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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H32ClFO5
Molecular Weight 466.97
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLOBETASOL PROPIONATE

SMILES

[H][C@@]12C[C@H](C)[C@](OC(=O)CC)(C(=O)CCl)[C@@]1(C)C[C@H](O)[C@@]3(F)[C@@]2([H])CCC4=CC(=O)C=C[C@]34C

InChI

InChIKey=CBGUOGMQLZIXBE-XGQKBEPLSA-N
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

HIDE SMILES / InChI

Molecular Formula C25H32ClFO5
Molecular Weight 466.97
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

CLOBETASOL, a derivative of prednisolone with high glucocorticoid activity and low mineralocorticoid activity. Absorbed through the skin faster than fluocinonide, it is used topically in the treatment of psoriasis but may cause marked adrenocortical suppression. For short-term topical treatment of the inflammatory and pruritic manifestations of moderate to severe corticosteroid-responsive dermatoses of the scalp. 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. Topical corticosteroids share anti-inflammatory, antipruritic, and vasoconstrictive properties. The mechanism of the anti-inflammatory activity of topical steroids is unclear. However, corticosteroids are thought to act by the induction of phospholipase A2 inhibitory proteins, collectively called lipocortins. It is postulated that these proteins control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes by inhibiting the release of their common precursor, arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A2. Initially, however, clobetasol, like other corticosteroids, bind to the glucocorticoid receptor, which complexes, enters the cell nucleus and modifies genetic transcription (transrepression/transactivation).

CNS Activity

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
OLUX E

Cmax

ValueDoseCo-administeredAnalytePopulation
59 pg/mL
3.57 g 2 times / day multiple, topical
CLOBETASOL plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
562 pg × h/mL
3.57 g 2 times / day multiple, topical
CLOBETASOL plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
18 h
12.5 mg single, topical
CLOBETASOL plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
2.5%
CLOBETASOL plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
Apply a thin layer of Olux-E Foam (clobetasol propionate) to the affected area(s) twice daily, morning and evening.
Route of Administration: Topical
In Vitro Use Guide
Clobetasol treatment of U937 cells induced an up- and down-regulation of secretory leukocyte peptidase inhibitor (SLPI) expression in a dose-dependent manner.
Substance Class Chemical
Record UNII
779619577M
Record Status Validated (UNII)
Record Version