Basic information
- CAS
426-13-1- Standard SMILES
CC(=O)[C@@]1(O)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C- InChIKey
FAOZLTXFLGPHNG-KNAQIMQKSA-N- Molecular formula
- C22H29FO4
- Average molar mass
- 376.5 g/mol
- Monoisotopic mass
- 376.20498756
Overview
Fluorometholone is a member of the class of glucocorticoids that is 1-progesterone substituted at positions 11beta and 17 by hydroxy groups, at position 6alpha by a methyl group and at position 9 by a fluoro group. Used for the treatment of corticosteroid-responsive inflammation of the palpebral and bulbar conjunctiva, cornea and anterior segment of the globe. It has a role as an anti-inflammatory drug. It is a tertiary alpha-hydroxy ketone, a glucocorticoid, a 17alpha-hydroxy steroid, an 11beta-hydroxy steroid, a 20-oxo steroid, a fluorinated steroid and a 3-oxo-Delta(1),Delta(4)-steroid. It is functionally related to a Delta(1)-progesterone.
Names & identifiers
- Preferred name
- Fluorometholone
- IUPAC
- (6S,8S,9R,10S,11S,13S,14S,17R)-17-acetyl-9-fluoro-11,17-dihydroxy-6,10,13-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
- English name
- Fluorometholone
- Molecular formula
- C22H29FO4
- Molecular weight
- 376.46
Names & synonyms
fluorometholone426-13-1OxyloneFluor-OpFML ForteFluorometolonaFluorometholonumFluorometoloneDTXSID70474359-Fluoro-11beta,17-dihydroxy-6alpha-methylpregna-1,4-diene-3,20-dioneFluaton(6S,8S,9R,10S,11S,13S,14S,17R)-17-acetyl-9-fluoro-11,17-dihydroxy-6,10,13-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
Show more names
fluoromethaloneFlurometholoneFMLFlulonU 8614UrsnonFluoronFML SOP
SV0CSG527LNSC-33001Fluoro OphtalIsopto FluconCHEBI:31625NSC33001DTXCID5027435Pregna-1,4-diene-3,20-dione, 9-fluoro-11,17-dihydroxy-6-methyl-, (6alpha,11beta)-
Database identifiers
- CAS
426-13-1- PubChem CID
- 9878
Properties
Computed structural properties
- XLogP
- 2
- Topological polar surface area
- 74.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 1
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 787
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Dermatologicals -> Corticosteroids, dermatological preparations
Pharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesMagnetic anisotropy
LogP
2
2.65
Solubility1.66e-02 g/L
Human Drugs
Breast Feeding; Lactation; Anti-Inflammatory Agents; Corticosteroids, Ophthalmic; Glucocorticoids;
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Pharmaceuticals
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point
292-303
297 °C
Physical DescriptionSolid
Collision Cross Section
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
H302 (89.1%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 46 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Other Safety InformationIMAP assessments - Pregna-1,4-diene-3,20-dione, 9-fluoro-11,17-dihydroxy-6-methyl-, (6.alpha.,11.beta.)-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (89.1%)
Toxicology
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- TU3834100
- hs_code
- 29189900
- Toxicity
- rat,LD,oral,> 2gm/kg (2000mg/kg),Kiso to Rinsho. Clinical Report. Vol. 8, Pg. 2349, 1974.
- risk_code
- 20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
Chemistry & industry
Pharmacology
ATC Code
S01BA07
S - Sensory organs
D - Dermatologicals
D - Dermatologicals
S - Sensory organs
C - Cardiovascular system
Pharmacodynamics
Corticosteroids such as fluorometholone inhibit the inflammatory response to a variety of inciting agents and probably delay or slow healing. They inhibit the edema, fibrin deposition, capillary dilation, leukocyte migration, capillary proliferation, fibroblast proliferation, deposition of collagen, and scar formation associated with inflammation.
Mechanism of Action
There is no generally accepted explanation for the mechanism of action of ocular corticosteroids. However, corticosteroids are thought to act by the induction of phospholipase A2 inhibitory proteins, collectively called lipocortins. It is postulated that these proteins control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes by inhibiting the release of their common precursor, arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A2. Their primary target is the cytosolic glucocorticoid receptor. After binding the receptor the newly formed receptor-ligand complex translocates itself into the cell nucleus, where it binds to many glucocorticoid response elements (GRE) in the promoter region of the target genes. The DNA bound receptor then interacts with basic transcription factors, causing the increase in expression of specific target genes.
FDA Pharmacological Classification
SV0CSG527L
FLUOROMETHOLONE
Established Pharmacologic Class [EPC] - Corticosteroid
Mechanisms of Action [MoA] - Corticosteroid Hormone Receptor Agonists
Fluorometholone is a Corticosteroid. The mechanism of action of fluorometholone is as a Corticosteroid Hormone Receptor Agonist.
FLUOROMETHOLONE
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.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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