CLOBETASOL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H28ClFO4
Molecular Weight	410.907
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12C[C@H](C)[C@](O)(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=FCSHDIVRCWTZOX-DVTGEIKXSA-N

InChI=1S/C22H28ClFO4/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,24)17(26)10-20(16,3)22(12,28)18(27)11-23/h6-7,9,12,15-17,26,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,17-,19-,20-,21-,22-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C22H28ClFO4
Molecular Weight	410.907
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022013lbl.pdf

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 Target	Pharmacology	Condition	Potency
Glucocorticoid receptor 172 Target ID: CHEMBL2034 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9891987	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Inflammatory and pruritic dermatoses 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022013lbl.pdf	Palliative		Approved 8429	OLUX E Approved Use Olux-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 Date 1.16847359E12

C_max

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

T_1/2

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

F_unbound

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: https://pubmed.ncbi.nlm.nih.gov/7152080 Page: p.420	unhealthy, 36 n = 25 Health Status: unhealthy Condition: Psoriasis Age Group: 36 Sex: M+F Population Size: 25 Sources: https://pubmed.ncbi.nlm.nih.gov/7152080 Page: p.420	Disc. AE: Pruritus... AEs leading to discontinuation/dose reduction: Pruritus (4%) Sources: https://pubmed.ncbi.nlm.nih.gov/7152080 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: https://pubmed.ncbi.nlm.nih.gov/7152080 Page: p.420	unhealthy, 36 n = 25 Health Status: unhealthy Condition: Psoriasis Age Group: 36 Sex: M+F Population Size: 25 Sources: https://pubmed.ncbi.nlm.nih.gov/7152080 Page: p.420

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 781 inhibitor 1587			inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP3A5 73		CYP3A5 76

Drug as perpetrator

Target	Modality	Activity
CYP3A4 1925	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/16882163/ Page: 3.0	no
CYP3A4 1925	inhibitor 3277 Sources: https://pubs.acs.org/doi/abs/10.1021/acs.jmedchem.9b02067	no
CYP3A5 130	inhibitor 3277 Sources: https://pubs.acs.org/doi/abs/10.1021/acs.jmedchem.9b02067	yes [IC50 1.8 uM]
CYP3A5 130	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/16882163/ Page: 3.0	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209483Orig1s000ClinPharmR.pdf#page=4

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:205919	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:205919
ChemicalBook	CB8715108	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8715108
ZINC	ZINC000026892643	http://zinc15.docking.org/substances/ZINC000026892643
eMolecules	36755839	https://www.emolecules.com/cgi-bin/more?vid=36755839

PubMed

Title	Date	PubMed
Clobetasol down-regulates SLPI expression in U937 monocytoid cells.	2012 Feb	22076618
Clobetasol synergistically diminishes Ciz1 expression with genistein in U937 cells.	2012 Feb	22075938

Patents

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 Created by `admin` on `Fri Dec 15 15:59:47 UTC 2023` Edited by `admin` on `Fri Dec 15 15:59:47 UTC 2023`
Record UNII	ADN79D536H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CLOBETASOL

Official Name

English

BETAMETHASONE IMPURITY B [EP IMPURITY]

Common Name

English

CLOBETASOL [VANDF]

Common Name

English

CLOBETASOL [MI]

Common Name

English

DOVATE

Brand Name

English

CLOBETASOL PROPIONATE IMPURITY G [EP IMPURITY]

Common Name

English

21-Chloro-9-fluoro-11β,17-dihydroxy-16β-methylpregna-1,4-diene-3,20-dione

Systematic Name

English

CLOBECORT AMEX

Brand Name

English

(11β,16β)-21-Chloro-9-fluoro-11,17-dihydroxy-16-methylpregna-1,4-diene-3,20-dione

Systematic Name

English

PREGNA-1,4-DIENE-3,20-DIONE, 21-CHLORO-9-FLUORO-11,17-DIHYDROXY-16-METHYL-, (11.BETA.,16.BETA.)-

Systematic Name

English

Clobetasol [WHO-DD]

Common Name

English

clobetasol [INN]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QD07CD01