Details of the Drug

General Information of Drug (ID: DMUXP52)

Drug Name

Clobetasol

Synonyms

Clobetasolum; Clofenazon; Clobecort Amex; Butavate (TN); Clobecort Amex (TN); Clobetasol (INN); Clobetasol [INN:BAN]; Clobetasolum [INN-Latin]; Clobex (TN); Dermatovate (TN); Dermovate (TN); Movate (TN); Olux (TN); Temovate (TN); Tenovate (TN); (11beta,16beta)-21-chloro-9-fluoro-11,17-dihydroxy-16-methylpregna-1,4-diene-3,20-dione; (8S,9R,10S,11S,13S,14S,16S,17R)-17-(2-chloroacetyl)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one; (9R,17R)-17-(2-chloroacetyl)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one; 17-(2-chloroacetyl)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one; 21-Chloro-9-fluoro-11beta,17-dihydroxy-16beta-methylpregna-1,4-diene-3,20-dione; 21-chloro-9-fluoro-11,17-dihydroxy-16-methylpregna-1,4-diene-3,20-dione

Indication

Disease Entry	ICD 11	Status	REF
Rosacea	ED90.0	Approved	[1]
Oral lichen planus	EA91.4	Phase 2	[2]

Therapeutic Class

Antiinflammatory Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

410.9

Topological Polar Surface Area (xlogp)

2.5

Rotatable Bond Count (rotbonds)

2

Hydrogen Bond Donor Count (hbonddonor)

2

Hydrogen Bond Acceptor Count (hbondacc)

5

Chemical Identifiers

Formula: C22H28ClFO4
IUPAC Name: (8S,9R,10S,11S,13S,14S,16S,17R)-17-(2-chloroacetyl)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
Canonical SMILES: C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)CCl)O)C)O)F)C
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
InChIKey: FCSHDIVRCWTZOX-DVTGEIKXSA-N

Cross-matching ID

PubChem CID: 5311051
ChEBI ID: CHEBI:205919
CAS Number: 25122-41-2
DrugBank ID: DB11750
TTD ID: D0FL5V

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Phospholipase A2 (PLA2G1B)	TT9V5JH	PA21B_HUMAN	Inhibitor	[3]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Rosacea

ICD Disease Classification

ED90.0

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Phospholipase A2 (PLA2G1B)	DTT	PLA2G1B	2.65E-01	-0.08	-0.21

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2	Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
3	Utilization of epidermal phospholipase A2 inhibition to monitor topical steroid action. Br J Dermatol. 1984 Jul;111 Suppl 27:195-203.
4	How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
5	Novel antifungal agents, targets or therapeutic strategies for the treatment of invasive fungal diseases: a review of the literature (2005-2009). Rev Iberoam Micol. 2009 Mar 31;26(1):15-22.
6	Clocortolone pivalate: a paired comparison clinical trial of a new topical steroid in eczema/atopic dermatitis. Cutis. 1980 Jan;25(1):96-8.
7	Structures from powders: diflorasone diacetate. Steroids. 2009 Jan;74(1):102-11.
8	Successful immunotherapy with T-cell epitope peptides of bee venom phospholipase A2 induces specific T-cell anergy in patients allergic to bee venom. J Allergy Clin Immunol. 1998 Jun;101(6 Pt 1):747-54.
9	Synthesis of benzoyl phenyl benzoates as effective inhibitors for phospholipase A2 and hyaluronidase enzymes. Bioorg Med Chem Lett. 2005 Sep 15;15(18):4100-4.
10	Manoalide, a phospholipase A2 inhibitor, inhibits arachidonate incorporation and turnover in brain phospholipids of the awake rat. Neurochem Res. 1998 Oct;23(10):1251-7.
11	Phospholipase A2, group IVA (cytosolic, calcium-dependent) (PLA2G4A). SciBX 1(41); doi:10.1038/scibx.2008.999. Nov. 13 2008
12	A novel treatment of contact dermatitis by topical application of phospholipase A2 inhibitor: a double-blind placebo-controlled pilot study. Int J Immunopathol Pharmacol. 2007 Jan-Mar;20(1):191-5.
13	Effect of treatment for 12 weeks with rilapladib, a lipoprotein-associated phospholipase A2 inhibitor, on arterial inflammation as assessed with 18F-fluorodeoxyglucose-positron emission tomography imaging.J Am Coll Cardiol.2014 Jan 7-14;63(1):86-8.