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Identification
Name Halobetasol Propionate
Accession Number DB00596 (APRD01010)
Type small molecule
Groups approved
Description

Halobetasol propionate is thought to act by the induction of phospholipase A2 inhibitory proteins, collectively called lipocortins. It is postulated that these proteins control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes by inhibiting the release of their common precursor arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A2. It is used for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
Halobetasol
Ulobetasol Propionate
Ultravate
Brand mixtures Not Available
Categories
  • Vasoconstrictor Agents
  • Anti-inflammatory Agents
CAS number 66852-54-8
Weight Average: 484.96
Monoisotopic: 484.182808219
Chemical Formula C25H31ClF2O5
InChI Key InChIKey=BDSYKGHYMJNPAB-YKQIDFLYSA-N
InChI
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
Plain Text
IUPAC Name
(1R,8S,13S,14R)-14-(2-chloroacetyl)-1,8-difluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl propanoate
SMILES
[H][C@]1(F)CC2C3C[C@H](C)[C@](OC(=O)CC)(C(=O)CCl)C3(C)CC(O)[C@]2(F)C2(C)C=CC(=O)C=C12
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes
  • Steroids and Steroid Derivatives
Substructures
  • Steroids and Steroid Derivatives
  • Carboxylic Acids and Derivatives
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Acetates
  • Alkyl Halides
  • Ethers
  • Alcohols and Polyols
  • Ketones
Pharmacology
Indication For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.
Pharmacodynamics Not Available
Mechanism of action Halobetasol propionate is thought to act by the induction of phospholipase A2 inhibitory proteins, collectively called lipocortins. It is postulated that these proteins control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes by inhibiting the release of their common precursor arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A2. 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.
Absorption The extent of percutaneous absorption of topical corticosteroids is determined by many factors including the vehicle and the integrity of the epidermal barrier. Inflammation and/or other disease processes in the skin may increase percutaneous absorption.
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Altana inc
  • G and w laboratories inc
  • Perrigo israel pharmaceuticals ltd
  • Taro pharmaceuticals usa inc
  • Ranbaxy laboratories inc
  • Actavis mid atlantic llc
  • Perrigo co
Packagers
Dosage forms
Form Route Strength
Cream Topical
Ointment Topical
Prices
Unit description Cost Unit
Ultravate 0.05% Ointment 50 gm Tube 180.27 USD tube
Ultravate 0.05% Cream 50 gm Tube 152.54 USD tube
Halobetasol Propionate 0.05% Cream 50 gm Tube 79.14 USD tube
Halobetasol Propionate 0.05% Ointment 50 gm Tube 79.14 USD tube
Ultravate 0.05% Ointment 15 gm Tube 64.78 USD tube
Ultravate 0.05% Cream 15 gm Tube 63.16 USD tube
Halobetasol Propionate 0.05% Cream 15 gm Tube 32.92 USD tube
Halobetasol Propionate 0.05% Ointment 15 gm Tube 32.92 USD tube
Ultravate 0.05% cream 4.07 USD g
Halobetasol prop 0.05% cream 1.8 USD g
Ultravate 0.05 % Cream 0.9 USD g
Ultravate pac kit 0.59 USD g
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Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
water solubility Mostly insoluble Not Available
logP 2.9 Not Available
Predicted Properties
Property Value Source
water solubility 7.57e-03 g/l ALOGPS
logP 3.81 ALOGPS
logP 3.84 ChemAxon
logS -4.8 ALOGPS
pKa (strongest acidic) 13.55 ChemAxon
pKa (strongest basic) -3.4 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 4 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 80.67 ChemAxon
rotatable bond count 5 ChemAxon
refractivity 119.15 ChemAxon
polarizability 47.93 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
PubChem Compound 48175 Link_out
PubChem Substance 46506187 Link_out
ChemSpider 43819 Link_out
Therapeutic Targets Database DAP001186 Link_out
PharmGKB PA164768832 Link_out
Drug Product Database 1962701 Link_out
RxList http://www.rxlist.com/cgi/generic3/halobetasol.htm Link_out
Drugs.com http://www.drugs.com/cdi/halobetasol-cream.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/ult1649.shtml Link_out
ATC Codes
  • D07AC21
AHFS Codes
  • 84:06.00
PDB Entries Not Available
FDA label show (399 KB)
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Glucocorticoid receptor

Pharmacological action: yes
Actions: agonist

Receptor for glucocorticoids (GC). Has a dual mode of action:as a transcription factor that binds to glucocorticoid response elements (GRE) and as a modulator of other transcription factors. Affects inflammatory responses, cellular proliferation and differentiation in target tissues. Could act as a coactivator for STAT5-dependent transcription upon growth hormone (GH) stimulation and could reveal an essential role of hepatic GR in the control of body growth

Organism class: human
UniProt ID: P04150 Link_out
Gene: NR3C1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Mohandas S, Rai R, Srinivas CR: Halobetasol versus clobetasol: a study of potency. Indian J Dermatol Venereol Leprol. 2009 Mar-Apr;75(2):186-7. Pubmed
  2. Hofmann TG, Hehner SP, Bacher S, Droge W, Schmitz ML: Various glucocorticoids differ in their ability to induce gene expression, apoptosis and to repress NF-kappaB-dependent transcription. FEBS Lett. 1998 Dec 28;441(3):441-6. Pubmed
Carriers

1. Corticosteroid-binding globulin

Major transport protein for glucocorticoids and progestins in the blood of almost all vertebrate species

UniProt ID: P08185 Link_out
Gene: SERPINA6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19