U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of FLUOROMETHOLONE

SMILES

[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)C[C@H](O)[C@@]3(F)[C@@]2([H])C[C@H](C)C4=CC(=O)C=C[C@]34C

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
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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

6.4022401E10
Doses

Doses

DosePopulationAdverse 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:
healthy, 41.7 years
n = 76
Health Status: healthy
Age Group: 41.7 years
Sex: M+F
Population Size: 76
Sources:
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:
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:
unhealthy
Health Status: unhealthy
Condition: orticosteroid-responsive inflammation of the palpebral and bulbar conjunctiva
Sources:
Disc. AE: Glaucoma, Posterior subcapsular cataract...
AEs leading to
discontinuation/dose reduction:
Glaucoma
Posterior subcapsular cataract
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
healthy, 41.7 years
n = 76
Health Status: healthy
Age Group: 41.7 years
Sex: M+F
Population Size: 76
Sources:
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:
healthy, 41.7 years
n = 76
Health Status: healthy
Age Group: 41.7 years
Sex: M+F
Population Size: 76
Sources:
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:
unhealthy
Health Status: unhealthy
Condition: orticosteroid-responsive inflammation of the palpebral and bulbar conjunctiva
Sources:
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:
unhealthy
Health Status: unhealthy
Condition: orticosteroid-responsive inflammation of the palpebral and bulbar conjunctiva
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Ocular-hypertensive and anti-inflammatory response to rimexolone therapy in children.
2003 Dec
In vitro drug-induced spoliation of a keratoprosthetic hydrogel.
2004 Aug
Effect of topical 0.1% indomethacin solution versus 0.1% fluorometholon acetate on ocular surface and pain control following laser subepithelial keratomileusis (LASEK).
2004 Aug
Quantitative, highly sensitive liquid chromatography-tandem mass spectrometry method for detection of synthetic corticosteroids.
2004 Dec
Ocular rosacea in childhood.
2004 Jan
[A retrospective analysis of infection after corneal transplantation].
2004 Jun
Evaluation of ophthalmic suspensions using surface tension.
2004 Mar
Thygeson's superficial punctate keratitis recurrence after laser in situ keratomileusis.
2004 Sep
The efficacy of hourly prophylactic steroids in diffuse lamellar keratitis epidemic.
2004 Sep-Oct
US trends in refractive surgery: 2003 ISRS/AAO survey.
2005 Jan-Feb
Experimental study of an automated system for the delivery of eyedrops using a microinfusion pump.
2005 Mar
[Intraocular pressure after ND: YAG laser capsulotomy in pseudophakic patients with glaucoma].
2006
Effects of antibiotics and corticosteroid eyedrops on cellular proliferation in cultured human corneal keratocytes.
2006 Aug
A clinical study of the efficacy of topical corticosteroids on dry eye.
2006 Aug
Corneal perforation during laser blepharoplasty.
2006 Jul-Aug
Conjunctival mucoepidermoid carcinoma in a patient with ocular cicatricial pemphigoid and a review of the literature.
2006 Sep-Oct
Comparison of topical dry eye medications for the treatment of keratoconjunctivitis sicca in a botulinum toxin B-induced mouse model.
2007 Jan
Isolated large limbal nodule as the presenting feature of vernal keratoconjunctivitis.
2007 Jan-Feb
Diagnosis and management of Thygeson's superficial punctate keratitis.
2007 Jul
Effect of base curve radius of therapeutic lenses on epithelial healing after laser-assisted subepithelial keratectomy.
2007 Jun
Lacrimal gland inflammatory cytokine gene expression in the botulinum toxin B-induced murine dry eye model.
2007 Nov 29
Infectious crystalline keratopathy caused by Serratia marcescens.
2007 Sep
Mitomycin C in photorefractive keratectomy: effect on epithelialization and predictability.
2008 Apr
Bacterial keratitis after nonpenetrating glaucoma surgery.
2008 Apr
Delayed-onset Actinomyces keratitis after laser in situ keratomileusis.
2008 Aug
Delayed epithelial ingrowth caused by viral conjunctivitis after LASIK.
2008 Aug 30
A case of epithelial inclusion cyst of iris.
2008 Dec
Posttraumatic Stenotrophomonas maltophilia infectious scleritis.
2008 Feb
Aggravated dry eye after laser in situ keratomileusis in patients with Sjögren syndrome.
2008 Jan
Treatment of recurrent corneal erosion syndrome using the combination of oral doxycycline and topical corticosteroid.
2008 Jan-Feb
Juvenile xanthogranuloma of the corneal limbus: report of two cases and review of the literature.
2008 Jul
Phosphate concentration in ophthalmic corticoid preparations.
2008 Jul
Post-penetrating keratoplasty glaucoma.
2008 Jul-Aug
Recurrent occlusion of laser iridotomy sites after posterior chamber phakic IOL implantation.
2008 Jun
A simple new method for identifying the proximal cut end in lower canalicular laceration.
2008 Jun
Effect of nepafenac sodium 0.1% on delayed corneal epithelial healing and haze after photorefractive keratectomy: retrospective comparative study.
2008 Sep
[Post-traumatic striate melanokeratosis in a Caucasian woman].
2009 Apr
Effect of chitosan-N-acetylcysteine conjugate in a mouse model of botulinum toxin B-induced dry eye.
2009 Apr
Mitomycin-C in hyperopic photorefractive keratectomy.
2009 Apr
Steroid-induced intraocular pressure elevation or glaucoma after penetrating keratoplasty in patients with keratoconus or Fuchs dystrophy.
2009 Aug
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 Aug
Diagnosis of steroid-induced elevated intraocular pressure and associated lamellar keratitis after laser in situ keratomileusis using optical coherence tomography.
2009 Feb
Scleral ulceration after vitreoretinal surgery.
2009 Jul-Aug
Dry eye after cataract surgery and associated intraoperative risk factors.
2009 Jun
Comparison of efficacy of bromfenac sodium 0.1% ophthalmic solution and fluorometholone 0.02% ophthalmic suspension for the treatment of allergic conjunctivitis.
2009 Jun
The evaluation of the treatment response in obstructive meibomian gland disease by in vivo laser confocal microscopy.
2009 Jun
Topical and oral voriconazole in the treatment of fungal keratitis.
2009 Mar
Intravitreal triamcinolone acetonide injection at the time of pars plana vitrectomy for retained lens material.
2009 Mar
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 Mar-Apr
Safety and efficacy of Intacs in Indian eyes with keratoconus: an initial report.
2009 Mar-Apr
Patents

Sample Use Guides

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
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 Thu Jul 06 21:35:36 UTC 2023
Edited
by admin
on Thu Jul 06 21:35:36 UTC 2023
Record UNII
SV0CSG527L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FLUOROMETHOLONE
INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
FML
Brand Name English
fluorometholone [INN]
Common Name English
FLUOROMETHOLONE COMPONENT OF FML-S
Common Name English
FLUOROMETHOLONE [MI]
Common Name English
OXYLONE
Brand Name English
FLUOROMETHOLONE [VANDF]
Common Name English
9-Fluoro-11β,17-dihydroxy-6α-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
FML-S COMPONENT FLUOROMETHOLONE
Common 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
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
NDF-RT N0000175576
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
WHO-VATC QD07AB06
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
NCI_THESAURUS C521
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
WHO-ATC C05AA06
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
WHO-ATC D07AB06
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
WHO-VATC QC05AA06
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
WHO-VATC QD07XB04
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
WHO-ATC D10AA01
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
WHO-ATC S01CA07
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
WHO-VATC QS01BA07
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
WHO-ATC D07CB03
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
WHO-VATC QS01CB05
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
WHO-ATC S01BB03
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
WHO-VATC QD07CB03
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
WHO-VATC QS01BB03
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
WHO-VATC QD10AA01
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
WHO-VATC QS01CA07
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
WHO-ATC S01BA07
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
WHO-ATC D07XB04
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
WHO-ATC S01CB05
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C29058
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
PRIMARY
FDA UNII
SV0CSG527L
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
PRIMARY
WIKIPEDIA
FLUOROMETHOLONE
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
PRIMARY
DRUG BANK
DB00324
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
PRIMARY
IUPHAR
7079
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
PRIMARY
MERCK INDEX
M5477
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
PRIMARY Merck Index
EVMPD
SUB07720MIG
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
PRIMARY
DRUG CENTRAL
1208
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
PRIMARY
RXCUI
4491
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
PRIMARY RxNorm
RS_ITEM_NUM
1278007
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
PRIMARY
ECHA (EC/EINECS)
207-041-5
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
PRIMARY
LACTMED
Fluorometholone
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
PRIMARY
CAS
426-13-1
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
PRIMARY
SMS_ID
100000091928
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
PRIMARY
PUBCHEM
9878
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
PRIMARY
DAILYMED
SV0CSG527L
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
PRIMARY
EPA CompTox
DTXSID7047435
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
PRIMARY
ChEMBL
CHEMBL1200600
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
PRIMARY
CHEBI
31625
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
PRIMARY
NSC
33001
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
PRIMARY
MESH
D005469
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
PRIMARY
INN
803
Created by admin on Thu Jul 06 21:35:36 UTC 2023 , Edited by admin on Thu Jul 06 21:35:36 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST
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PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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ACTIVE MOIETY