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
[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
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 |
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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 |
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Target ID: CHEMBL2034 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19293512 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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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 |
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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 |
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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 |
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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) 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 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%) 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 |
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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: |
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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
Created by
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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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ACTIVE MOIETY