You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameUlobetasol
Accession NumberDB00596  (APRD01010)
TypeSmall Molecule
GroupsApproved
Description

Ulobetasol (as ulobetasol 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
21-chloro diflorasone
Halobetasol
Ulobetasol
Ulobétasol
Ulobetasolum
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ultravatelotion.5 mg/gtopicalRanbaxy Laboratories, Inc.2016-03-01Not applicableUs
Ultravateointment.5 mg/gtopicalRanbaxy Laboratories Inc.2009-02-20Not applicableUs
Ultravatecream.5 mg/gtopicalRanbaxy Laboratories Inc.2009-03-16Not applicableUs
Ultravate Creamcream0.05 %topicalValeant Canada Lp Valeant Canada S.E.C.1993-12-31Not applicableCanada
Ultravate Ointment 0.05%ointment0.05 %topicalValeant Canada Lp Valeant Canada S.E.C.1993-12-31Not applicableCanada
Ultravate Pacointment.5 mg/gtopicalRanbaxy Laboratories Inc.2008-05-13Not applicableUs
Ultravate Pac-creamcream.5 mg/gtopicalRanbaxy Laboratories Inc.2010-02-10Not applicableUs
Ultravate XkitRanbaxy Laboratories Inc.2012-07-09Not applicableUs
Ultravate XkitRanbaxy Laboratories Inc.2012-07-01Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Halobetasol Propionateointment.5 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.2004-12-16Not applicableUs
Halobetasol Propionatecream.5 mg/gtopicalE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.2004-12-16Not applicableUs
Halobetasol Propionatecream.5 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.2005-08-04Not applicableUs
Halobetasol Propionateointment.5 mg/gtopicalPerrigo New York Inc2009-02-05Not applicableUs
Halobetasol Propionatecream.5 mg/gtopicalPerrigo New York Inc2008-08-04Not applicableUs
Halobetasol Propionatecream.5 mg/gtopicalRebel Distributors Corp2007-07-16Not applicableUs
Halobetasol Propionateointment.5 mg/gtopicalPhysicians Total Care, Inc.2005-12-05Not applicableUs
Halobetasol Propionatecream.5 mg/gtopicalG&W Laboratories, Inc.2007-07-16Not applicableUs
Halobetasol Propionatecream.5 mg/gtopicalPhysicians Total Care, Inc.2005-05-25Not applicableUs
Halobetasol Propionateointment.5 mg/gtopicalG&W Laboratories, Inc.2007-04-27Not applicableUs
Halobetasol Propionateointment.5 mg/gtopicalH.J. Harkins Company, Inc.2009-02-05Not applicableUs
Halobetasol Propionateointment.5 mg/gtopicalE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.2004-12-16Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
HalobetasolFougera
HalovateGlenmark
HobsAamorb
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Ulobetasol propionate
66852-54-8
Thumb
  • InChI Key: BDSYKGHYMJNPAB-LICBFIPMSA-N
  • Monoisotopic Mass: 484.1828081
  • Average Mass: 484.96
DBSALT001867
Categories
UNII9P6159HM7T
CAS number98651-66-2
WeightAverage: 428.9
Monoisotopic: 428.1565934
Chemical FormulaC22H27ClF2O4
InChI KeyLEHFPXVYPMWYQD-XHIJKXOTSA-N
InChI
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
IUPAC Name
(1R,2S,8S,10S,11S,13S,14R,15S,17S)-14-(2-chloroacetyl)-1,8-difluoro-14,17-dihydroxy-2,13,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one
SMILES
[H][C@@]12C[[email protected]](C)[C@](O)(C(=O)CCl)[C@@]1(C)C[[email protected]](O)[C@@]1(F)[C@@]2([H])C[[email protected]](F)C2=CC(=O)C=C[C@]12C
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPregnane steroids
Direct ParentGluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 20-oxosteroid
  • 3-oxo-delta-1,4-steroid
  • 3-oxosteroid
  • 9-halo-steroid
  • 6-halo-steroid
  • 17-hydroxysteroid
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • Halo-steroid
  • Hydroxysteroid
  • Oxosteroid
  • Delta-1,4-steroid
  • Alpha-haloketone
  • Alpha-chloroketone
  • Alpha-hydroxy ketone
  • Cyclic alcohol
  • Tertiary alcohol
  • Secondary alcohol
  • Halohydrin
  • Ketone
  • Cyclic ketone
  • Fluorohydrin
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Alkyl halide
  • Alkyl fluoride
  • Alkyl chloride
  • Organohalogen compound
  • Organochloride
  • Organofluoride
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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.
Related Articles
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
MetabolismNot Available
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
PropertyValueProbability
Human Intestinal Absorption+0.9974
Blood Brain Barrier+0.9789
Caco-2 permeable+0.5865
P-glycoprotein substrateSubstrate0.7448
P-glycoprotein inhibitor IInhibitor0.6948
P-glycoprotein inhibitor IINon-inhibitor0.8943
Renal organic cation transporterNon-inhibitor0.857
CYP450 2C9 substrateNon-substrate0.8553
CYP450 2D6 substrateNon-substrate0.9136
CYP450 3A4 substrateSubstrate0.7689
CYP450 1A2 substrateNon-inhibitor0.9093
CYP450 2C9 inhibitorNon-inhibitor0.885
CYP450 2D6 inhibitorNon-inhibitor0.7394
CYP450 2C19 inhibitorNon-inhibitor0.8972
CYP450 3A4 inhibitorInhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8771
Ames testNon AMES toxic0.8762
CarcinogenicityNon-carcinogens0.8902
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.3204 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9723
hERG inhibition (predictor II)Non-inhibitor0.6521
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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.5 mg/g
Ointmenttopical.5 mg/g
Lotiontopical.5 mg/g
Creamtopical0.05 %
Ointmenttopical0.05 %
Kit
Prices
Unit descriptionCostUnit
Ultravate 0.05% Ointment 50 gm Tube180.27USD tube
Ultravate 0.05% Cream 50 gm Tube152.54USD tube
Halobetasol Propionate 0.05% Cream 50 gm Tube79.14USD tube
Halobetasol Propionate 0.05% Ointment 50 gm Tube79.14USD tube
Ultravate 0.05% Ointment 15 gm Tube64.78USD tube
Ultravate 0.05% Cream 15 gm Tube63.16USD tube
Halobetasol Propionate 0.05% Cream 15 gm Tube32.92USD tube
Halobetasol Propionate 0.05% Ointment 15 gm Tube32.92USD tube
Ultravate 0.05% cream4.07USD g
Halobetasol prop 0.05% cream1.8USD g
Ultravate 0.05 % Cream0.9USD g
Ultravate pac kit0.59USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US8962028 No2013-06-192033-06-19Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubilityMostly insolubleNot Available
logP2.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.022 mg/mLALOGPS
logP2.93ALOGPS
logP2.7ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)12.46ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity105.37 m3·mol-1ChemAxon
Polarizability42.07 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
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 ReferencesNot Available
External Links
ATC CodesD07AC21
AHFS Codes
  • 84:06.00
PDB EntriesNot Available
FDA labelDownload (399 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AldesleukinHalobetasol Propionate may decrease the antineoplastic activities of Aldesleukin.
CeritinibHalobetasol Propionate may increase the hyperglycemic activities of Ceritinib.
Corticorelin ovine triflutateThe therapeutic efficacy of Corticorelin can be decreased when used in combination with Halobetasol Propionate.
DeferasiroxThe risk or severity of adverse effects can be increased when Halobetasol Propionate is combined with Deferasirox.
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Halobetasol Propionate.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, 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 grow...
Gene Name:
NR3C1
Uniprot ID:
P04150
Molecular Weight:
85658.57 Da
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:19293512 ]
  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:9891987 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Steroid binding
Specific Function:
Major transport protein for glucocorticoids and progestins in the blood of almost all vertebrate species.
Gene Name:
SERPINA6
Uniprot ID:
P08185
Molecular Weight:
45140.49 Da
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:17139284 ]
  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:17016423 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on June 30, 2016 01:52