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
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
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).
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2034 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9891987 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | OLUX E Approved UseOlux-E Foam is indicated for the treatment of inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses in patients 12 years of age or older. Treatment should be limited to 2 consecutive weeks and patients should not use greater than 50 grams per week. Patients should be instructed to use Olux-E Foam for the minimum amount of time necessary to achieve the desired results. Use in pediatric patients under 12 years of age is not recommended because of numerically high rates of hypothalamic-pituitary-adrenal (HPA) axis suppression seen in patients under 12 years of age Launch Date2007 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
59 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18539358 |
3.57 g 2 times / day multiple, topical dose: 3.57 g route of administration: Topical experiment type: MULTIPLE co-administered: |
CLOBETASOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
562 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18539358 |
3.57 g 2 times / day multiple, topical dose: 3.57 g route of administration: Topical experiment type: MULTIPLE co-administered: |
CLOBETASOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
18 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6851236/ |
12.5 mg single, topical dose: 12.5 mg route of administration: Topical experiment type: SINGLE co-administered: |
CLOBETASOL plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.5% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21965623 |
CLOBETASOL plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
0.05 % 2 times / day multiple, topical Recommended Dose: 0.05 %, 2 times / day Route: topical Route: multiple Dose: 0.05 %, 2 times / day Sources: Page: p.420 |
unhealthy, 36 n = 25 Health Status: unhealthy Condition: Psoriasis Age Group: 36 Sex: M+F Population Size: 25 Sources: Page: p.420 |
Disc. AE: Pruritus... AEs leading to discontinuation/dose reduction: Pruritus (4%) Sources: Page: p.420 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Pruritus | 4% Disc. AE |
0.05 % 2 times / day multiple, topical Recommended Dose: 0.05 %, 2 times / day Route: topical Route: multiple Dose: 0.05 %, 2 times / day Sources: Page: p.420 |
unhealthy, 36 n = 25 Health Status: unhealthy Condition: Psoriasis Age Group: 36 Sex: M+F Population Size: 25 Sources: Page: p.420 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/16882163/ Page: 3.0 |
no | |||
no | ||||
yes [IC50 1.8 uM] | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/16882163/ Page: 3.0 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22076618
Clobetasol treatment of U937 cells induced an up- and down-regulation of secretory leukocyte peptidase inhibitor (SLPI) expression in a dose-dependent manner.
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NCI_THESAURUS |
C521
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U-34
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CLOBETASOL PROPIONATE
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ACTIVE MOIETY
SUBSTANCE RECORD