CAS 25122-46-7|Clobetasolpropionat mikron.|Clobetasole propionate|Temovate E|clobetasol|Embeline E|(1R,2S,10S,11S,13S,14R,15S,17S)-14-(2-chloroacetyl)-1-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetr...

General Information

Structure

Molecular Formula

C₂₅H₃₂ClFO₅

Molecular Mass

466.9699832

Exact Mass

466.19223002

Charge

InChI

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

InChIKey

CBGUOGMQLZIXBE-XGQKBEPLSA-N

Canonic Smiles

CCC(=O)O[C@@]1([C@@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2CCC2=CC(=O)C=C[C@]12C)F)C(=O)CCl

Isomeric Smiles

ClCC(=O)[C@]1(OC(=O)CC)[C@@]2([C@H]([C@H]3[C@](F)([C@@H](O)C2)[C@@]2(C(=CC(=O)C=C2)CC3)C)C[C@@H]1C)C

Calculated Properties

JChem

Acid pKa

13.626671

H Acceptors

H Donor

LogD (pH = 5.5)

4.1778226

LogD (pH = 7.4)

4.1778226

Log P

4.1778226

Molar Refractivity

119.3223

Polarizability

46.51583

Polar Surface Area

80.67

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

3.49

LOG S

-5.05

Solubility (Water)

4.13e-03 g/l

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Brand Name

DermovateTemovate EEmbeline EOluxClobetasol propionate [USAN:JAN]Clobetasole propionateClobetasol PropionateClobexEmbelineTemovateClobesolClobetasolpropionat mikron.

IUPAC name

(1R,2S,10S,11S,13S,14R,15S,17S)-14-(2-chloroacetyl)-1-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl propanoate (1R,2S,10S,11S,13S,14R,15S,17S)-14-(2-chloroacetyl)-1-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-14-yl propanoate

Synonyms

Clobetasol丙酸氯倍他索Clobetasol propionateClobetasol propionateOlux21-Chloro-21-deoxybetamethasone 17-PropionateTemovate(11β,16β)-21-Chloro-9-fluoro-11-hydroxy-16-methyl-17-(1-oxopropoxy)pregna-1,4-diene-3,20-dioneDermovalClobesolKarisonDermoxinClobexSkin CapClobedermDermoxinaleDermovateClobetasol 17-PropionateGR 2/925

IUPAC Traditional name

clobetasol temovate

Names and Identifiers

Registration numbers

PubChem CID

CAS Number

PubChem SID

EC Number

MDL Number

Registration numbers

Properties

Product Information

Salt Data

propionate

Purity

≥98%

Grade

analytical standard

Certificate of Analysis

Download link

Pharmacology Properties

Gene Information

rat ... Nr3c1(24413)

Target Organ

Adrenal gland, Immune system

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB01013

Drug Groups

approved

Description

A derivative of prednisolone with high glucocorticoid activity and low mineralocorticoid activity. Absorbed through the skin faster than fluocinonide, it is used topically in treatment of psoriasis but may cause marked adrenocortical suppression. [PubChem]

Indication

For short-term topical treatment of the inflammatory and pruritic manifestations of moderate to severe corticosteroid-responsive dermatoses of the scalp.

Pharmacology

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. It is recommended that treatment should be limited to 2 consecutive weeks and therapy should be discontinued when adequate results have been achieved.

Toxicity

Oral LD₅₀ in rat and mouse is >3000 mg/kg. Topically applied clobetasol can be absorbed in sufficient amounts to produce systemic effects. Symptoms of overdose include thinning of skin and suppression of adrenal cortex (decreased ability to respond to stress).

Affected Organisms

Humans and other mammals

Biotransformation

Metabolized, primarily in the liver, and then excreted by the kidneys.

Absorption

Topical corticosteroids can be absorbed from intact healthy skin. The extent of percutaneous absorption of topical corticosteroids is determined by many factors, including the vehicle and the integrity of the epidermal barrier. Occlusion, inflammation and/or other disease processes in the skin may also increase percutaneous absorption.

Elimination

Corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys. Some of the topical corticosteroids, including clobetasol propionate and its metabolites, are also excreted into the bile.

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

Selleck Chemicals

S2584

Research Area: Inflammation
Biological Activity:
Clobetasol propionate is a anti-inflammatory corticosteroid used to treat various skin disorders including eczema and psoriasis. Clobetasol propionate is also highly effective for contact dermatitis caused by exposure to poison ivy/oak. Clobetasol belongs to US Class I (Europe: class IV) of the corticosteroids, making it one of the most potent available. Clobetasol propionate has very high potency and typically should not be used with occlusive dressings, or for extended continuous use (beyond two weeks). Clobetasol propionate is also used to treat several auto-immune diseases including alopecia areata, vitiligo and lichen planus. [1][2]References on Clobetasol propionate[1] http://en.wikipedia.org/wiki/Clobetasol_propionate, , [2] Forensic Sci Int. , 2011 Apr 5,

Sigma Aldrich

C8037

Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C8037.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

TRC

C583500

Topical corticosteroid. Glucocorticoid; anti-inflammatory.

Molecule Details

References

PubChem Literature

From Data Sources

• Nam YS et al. Forensic Sci Int. 2011 Apr 5

• Olsen, E.A., et al.: J. Am. Acad. Dermatol., 15, 246 (1986)

References

Bioactivity

PubChem BioAssay

Bioactivity

Data Source

Academic Data

Commercial Catalog

Names and Identifiers

Brand Name

DermovateTemovate EEmbeline EOluxClobetasol propionate [USAN:JAN]Clobetasole propionateClobetasol PropionateClobexEmbelineTemovateClobesolClobetasolpropionat mikron.

IUPAC name

Synonyms

IUPAC Traditional name

clobetasol temovate

Registration numbers

PubChem CID

CAS Number

PubChem SID

EC Number

MDL Number

Properties

Product Information

Salt Data

propionate

Purity

≥98%

Grade

analytical standard

Certificate of Analysis

Download link

Pharmacology Properties

Gene Information

rat ... Nr3c1(24413)

Target Organ

Adrenal gland, Immune system

Molecule Details

DrugBank

DB01013

Drug Groups

approved

Description

Indication

For short-term topical treatment of the inflammatory and pruritic manifestations of moderate to severe corticosteroid-responsive dermatoses of the scalp.

Pharmacology

Toxicity

Affected Organisms

Humans and other mammals

Biotransformation

Metabolized, primarily in the liver, and then excreted by the kidneys.

Absorption

Elimination

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]