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Identification
Name Flumethasone Pivalate
Accession Number DB00663 (APRD00975)
Type small molecule
Groups approved
Description

Flumethasone pivalate is a moderately potent difluorinated corticosteroid ester with anti-inflammatory, antipruritic and vasoconstrictive properties. As it is a privalate salt, its anti-inflammatory action is concentrated at the site of application. This local effect on diseased areas results in a prompt decrease in inflammation, exudation and itching.
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Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
Locorten
Brand mixtures
Brand Name Ingredients
Locacorten Vioform Clioquinol + Flumethasone Pivalate
Locacorten Vioform Cream Clioquinol + Flumethasone Pivalate
Locacorten Vioform Eardrops Clioquinol + Flumethasone Pivalate
Locasalen Flumethasone Pivalate + Salicylic Acid
Categories
  • Anti-inflammatory Agents
  • Antipruritics
  • Glucocorticoids
CAS number 2002-29-1
Weight Average: 494.5679
Monoisotopic: 494.247995294
Chemical Formula C27H36F2O6
InChI Key InChIKey=JWRMHDSINXPDHB-OJAGFMMFSA-N
InChI
InChI=1S/C27H36F2O6/c1-14-9-16-17-11-19(28)18-10-15(30)7-8-24(18,5)26(17,29)20(31)12-25(16,6)27(14,34)21(32)13-35-22(33)23(2,3)4/h7-8,10,14,16-17,19-20,31,34H,9,11-13H2,1-6H3/t14-,16+,17+,19+,20+,24+,25+,26+,27+/m1/s1
Plain Text
IUPAC Name
2-[(1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl]-2-oxoethyl 2,2-dimethylpropanoate
SMILES
C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O)C(=O)COC(=O)C(C)(C)C
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes
  • Steroids and Steroid Derivatives
Substructures
  • Steroids and Steroid Derivatives
  • Carbonyl Compounds
  • Carboxylic Acids and Derivatives
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Acetates
  • Alkyl Halides
  • Ethers
  • Alcohols and Polyols
  • Ketones
Pharmacology
Indication For the treatment of contact dermatitis, atopic dermatitis, exczema, psoriasis, diaper rash and other skin conditions
Pharmacodynamics Flumethasone pivalate is a moderately potent difluorinated corticosteroid ester with anti-inflammatory, antipruritic and vasoconstrictive properties. As it is a privalate salt, its anti-inflammatory action is concentrated at the site of application. This local effect on diseased areas results in a prompt decrease in inflammation, exudation and itching.
Mechanism of action Flumethasone is a glucocorticoid receptor agonist. This complex binds to the nucleus causing a variety of genetic activation and repressions. The antiinflammatory actions of corticosteroids are thought to involve lipocortins, phospholipase A2 inhibitory proteins which, through inhibition arachidonic acid, control the biosynthesis of prostaglandins and leukotrienes. The immune system is suppressed by corticosteroids due to a decrease in the function of the lymphatic system, a reduction in immunoglobulin and complement concentrations, the precipitation of lymphocytopenia, and interference with antigen-antibody binding. Flumethasone binds to plasma transcortin, and it becomes active when it is not bound to transcortin.
Absorption Minimal if applied topically
Volume of distribution Not Available
Protein binding Not Available
Metabolism Primarily hepatic
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Can lead to signs of irritation such as burning sensation, itching or skin rash at the site of application; hypersensitivity reactions.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Novartis pharmaceuticals corp
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 219 °C (base only) Not Available
water solubility 0.392 mg/L Not Available
logP 3.86 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
water solubility 1.07e-02 g/l ALOGPS
logP 3.21 ALOGPS
logP 3.58 ChemAxon
logS -4.7 ALOGPS
pKa (strongest acidic) 12.44 ChemAxon
pKa (strongest basic) -3.4 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 5 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 100.9 ChemAxon
rotatable bond count 5 ChemAxon
refractivity 125.17 ChemAxon
polarizability 50.96 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D01464 Link_out
PubChem Compound 443980 Link_out
PubChem Substance 46505121 Link_out
ChemSpider 392021 Link_out
ChEBI 31620 Link_out
ChEMBL 31620 Link_out
Therapeutic Targets Database DAP000814 Link_out
PharmGKB PA164749388 Link_out
Drug Product Database 5134 Link_out
ATC Codes
  • C05AA10
  • D07AC04
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Glucocorticoid receptor

Pharmacological action: yes
Actions: agonist

Receptor for glucocorticoids (GC). Has a dual mode of action:as a transcription factor that binds to glucocorticoid response elements (GRE) 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 growth hormone (GH) stimulation and could reveal an essential role of hepatic GR in the control of body growth

Organism class: human
UniProt ID: P04150 Link_out
Gene: NR3C1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  3. Maier C, Runzler D, Schindelar J, Grabner G, Waldhausl W, Kohler G, Luger A: G-protein-coupled glucocorticoid receptors on the pituitary cell membrane. J Cell Sci. 2005 Aug 1;118(Pt 15):3353-61. Pubmed
  4. Labeur M, Holsboer F: Molecular mechanisms of glucocorticoid receptor signaling. Medicina (B Aires). 2010;70(5):457-462. Pubmed
Carriers

1. Corticosteroid-binding globulin

Actions: binder

Major transport protein for glucocorticoids and progestins in the blood of almost all vertebrate species

UniProt ID: P08185 Link_out
Gene: SERPINA6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19