Identification

Name
Alclometasone
Accession Number
DB00240  (APRD00783)
Type
Small Molecule
Groups
Approved
Description

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

Structure
Thumb
Synonyms
  • (7alpha,11beta,16alpha)-7-chloro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione
  • 7α-Chloro-16α-methylprednisolone
Product Ingredients
IngredientUNIICASInChI Key
Alclometasone dipropionateS56PQL4N1V66734-13-2DJHCCTTVDRAMEH-DUUJBDRPSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AclovateOintment0.05 mg/1TopicalGlaxoSmithKline2006-10-11Not applicableUs
AclovateCream0.5 mg/1gTopicalGlaxosmithkline Inc2006-02-102011-02-11Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AclovateOintment0.5 mg/1gTopicalPharma Derm, A Division Of Nycomed Us Inc.2009-10-01Not applicableUs
AclovateCream0.5 mg/1gTopicalPhysicians Total Care, Inc.2009-09-012011-09-30Us
AclovateCream0.5 mg/1gTopicalPharma Derm, A Division Of Nycomed Us Inc.2009-09-01Not applicableUs
AclovateOintment0.5 mg/1gTopicalPhysicians Total Care, Inc.2009-10-012011-09-30Us
Alclometasone DipropionateOintment0.5 mg/1gTopicalTaro Pharmaceuticals U.S.A., Inc.2004-07-29Not applicableUs
Alclometasone DipropionateCream0.5 mg/1gTopicalGlenmark Pharmaceuticals Inc.,Usa2009-06-23Not applicableUs
Alclometasone DipropionateOintment0.5 mg/1gTopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2005-07-18Not applicableUs
Alclometasone dipropionateCream0.5 mg/1gTopicalTaro Pharmaceuticals U.S.A., Inc.2005-09-15Not applicableUs
Alclometasone DipropionateCream0.5 mg/1gTopicalPhysicians Total Care, Inc.2009-06-23Not applicableUs
Alclometasone DipropionateCream0.5 mg/1gTopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2005-07-12Not applicableUs
Categories
UNII
136H45TB7B
CAS number
67452-97-5
Weight
Average: 408.916
Monoisotopic: 408.170351745
Chemical Formula
C22H29ClO5
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
(1S,2R,9R,10S,11S,13R,14R,15S,17S)-9-chloro-14,17-dihydroxy-14-(2-hydroxyacetyl)-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)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])[C@H](Cl)CC2=CC(=O)C=C[C@]12C

Pharmacology

Indication

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

Associated Conditions
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
Human
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
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.

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

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Alclometasone.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Alclometasone.
3,5-diiodothyropropionic acidThe metabolism of Alclometasone can be decreased when combined with 3,5-diiodothyropropionic acid.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Alclometasone.
6-Deoxyerythronolide BThe metabolism of Alclometasone can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Alclometasone.
AbemaciclibThe metabolism of Alclometasone can be decreased when combined with Abemaciclib.
AbirateroneThe metabolism of Alclometasone can be decreased when combined with Abiraterone.
AcalabrutinibThe metabolism of Alclometasone can be decreased when combined with Acalabrutinib.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Alclometasone.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0014385
KEGG Drug
D01820
PubChem Compound
5311000
PubChem Substance
46508296
ChemSpider
4470541
ChEBI
53776
ChEMBL
CHEMBL1201361
Therapeutic Targets Database
DAP000415
PharmGKB
PA164747650
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Alclometasone
ATC Codes
D07AB10 — AlclometasoneS01BA10 — Alclometasone
FDA label
Download (191 KB)
MSDS
Download (26.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentAllergy Symptoms / Dermatitis, Eczematous / Itching / Psoriasis1
2CompletedTreatmentLung Cancer Non-Small Cell Cancer (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
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
Polarizability42.62 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

Taxonomy

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
show 7 more
Substituents
21-hydroxysteroid / Progestogin-skeleton / 20-oxosteroid / Pregnane-skeleton / Halo-steroid / 3-oxo-delta-1,4-steroid / 7-halo-steroid / 3-oxosteroid / Oxosteroid / 11-beta-hydroxysteroid
show 21 more
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)

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. Labeur M, Holsboer F: Molecular mechanisms of glucocorticoid receptor signaling. Medicina (B Aires). 2010;70(5):457-62. [PubMed:20920967]
  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]

Enzymes

Kind
Protein
Organism
Human
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
Human
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. [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]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Drug created on June 13, 2005 07:24 / Updated on October 11, 2018 22:27