Identification

Name
Ulobetasol
Accession Number
DB00596  (APRD01010)
Type
Small Molecule
Groups
Approved
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
Product Ingredients
IngredientUNIICASInChI Key
Ulobetasol propionate91A0K1TY3Z66852-54-8BDSYKGHYMJNPAB-LICBFIPMSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
UltravateCream0.5 mg/1gTopicalRanbaxy Inc.2009-03-16Not applicableUs
UltravateOintment0.5 mg/1gTopicalBristol Myers Squibb Pharma Company2009-06-012009-12-31Us
UltravateLotion0.5 mg/1gTopicalSun Pharmaceutical Industries Limited2016-03-01Not applicableUs
UltravateOintment0.5 mg/1gTopicalRanbaxy Inc.2009-02-20Not 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 PACOintment0.5 mg/1gTopicalSun Pharmaceutical Industries Limited2008-05-132008-05-13Us
Ultravate PAC-CreamCream0.5 mg/1gTopicalSun Pharmaceutical Industries Limited2010-02-102010-02-10Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Halobetasol PropionateOintment0.5 mg/1gTopicalE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.2004-12-16Not applicableUs
Halobetasol PropionateCream0.5 mg/1gTopicalE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.2004-12-16Not applicableUs
Halobetasol PropionateOintment0.5 mg/1gTopicalPerrigo New York Inc.2009-02-05Not applicableUs
Halobetasol PropionateOintment0.5 mg/1gTopicalPhysicians Total Care, Inc.2005-12-05Not applicableUs
Halobetasol PropionateCream0.5 mg/1gTopicalTaro Pharmaceuticals U.S.A., Inc.2005-08-04Not applicableUs
Halobetasol PropionateOintment0.5 mg/1gTopicalTaro Pharmaceuticals U.S.A., Inc.2004-12-16Not applicableUs
Halobetasol PropionateOintment0.5 mg/1gTopicalH.J. Harkins Company2009-02-05Not applicableUs
Halobetasol PropionateOintment0.5 mg/1gTopicalTeligent Pharma, Inc.2018-03-20Not applicableUs
Halobetasol PropionateCream.5 mg/1gTopicalGw Pharmaceuticals Ltd.2007-07-16Not applicableUs
Halobetasol PropionateOintment.5 mg/1gTopicalGw Pharmaceuticals Ltd.2005-06-14Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Ultravate XUlobetasol propionate (0.50 mg/1g) + Ammonium lactate (100 mg/1g)KitRanbaxy Inc.2012-07-01Not applicableUs
Ultravate XUlobetasol propionate (0.5 mg/1g) + Ammonium lactate (100 mg/1g)KitRanbaxy Inc.2012-07-09Not applicableUs
International/Other Brands
Halobetasol (Fougera) / Halovate (Glenmark) / Hobs (Aamorb)
Categories
UNII
9P6159HM7T
CAS number
98651-66-2
Weight
Average: 428.9
Monoisotopic: 428.1565934
Chemical Formula
C22H27ClF2O4
InChI Key
LEHFPXVYPMWYQD-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[C@H](C)[C@](O)(C(=O)CCl)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])C[C@H](F)C2=CC(=O)C=C[C@]12C

Pharmacology

Indication

For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.

Associated Conditions
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.

TargetActionsOrganism
AGlucocorticoid receptor
agonist
Human
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
1-TestosteroneThe risk or severity of edema formation can be increased when 1-Testosterone is combined with Ulobetasol.
1,10-PhenanthrolineThe therapeutic efficacy of 1,10-Phenanthroline can be decreased when used in combination with Ulobetasol.
16-BromoepiandrosteroneThe risk or severity of edema formation can be increased when 16-Bromoepiandrosterone is combined with Ulobetasol.
19-norandrostenedioneThe risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Ulobetasol.
1alpha-Hydroxyvitamin D5The therapeutic efficacy of 1alpha-Hydroxyvitamin D5 can be decreased when used in combination with Ulobetasol.
2-MethoxyethanolThe risk or severity of adverse effects can be increased when 2-Methoxyethanol is combined with Ulobetasol.
4-HydroxytestosteroneThe risk or severity of edema formation can be increased when 4-Hydroxytestosterone is combined with Ulobetasol.
5-androstenedioneThe risk or severity of edema formation can be increased when 5-androstenedione is combined with Ulobetasol.
9-(N-methyl-L-isoleucine)-cyclosporin AThe risk or severity of adverse effects can be increased when 9-(N-methyl-L-isoleucine)-cyclosporin A is combined with Ulobetasol.
AbataceptThe risk or severity of adverse effects can be increased when Abatacept is combined with Ulobetasol.
Food Interactions
Not 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 References
Not Available
External Links
PubChem Compound
5311167
PubChem Substance
46506187
ChemSpider
4470691
ChEMBL
CHEMBL1201360
Therapeutic Targets Database
DAP001186
PharmGKB
PA164768832
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Ulobetasol
ATC Codes
D07AC21 — Ulobetasol
AHFS Codes
  • 84:06.00 — Anti-inflammatory Agents
FDA label
Download (399 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealthy Volunteers2
1CompletedTreatmentPsoriasis1
2CompletedTreatmentPsoriasis2
2CompletedTreatmentPsoriasis Vulgaris (Plaque Psoriasis)1
2WithdrawnTreatmentPsoriasis Vulgaris (Plaque Psoriasis)1
2, 3CompletedTreatmentPsoriasis1
3CompletedTreatmentPsoriasis Vulgaris (Plaque Psoriasis)1
3RecruitingTreatmentPsoriasis Vulgaris (Plaque Psoriasis)2

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
  • Actavis Group
  • Contract Pharm
  • E. Fougera and Co.
  • G & W Labs
  • JSJ Pharmaceuticals Inc.
  • Nycomed Inc.
  • Perrigo Co.
  • Physicians Total Care Inc.
  • Ranbaxy Laboratories
  • Taro Pharmaceuticals USA
Dosage forms
FormRouteStrength
CreamTopical.5 mg/1g
CreamTopical0.5 mg/1g
OintmentTopical.5 mg/1g
OintmentTopical0.5 mg/1g
LotionTopical0.5 mg/1g
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)
US8962028No2013-06-192033-06-19Us

Properties

State
Solid
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Pregnane steroids
Direct Parent
Gluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
20-oxosteroids / 11-beta-hydroxysteroids / 17-hydroxysteroids / 3-oxo delta-1,4-steroids / Halogenated steroids / Delta-1,4-steroids / Tertiary alcohols / Alpha-hydroxy ketones / Alpha-chloroketones / Secondary alcohols
show 9 more
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
show 26 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
Not 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 modula...
Gene Name
NR3C1
Uniprot ID
P04150
Uniprot Name
Glucocorticoid receptor
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
Uniprot Name
Corticosteroid-binding globulin
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]

Drug created on June 13, 2005 07:24 / Updated on September 25, 2018 03:05