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Identification
NameAlclometasone
Accession NumberDB00240  (APRD00783)
TypeSmall Molecule
GroupsApproved
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
External Identifiers Not Available
Prescription ProductsNot Available
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Aclovateointment.5 mg/gtopicalPharmaDerm, A division of Nycomed US Inc.2009-10-012016-04-23Us
Aclovatecream.5 mg/gtopicalPharmaDerm, A division of Nycomed US Inc.2009-09-012016-04-23Us
Alclometasone Dipropionatecream.5 mg/gtopicalGlenmark Pharmaceuticals Inc., Usa2009-06-232016-04-05Us
Alclometasone Dipropionatecream.5 mg/gtopicalE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.2005-07-122016-04-23Us
Alclometasone Dipropionateointment.5 mg/gtopicalGlenmark Pharmaceuticals Inc., Usa2009-07-302016-04-05Us
Alclometasone Dipropionatecream.5 mg/gtopicalPhysicians Total Care, Inc.2009-06-232016-04-05Us
Alclometasone Dipropionateointment.5 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.2004-07-292016-04-05Us
Alclometasone Dipropionatecream.5 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.2005-09-152016-04-05Us
Alclometasone Dipropionateointment.5 mg/gtopicalE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.2005-07-182016-04-23Us
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Alclometasone dipropionate
66734-13-2
Thumb
  • InChI Key: DJHCCTTVDRAMEH-DUUJBDRPSA-N
  • Monoisotopic Mass: 520.2227812
  • Average Mass: 521.05
DBSALT000893
Categories
UNII136H45TB7B
CAS number67452-97-5
WeightAverage: 408.916
Monoisotopic: 408.170351745
Chemical FormulaC22H29ClO5
InChI KeyInChIKey=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[[email protected]](O)[C@@]1([H])[C@@]2([H])[[email protected]](Cl)CC2=CC(=O)C=C[C@]12C
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassHydroxysteroids
Direct Parent21-hydroxysteroids
Alternative Parents
Substituents
  • 21-hydroxysteroid
  • Progestogin-skeleton
  • Pregnane-skeleton
  • 20-oxosteroid
  • 17-hydroxysteroid
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • Oxosteroid
  • Halo-steroid
  • 7-halo-steroid
  • 3-oxosteroid
  • 3-oxo-delta-1,4-steroid
  • Delta-1,4-steroid
  • Tertiary alcohol
  • Cyclic alcohol
  • Alpha-hydroxy ketone
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Alkyl chloride
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.
PharmacodynamicsAlclometasone 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 actionThe 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.
Related Articles
AbsorptionTopical 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 distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic.

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySymptoms 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
Manufacturers
  • Nycomed us inc
  • Altana inc
  • Glenmark generics ltd
  • Taro pharmaceuticals usa inc
  • Glaxosmithkline
Packagers
Dosage forms
FormRouteStrength
Creamtopical.5 mg/g
Ointmenttopical.5 mg/g
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.
PatentsNot Available
Properties
StateSolid
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesD07AB10S01BA10
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (191 KB)
MSDSDownload (26.3 KB)
Interactions
Drug Interactions
Drug
AldesleukinAlclometasone may decrease the antineoplastic activities of Aldesleukin.
CeritinibAlclometasone may increase the hyperglycemic activities of Ceritinib.
CorticorelinThe therapeutic efficacy of Corticorelin can be decreased when used in combination with Alclometasone.
DeferasiroxThe risk or severity of adverse effects can be increased when Alclometasone is combined with Deferasirox.
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Alclometasone.
Food InteractionsNot Available

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 modulator of other transcription factors. Affects inflammatory responses, cellular proliferation and differentiation in target tissues. Could act as a coactivator for STAT5-dependent transcription upon grow...
Gene Name:
NR3C1
Uniprot ID:
P04150
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
unknown
Actions
substrateinducer
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. El-Sankary W, Bombail V, Gibson GG, Plant N: Glucocorticoid-mediated induction of CYP3A4 is decreased by disruption of a protein: DNA interaction distinct from the pregnane X receptor response element. Drug Metab Dispos. 2002 Sep;30(9):1029-34. [PubMed:12167569 ]
  2. Cooper BW, Cho TM, Thompson PM, Wallace AD: Phthalate induction of CYP3A4 is dependent on glucocorticoid regulation of PXR expression. Toxicol Sci. 2008 Jun;103(2):268-77. doi: 10.1093/toxsci/kfn047. Epub 2008 Mar 10. [PubMed:18332045 ]

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
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 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on April 28, 2016 16:20