This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Clobetasol
Accession Number
DB11750
Type
Small Molecule
Groups
Approved, Experimental, Investigational
Description

Clobetasol is under investigation for the treatment of Scleroderma. Clobetasol has been investigated for the prevention of Psoriasis and Cutaneous Atrophy Due to Corticosteroids.

Structure
Thumb
Synonyms
Not Available
Categories
UNII
ADN79D536H
CAS number
25122-41-2
Weight
Average: 410.907
Monoisotopic: 410.166015296
Chemical Formula
C22H28ClFO4
InChI Key
FCSHDIVRCWTZOX-DVTGEIKXSA-N
InChI
InChI=1S/C22H28ClFO4/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,24)17(26)10-20(16,3)22(12,28)18(27)11-23/h6-7,9,12,15-17,26,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,17-,19-,20-,21-,22-/m0/s1
IUPAC Name
(1R,2S,10S,11S,13S,14R,15S,17S)-14-(2-chloroacetyl)-1-fluoro-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])CCC2=CC(=O)C=C[C@]12C

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
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
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be increased when combined with Clobetasol.
(S)-WarfarinThe metabolism of (S)-Warfarin can be increased when combined with Clobetasol.
1-TestosteroneThe risk or severity of edema formation can be increased when 1-Testosterone is combined with Clobetasol.
1,10-PhenanthrolineThe therapeutic efficacy of 1,10-Phenanthroline can be decreased when used in combination with Clobetasol.
16-BromoepiandrosteroneThe risk or severity of edema formation can be increased when 16-Bromoepiandrosterone is combined with Clobetasol.
19-norandrostenedioneThe risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Clobetasol.
1alpha-Hydroxyvitamin D5The therapeutic efficacy of 1alpha-Hydroxyvitamin D5 can be decreased when used in combination with Clobetasol.
2-MethoxyethanolThe risk or severity of adverse effects can be increased when 2-Methoxyethanol is combined with Clobetasol.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be decreased when used in combination with Clobetasol.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be increased when combined with Clobetasol.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0015148
PubChem Compound
5311051
PubChem Substance
347828107
ChemSpider
4470588
ChEBI
205919
ChEMBL
CHEMBL1201362
Wikipedia
Clobetasol
ATC Codes
D07CD01 — Clobetasol and antibioticsD07AD01 — Clobetasol

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealthy Volunteers2
1CompletedTreatmentPsoriasis1
1WithdrawnTreatmentScleroderma1
2CompletedPreventionCutaneous Atrophy Due to Corticosteroids1
2CompletedTreatmentHerpes Labialis1
2CompletedTreatmentLichen Sclerosus et Atrophicus1
2CompletedTreatmentOral Lichen Planus1
2RecruitingTreatmentBullous Pemphigoid (BP)1
2, 3CompletedTreatmentPsoriasis1
3CompletedTreatmentGraft Versus Host Disease (GVHD) / Oral Manifestations1
3CompletedTreatmentPsoriasis1
4RecruitingTreatmentPsoriasis1
4Unknown StatusTreatmentDermatitis, Contact / Dermatitis, Occupational1
Not AvailableCompletedTreatmentPsoriasis1
Not AvailableNot Yet RecruitingTreatmentLichen Planus, Oral / Low-level Light Therapy1
Not AvailableRecruitingTreatmentDrug Reaction With Eosinophilia and Systemic Symptoms1
Not AvailableTerminatedNot AvailablePsoriasis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0142 mg/mLALOGPS
logP2.72ALOGPS
logP3.04ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)12.47ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity105.54 m3·mol-1ChemAxon
Polarizability41.97 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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 / Hydroxysteroid / Halo-steroid / 9-halo-steroid / Oxosteroid / 11-beta-hydroxysteroid / 11-hydroxysteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid
show 25 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
11beta-hydroxy steroid, 17alpha-hydroxy steroid, glucocorticoid, 20-oxo steroid, fluorinated steroid, 3-oxo-Delta(1),Delta(4)-steroid, chlorinated steroid (CHEBI:205919)

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Ahmad N, Mukhtar H: Cytochrome p450: a target for drug development for skin diseases. J Invest Dermatol. 2004 Sep;123(3):417-25. doi: 10.1111/j.0022-202X.2004.23307.x. [PubMed:15304077]
  2. Olux monograph [File]

Drug created on October 20, 2016 14:44 / Updated on November 02, 2018 07:15