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2135-17-3 molecular structure
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(1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

ChemBase ID: 134258
Molecular Formular: C22H28F2O5
Molecular Mass: 410.4515264
Monoisotopic Mass: 410.19048044
SMILES and InChIs

SMILES:
C[C@@H]1C[C@H]2[C@@H]3C[C@@H](C4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)CO)O)C)O)F)C)F
Canonical SMILES:
OCC(=O)[C@@]1(O)[C@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2C[C@@H](C2=CC(=O)C=C[C@]12C)F)F
InChI:
InChI=1S/C22H28F2O5/c1-11-6-13-14-8-16(23)15-7-12(26)4-5-19(15,2)21(14,24)17(27)9-20(13,3)22(11,29)18(28)10-25/h4-5,7,11,13-14,16-17,25,27,29H,6,8-10H2,1-3H3/t11-,13+,14+,16+,17+,19+,20+,21+,22+/m1/s1
InChIKey:
WXURHACBFYSXBI-GQKYHHCASA-N

Cite this record

CBID:134258 http://www.chembase.cn/molecule-134258.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one
IUPAC Traditional name
flumethasone
Synonyms
6α,9α-Difluoro-16α-methyl-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione
6α,9α-Difluoro-16α-methylprednisolone
6α-Fluorodexamethasone
Flumethasone
(6α,11β,16α)-6,9-Difluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione
6α-Fluorodexamethazone
Anaprime
Aniprime
Aniprome
Cortexillar
Flucort
Flucorticin
Flumetasone
Flumethason
Fluvet
Methagon
NSC 5402
NSC 54702
RS 2177
U 10974
Vecort
Flumethasone
CAS Number
2135-17-3
EC Number
218-370-9
MDL Number
MFCD00056464
PubChem SID
24894998
162228535
PubChem CID
16490

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 16490 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 12.418192  H Acceptors
H Donor LogD (pH = 5.5) 1.3418503 
LogD (pH = 7.4) 1.3418462  Log P 1.3418504 
Molar Refractivity 102.3163 cm3 Polarizability 39.40079 Å3
Polar Surface Area 94.83 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Methanol expand Show data source
Apperance
White Solid expand Show data source
Melting Point
237-240°C expand Show data source
Storage Condition
-20°C Freezer expand Show data source
RTECS
TU3832000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
40 expand Show data source
Safety Statements
22-36 expand Show data source
GHS Pictograms
GHS08 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H351 expand Show data source
GHS Precautionary statements
P281 expand Show data source
Personal Protective Equipment
Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
Storage Temperature
2-8°C expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich TRC TRC
Sigma Aldrich - F9507 external link
Application
Flumethasone pivalate is a topical corticosteroid. Prompt decrease in inflammation, exudation and itching is experienced after application. It is a difluorinated corticosteroid ester with anti-inflammatory, antipruritic and vasoconstrictive properties. Flumethasone is a corticosteroid commonly used in veterinary practice1 and has been used in cortisol assays to study early porcine conceptus development2.
Biochem/physiol Actions
Flumethasone is a glucocorticoid receptor agonist used in studies on plasma transcortin binding.
Flumethasone is a glucocorticoid receptor agonist. It binds to the nucleus causing a variety of genetic activation and repressions. The anti-inflammatory actions of flumethasone is thought to involve lipocortins and phospholipase A2 inhibitory proteins, which results in the inhibition of arachidonic acid and the control of prostaglandin and leukotriene biosynthesis. Flumethasone suppresses the immune system 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 .
Toronto Research Chemicals - F455000 external link
A glucocorticoid. An anti-inflammatory.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Matuszewski, B, et al.: Anal. Chem., 75, 3019 (2003)
  • • Fekete, S., et al.: J. Pharm. Biomed. Anal., 49, 64 (2003)
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PATENTS

PATENTS

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INTERNET

INTERNET

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