.0 Gene Symbol: ANXA1 Target Organism: Homo sapiens (Human) Sources: https://web.archive.org/web/20170630002752/http://ca.gsk.com/media/1187415/nerisone.pdf	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Acute and chronic skin diseases 2 Sources: https://web.archive.org/web/20170630002752/http://ca.gsk.com/media/1187415/nerisone.pdf	Primary		Approved 8429	NERISONE Approved Use NERISONE® (diflucortolone valerate) preparations are indicated for the topical treatment of corticosteroid-responsive acute and chronic skin diseases, where anti-inflammatory, anti-allergic and anti-pruritic action is required for a maximum duration of 4 weeks.

PubMed

Title	Date	PubMed
[Use of diflucortolone in various dermatological processes].	1976 Oct	1015587
[Clinical comparative study of between difluocortolone and flumethasone].	1977	364210
[Clinical trial of diflucortolone. Preliminary report].	1981	7026942
A test of the half-side comparative design in the clinical evaluation of topical steroids, using diflucortolone and betamethasone creams.	1985 Oct	3907679
Local anti-inflammatory activity and systemic side effects of NM-135, a new prodrug glucocorticoid, in an experimental inflammatory rat model.	1998 Dec	9920209
Congenital infantile digital fibromatosis: a case report and review of the literature.	2009 Dec 28	21139926
Enhanced dermal delivery of diflucortolone valerate using lecithin/chitosan nanoparticles: in-vitro and in-vivo evaluations.	2013	23390364
Cutaneous polyarteritis nodosa successfully treated with topical diflucortolone valerate: a case report & review of the literature.	2014	25328491

Patents

Sample Use Guides

In Vivo Use Guide

Apply a thin layer and gently rub in using only enough to cover the affected area once or twice a day for a maximum of 4 weeks.

Route of Administration: Topical

In Vitro Use Guide

In the vasoconstriction test on human skin, in which hyperemia has been experimentally induced, a water/oil emulsion with 0.001% diflucortolone valerate is as effective as a similar preparation containing 0.1% fluocortolone.

Name

Type

Language

DIFLUCORTOLONE

Official Name

English

PREGNA-1,4-DIENE-3,20-DIONE, 6,9-DIFLUORO-11,21-DIHYDROXY-16-METHYL-, (6.ALPHA.,11.BETA.,16.ALPHA.)-

Systematic Name

English

DIFLUCORTOLONE [USAN]

Common Name

English

DIFLUCORTOLONE [MART.]

Common Name

English

6α,9-Difluoro-11β,21-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione

Systematic Name

English

diflucortolone [INN]

Common Name

English

Diflucortolone [WHO-DD]

Common Name

English

DIFLUCORTOLONE [MI]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QD07XC04