FLUOROMETHOLONE

First approved in 1959

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H29FO4
Molecular Weight	376.4617
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H]1C[C@H]2[C@@H]3CC[C@](O)(C(C)=O)[C@@]3(C)C[C@H](O)[C@]2(F)[C@@]4(C)C=CC(=O)C=C14

InChI

InChIKey=FAOZLTXFLGPHNG-KNAQIMQKSA-N

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

HIDE SMILES / InChI

Molecular Formula	C22H29FO4
Molecular Weight	376.4617
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/016851s063lbl.pdf
Curator's Comment: description was created based on several sources, including

Fluorometholone is a glucocorticoid employed, usually as eye drops, in the treatment of allergic and inflammatory conditions of the eye. Corticosteroids such as fluorometholone inhibit the inflammatory response to a variety of inciting agents and probably delay or slow healing. 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. Corticosteroids are capable of producing a rise in intraocular pressure. In clinical studies of documented steroid-responders, fluorometholone demonstrated a significantly longer average time to produce a rise in intraocular pressure than dexamethasone phosphate.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glucocorticoid receptor 173 Target ID: CHEMBL2034 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15684812	Agonist 2752
Glucocorticoid receptor 173 Target ID: CHEMBL2034 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7073584	Binding Agent 1076

Conditions

Condition	Modality	Targets	Highest Phase	Product
Inflammation of the palpebral and bulbar conjunctiva, cornea and anterior segment of the globe 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/016851s063lbl.pdf	Primary		Approved 8583	FML Approved Use FML ® ointment is indicated for the treatment of corticosteroid-responsive inflammation of the palpebral and bulbar conjunctiva, cornea and anterior segment of the globe. Launch Date 1972

Doses

Dose	Population	Adverse events
0.1 % 4 times / day steady, ophthalmic Dose: 0.1 %, 4 times / day Route: ophthalmic Route: steady Dose: 0.1 %, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/30267699	healthy, 41.7 years Health Status: healthy Age Group: 41.7 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/30267699	DLT: Allergic reaction... Disc. AE: Intraocular pressure increased... Dose limiting toxicities: Allergic reaction (1 patient) AEs leading to discontinuation/dose reduction: Intraocular pressure increased (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/30267699
0.25 % 3 times / day steady, ophthalmic Recommended Dose: 0.25 %, 3 times / day Route: ophthalmic Route: steady Dose: 0.25 %, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019216s025lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019216s025lbl.pdf	Disc. AE: Glaucoma, Posterior subcapsular cataract... AEs leading to discontinuation/dose reduction: Glaucoma Posterior subcapsular cataract Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019216s025lbl.pdf

AEs

AE	Significance	Dose	Population
Allergic reaction	1 patient DLT, Disc. AE	0.1 % 4 times / day steady, ophthalmic Dose: 0.1 %, 4 times / day Route: ophthalmic Route: steady Dose: 0.1 %, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/30267699	healthy, 41.7 years Health Status: healthy Age Group: 41.7 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/30267699
Intraocular pressure increased	1 patient Disc. AE	0.1 % 4 times / day steady, ophthalmic Dose: 0.1 %, 4 times / day Route: ophthalmic Route: steady Dose: 0.1 %, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/30267699	healthy, 41.7 years Health Status: healthy Age Group: 41.7 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/30267699
Glaucoma	Disc. AE	0.25 % 3 times / day steady, ophthalmic Recommended Dose: 0.25 %, 3 times / day Route: ophthalmic Route: steady Dose: 0.25 %, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019216s025lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019216s025lbl.pdf
Posterior subcapsular cataract	Disc. AE	0.25 % 3 times / day steady, ophthalmic Recommended Dose: 0.25 %, 3 times / day Route: ophthalmic Route: steady Dose: 0.25 %, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019216s025lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019216s025lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
Nav1.5 116	P-gp 2052

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://cdnsciencepub.com/doi/abs/10.1139/o94-075 Page: 567.0	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
Nav1.5 119	inhibitor 2237 Sources: https://bpspubs.onlinelibrary.wiley.com/doi/full/10.1111/j.1476-5381.2011.01415.x Page: 262.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:31625	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31625
eMolecules	30316174	https://www.emolecules.com/cgi-bin/more?vid=30316174
eMolecules	538523	https://www.emolecules.com/cgi-bin/more?vid=538523
MolPort	MolPort-003-941-413	https://www.molport.com/shop/molecule-link/MolPort-003-941-413
ZINC	ZINC000118912517	http://zinc15.docking.org/substances/ZINC000118912517

PubMed

Title	Date	PubMed
Steroid-induced intraocular pressure elevation or glaucoma after penetrating keratoplasty in patients with keratoconus or Fuchs dystrophy.	2009-08	19574912
Efficacy of olopatadine HCI 0.1%, ketotifen fumarate 0.025%, epinastine HCI 0.05%, emedastine 0.05% and fluorometholone acetate 0.1% ophthalmic solutions for seasonal allergic conjunctivitis: a placebo-controlled environmental trial.	2009-08	18631332
Scleral ulceration after vitreoretinal surgery.	2009-07-04	19574702
Validation of a solid-phase extraction and ultra-performance liquid chromatographic tandem mass spectrometric method for the detection of 16 glucocorticoids in pig tissues.	2009-06-03	19485221
Dry eye after cataract surgery and associated intraoperative risk factors.	2009-06	19568353
Comparison of efficacy of bromfenac sodium 0.1% ophthalmic solution and fluorometholone 0.02% ophthalmic suspension for the treatment of allergic conjunctivitis.	2009-06	19348602
The evaluation of the treatment response in obstructive meibomian gland disease by in vivo laser confocal microscopy.	2009-06	19101718
[Post-traumatic striate melanokeratosis in a Caucasian woman].	2009-04	19384762
Effect of chitosan-N-acetylcysteine conjugate in a mouse model of botulinum toxin B-induced dry eye.	2009-04	19365035
Mitomycin-C in hyperopic photorefractive keratectomy.	2009-04	19304089
Topical and oral voriconazole in the treatment of fungal keratitis.	2009-03	19337480
Intravitreal triamcinolone acetonide injection at the time of pars plana vitrectomy for retained lens material.	2009-03	19337473
Safety and efficacy of Intacs in Indian eyes with keratoconus: an initial report.	2009-02-25	19237784
Diagnosis of steroid-induced elevated intraocular pressure and associated lamellar keratitis after laser in situ keratomileusis using optical coherence tomography.	2009-02	19185259
A case of epithelial inclusion cyst of iris.	2008-12	19096245
Effect of nepafenac sodium 0.1% on delayed corneal epithelial healing and haze after photorefractive keratectomy: retrospective comparative study.	2008-09	18721717
Delayed epithelial ingrowth caused by viral conjunctivitis after LASIK.	2008-08-30	18729311
Delayed-onset Actinomyces keratitis after laser in situ keratomileusis.	2008-08	18650675
Juvenile xanthogranuloma of the corneal limbus: report of two cases and review of the literature.	2008-07	18580271
Phosphate concentration in ophthalmic corticoid preparations.	2008-07	18357463
Post-penetrating keratoplasty glaucoma.	2008-06-27	18579984
Recurrent occlusion of laser iridotomy sites after posterior chamber phakic IOL implantation.	2008-06	18612232
A simple new method for identifying the proximal cut end in lower canalicular laceration.	2008-06	18612222
Short-term effect of topical brinzolamide on human central corneal thickness.	2008-05-10	18465712
Diagnosis of steroid-induced glaucoma after photorefractive keratectomy.	2008-04	18500094
Mitomycin C in photorefractive keratectomy: effect on epithelialization and predictability.	2008-04	18362654
Bacterial keratitis after nonpenetrating glaucoma surgery.	2008-04	18361998
Systematic review of the clinical effect of glucocorticoids on nonhematologic malignancy.	2008-03-28	18373855
Treatment of recurrent corneal erosion syndrome using the combination of oral doxycycline and topical corticosteroid.	2008-02-23	18290949
Posttraumatic Stenotrophomonas maltophilia infectious scleritis.	2008-02	18216585
Aggravated dry eye after laser in situ keratomileusis in patients with Sjögren syndrome.	2008-01	18245981
The effect of topical diclofenac on choroidal blood flow in early postoperative pseudophakias with regard to cystoid macular edema formation.	2007-12	18055815
Lacrimal gland inflammatory cytokine gene expression in the botulinum toxin B-induced murine dry eye model.	2007-11-29	18087241
Bilateral peripheral infiltrative keratitis after LASIK.	2007-09	17804925
Infectious crystalline keratopathy caused by Serratia marcescens.	2007-09	17721309
Diagnosis and management of Thygeson's superficial punctate keratitis.	2007-07	17601570
Preclinical investigation of fluorometholone acetate as a potential new adjuvant during vitreous surgery.	2007-07	17186258
Effect of base curve radius of therapeutic lenses on epithelial healing after laser-assisted subepithelial keratectomy.	2007-06	17592238
The variant N363S of glucocorticoid receptor in steroid-induced ocular hypertension in Hungarian patients treated with photorefractive keratectomy.	2007-04-27	17563720
Isolated large limbal nodule as the presenting feature of vernal keratoconjunctivitis.	2007-02-06	17274337
Effects of topical anti-inflammatory agents in a botulinum toxin B-induced mouse model of keratoconjunctivitis sicca.	2007-02	17341147
The safety of 250 microm residual stromal bed in preventing keratectasia after laser in situ keratomileusis (LASIK).	2007-02	17297268
Comparison of topical dry eye medications for the treatment of keratoconjunctivitis sicca in a botulinum toxin B-induced mouse model.	2007-01	17198019
Multifocal lamellar keratitis following laser in situ keratomileusis.	2007-01	17189812
Comparison of laser epithelial keratomileusis with and without the use of mitomycin C.	2006-10	17061715
Conjunctival mucoepidermoid carcinoma in a patient with ocular cicatricial pemphigoid and a review of the literature.	2006-09-05	16950250
Corneal perforation during laser blepharoplasty.	2006-08-11	16898397
Effects of antibiotics and corticosteroid eyedrops on cellular proliferation in cultured human corneal keratocytes.	2006-08	16911920
Subconjunctival crystals in paediatric blepharokeratoconjunctivitis.	2006-08	16879584
Haze after photorefractive keratectomy caused by iatrogenic lagophthalmos.	2006-08	16863982

Patents

Sample Use Guides

In Vivo Use Guide

Instill one drop into the conjunctival sac two to four times daily. During the initial 24 to 48 hours, the dosing frequency may be increased to one application every four hours

Route of Administration: Other

In Vitro Use Guide

IC50 values for hCA-I (Carbonic anhydrase I) and hCA-II were 11.7, 0.11 μm using fluorometholone acetate. For fluorometholone acetate and dexamethasone, Ki values from Lineweaver-Burk plots were obtained as 1.044 and 21.2 μm (noncompetitive) for hCA-I and 9.98 and 8.66 μm (non-competitive) for hCA-II. Fluorometholone acetate showed potent inhibitory effects on esterase activity of hCA-I and hCA-II isozymes.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 07:04:45 GMT 2025` Edited by `admin` on `Wed Apr 02 07:04:45 GMT 2025`
Record UNII	SV0CSG527L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FLUOROMETHOLONE

Official Name

English

FML-S COMPONENT FLUOROMETHOLONE

Preferred Name

English

FML

Brand Name

English

fluorometholone [INN]

Common Name

English

FLUOROMETHOLONE [MI]

Common Name

English

OXYLONE

Brand Name

English

FLUOROMETHOLONE [VANDF]

Common Name

English

9-Fluoro-11?,17-dihydroxy-6?-methylpregna-1,4-diene-3,20-dione

Systematic Name

English

Fluorometholone [WHO-DD]

Common Name

English

PREGNA-1,4-DIENE-3,20-DIONE, 9-FLUORO-11,17-DIHYDROXY-6-METHYL-, (6.ALPHA.,11.BETA.)-

Systematic Name

English

FLUOR-OP

Brand Name

English

NSC-33001

Code

English

FLUOROMETHOLONE [USP-RS]

Common Name

English

FLUOROMETHOLONE [USP MONOGRAPH]

Common Name

English

FLUOROMETHOLONE [JAN]

Common Name

English

FLUOROMETHOLONE [ORANGE BOOK]

Common Name

English

FLUOROMETHOLONE [MART.]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000175450