Basic information
- CAS
2135-17-3- Standard SMILES
CC1CC2C3CC(F)C4=CC(=O)C=CC4(C)C3(F)C(O)CC2(C)C1(O)C(=O)CO- InChIKey
WXURHACBFYSXBI-UHFFFAOYSA-N- Molecular formula
- C22H28F2O5
- Average molar mass
- 410.5 g/mol
- Monoisotopic mass
- 410.19048031
Names & identifiers
- Preferred name
- 6,9-Difluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
- IUPAC
- 6,9-difluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
- English name
- Flumethasone
- Molecular formula
- C22H28F2O5
- Molecular weight
- 410.45
Names & synonyms
Aniprime6,9-Difluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione6.alpha.-FluorodexamethasoneC22H28F2O5MFCD000564646,9-difluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-oneCHEMBL2007346DTXSID30859700HMS5082O10HMS5084O12s4088s5360
Show more names
flumetasonefluvetFLUCORTrs-2177anaprimemethagonNSC-54702CORTEXILARha-methyl-
AKOS025149901LS-14954NCI60_004347U 109746.alpha.,9.alpha.-Difluoro-16.alpha.-methylprednisolone6.alpha.,17,21-trihydroxy-16.alpha.-methylpregna-1,4-diene-3,20-dionePregna-1,20-dione, 6.alpha.,9-difluoro-11.beta.,17,21-trihydroxy-16.alpha.-methyl-6|A-Fluorodexamethasone;6|A,9|A-Difluoro-16|A-methylprednisolone;Aniprime;Flumethasone;Fluvet
Database identifiers
Properties
Computed structural properties
- XLogP
- 1.9
- Topological polar surface area
- 94.8 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 2
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 839
Physicochemical properties
- Melting point
- 237 · 237-240°C
- Boiling point
- 569.8 · 569.8±50.0 °C(Predicted)
- Density
- 1.1621 · 1.1621 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- 10 mg/mL · acetic acid: soluble10mg/mL
- form
- solid
- pka
- 11.98 · 11.98±0.70(Predicted)
- color
- white
- optical activity
- 25 · [α]25/D 67.0 to 71.0°, c = 1 in dioxane
- Water Solubility
- 1 mg/L · 1mg/L(20 ºC)
- Merck
- 14 · 14,4138
- InChIKey
- WXURHACBFYSXBI-GQKYHHCASA-N
- SMILES
- C1(=O)C=C2[C@](C)(C=C1)[C@]1(F)[C@]([H])([C@@]3([H])[C@@](C[C@@H]1O)(C)[C@@](O)(C(=O)CO)[C@H](C)C3)C[C@@H]2F
- CAS DataBase Reference
- 2135 · 2135-17-3(CAS DataBase Reference)
- FDA UNII
- 3 CD8SX89 · LR3CD8SX89
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- rtecs
- TU3832000
- hs_code
- 29144000
- risk_code
- 40
- Signal word
- Warning
- Symbol(GHS)
- GHS08
- hazard_code
- Xn
- safety_code
- 22-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H351
- REACH Registrations
- Active
- Hazard Classifications
- Carc. 2
- Precautionary statements
- P281
Chemistry & industry
Applications
DescriptionFlumethasone is a moderately potent difluorinated corticosteroid ester with anti-inflammatory, antipruritic and vasoconstrictive properties. Its mechanism of action is thought to inhibit arachidonic acids role in the biosynthesis of prostaglandins and leukotrienes. Flumethasone is active when it is not bound to the plasma protein transcortin. The drug flumethasone can be used to treat a variety of skin conditions, such as contact dermatitis, bug bites and eczema.
UsesFlumethasone is an anti-inflammatory glucocorticoid used in veterinary practice and used as an anti-inflammatory for a variety of animals. It is commonly investigated for its effectiveness in animals to combat inflammatory symptoms caused by pathogens and to better understand inflammatory mechanisms. It is also used as to investigate novel techniques that detect and quantify steroid compounds within muscles. For the treatment of contact dermatitis, atopic dermatitis, exczema, psoriasis, diaper rash and other skin conditions. Flumethasone is a corticosteroid for topical use, in combination with Clioquinol for the treatment of otitis externa and otomycosis. Flumethasone shows fully 420 times the potency of cortisone in an animal model for anti-inflammatory activity. Flumethasone has been shown to exert anti-inflammtory effects by functioning as a glucocorticoid receptor agonist. Stimulating this receptor promotes inhibition of phospholipase A2 activity. This enzyme catalyzes arachidonic acid into eicosanoids most of which stimulate anti-inflammation mechanisms.
DescriptionFlumethasone is an agonist of glucocorticoid and mineralocorticoid receptors with EC50 values of 0.26 and 0.494 nM, respectively, in CV-1 cells expressing human receptors. In vitro, it inhibits the growth of UM-UC-3, TCC-SUP, and 5637 urothelial carcinoma cell lines at a concentration of 100 nM. Flumethasone (5 mg per animal) decreases tumor necrosis factor (TNF) production ex vivo in blood cells collected by bronchoalveolar lavage (BAL) from calves with experimentally-induced local lung inflammation. It also inhibits phytohemagglutinin-induced delayed hypersensitivity in calf skin. In vivo, flumethasone (5 μM) impairs cell cycle re-entry of cardiac cells seven days post cryo-injury to the heart and impairs cardiac regeneration in zebrafish.
Usestopical anti-inflammatory corticosteroid
UsesA glucocorticoid. An anti-inflammatory.
Related reactions
0 records
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Compound notes
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