Overview Clinical application Precautions
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Fluorometholone

Overview Clinical application Precautions
Product Name
Fluorometholone
CAS No.
426-13-1
Chemical Name
Fluorometholone
Synonyms
FML;Flulon;U 8614;Ursnon;Fluoron;Fluaton;FML SOP;oxylone;trilcin;Fluor-Op
CBNumber
CB9461978
Molecular Formula
C22H29FO4
Formula Weight
376.46
MOL File
426-13-1.mol
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Fluorometholone Property

Melting point:
292-303°
alpha 
+52～+60°(c=1, pyridine) (D/20℃)
Boiling point:
527.1±50.0 °C(Predicted)
Density 
1.0573 (rough estimate)
refractive index 
55 ° (C=1, Pyridine)
storage temp. 
2-8°C
solubility 
DMSO (Slightly), Methanol (Slightly), Pyridine (Slightly)
form 
Solid
pka
12.50±0.70(Predicted)
color 
White to Off-White
Water Solubility 
30mg/L(25 ºC)
Merck 
14,4175
CAS DataBase Reference
426-13-1(CAS DataBase Reference)
EPA Substance Registry System
Fluorometholone (426-13-1)
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Safety

Hazard Codes 
Xn
Risk Statements 
20/21/22
Safety Statements 
36
WGK Germany 
3
RTECS 
TU3834100
HS Code 
29189900
Toxicity
rat,LD,oral,> 2gm/kg (2000mg/kg),Kiso to Rinsho. Clinical Report. Vol. 8, Pg. 2349, 1974.
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
F9381
Product name
Fluorometholone
Purity
≥98%
Packaging
100mg
Price
$140
Updated
2024/03/01
Sigma-Aldrich
Product number
PHR3405
Product name
Fluorometholone
Purity
certified reference material, pharmaceutical secondary standard
Packaging
400MG
Price
$241
Updated
2024/03/01
Sigma-Aldrich
Product number
BP573
Product name
Fluorometholone
Purity
British Pharmacopoeia (BP) Reference Standard
Packaging
100MG
Price
$223
Updated
2024/03/01
Sigma-Aldrich
Product number
1278007
Product name
Fluorometholone
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$436
Updated
2024/03/01
TCI Chemical
Product number
F0414
Product name
Fluorometholone
Purity
>98.0%(HPLC)
Packaging
1g
Price
$201
Updated
2024/03/01
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Fluorometholone Chemical Properties,Usage,Production

Overview

Fluorometholone is the topical synthetic glucocorticoid. Its tropical anti-inflammatory effect is 40 times as much as hydrocortisone, but their effects of oral administration are almost equal. It is mainly used for local treatment of skin allergy, pruritus, rash and other diseases related to allergy. Oral administration is also used for the treatment of breast cancer, childhood leukemia, connective tissue disease, and so on.

Clinical application

It is mainly the topical medication for various skin diseases that are suitable for glucocorticoid treatment, for allergic and inflammatory eye diseases, and for breast cancer and childhood leukemia.

Precautions

  1. The adverse reaction of this drug is similar to that of other glucocorticoid hormones, but the degree is lighter. The transocular administration of this drug can cause irritation of local burning sensation and foreign body sensation. Long-term use of this drug can cause the increase of intraocular pressure and even glaucoma. It can occasionally cause optic nerve damage, subcapsular cataract, secondary ocular tissue fungal and virus infection, perforation of eyeball and delayed wound healing, 
  2. Cross allergy: People allergic to other adrenocortical hormone drugs may also be allergic to this drug.
  3. Contraindications: Allergic to glucocorticoid, acute superficial herpes simplex viral keratitis, varicella, cowpox and most other viral infections, ocular fungal infection and ophthalmic tuberculosis.
  4. Cautious use: Any person who suffers the pathological changes that can make the cornea and sclera thinner or who have a history of herpes simplex viral keratitis, pregnant women and breast-feeding women.

Chemical Properties

White powder

Originator

Oxylone, Upjohn, US,1959

Uses

Fluorometholone is a glucocorticoid; anti-inflammatory.

Definition

ChEBI: A member of the class of glucocorticoids that is Delta1-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.

Manufacturing Process

The following description is taken from US Patent 2,867,637.
(a) Preparation of 6α-Methyl-9α-Fluoro-11β,17α,21-Trihydroxy-1,4Pregnadiene-3,20-Dione 21-Methanesulfonate: A solution was prepared containing 250 mg of 1-dehydro-6α-methyl-9α-fluorohydrocortisone [G.B. Spero et al, J. Am. Chem. Soc.79, 1515 (1957)] in 6 ml of pyridine. This solution was cooled to 0°C and treated with 0.25 ml of methanesulfonyl chloride. Thereafter the solution was allowed to stir at a temperature between 0° and 5°C for a period of 18 hours. Thereafter ice and 2 ml of water were added, followed by 30 ml of sufficient dilute (5%) hydrochloric acid to neutralize the pyridine. The mixture was then filtered, the precipitate washed with water and dried to give 197 mg of crude 6α-methyl-9α-fluoro11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione 21-methanesulfonate of MP 165° to 185°C.
(b) Preparation of 6α-Methyl-9α-Fluoro-11β,17α-Dihydroxy-21-Iodo-1,4Pregnadiene-3,20-Dione: The crude 197 mg of methanesulfonate of 6αmethyl-9α-fluoro-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione was dissolved in 5 ml of acetone and treated with a solution of 197 mg of sodium iodide in 5 ml of acetone. The mixture was heated under reflux with stirring for a period of 15 minutes. The heating was then discontinued and the mixture concentrated to dryness at reduced pressure to give 6α-methyl-9αfluoro-11β,17α-dihydroxy-21-iodo-1,4-pregnadiene-3,20-dione.
(c) Preparation of 6α-Methyl-9α-Fluoro-11β,17α-Dihydroxy-1,4-Pregnadiene3,20-Dione: The crude 6α-methyl-9α-fluoro-11β,17α-dihydroxy-21-iodo-1,4pregnadiene-3,20-dione was slurried with 5 ml of acetic acid and stirred for a period of 45 minutes. Thereafter was added a solution of 250 mg of sodium thiosulfate pentahydrate in 5 ml of water causing the iodine color to disappear. Additional water was added (30 ml) and the reaction mixture was filtered. The resulting solid precipitate was washed with water and dried to give 146 mg of crude 6α-methyl-9α-fluoro-11β,17α-dihydroxy-1,4pregnadiene-3,20-dione.
The crude material was then chromatographed by dissolving 120 mg of 6αmethyl-9α-fluoro-11β,17α-dihydroxy-1,4-pregnadiene-3,20-dione in 300 ml of methylene chloride and allowing the thus obtained solution to be absorbed by a chromatographic column containing 10 grams of Florisil anhydrous magnesium silicate. The column was developed taking fractions of 20 ml each as follows:Fractions 11 through 24 inclusive were combined, evaporated and twice recrystallized from acetone to give pure 6α-methyl-9α-fluoro-11β,17αdihydroxy-1,4-pregnadiene-3,20-dione of melting point 292° to 303°C.

brand name

Flarex (Alcon).

Therapeutic Function

Glucocorticoid, Antiinflammatory

General Description

Fluorometholone, 9-fluoro-11β,17-dihydroxy-6α-methylpregn-4-ene-3,20-dione(Fluor-Op, FML), lacks the typical C21 OH group of GCsand is used exclusively in ophthalmic products. The 17-acetateof fluorometholone is also used as an ophthalmic suspension(Flarex).

Biochem/physiol Actions

Clinically significant in allergic conjunctivitis and as anti-inflammatory following cataract surgery.

Fluorometholone Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Fluorometholone manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Fluorometholone 426-13-1
Price
US $0.00/g/Bag
Min. Order
100g
Purity
97%-103%
Supply Ability
1000g
Release date
2021-08-03
Wuhan Senwayer Century Chemical Co.,Ltd
Product
Fluorometholone 426-13-1
Price
US $1500.00/gram
Min. Order
100gram
Purity
99% HPLC
Supply Ability
20 tons
Release date
2022-10-21
Weijer International Trade (Hebei) Co., Ltd
Product
fluoromethalone 426-13-1
Price
US $1.00/kg
Min. Order
1kg
Purity
>99%
Supply Ability
3000T
Release date
2023-03-16

426-13-1, FluorometholoneRelated Search:

Thiophanate-methyl Bensulfuron methyl Kresoxim-methyl Flumethasone (6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic acid Methyl Methyl bromide Fluorine Eflone FLUOROCYCLOHEXANE (1-FLUOROCYCLOHEXYL)METHANOL TRANS-2-FLUOROCYCLOHEXANOL CIS,CIS,CIS-1,3,5-TRIMETHYLCYCLOHEXANE Methylprednisolone 2-FLUORO-2-METHYL-PROPAN-1-OL 1-FLUOROTETRADECANE TERT-BUTYL FLUORIDE 1,1,3,5-TETRAMETHYLCYCLOHEXANE

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  • Pregna-1,4-diene-3,20-dione,9-fluoro-11,17-dihydroxy-6-Methyl-, (6a,11b)-
  • Fluorometholone 426-13-1
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