CAS 66852-54-8|Ultravate|halobetasol propionate|(1R,8S,13S,14R)-14-(2-chloroacetyl)-1,8-difluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl propano...

General Information

Structure

Molecular Formula

C₂₅H₃₁ClF₂O₅

Molecular Mass

484.9604464

Exact Mass

484.18280821

Charge

InChI

InChI=1S/C25H31ClF2O5/c1-5-21(32)33-25(20(31)12-26)13(2)8-15-16-10-18(27)17-9-14(29)6-7-22(17,3)24(16,28)19(30)11-23(15,25)4/h6-7,9,13,15-16,18-19,30H,5,8,10-12H2,1-4H3/t13-,15?,16?,18-,19?,22?,23?,24-,25-/m0/s1

InChIKey

BDSYKGHYMJNPAB-YKQIDFLYSA-N

Canonic Smiles

CCC(=O)O[C@@]1([C@@H](C)CC2C1(C)CC(O)[C@]1(C2C[C@@H](C2=CC(=O)C=CC12C)F)F)C(=O)CCl

Isomeric Smiles

ClCC(=O)[C@]1(OC(=O)CC)C2(C(C3[C@](F)(C(O)C2)C2(C(=CC(=O)C=C2)[C@@H](F)C3)C)C[C@@H]1C)C

Calculated Properties

JChem

Acid pKa

13.545719

H Acceptors

H Donor

LogD (pH = 5.5)

3.8381035

LogD (pH = 7.4)

3.8381033

Log P

3.8381035

Molar Refractivity

119.1457

Polarizability

46.300114

Polar Surface Area

80.67

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

3.81

LOG S

-4.81

Solubility (Water)

7.57e-03 g/l

Data Source

Academic Data

Data Source

Names and Identifiers

Brand Name

UltravateUlobetasol PropionateHalobetasol

IUPAC Traditional name

halobetasol propionate

IUPAC name

(1R,8S,13S,14R)-14-(2-chloroacetyl)-1,8-difluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl propanoate

Synonyms

Halobetasol Propionate

Names and Identifiers

Registration numbers

CAS Number

66852-54-8

PubChem CID

48175

PubChem SID

46506187160963941

Registration numbers

Properties

Physical Property

Solubility

Mostly insoluble

Hydrophobicity(logP)

2.9

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB00596

Drug Groups

approved

Description

Halobetasol propionate is 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. It is used for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.

Indication

For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.

Affected Organisms

Humans and other mammals

Absorption

The extent of percutaneous absorption of topical corticosteroids is determined by many factors including the vehicle and the integrity of the epidermal barrier. Inflammation and/or other disease processes in the skin may increase percutaneous absorption.

External Links

• [RxList]

• [PDRhealth]

• [Drugs.com]

Molecule Details

References

PubChem Literature

No Data Available

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References

Bioactivity

PubChem BioAssay