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Identification
NameHalobetasol Propionate
Accession NumberDB00596  (APRD01010)
Typesmall molecule
Groupsapproved
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
Synonyms
SynonymLanguageCode
MiracortenNot AvailableIS
UlobetasolNot AvailableINN
UlobétasolFrenchINN
UlobetasolumLatinINN
SaltsNot Available
Brand names
NameCompany
HalobetasolFougera
HalovateGlenmark
HobsAamorb
UltravateRanbaxy
Brand mixtures
Brand NameIngredients
Halovate-SUlobetasol and Salicylic Acid
Hobs-SUlobetasol and Salicylic Acid
CategoriesNot Available
CAS number66852-54-8
WeightAverage: 484.96
Monoisotopic: 484.182808219
Chemical FormulaC25H31ClF2O5
InChI KeyInChIKey=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
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassSteroids and Steroid Derivatives
SubclassGluco/mineralocorticoids, Progestogins and Derivatives
Direct parentGluco/mineralocorticoids, Progestogins and Derivatives
Alternative parentsSteroid Esters; Halogenated Steroids; Hydroxysteroids; Ketosteroids; Iridoids and Derivatives; Cyclohexanols; Carboxylic Acid Esters; Ketones; Fluorohydrins; Cyclic Alcohols and Derivatives; Ethers; Polyamines; Enolates; Organofluorides; Organochlorides; Alkyl Fluorides; Alkyl Chlorides
Substituents11-hydroxy-steroid; 20-keto-steroid; 9-halo-steroid; 6-halo-steroid; 3-keto-steroid; monoterpene; 11-noriridane monoterpene; cyclohexanol; cyclic alcohol; secondary alcohol; halohydrin; ketone; fluorohydrin; carboxylic acid ester; ether; polyamine; enolate; carboxylic acid derivative; organochloride; organohalogen; organofluoride; alcohol; carbonyl group; alkyl halide; alkyl fluoride; alkyl chloride
Classification descriptionThis compound belongs to the gluco/mineralocorticoids, progestogins and derivatives. These are steroids whose structure is based on an hydroxylated prostane moiety.
Pharmacology
IndicationFor the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.
PharmacodynamicsNot Available
Mechanism of actionHalobetasol 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.
AbsorptionThe 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 distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9974
Blood Brain Barrier + 0.9789
Caco-2 permeable + 0.5865
P-glycoprotein substrate Substrate 0.7448
P-glycoprotein inhibitor I Inhibitor 0.6948
P-glycoprotein inhibitor II Non-inhibitor 0.8943
Renal organic cation transporter Non-inhibitor 0.857
CYP450 2C9 substrate Non-substrate 0.8553
CYP450 2D6 substrate Non-substrate 0.9136
CYP450 3A4 substrate Substrate 0.7689
CYP450 1A2 substrate Non-inhibitor 0.9093
CYP450 2C9 substrate Non-inhibitor 0.885
CYP450 2D6 substrate Non-inhibitor 0.7394
CYP450 2C19 substrate Non-inhibitor 0.8972
CYP450 3A4 substrate Inhibitor 0.8309
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8771
Ames test Non AMES toxic 0.8762
Carcinogenicity Non-carcinogens 0.8902
Biodegradation Not ready biodegradable 1.0
Rat acute toxicity 2.3204 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9723
hERG inhibition (predictor II) Non-inhibitor 0.6521
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
FormRouteStrength
CreamTopical
OintmentTopical
Prices
Unit descriptionCostUnit
Ultravate 0.05% Ointment 50 gm Tube180.27USDtube
Ultravate 0.05% Cream 50 gm Tube152.54USDtube
Halobetasol Propionate 0.05% Cream 50 gm Tube79.14USDtube
Halobetasol Propionate 0.05% Ointment 50 gm Tube79.14USDtube
Ultravate 0.05% Ointment 15 gm Tube64.78USDtube
Ultravate 0.05% Cream 15 gm Tube63.16USDtube
Halobetasol Propionate 0.05% Cream 15 gm Tube32.92USDtube
Halobetasol Propionate 0.05% Ointment 15 gm Tube32.92USDtube
Ultravate 0.05% cream4.07USDg
Halobetasol prop 0.05% cream1.8USDg
Ultravate 0.05 % Cream0.9USDg
Ultravate pac kit0.59USDg
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
water solubilityMostly insolubleNot Available
logP2.9Not Available
Predicted Properties
PropertyValueSource
water solubility7.57e-03 g/lALOGPS
logP3.81ALOGPS
logP3.84ChemAxon
logS-4.8ALOGPS
pKa (strongest acidic)13.55ChemAxon
pKa (strongest basic)-3.4ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count1ChemAxon
polar surface area80.67ChemAxon
rotatable bond count5ChemAxon
refractivity119.15ChemAxon
polarizability47.93ChemAxon
number of rings4ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Daniella Gutman, Shimon Chernyak, “Process for preparing a crystalline form of halobetasol propionate.” U.S. Patent US20070167420, issued July 19, 2007.

US20070167420
General ReferenceNot Available
External Links
ResourceLink
PubChem Compound48175
PubChem Substance46506187
ChemSpider43819
Therapeutic Targets DatabaseDAP001186
PharmGKBPA164768832
Drug Product Database1962701
RxListhttp://www.rxlist.com/cgi/generic3/halobetasol.htm
Drugs.comhttp://www.drugs.com/cdi/halobetasol-cream.html
PDRhealthhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/ult1649.shtml
ATC CodesD07AC21
AHFS Codes
  • 84:06.00
PDB EntriesNot Available
FDA labelshow(399 KB)
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. Glucocorticoid receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Glucocorticoid receptor P04150 Details

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

1. Corticosteroid-binding globulin

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Corticosteroid-binding globulin P08185 Details

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 13, 2014 10:44