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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

CCC(=O)O[C@@]1([C@@H](C)C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]12C)C(=O)CCl

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
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including

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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P04150
Gene ID: 2908.0
Gene Symbol: NR3C1
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
ULTRAVATE

Approved Use

Ultravate is a super-high potency corticosteroid indicated for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses. Treatment beyond two consecutive weeks is not recommended, and the total dosage should not exceed 50 g/week because of the potential for the drug to suppress the hypothalamic-pituitary-adrenal (HPA) axis. Use in children under 12 years of age is not recommended. As with other highly active corticosteroids, therapy should be discontinued when control has been achieved. If no improvement is seen within 2 weeks, reassessment of the diagnosis may be necessary.

Launch Date

1990
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
201.1 pg/mL
1.75 mg 2 times / day steady-state, topical
dose: 1.75 mg
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
HALOBETASOL PROPIONATE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
199.7 pg/mL
1.85 mg 2 times / day steady-state, topical
dose: 1.85 mg
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
HALOBETASOL PROPIONATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1632 pg × h/mL
1.75 mg 2 times / day steady-state, topical
dose: 1.75 mg
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
HALOBETASOL PROPIONATE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1434.9 pg × h/mL
1.85 mg 2 times / day steady-state, topical
dose: 1.85 mg
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
HALOBETASOL PROPIONATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
2 g 2 times / day multiple, topical
Recommended
Dose: 2 g, 2 times / day
Route: topical
Route: multiple
Dose: 2 g, 2 times / day
Sources:
unhealthy, 51 years (range: 18-86 years)
Health Status: unhealthy
Age Group: 51 years (range: 18-86 years)
Sex: M+F
Sources:
Other AEs: Telangiectasia, Skin atrophy...
Other AEs:
Telangiectasia (3 patients)
Skin atrophy (4 patients)
Burning sensation (10 patients)
Application site atrophy (2 patients)
Headache (2 patients)
Sources:
0.01 % 1 times / day multiple, topical
Recommended
Dose: 0.01 %, 1 times / day
Route: topical
Route: multiple
Dose: 0.01 %, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Other AEs: Dermatitis contact, Skin atrophy...
Other AEs:
Dermatitis contact (7.4%)
Skin atrophy (1.9%)
Rash (1.5%)
Upper respiratory tract infection (1.9%)
Folliculitis (1.9%)
Sinusitis (1.1%)
Excoriation (1.9%)
Skin abrasion (1.1%)
Application site pain (2.6%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Burning sensation 10 patients
2 g 2 times / day multiple, topical
Recommended
Dose: 2 g, 2 times / day
Route: topical
Route: multiple
Dose: 2 g, 2 times / day
Sources:
unhealthy, 51 years (range: 18-86 years)
Health Status: unhealthy
Age Group: 51 years (range: 18-86 years)
Sex: M+F
Sources:
Application site atrophy 2 patients
2 g 2 times / day multiple, topical
Recommended
Dose: 2 g, 2 times / day
Route: topical
Route: multiple
Dose: 2 g, 2 times / day
Sources:
unhealthy, 51 years (range: 18-86 years)
Health Status: unhealthy
Age Group: 51 years (range: 18-86 years)
Sex: M+F
Sources:
Headache 2 patients
2 g 2 times / day multiple, topical
Recommended
Dose: 2 g, 2 times / day
Route: topical
Route: multiple
Dose: 2 g, 2 times / day
Sources:
unhealthy, 51 years (range: 18-86 years)
Health Status: unhealthy
Age Group: 51 years (range: 18-86 years)
Sex: M+F
Sources:
Telangiectasia 3 patients
2 g 2 times / day multiple, topical
Recommended
Dose: 2 g, 2 times / day
Route: topical
Route: multiple
Dose: 2 g, 2 times / day
Sources:
unhealthy, 51 years (range: 18-86 years)
Health Status: unhealthy
Age Group: 51 years (range: 18-86 years)
Sex: M+F
Sources:
Skin atrophy 4 patients
2 g 2 times / day multiple, topical
Recommended
Dose: 2 g, 2 times / day
Route: topical
Route: multiple
Dose: 2 g, 2 times / day
Sources:
unhealthy, 51 years (range: 18-86 years)
Health Status: unhealthy
Age Group: 51 years (range: 18-86 years)
Sex: M+F
Sources:
Sinusitis 1.1%
0.01 % 1 times / day multiple, topical
Recommended
Dose: 0.01 %, 1 times / day
Route: topical
Route: multiple
Dose: 0.01 %, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Skin abrasion 1.1%
0.01 % 1 times / day multiple, topical
Recommended
Dose: 0.01 %, 1 times / day
Route: topical
Route: multiple
Dose: 0.01 %, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Rash 1.5%
0.01 % 1 times / day multiple, topical
Recommended
Dose: 0.01 %, 1 times / day
Route: topical
Route: multiple
Dose: 0.01 %, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Excoriation 1.9%
0.01 % 1 times / day multiple, topical
Recommended
Dose: 0.01 %, 1 times / day
Route: topical
Route: multiple
Dose: 0.01 %, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Folliculitis 1.9%
0.01 % 1 times / day multiple, topical
Recommended
Dose: 0.01 %, 1 times / day
Route: topical
Route: multiple
Dose: 0.01 %, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Skin atrophy 1.9%
0.01 % 1 times / day multiple, topical
Recommended
Dose: 0.01 %, 1 times / day
Route: topical
Route: multiple
Dose: 0.01 %, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Upper respiratory tract infection 1.9%
0.01 % 1 times / day multiple, topical
Recommended
Dose: 0.01 %, 1 times / day
Route: topical
Route: multiple
Dose: 0.01 %, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Application site pain 2.6%
0.01 % 1 times / day multiple, topical
Recommended
Dose: 0.01 %, 1 times / day
Route: topical
Route: multiple
Dose: 0.01 %, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Dermatitis contact 7.4%
0.01 % 1 times / day multiple, topical
Recommended
Dose: 0.01 %, 1 times / day
Route: topical
Route: multiple
Dose: 0.01 %, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Tox targets

Tox targets

PubMed

PubMed

TitleDatePubMed
Patents

Patents

Sample Use Guides

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
Created
by admin
on Mon Mar 31 18:01:17 GMT 2025
Edited
by admin
on Mon Mar 31 18:01:17 GMT 2025
Record UNII
91A0K1TY3Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ULOBETASOL PROPIONATE
MART.   WHO-DD  
Preferred Name English
HALOBETASOL PROPIONATE
MI   ORANGE BOOK   USAN   USP-RS   VANDF  
USAN  
Official Name English
DUOBRII COMPONENT HALOBETASOL PROPIONATE
Brand Name English
ULTRAVATE
Brand Name English
ULOBETASOL PROPIONATE [MART.]
Common Name English
CGP-14458
Code English
HALOBETASOL PROPIONATE [USAN]
Common Name English
HALOBETASOL PROPIONATE [USP MONOGRAPH]
Common Name English
Ulobetasol propionate [WHO-DD]
Common Name English
CGP-14,458
Code English
IDP-118 COMPONENT HALOBETASOL PROPIONATE
Common Name English
JEMDEL
Brand Name English
PREGNA-1,4-DIENE-3,20-DIONE, 21-CHLORO-6,9-DIFLUORO-11-HYDROXY-16-METHYL-17-(1-OXOPROPOXY)-, (6.ALPHA.,11.BETA.,16.BETA.)-
Systematic Name English
HALOBETASOL PROPIONATE [USP-RS]
Common Name English
HALOBETASOL PROPIONATE [ORANGE BOOK]
Common Name English
HALOBETASOL PROPIONATE [VANDF]
Common Name English
BMY-30056
Code English
BRYHALI
Brand Name English
HALOBETASOL PROPIONATE [MI]
Common Name English
21-Chloro-6?,9-difluoro-11?,17-dihydroxy-16?-methylpregna-1,4-diene-3,20-dione 17-propionate
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C521
Created by admin on Mon Mar 31 18:01:17 GMT 2025 , Edited by admin on Mon Mar 31 18:01:17 GMT 2025
Code System Code Type Description
MERCK INDEX
m5899
Created by admin on Mon Mar 31 18:01:17 GMT 2025 , Edited by admin on Mon Mar 31 18:01:17 GMT 2025
PRIMARY Merck Index
DRUG CENTRAL
1349
Created by admin on Mon Mar 31 18:01:17 GMT 2025 , Edited by admin on Mon Mar 31 18:01:17 GMT 2025
PRIMARY
WIKIPEDIA
Ulobetasol propionate
Created by admin on Mon Mar 31 18:01:17 GMT 2025 , Edited by admin on Mon Mar 31 18:01:17 GMT 2025
PRIMARY
RS_ITEM_NUM
1302906
Created by admin on Mon Mar 31 18:01:17 GMT 2025 , Edited by admin on Mon Mar 31 18:01:17 GMT 2025
PRIMARY
SMS_ID
100000084781
Created by admin on Mon Mar 31 18:01:17 GMT 2025 , Edited by admin on Mon Mar 31 18:01:17 GMT 2025
PRIMARY
DAILYMED
91A0K1TY3Z
Created by admin on Mon Mar 31 18:01:17 GMT 2025 , Edited by admin on Mon Mar 31 18:01:17 GMT 2025
PRIMARY
CAS
66852-54-8
Created by admin on Mon Mar 31 18:01:17 GMT 2025 , Edited by admin on Mon Mar 31 18:01:17 GMT 2025
PRIMARY
DRUG BANK
DB00596
Created by admin on Mon Mar 31 18:01:17 GMT 2025 , Edited by admin on Mon Mar 31 18:01:17 GMT 2025
PRIMARY
ChEMBL
CHEMBL1200908
Created by admin on Mon Mar 31 18:01:17 GMT 2025 , Edited by admin on Mon Mar 31 18:01:17 GMT 2025
PRIMARY
USAN
BB-2
Created by admin on Mon Mar 31 18:01:17 GMT 2025 , Edited by admin on Mon Mar 31 18:01:17 GMT 2025
PRIMARY
EVMPD
SUB05030MIG
Created by admin on Mon Mar 31 18:01:17 GMT 2025 , Edited by admin on Mon Mar 31 18:01:17 GMT 2025
PRIMARY
PUBCHEM
6918178
Created by admin on Mon Mar 31 18:01:17 GMT 2025 , Edited by admin on Mon Mar 31 18:01:17 GMT 2025
PRIMARY
EPA CompTox
DTXSID6046636
Created by admin on Mon Mar 31 18:01:17 GMT 2025 , Edited by admin on Mon Mar 31 18:01:17 GMT 2025
PRIMARY
FDA UNII
91A0K1TY3Z
Created by admin on Mon Mar 31 18:01:17 GMT 2025 , Edited by admin on Mon Mar 31 18:01:17 GMT 2025
PRIMARY
NCI_THESAURUS
C47553
Created by admin on Mon Mar 31 18:01:17 GMT 2025 , Edited by admin on Mon Mar 31 18:01:17 GMT 2025
PRIMARY
RXCUI
45318
Created by admin on Mon Mar 31 18:01:17 GMT 2025 , Edited by admin on Mon Mar 31 18:01:17 GMT 2025
PRIMARY RxNorm
Related Record Type Details
TARGET -> AGONIST
Halobetasol propionate is thought to act by the induction of phospholipase A2 inhibitory proteins, collectively called lipocortins.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.
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY