Alclometasone

Identification

Summary

Alclometasone is a topical corticosteroid used to relieve the symptoms of corticosteroid-responsive dermatoses.

Generic Name
Alclometasone
DrugBank Accession Number
DB00240
Background

Alclometasone is synthetic glucocorticoid steroid for topical use in dermatology as anti-inflammatory, antipruritic, antiallergic, antiproliferative and vasoconstrictive agent.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 408.916
Monoisotopic: 408.170351745
Chemical Formula
C22H29ClO5
Synonyms
  • (7alpha,11beta,16alpha)-7-chloro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione
  • 7α-Chloro-16α-methylprednisolone
  • Alclometasone

Pharmacology

Indication

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

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Alclometasone is a synthetic corticosteroid for topical dermatologic use. The corticosteroids constitute a class of primarily synthetic steroids used topically as anti-inflammatory and antipruritic agents. Alclometasone is a selective glucocorticoid receptor agonist.

Mechanism of action

The mechanism of the anti-inflammatory activity of the topical steroids, in general, is unclear. However, corticosteroids are 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. Alclometasone initially binds the corticosteroid receptor. This complex migrates to the nucleus where it binds to different glucocorticoid response elements on the DNA. This in turn enhances and represses various genes, especially those involved in inflammatory pathways.

TargetActionsOrganism
AGlucocorticoid receptor
agonist
Humans
Absorption

Topical corticosteroids can be absorbed from normal intact skin. Studies have shown that approximately 3% of steroid is absorbed during 8 hours of contact with intact skin of normal volunteers.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Hepatic.

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Symptoms of overdose include suppression of adrenal glands, temporary decrease in white blood cell counts, symptoms of hypersensitivity (such as skin rash, hives, itching, and difficulty breathing), and increased susceptibility to infection.

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
AbametapirThe serum concentration of Alclometasone can be increased when it is combined with Abametapir.
AcarboseThe risk or severity of hyperglycemia can be increased when Alclometasone is combined with Acarbose.
AcetohexamideThe risk or severity of hyperglycemia can be increased when Alclometasone is combined with Acetohexamide.
AcetyldigitoxinThe risk or severity of adverse effects can be increased when Alclometasone is combined with Acetyldigitoxin.
AlbiglutideThe risk or severity of hyperglycemia can be increased when Alclometasone is combined with Albiglutide.
AlogliptinThe risk or severity of hyperglycemia can be increased when Alclometasone is combined with Alogliptin.
AminoglutethimideThe therapeutic efficacy of Alclometasone can be decreased when used in combination with Aminoglutethimide.
BendroflumethiazideThe risk or severity of electrolyte imbalance can be increased when Alclometasone is combined with Bendroflumethiazide.
BenzthiazideThe risk or severity of electrolyte imbalance can be increased when Alclometasone is combined with Benzthiazide.
BromocriptineThe risk or severity of hyperglycemia can be increased when Alclometasone is combined with Bromocriptine.
Interactions
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Food Interactions
No interactions found.

Products

Products
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Product Ingredients
IngredientUNIICASInChI Key
Alclometasone dipropionateS56PQL4N1V66734-13-2DJHCCTTVDRAMEH-DUUJBDRPSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AclovateOintment0.05 mg/1TopicalGlaxoSmithKline2006-10-112007-06-29US flag
AclovateCream0.5 mg/1gTopicalGlaxosmithkline Inc2006-02-102011-02-11US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AclovateCream0.5 mg/1gTopicalPhysicians Total Care, Inc.2009-09-012011-09-30US flag
AclovateOintment0.5 mg/1gTopicalPharmaDerm a division of Fougera Pharmaceuticals Inc.2009-10-012015-02-28US flag
AclovateCream0.5 mg/1gTopicalPharmaDerm a division of Fougera Pharmaceuticals Inc.2009-09-012015-02-28US flag
AclovateOintment0.5 mg/1gTopicalPhysicians Total Care, Inc.2009-10-012011-09-30US flag
Alclometasone DipropionateCream0.5 mg/1gTopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2005-07-12Not applicableUS flag
Alclometasone DipropionateOintment0.5 mg/1gTopicalTaro Pharmaceuticals U.S.A., Inc.2004-07-29Not applicableUS flag
Alclometasone dipropionateCream0.5 mg/1gTopicalTaro Pharmaceuticals U.S.A., Inc.2005-09-15Not applicableUS flag
Alclometasone DipropionateOintment.5 mg/1gTopicalGlenmark Pharmaceuticals Inc., USA2009-07-30Not applicableUS flag
Alclometasone DipropionateCream0.5 mg/1gTopicalPhysicians Total Care, Inc.2009-06-23Not applicableUS flag
Alclometasone DipropionateOintment0.5 mg/1gTopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2005-07-18Not applicableUS flag

Categories

ATC Codes
D07AB10 — AlclometasoneS01BA10 — Alclometasone
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Hydroxysteroids
Direct Parent
21-hydroxysteroids
Alternative Parents
Gluco/mineralocorticoids, progestogins and derivatives / 20-oxosteroids / 11-beta-hydroxysteroids / 17-hydroxysteroids / 3-oxo delta-1,4-steroids / Halogenated steroids / Delta-1,4-steroids / Tertiary alcohols / Alpha-hydroxy ketones / Secondary alcohols
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Substituents
11-beta-hydroxysteroid / 11-hydroxysteroid / 17-hydroxysteroid / 20-oxosteroid / 21-hydroxysteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / 7-halo-steroid / Alcohol / Aliphatic homopolycyclic compound
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Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
11beta-hydroxy steroid, 17alpha-hydroxy steroid, glucocorticoid, 20-oxo steroid, 3-oxo-Delta(1),Delta(4)-steroid, chlorinated steroid, 21-hydroxy steroid (CHEBI:53776)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
136H45TB7B
CAS number
67452-97-5
InChI Key
FJXOGVLKCZQRDN-PHCHRAKRSA-N
InChI
InChI=1S/C22H29ClO5/c1-11-6-14-18-15(23)8-12-7-13(25)4-5-20(12,2)19(18)16(26)9-21(14,3)22(11,28)17(27)10-24/h4-5,7,11,14-16,18-19,24,26,28H,6,8-10H2,1-3H3/t11-,14+,15-,16+,18-,19+,20+,21+,22+/m1/s1
IUPAC Name
(1R,2R,3aS,3bS,4R,9aR,9bS,10S,11aS)-4-chloro-1,10-dihydroxy-1-(2-hydroxyacetyl)-2,9a,11a-trimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
SMILES
[H][C@@]12C[C@@H](C)[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])[C@H](Cl)CC2=CC(=O)C=C[C@]12C

References

General References
  1. Matoulkova P, Pavek P, Maly J, Vlcek J: Cytochrome P450 enzyme regulation by glucocorticoids and consequences in terms of drug interaction. Expert Opin Drug Metab Toxicol. 2014 Mar;10(3):425-35. doi: 10.1517/17425255.2014.878703. Epub 2014 Jan 23. [Article]
Human Metabolome Database
HMDB0014385
KEGG Drug
D07116
PubChem Compound
5311000
PubChem Substance
46508296
ChemSpider
4470541
RxNav
108088
ChEBI
53776
ChEMBL
CHEMBL1201361
ZINC
ZINC000030691420
Therapeutic Targets Database
DAP000415
PharmGKB
PA164747650
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Alclometasone
FDA label
Download (191 KB)
MSDS
Download (26.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentAllergy Symptoms / Dermatitis, Eczematous / Pruritus / Psoriasis1
2CompletedTreatmentNon-Small Cell Lung Carcinoma (NSCLC)1

Pharmacoeconomics

Manufacturers
  • Nycomed us inc
  • Altana inc
  • Glenmark generics ltd
  • Taro pharmaceuticals usa inc
  • Glaxosmithkline
Packagers
  • Dispensing Solutions
  • E. Fougera and Co.
  • Glenmark Generics Ltd.
  • Nycomed Inc.
  • Pharmaderm
  • Physicians Total Care Inc.
  • Taro Pharmaceuticals USA
Dosage Forms
FormRouteStrength
CreamTopical0.5 mg/1g
OintmentTopical0.05 mg/1
OintmentTopical0.5 mg/1g
OintmentTopical.5 mg/1g
CreamTopical
LotionTopical
OintmentTopical
SolutionTopical
Prices
Unit descriptionCostUnit
Aclovate 0.05% Ointment 60 gm Tube141.1USD tube
Aclovate 0.05% Cream 60 gm Tube103.1USD tube
Aclovate 0.05% Cream 45 gm Tube81.19USD tube
Aclovate 0.05% Cream 15 gm Tube54.54USD tube
Aclovate 0.05% Ointment 15 gm Tube52.99USD tube
Alclometasone Dipropionate 0.05% Cream 60 gm Tube52.99USD tube
Alclometasone Dipropionate 0.05% Cream 45 gm Tube41.31USD tube
Alclometasone Dipropionate 0.05% Ointment 60 gm Tube39.27USD tube
Alclometasone Dipropionate 0.05% Cream 15 gm Tube19.81USD tube
Alclometasone Dipropionate 0.05% Ointment 15 gm Tube16.99USD tube
Aclovate 0.05% cream2.91USD g
Alclometasone dipro 0.05% crm1.21USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilityInsolubleNot Available
logP2.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.137 mg/mLALOGPS
logP2.11ALOGPS
logP1.68ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity107.61 m3·mol-1ChemAxon
Polarizability42.88 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9948
Blood Brain Barrier+0.9518
Caco-2 permeable+0.6337
P-glycoprotein substrateSubstrate0.7572
P-glycoprotein inhibitor INon-inhibitor0.8049
P-glycoprotein inhibitor IINon-inhibitor0.8763
Renal organic cation transporterNon-inhibitor0.8262
CYP450 2C9 substrateNon-substrate0.8524
CYP450 2D6 substrateNon-substrate0.9027
CYP450 3A4 substrateSubstrate0.717
CYP450 1A2 substrateNon-inhibitor0.9228
CYP450 2C9 inhibitorNon-inhibitor0.9215
CYP450 2D6 inhibitorNon-inhibitor0.9372
CYP450 2C19 inhibitorNon-inhibitor0.8962
CYP450 3A4 inhibitorNon-inhibitor0.7736
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8568
Ames testNon AMES toxic0.8448
CarcinogenicityNon-carcinogens0.9132
BiodegradationNot ready biodegradable0.9974
Rat acute toxicity2.2398 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9651
hERG inhibition (predictor II)Non-inhibitor0.6522
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 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

Targets

Drugtargets
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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. Labeur M, Holsboer F: Molecular mechanisms of glucocorticoid receptor signaling. Medicina (B Aires). 2010;70(5):457-62. [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]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
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. Vallerand A. and Sanoski C. (2017). David's Canadian Drug Guide for Nurses (16th ed.). FA Davis Company. [ISBN:978-0-803-669468]

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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  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. [Article]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Drug created on June 13, 2005 13:24 / Updated on July 03, 2021 09:00