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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H31ClF2O5
Molecular Weight 484.96
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HALOBETASOL PROPIONATE

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])C[C@H](F)C4=CC(=O)C=C[C@]34C

InChI

InChIKey=BDSYKGHYMJNPAB-LICBFIPMSA-N
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

HIDE SMILES / InChI

Molecular Formula C25H31ClF2O5
Molecular Weight 484.96
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Halobetasol Propionate is the propionate salt form of halobetasol, a synthetic corticosteroid with anti-inflammatory, antipruritic, and vasoconstrictor activities. Halobetasol, a topical steroid, diffuses across cell membranes to interact with cytoplasmic corticosteroid receptors located in both the dermal and intradermal cells, thereby activating gene expression of anti-inflammatory proteins mediated via corticosteroid receptor response element. Specifically, this agent induces phospholipase A2 inhibitory proteins, which inhibit the release of arachidonic acid, thereby inhibiting the biosynthesis of potent mediators of inflammation, such as prostaglandins and leukotrienes. As a result, halobetasol reduces edema, erythema, and pruritus through its cutaneous effects on vascular dilation and permeability. The initial interaction, however, is due to the drug binding to the cytosolic glucocorticoid receptor. After binding the receptor the newly formed receptor-ligand complex translocates itself into the cell nucleus, where it binds to many glucocorticoid response elements (GRE) in the promoter region of the target genes. The DNA bound receptor then interacts with basic transcription factors, causing the increase in expression of specific target genes.

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
ULTRAVATE

Cmax

ValueDoseCo-administeredAnalytePopulation
201.1 pg/mL
1.75 mg 2 times / day steady-state, topical
HALOBETASOL PROPIONATE plasma
Homo sapiens
199.7 pg/mL
1.85 mg 2 times / day steady-state, topical
HALOBETASOL PROPIONATE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1632 pg × h/mL
1.75 mg 2 times / day steady-state, topical
HALOBETASOL PROPIONATE plasma
Homo sapiens
1434.9 pg × h/mL
1.85 mg 2 times / day steady-state, topical
HALOBETASOL PROPIONATE plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Tox targets

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Apply a thin layer of Ultravate Cream ((halobetasol propionate) or Ointment to the affected skin once or twice daily
Route of Administration: Topical
In Vitro Use Guide
Unknown
Substance Class Chemical
Record UNII
91A0K1TY3Z
Record Status Validated (UNII)
Record Version