Identification

Name
Ulobetasol
Accession Number
DB00596
Description

Ulobetasol is a highly potent corticosteroid.6 It is structurally related to clobetasol.6 Due to its high potency, it is mainly prescribed in the treatment of severe plaque psoriasis and corticosteroid responsive dermatoses.7,8,10

Ulobetasol was granted FDA approval on 17 December 1990.7

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 428.9
Monoisotopic: 428.1565934
Chemical Formula
C22H27ClF2O4
Synonyms
  • 21-chloro diflorasone
  • Halobetasol
  • Ulobetasol
  • Ulobétasol
  • Ulobetasolum

Pharmacology

Indication

Ulobetasol cream and ointment are indicated in the treatment of inflammatory and pruritic corticosteroid responsive dermatoses.7 Ulobetasol lotion is indicated in the treatment of plaque psoriasis.8

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More
Pharmacodynamics

Corticosteroids bind to the glucocorticoid receptor, inhibiting pro-inflammatory signals, and promoting anti-inflammatory signals.2 Ulobetasol has a moderate duration of action as it is applied once or twice daily.7,8 Corticosteroids have a wide therapeutic window as patients may require doses that are multiples of what the body naturally produces.2 Patients taking corticosteroids should be counselled regarding the risk of hypothalamic-pituitary-adrenal axis suppression and increased susceptibility to infections.2

Mechanism of action

The short term effects of corticosteroids are decreased vasodilation and permeability of capillaries, as well as decreased leukocyte migration to sites of inflammation.2 Corticosteroids binding to the glucocorticoid receptor mediates changes in gene expression that lead to multiple downstream effects over hours to days.2

Glucocorticoids inhibit phospholipase 2 and neutrophil apoptosis and demargination, resulting in decreased formation of arachidonic acid derivatives. They also inhibit NF-Kappa B and other inflammatory transcription factors while promoting anti-inflammatory genes like interleukin-10.1,2

Lower doses of corticosteroids provide an anti-inflammatory effect, while higher doses are immunosuppressive.2 High doses of glucocorticoids for an extended period bind to the mineralocorticoid receptor, raising sodium levels and decreasing potassium levels.2

TargetActionsOrganism
AGlucocorticoid receptor
agonist
Humans
Absorption

Ulobetasol lotion reaches a Cmax of 201.1 ± 157.5 pg/mL, with a Tmax of 3 hours, and an AUC of 1632 ± 1147 pg*h/mL.8 Absorption can be influenced by skin integrity, the vehicle used, inflammation, or disease processes.7,8

Volume of distribution
Not Available
Protein binding

Ulobetasol is likely bound to corticosteroid binding globulin in serum.3

Metabolism
Not Available
Route of elimination

Corticosteroids are eliminated predominantly in the urine.4

Half-life

In vitro experiments show halobetasol propionate, a derivative of ulobetasol, has a half life of 33 minutes.9

Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
Toxicity

Data regarding acute overdoses of glucocorticoids are rare.7,8 Chronic high doses of glucocorticoids can lead to the development of cataract, glaucoma, hypertension, water retention, hyperlipidemia, peptic ulcer, pancreatitis, myopathy, osteoporosis, mood changes, psychosis, dermal atrophy, allergy, acne, hypertrichosis, immune suppression, decreased resistance to infection, moon face, hyperglycemia, hypocalcemia, hypophosphatemia, metabolic acidosis, growth suppression, and secondary adrenal insufficiency.5 Overdose may be treated by adjusting the dose or stopping the corticosteroid as well as initiating symptomatic and supportive treatment.5,10

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcarboseThe risk or severity of hyperglycemia can be increased when Ulobetasol is combined with Acarbose.
AcetohexamideThe risk or severity of hyperglycemia can be increased when Ulobetasol is combined with Acetohexamide.
AcetyldigitoxinThe risk or severity of adverse effects can be increased when Ulobetasol is combined with Acetyldigitoxin.
AlbiglutideThe risk or severity of hyperglycemia can be increased when Ulobetasol is combined with Albiglutide.
AlogliptinThe risk or severity of hyperglycemia can be increased when Ulobetasol is combined with Alogliptin.
AminoglutethimideThe therapeutic efficacy of Ulobetasol can be decreased when used in combination with Aminoglutethimide.
BendroflumethiazideThe risk or severity of electrolyte imbalance can be increased when Ulobetasol is combined with Bendroflumethiazide.
BenzthiazideThe risk or severity of electrolyte imbalance can be increased when Ulobetasol is combined with Benzthiazide.
BromocriptineThe risk or severity of hyperglycemia can be increased when Ulobetasol is combined with Bromocriptine.
CanagliflozinThe risk or severity of hyperglycemia can be increased when Ulobetasol is combined with Canagliflozin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
No interactions found.

Products

Product Ingredients
IngredientUNIICASInChI Key
Ulobetasol propionate91A0K1TY3Z66852-54-8BDSYKGHYMJNPAB-LICBFIPMSA-N
International/Other Brands
Halobetasol (Fougera) / Halovate (Glenmark) / Hobs (Aamorb)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BryhaliLotion0.1 mg/1gTopicalBausch Health US, LLC2018-11-06Not applicableUs
Halobetasol propionateAerosol, foam0.5 mg/1gTopicalPharmasol Corporation2019-02-042022-01-31Us
Halobetasol propionateAerosol, foam0.5 mg/1gTopicalMayne Pharma2019-02-04Not applicableUs
LexetteAerosol, foam0.5 mg/1gTopicalMayne Pharma2019-04-23Not applicableUs
UltravateOintment0.5 mg/1gTopicalBristol Myers Squibb Pharma Company2009-06-012009-12-31Us
UltravateOintment0.5 mg/1gTopicalSun Pharmaceutical Industries, Inc.2009-02-202017-06-30Us
UltravateCream0.05 %TopicalBausch Health, Canada Inc.1993-12-31Not applicableCanada
UltravateCream0.5 mg/1gTopicalSun Pharmaceutical Industries, Inc.2009-03-162017-06-30Us
UltravateLotion0.5 mg/1gTopicalSun Pharmaceutical Industries, Inc.2016-03-01Not applicableUs
UltravateOintment0.05 %TopicalBausch Health, Canada Inc.1993-12-31Not applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Halobetasol PropionateOintment.5 mg/1gTopicalCosette Pharmaceuticals, Inc.2016-09-21Not applicableUs
Halobetasol PropionateCream0.5 mg/1gTopicalRebel Distributors2007-07-16Not applicableUs
Halobetasol PropionateOintment0.5 mg/1gTopicalSola Pharmaceuticals2019-02-04Not applicableUs
Halobetasol PropionateOintment0.5 mg/1gTopicalMcKesson Corporation2020-03-11Not 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/1gTopicalPerrigo New York Inc2009-02-05Not applicableUs
Halobetasol PropionateCream.5 mg/1gTopicalCosette Pharmaceuticals, Inc.2007-07-16Not applicableUs
Halobetasol PropionateOintment0.5 mg/1gTopicalH.J. Harkins Company2009-02-05Not applicableUs
Halobetasol PropionateCream0.5 mg/1gTopicalFougera Pharmaceuticals Inc.2004-12-16Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
DuobriiUlobetasol propionate (0.01 %) + Tazarotene (0.045 %)LotionTopicalBausch Health, Canada Inc.Not applicableNot applicableCanada
DuobriiUlobetasol propionate (0.1 mg/1g) + Tazarotene (0.45 mg/1g)LotionTopicalBausch Health US, LLC2019-04-25Not applicableUs
Ultravate XUlobetasol propionate (0.50 mg/1g) + Ammonium lactate (100 mg/1g)KitTopicalRanbaxy Inc.2012-07-01Not applicableUs
Ultravate XUlobetasol propionate (0.5 mg/1g) + Ammonium lactate (100 mg/1g)TopicalSun Pharmaceutical Industries, Inc.2012-07-092017-08-31Us

Categories

ATC Codes
D07AC21 — Ulobetasol
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
11-beta-hydroxysteroid / 11-hydroxysteroid / 17-hydroxysteroid / 20-oxosteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / 6-halo-steroid / 9-halo-steroid / Alcohol / Aliphatic homopolycyclic compound
show 26 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
Not Available

Chemical Identifiers

UNII
9P6159HM7T
CAS number
98651-66-2
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

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
  1. Awad N, Preuss CV: Halobetasol Cream . [PubMed:31334954]
  2. Yasir M, Sonthalia S: Corticosteroid Adverse Effects . [PubMed:30285357]
  3. Gardill BR, Vogl MR, Lin HY, Hammond GL, Muller YA: Corticosteroid-binding globulin: structure-function implications from species differences. PLoS One. 2012;7(12):e52759. doi: 10.1371/journal.pone.0052759. Epub 2012 Dec 26. [PubMed:23300763]
  4. Czock D, Keller F, Rasche FM, Haussler U: Pharmacokinetics and pharmacodynamics of systemically administered glucocorticoids. Clin Pharmacokinet. 2005;44(1):61-98. doi: 10.2165/00003088-200544010-00003. [PubMed:15634032]
  5. Ciriaco M, Ventrice P, Russo G, Scicchitano M, Mazzitello G, Scicchitano F, Russo E: Corticosteroid-related central nervous system side effects. J Pharmacol Pharmacother. 2013 Dec;4(Suppl 1):S94-8. doi: 10.4103/0976-500X.120975. [PubMed:24347992]
  6. Watson WA, Kalb RE, Siskin SB, Freer JP, Krochmal L: The safety of halobetasol 0.05% ointment in the treatment of psoriasis. Pharmacotherapy. 1990;10(2):107-11. [PubMed:2349135]
  7. FDA Approved Drug Products: Halobetasol Propionate Cream or Ointment [Link]
  8. FDA Approved Drug Products: Halobetasol Propionate Topical Lotion [Link]
  9. FDA Summary Review: Halobetasol Propionate [Link]
  10. Health Canada Approved Drug Products: Ultravate Halobetasol Propionate Topical Cream or Ointment [Link]
PubChem Compound
5311167
PubChem Substance
46506187
ChemSpider
4470691
RxNav
41208
ChEMBL
CHEMBL1201360
ZINC
ZINC000004214603
Therapeutic Targets Database
DAP001186
PharmGKB
PA164768832
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Ulobetasol
AHFS Codes
  • 84:06.00 — Anti-inflammatory Agents
FDA label
Download (399 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedOtherPsoriasis Vulgaris (Plaque Psoriasis)1
4CompletedTreatmentPsoriasis Vulgaris (Plaque Psoriasis)2
4CompletedTreatmentStable Plaque Psoriasis1
4RecruitingTreatmentPsoriasis1
3RecruitingTreatmentPsoriasis Vulgaris (Plaque Psoriasis)2
2CompletedTreatmentPsoriasis2
2CompletedTreatmentPsoriasis Vulgaris (Plaque Psoriasis)1
2CompletedTreatmentPsoriasis / Psoriasis Vulgaris (Plaque Psoriasis)1
2TerminatedTreatmentAtopic Dermatitis (AD)1
2WithdrawnTreatmentPsoriasis Vulgaris (Plaque Psoriasis)1

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
LotionTopical0.1 mg/1g
LotionTopical
CreamTopical.5 mg/1g
CreamTopical0.5 mg/1g
OintmentTopical.5 mg/1g
OintmentTopical0.5 mg/1g
Aerosol, foamTopical0.5 mg/1g
CreamTopical0.05 %
LotionTopical0.5 mg/1g
OintmentTopical0.05 %
KitTopical
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)Region
US8962028No2015-02-242033-06-19Us
US8809307No2014-08-192031-11-02Us
US6517847No2003-02-112020-08-03Us
US10251895No2019-04-092036-06-06Us
US10478502No2019-11-192031-11-02Us
US10426787No2019-10-012036-06-06Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)200-216Health Canada Label
water solubilityPractically insolubleFDA Label
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

Targets

Kind
Protein
Organism
Humans
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
Humans
Pharmacological action
Unknown
Actions
Binder
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. Schoepe S, Schacke H, May E, Asadullah K: Glucocorticoid therapy-induced skin atrophy. Exp Dermatol. 2006 Jun;15(6):406-20. doi: 10.1111/j.0906-6705.2006.00435.x. [PubMed:16689857]
  2. Gardill BR, Vogl MR, Lin HY, Hammond GL, Muller YA: Corticosteroid-binding globulin: structure-function implications from species differences. PLoS One. 2012;7(12):e52759. doi: 10.1371/journal.pone.0052759. Epub 2012 Dec 26. [PubMed:23300763]

Drug created on June 13, 2005 07:24 / Updated on August 14, 2020 04:24

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