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
SMILES
C[C@H]1C[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@]2(C)[C@@]1(O)C(=O)CCl
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
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 |
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 Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P04150 Gene ID: 2908.0 Gene Symbol: NR3C1 Target Organism: Homo sapiens (Human) Sources: https://www.genome.jp/dbget-bin/www_bget?dr:D04409 |
|||
Target ID: CHEMBL2034 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19293512 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | ULTRAVATE Approved UseUltravate 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 Date1990 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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) Sources: Skin atrophy (4 patients) Burning sensation (10 patients) Application site atrophy (2 patients) Headache (2 patients) |
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 |
Other AEs: Dermatitis contact, Skin atrophy... Other AEs: Dermatitis contact (7.4%) Sources: 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%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
PubMed
Title | Date | PubMed |
---|---|---|
Halobetasol propionate-loaded solid lipid nanoparticles (SLN) for skin targeting by topical delivery. | 2014 Jun |
|
Impurity profiling and a stability-indicating UPLC method development and validation for the estimation of related impurities of halobetasol propionate in halobetasol propionate 0.05% (w/w) cream. | 2015 Jan |
Patents
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:32:22 GMT 2025
by
admin
on
Mon Mar 31 18:32:22 GMT 2025
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Record UNII |
9P6159HM7T
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C521
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NDF-RT |
N0000175450
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WHO-VATC |
QD07AC21
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NDF-RT |
N0000175576
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WHO-ATC |
D07AC21
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Code System | Code | Type | Description | ||
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Halobetasol
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DTXSID60243759
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C064466
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5311167
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DB00596
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SUB11379MIG
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CHEMBL1200908
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5829
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9P6159HM7T
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98651-66-2
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Halobetasol
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9P6159HM7T
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100000076641
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41208
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C61781
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
Related Record | Type | Details | ||
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ACTIVE MOIETY |