Ulobetasol

Identification

Summary

Ulobetasol is a lipocortin corticosteroid used to treat inflammatory and pruritic corticosteroid-responsive dermatoses.

Brand Names
Bryhali, Duobrii, Lexette, Ultravate, Ultravate X Ointment
Generic Name
Ulobetasol
DrugBank Accession Number
DB00596
Background

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
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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofPsoriasis vulgaris (plaque psoriasis)••••••••••••••••••••••• •••••
Treatment ofCorticosteroid responsive, inflammatory dermatosis•••••••••••••••••• ••••••••
Treatment ofCorticosteroid responsive, pruritic dermatosis•••••••••••••••••• ••••••••
Contraindications & Blackbox Warnings
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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
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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

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.
Allogeneic processed thymus tissueThe therapeutic efficacy of Allogeneic processed thymus tissue can be decreased when used in combination with Ulobetasol.
Food Interactions
No interactions found.

Products

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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
BryhaliLotion0.01 % w/wTopicalBausch Health, Canada Inc.2021-08-06Not applicableCanada flag
BryhaliLotion0.1 mg/1gTopicalBausch Health US, LLC2018-11-06Not applicableUS flag
Halobetasol propionateAerosol, foam0.5 mg/1gTopicalMayne Pharma2019-02-04Not applicableUS flag
Halobetasol propionateAerosol, foam0.5 mg/1gTopicalPharmasol Corporation2019-02-042022-01-31US flag
LexetteAerosol, foam0.5 mg/1gTopicalMayne Pharma2019-04-23Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Halobetasol PropionateOintment0.5 mg/1gTopicalbryant ranch prepack2009-02-05Not applicableUS flag
Halobetasol PropionateOintment0.5 mg/1gTopicalH.J. Harkins Company2009-02-05Not applicableUS flag
Halobetasol PropionateOintment0.5 mg/1gTopicalFougera Pharmaceuticals Inc.2004-12-162011-08-31US flag
Halobetasol PropionateOintment0.5 mg/1gTopicalTaro Pharmaceuticals U.S.A., Inc.2004-12-16Not applicableUS flag
Halobetasol PropionateOintment.5 mg/1gTopicalCosette Pharmaceuticals, Inc.2005-06-14Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
DuobriiUlobetasol propionate (0.1 mg/1g) + Tazarotene (0.45 mg/1g)LotionTopicalBausch Health US, LLC2019-04-25Not applicableUS flag
DuobriiUlobetasol propionate (0.01 % w/w) + Tazarotene (0.045 % w/w)LotionTopicalBausch Health, Canada Inc.2020-08-04Not applicableCanada flag
Ultravate XUlobetasol propionate (0.5 mg/1g) + Ammonium lactate (100 mg/1g)KitTopicalSun Pharmaceutical Industries, Inc.2012-07-092017-08-31US flag
Ultravate XUlobetasol propionate (0.50 mg/1g) + Ammonium lactate (100 mg/1g)KitTopicalRanbaxy Inc.2012-07-01Not applicableUS flag

Categories

ATC Codes
D05AX55 — Tazarotene and ulobetasolD07AC21 — 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
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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
Affected organisms
  • Humans and other mammals

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 . [Article]
  2. Yasir M, Sonthalia S: Corticosteroid Adverse Effects . [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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]
  11. FDA Approved Drug Products: LEXETTE (halobetasol propionate) topical foam [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
FDA label
Download (399 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentPalmoplantar Psoriasis / Psoriasis Vulgaris (Plaque Psoriasis)1
4CompletedTreatmentPsoriasis Vulgaris (Plaque Psoriasis)3
4CompletedTreatmentScalp Psoriasis1
4CompletedTreatmentStable Plaque Psoriasis1
4TerminatedOtherPsoriasis 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
LotionTopical0.01 % w/w
LotionTopical0.1 mg/1g
LotionTopical
OintmentCutaneous0.500 mg
CreamTopical.5 mg/1g
CreamTopical0.5 mg/1g
OintmentTopical.5 mg/1g
OintmentTopical0.5 mg/1g
Aerosol, foamTopical0.5 mg/1g
CreamTopical0.050 g
CreamTopical0.05 % w/w
LotionTopical0.5 mg/1g
OintmentTopical0.05 % w/w
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 flag
US8809307No2014-08-192031-11-02US flag
US6517847No2003-02-112020-08-03US flag
US10251895No2019-04-092036-06-06US flag
US10478502No2019-11-192031-11-02US flag
US10426787No2019-10-012036-06-06US flag
US10857159Yes2020-12-082037-05-30US flag
US11020407No2021-06-012036-11-30US flag
US11679115No2016-06-062036-06-06US flag
US11648256No2016-06-062036-06-06US flag
US11839656No2011-11-022031-11-02US flag

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/MSsplash10-06r6-0004900000-6ff1487d4b44fdb7f0bc
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0000900000-74929f2b0286af885e3a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01tc-0236900000-1e77a061ed99f8e6c9d3
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-5009100000-9efb3b69a63abecd8141
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0100-0719200000-35f0c78da8402a87d9c1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0kbg-2490000000-478e8dfd4ec3b35cdce4
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-194.93102
predicted
DeepCCS 1.0 (2019)
[M+H]+196.82643
predicted
DeepCCS 1.0 (2019)
[M+Na]+202.95409
predicted
DeepCCS 1.0 (2019)

Targets

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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. [Article]
  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. [Article]

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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48