Basic information
- CAS
2135-17-3- Standard 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)CO- InChIKey
WXURHACBFYSXBI-GQKYHHCASA-N- Molecular formula
- C22H28F2O5
- Average molar mass
- 410.5 g/mol
- Monoisotopic mass
- 410.19048031
Overview
Flumethasone is a primary alpha-hydroxy ketone, a tertiary alpha-hydroxy ketone, a glucocorticoid, a 17alpha-hydroxy steroid, a 21-hydroxy steroid, an 11beta-hydroxy steroid, a 20-oxo steroid, a fluorinated steroid and a 3-oxo-Delta(1),Delta(4)-steroid. It has a role as an anti-inflammatory drug. It derives from a hydride of a pregnane.
Names & identifiers
- Preferred name
- Flumethasone
- IUPAC
- (6S,8S,9R,10S,11S,13S,14S,16R,17R)-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
flumethasone2135-17-3FlumetasoneFlucortFlumetasonaFlumetasonumFluorodexamethasoneDTXSID20453656alpha,9-Difluoro-11beta,17,21-trihydroxy-16alpha-methylpregna-1,4-diene-3,20-dioneBimasoneFlucort TabletsFlucort Solution
Show more names
fluvetrs-2177ANIPRIMEanaprimemethagonCORTEXILARha-methyl-
U-10974LR3CD8SX89Anaprime Suspensionflumethasoni pivalasNSC-54702U-10,974DTXCID0025365CHEBI:34764
Database identifiers
- CAS
2135-17-3- PubChem CID
- 16490
- DTXSID
DTXSID2045365- ChEMBL
CHEMBL1201392- ChEBI
CHEBI:34764- UNII
- LR3CD8SX89
- EC Number
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
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
LogP1.94
Human DrugsPharmaceuticals
Animal DrugsFDA approved animal drugs -> Active ingredient
Collision Cross Section
213.7 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
193.2 Ų [M+H]+ [CCS Type: TW]
189.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
191.31 Ų [M+H]+
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
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H351 (89.1%): Suspected of causing cancer [Warning Carcinogenicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 46 reports by companies from 8 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
REACH registered substance: Flumetasone (EC: 218-370-9)
Pregna-1,4-diene-3,20-dione, 6,9-difluoro-11,17,21-trihydroxy-16-methyl-, (6.alpha.,11.beta.,16.alpha.)-: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Pregna-1,4-diene-3,20-dione, 6,9-difluoro-11,17,21-trihydroxy-16-methyl-, (6.alpha.,11.beta.,16.alpha.)-: Human health tier I assessment
Hazard Classes and CategoriesCarc. 2 (89.1%)
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
Chemistry & industry
Pharmacology
ATC Code
D - Dermatologicals
D - Dermatologicals
QD - Dermatologicals
QH - Systemic hormonal preparations, excl. sex hormones and insulin
QD - Dermatologicals
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.
Metabolism/MetabolitesPrimarily hepatic
MeSH Pharmacological Classification
Substances that reduce or suppress INFLAMMATION.
A group of CORTICOSTEROIDS that affect carbohydrate metabolism (GLUCONEOGENESIS, liver glycogen deposition, elevation of BLOOD SUGAR), inhibit ADRENOCORTICOTROPIC HORMONE secretion, and possess pronounced anti-inflammatory activity. They also play a role in fat and protein metabolism, maintenance of arterial blood pressure, alteration of the connective tissue response to injury, reduction in the number of circulating lymphocytes, and functioning of the central nervous system.
Absorption, Distribution and Excretion
Related reactions
2 records
Compound notes
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