U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H27ClF2O4
Molecular Weight 428.897
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HALOBETASOL

SMILES

[H][C@@]12C[C@H](C)[C@](O)(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=LEHFPXVYPMWYQD-XHIJKXOTSA-N
InChI=1S/C22H27ClF2O4/c1-11-6-13-14-8-16(24)15-7-12(26)4-5-19(15,2)21(14,25)17(27)9-20(13,3)22(11,29)18(28)10-23/h4-5,7,11,13-14,16-17,27,29H,6,8-10H2,1-3H3/t11-,13-,14-,16-,17-,19-,20-,21-,22-/m0/s1

HIDE SMILES / InChI

Molecular Formula C22H27ClF2O4
Molecular Weight 428.897
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 (median)
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)
n = 277
Health Status: unhealthy
Condition: plaque psoriasis
Age Group: 51 years (range: 18-86 years)
Sex: M+F
Population Size: 277
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
Co-administed with::
tazarotene(0.045%; 1/day)
Sources:
unhealthy, adult
n = 270
Health Status: unhealthy
Condition: plaque psoriasis
Age Group: adult
Sex: M+F
Population Size: 270
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 (median)
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)
n = 277
Health Status: unhealthy
Condition: plaque psoriasis
Age Group: 51 years (range: 18-86 years)
Sex: M+F
Population Size: 277
Sources:
Application site atrophy 2 patients
2 g 2 times / day multiple, topical (median)
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)
n = 277
Health Status: unhealthy
Condition: plaque psoriasis
Age Group: 51 years (range: 18-86 years)
Sex: M+F
Population Size: 277
Sources:
Headache 2 patients
2 g 2 times / day multiple, topical (median)
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)
n = 277
Health Status: unhealthy
Condition: plaque psoriasis
Age Group: 51 years (range: 18-86 years)
Sex: M+F
Population Size: 277
Sources:
Telangiectasia 3 patients
2 g 2 times / day multiple, topical (median)
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)
n = 277
Health Status: unhealthy
Condition: plaque psoriasis
Age Group: 51 years (range: 18-86 years)
Sex: M+F
Population Size: 277
Sources:
Skin atrophy 4 patients
2 g 2 times / day multiple, topical (median)
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)
n = 277
Health Status: unhealthy
Condition: plaque psoriasis
Age Group: 51 years (range: 18-86 years)
Sex: M+F
Population Size: 277
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
Co-administed with::
tazarotene(0.045%; 1/day)
Sources:
unhealthy, adult
n = 270
Health Status: unhealthy
Condition: plaque psoriasis
Age Group: adult
Sex: M+F
Population Size: 270
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
Co-administed with::
tazarotene(0.045%; 1/day)
Sources:
unhealthy, adult
n = 270
Health Status: unhealthy
Condition: plaque psoriasis
Age Group: adult
Sex: M+F
Population Size: 270
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
Co-administed with::
tazarotene(0.045%; 1/day)
Sources:
unhealthy, adult
n = 270
Health Status: unhealthy
Condition: plaque psoriasis
Age Group: adult
Sex: M+F
Population Size: 270
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
Co-administed with::
tazarotene(0.045%; 1/day)
Sources:
unhealthy, adult
n = 270
Health Status: unhealthy
Condition: plaque psoriasis
Age Group: adult
Sex: M+F
Population Size: 270
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
Co-administed with::
tazarotene(0.045%; 1/day)
Sources:
unhealthy, adult
n = 270
Health Status: unhealthy
Condition: plaque psoriasis
Age Group: adult
Sex: M+F
Population Size: 270
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
Co-administed with::
tazarotene(0.045%; 1/day)
Sources:
unhealthy, adult
n = 270
Health Status: unhealthy
Condition: plaque psoriasis
Age Group: adult
Sex: M+F
Population Size: 270
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
Co-administed with::
tazarotene(0.045%; 1/day)
Sources:
unhealthy, adult
n = 270
Health Status: unhealthy
Condition: plaque psoriasis
Age Group: adult
Sex: M+F
Population Size: 270
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
Co-administed with::
tazarotene(0.045%; 1/day)
Sources:
unhealthy, adult
n = 270
Health Status: unhealthy
Condition: plaque psoriasis
Age Group: adult
Sex: M+F
Population Size: 270
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
Co-administed with::
tazarotene(0.045%; 1/day)
Sources:
unhealthy, adult
n = 270
Health Status: unhealthy
Condition: plaque psoriasis
Age Group: adult
Sex: M+F
Population Size: 270
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Tox targets

Tox targets

PubMed

PubMed

TitleDatePubMed
Halobetasol propionate-loaded solid lipid nanoparticles (SLN) for skin targeting by topical delivery.
2014 Jun
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 Fri Dec 15 16:36:23 GMT 2023
Edited
by admin
on Fri Dec 15 16:36:23 GMT 2023
Record UNII
9P6159HM7T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HALOBETASOL
VANDF  
Common Name English
21-CHLORO-6.ALPHA.,9-DIFLUORO-11.BETA.,17-DIHYDROXY-16.BETA.-METHYLPREGNA-1,4-DIENE-3,20-DIONE
Systematic Name English
IDP-122
Code English
ulobetasol [INN]
Common Name English
HALOBETASOL [VANDF]
Common Name English
Ulobetasol [WHO-DD]
Common Name English
HALOBETASOL PROPIONATE IMPURITY, 21-CHLORO DIFLORASONE- [USP IMPURITY]
Common Name English
ULOBETASOL
INN   WHO-DD  
INN  
Official Name English
21-CHLORO DIFLORASONE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C521
Created by admin on Fri Dec 15 16:36:23 GMT 2023 , Edited by admin on Fri Dec 15 16:36:23 GMT 2023
NDF-RT N0000175450
Created by admin on Fri Dec 15 16:36:23 GMT 2023 , Edited by admin on Fri Dec 15 16:36:23 GMT 2023
WHO-VATC QD07AC21
Created by admin on Fri Dec 15 16:36:23 GMT 2023 , Edited by admin on Fri Dec 15 16:36:23 GMT 2023
NDF-RT N0000175576
Created by admin on Fri Dec 15 16:36:23 GMT 2023 , Edited by admin on Fri Dec 15 16:36:23 GMT 2023
WHO-ATC D07AC21
Created by admin on Fri Dec 15 16:36:23 GMT 2023 , Edited by admin on Fri Dec 15 16:36:23 GMT 2023
Code System Code Type Description
WIKIPEDIA
Halobetasol
Created by admin on Fri Dec 15 16:36:23 GMT 2023 , Edited by admin on Fri Dec 15 16:36:23 GMT 2023
PRIMARY
EPA CompTox
DTXSID60243759
Created by admin on Fri Dec 15 16:36:23 GMT 2023 , Edited by admin on Fri Dec 15 16:36:23 GMT 2023
PRIMARY
MESH
C064466
Created by admin on Fri Dec 15 16:36:23 GMT 2023 , Edited by admin on Fri Dec 15 16:36:23 GMT 2023
PRIMARY
PUBCHEM
5311167
Created by admin on Fri Dec 15 16:36:23 GMT 2023 , Edited by admin on Fri Dec 15 16:36:23 GMT 2023
PRIMARY
DRUG BANK
DB00596
Created by admin on Fri Dec 15 16:36:23 GMT 2023 , Edited by admin on Fri Dec 15 16:36:23 GMT 2023
PRIMARY
EVMPD
SUB11379MIG
Created by admin on Fri Dec 15 16:36:23 GMT 2023 , Edited by admin on Fri Dec 15 16:36:23 GMT 2023
PRIMARY
ChEMBL
CHEMBL1200908
Created by admin on Fri Dec 15 16:36:23 GMT 2023 , Edited by admin on Fri Dec 15 16:36:23 GMT 2023
PRIMARY
INN
5829
Created by admin on Fri Dec 15 16:36:23 GMT 2023 , Edited by admin on Fri Dec 15 16:36:23 GMT 2023
PRIMARY
FDA UNII
9P6159HM7T
Created by admin on Fri Dec 15 16:36:23 GMT 2023 , Edited by admin on Fri Dec 15 16:36:23 GMT 2023
PRIMARY
CAS
98651-66-2
Created by admin on Fri Dec 15 16:36:23 GMT 2023 , Edited by admin on Fri Dec 15 16:36:23 GMT 2023
PRIMARY
LACTMED
Halobetasol
Created by admin on Fri Dec 15 16:36:23 GMT 2023 , Edited by admin on Fri Dec 15 16:36:23 GMT 2023
PRIMARY
DAILYMED
9P6159HM7T
Created by admin on Fri Dec 15 16:36:23 GMT 2023 , Edited by admin on Fri Dec 15 16:36:23 GMT 2023
PRIMARY
SMS_ID
100000076641
Created by admin on Fri Dec 15 16:36:23 GMT 2023 , Edited by admin on Fri Dec 15 16:36:23 GMT 2023
PRIMARY
RXCUI
41208
Created by admin on Fri Dec 15 16:36:23 GMT 2023 , Edited by admin on Fri Dec 15 16:36:23 GMT 2023
PRIMARY RxNorm
NCI_THESAURUS
C61781
Created by admin on Fri Dec 15 16:36:23 GMT 2023 , Edited by admin on Fri Dec 15 16:36:23 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY