CAS 2002-29-1|Locorten|2-[(1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl]-2-oxoethyl 2,2-dimethylp...

General Information

Structure

Molecular Formula

C₂₇H₃₆F₂O₆

Molecular Mass

494.5679464

Exact Mass

494.24799531

Charge

InChI

InChI=1S/C27H36F2O6/c1-14-9-16-17-11-19(28)18-10-15(30)7-8-24(18,5)26(17,29)20(31)12-25(16,6)27(14,34)21(32)13-35-22(33)23(2,3)4/h7-8,10,14,16-17,19-20,31,34H,9,11-13H2,1-6H3/t14-,16+,17+,19+,20+,24+,25+,26+,27+/m1/s1

InChIKey

JWRMHDSINXPDHB-OJAGFMMFSA-N

Canonic Smiles

O=C1C=C[C@]2(C(=C1)[C@@H](F)C[C@@H]1[C@]2(F)[C@@H](O)C[C@]2([C@H]1C[C@H]([C@]2(O)C(=O)COC(=O)C(C)(C)C)C)C)C

Isomeric Smiles

F[C@@]12[C@H]([C@H]3[C@@]([C@](O)([C@@H](C3)C)C(=O)COC(=O)C(C)(C)C)(C[C@@H]1O)C)C[C@H](F)C1=CC(=O)C=C[C@]21C

Calculated Properties

JChem

Acid pKa

12.435035

H Acceptors

H Donor

LogD (pH = 5.5)

3.5825121

LogD (pH = 7.4)

3.5825083

Log P

3.5825121

Molar Refractivity

125.1702

Polarizability

48.730103

Polar Surface Area

100.9

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

3.21

LOG S

-4.67

Solubility (Water)

1.07e-02 g/l

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

IUPAC Traditional name

flumethasone pivalate

Synonyms

Flumethasone Pivalate6α,9-Difluoro-11β,17,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione 21-(2,2-dimethylpropionate)Flumethasone pivalateLorindenLocacortenNSC 107680(6α,11β,16α)-21-(2,2-Dimethyl-1-oxopropoxy)-6,9-difluoro-11,17-dihydroxy-16-methyl-pregna-1,4-diene-3,20-dioneFlumetasone PivalateLocortenFlumethasone 21-PivalateLosalen

IUPAC name

2-[(1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl]-2-oxoethyl 2,2-dimethylpropanoate 2-[(1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-14-yl]-2-oxoethyl 2,2-dimethylpropanoate

Brand Name

Locorten

Names and Identifiers

Registration numbers

PubChem CID

443980

PubChem SID

4650512116096400824894735

CAS Number

2002-29-1

MDL Number

MFCD00079287

EC Number

217-901-1

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

2.1

Solubility

0.392 mg/L

Product Information

Certificate of Analysis

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Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB00663

Drug Groups

approved

Description

Flumethasone pivalate is a moderately potent difluorinated corticosteroid ester with anti-inflammatory, antipruritic and vasoconstrictive properties. As it is a privalate salt, its anti-inflammatory action is concentrated at the site of application. This local effect on diseased areas results in a prompt decrease in inflammation, exudation and itching.

Indication

For the treatment of contact dermatitis, atopic dermatitis, exczema, psoriasis, diaper rash and other skin conditions

Pharmacology

Toxicity

Can lead to signs of irritation such as burning sensation, itching or skin rash at the site of application; hypersensitivity reactions.

Affected Organisms

Humans and other mammals

Biotransformation

Primarily hepatic

Absorption

Minimal if applied topically

Sigma Aldrich

F0891

Application
Flumethasone pivalate is a topical corticosteroid. Prompt decrease in inflammation, exudation and itching is experienced after application. It is a difluorinated corticosteroid ester with anti-inflammatory, antipruritic and vasoconstrictive properties. It is used to study adrenocortical suppression1, plasma transcortin binding, and cutaneous atrophy and telangiectasia2.
Biochem/physiol Actions
Flumethasone is a glucocorticoid receptor agonist. It binds to the nucleus causing a variety of genetic activation and repressions. The anti-inflammatory actions of flumethasone is thought to involve lipocortins and phospholipase A2 inhibitory proteins, which results in the inhibition of arachidonic acid and the control of prostaglandin and leukotriene biosynthesis. Flumethasone suppresses the immune system due to a decrease in the function of the lymphatic system, a reduction in immunoglobulin and complement concentrations, the precipitation of lymphocytopenia, and interference with antigen-antibody binding.
Flumethasone pivalate is a glucocorticoid receptor agonist used in studies on plasma transcortin binding.

TRC

F455015

An anti-inflammatory anti-itching corticosteroid found in topical creams.

Molecule Details

References

PubChem Literature

From Data Sources

• Fliri, A., et al.: J. Med. Chem., 52, 8038 (2009)

• Hoeller, S., et al.: J. Pharm. Sci., 98, 2686 (2009)

• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2009)

References

Bioactivity