(1R,2S,8S,10S,11S,14R,15S,17S)-14-acetyl-1-fluoro-14,17-dihydroxy-2,8,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

• ChemBase ID: 209
• Molecular Formular: C22H29FO4
• Molecular Mass: 376.4616632
• Monoisotopic Mass: 376.20498763
• SMILES: F[C@@]12[C@H]([C@H]3[C@@]([C@](O)(CC3)C(=O)C)(C[C@@H]1O)C)C[C@@H](C1=CC(=O)C=C[C@]21C)C
• Canonical SMILES: O=C1C=C[C@]2(C(=C1)[C@@H](C)C[C@@H]1[C@]2(F)[C@@H](O)C[C@]2([C@H]1CC[C@]2(O)C(=O)C)C)C
• InChI: InChI=1S/C22H29FO4/c1-12-9-17-15-6-8-21(27,13(2)24)20(15,4)11-18(26)22(17,23)19(3)7-5-14(25)10-16(12)19/h5,7,10,12,15,17-18,26-27H,6,8-9,11H2,1-4H3/t12-,15-,17-,18-,19-,20-,21-,22-/m0/s1
• InChIKey: FAOZLTXFLGPHNG-KNAQIMQKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,8S,10S,11S,14R,15S,17S)-14-acetyl-1-fluoro-14,17-dihydroxy-2,8,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one; (1R,2S,8S,10S,11S,14R,15S,17S)-14-acetyl-1-fluoro-14,17-dihydroxy-2,8,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one
• IUPAC Traditional name: fluorometholone
• Brand Name: Cortilet; Delmeson; Efflumidex; FML Liquifilm; Flarex; Fluaton; Flumetholon; Fluor-op; FML Forte; Loticort; Oxylone; Trilcin; Ursnon
• Synonyms: 11β,17α-Dihydroxy-9-fluoro-6-methyl-1,4-pregnadiene-3,20-dione; Fluorometholone; (6α,11β)-9-Fluoro-11,17-dihydroxy-6-methylpregna-1,4-diene-3,20-dione; 21-Desoxy-9α-fluoro-6-methylprednisolone; 6α-Methyl-9α-fluoro-11β,17α-dihydroxypregna-1,4-diene-3,20-dione; 6α-Methyl-9α-fluoro-21-desoxyprednisolone; 9α-Fluoro-11β,17α-dihydroxy-6α-methylpregna-1,4-diene-3,20-dione; Cortilet; Delmeson; Efflumidex; FML Forte; FML Liquifilm; FML SOP; Fluaton; Fluaton PVA; Flumetholon; Flumetholone; Fluor-Op; Loticort; NSC-33001; Oxylone; U 8614; Ursnon; FML; Fluoromethalone; Fluormetholone; Fluormetholon; Fluorometholone; 11β, 17α-Dihydroxy-9-fluoro-6-methyl-1,4-pregnadiene-3,-20-dione

Database IDs

• CAS Number: 426-13-1
• EC Number: 207-041-5
• MDL Number: MFCD00056461
• PubChem SID: 24894996; 160963672; 46505984
• PubChem CID: 9878

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.648287
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.4208639
• LogD (pH = 7.4): 2.4208615
• Log P: 2.420864
• Molar Refractivity: 100.8677 cm^3
• Polarizability: 38.960907 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.34
• LOG S: -4.36
• Solubility (Water): 1.66e-02 g/l

PROPERTIES

Physical Property

• Solubility: 30 mg/L; DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 274-276°C
• Hydrophobicity(logP): 2

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C), Protect from light
• RTECS: TU3834100
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98%

DETAILS

MP Biomedicals - 02190208

(11β, 17α-Dihydroxy-9-fluoro-6-methyl-1,4-pregnadiene-3,-20-dione)

DrugBank - DB00324

• Drug Groups: approved
• Description: A glucocorticoid employed, usually as eye drops, in the treatment of allergic and inflammatory conditions of the eye. It has also been used topically in the treatment of various skin disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p732)
• Indication: For the ophthalmic treatment of corticosteroid-responsive inflammation of the palpebral and bulbar conjunctiva, cornea and anterior segment of the globe.
• Pharmacology: 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.
• Toxicity: Side effects may include acute anterior uveitis and perforation of the globe. Keratitis, conjunctivitis, corneal ulcers, mydriasis, conjunctival hyperemia, loss of accommodation and ptosis have occasionally been reported following local use of corticosteroids. LD₅₀ = 234 mg/kg (rats)
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Sigma Aldrich - F9381

Biochem/physiol Actions
Clinically significant in allergic conjunctivitis and as anti-inflammatory following cataract surgery.1

Toronto Research Chemicals - F593145

Fluorometholone is a glucocorticoid; anti-inflammatory.

REFERENCES

• Kupferman, A., et al.: Arch. Ophthlmol., 640, 100 (1982)
• Tokunaga H., et al.: Chem. Pharm. Bull., 32, 4012 (1982)