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426-13-1

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426-13-1 Usage

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

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,? Cross allergy: People allergic to other adrenocortical hormone drugs may also be allergic to this drug. Contraindications: Allergic to glucocorticoid, acute superficial herpes simplex viral keratitis, varicella, cowpox and most other viral infections, ocular fungal infection and ophthalmic tuberculosis. 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.

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.

Check Digit Verification of cas no

The CAS Registry Mumber 426-13-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,2 and 6 respectively; the second part has 2 digits, 1 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 426-13:
(5*4)+(4*2)+(3*6)+(2*1)+(1*3)=51
51 % 10 = 1
So 426-13-1 is a valid CAS Registry Number.
InChI:InChI=1/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

426-13-1 Well-known Company Product Price

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  • TCI America

  • (F0414)  Fluorometholone  >98.0%(HPLC)

  • 426-13-1

  • 1g

  • 2,780.00CNY

  • Detail

426-13-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name fluorometholone

1.2 Other means of identification

Product number -
Other names 9-Fluoro-11,17-Dihydroxy-6-Methylpregna-1,4-Diene-3,20-Dione

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:426-13-1 SDS

426-13-1Synthetic route

fluorometholone acetate

fluorometholone acetate

fluorometholone
426-13-1

fluorometholone

Conditions
ConditionsYield
With methanol; sodium hydroxide at 0 - 5℃; for 5h; Reagent/catalyst; Temperature;96.3%
6α-methyl-9,11β-epoxy-17α-hydroxy-pregna-1,4-diene-3,20-dione
83873-16-9

6α-methyl-9,11β-epoxy-17α-hydroxy-pregna-1,4-diene-3,20-dione

fluorometholone
426-13-1

fluorometholone

Conditions
ConditionsYield
With triethylamine tris(hydrogen fluoride) at 25℃;90%
With hydrogen fluoride; water at -35℃; for 4h;80%
9-fluoro-11β,17,21-trihydroxy-6α-methyl-pregna-1,4-diene-3,20-dione
382-52-5

9-fluoro-11β,17,21-trihydroxy-6α-methyl-pregna-1,4-diene-3,20-dione

fluorometholone
426-13-1

fluorometholone

Conditions
ConditionsYield
ueber mehrere Stufen;
6α-methyl-17α-hydroxy-pregna-1,4,9(11)-triene-3,20-dione
110664-42-1

6α-methyl-17α-hydroxy-pregna-1,4,9(11)-triene-3,20-dione

fluorometholone
426-13-1

fluorometholone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydroxide; dihydrogen peroxide / methanol / 9 h / 35 - 45 °C / Inert atmosphere
2.1: hydrogen fluoride / N,N-dimethyl-formamide / 3 h / -4 - 0 °C
2.2: 3 h / pH 7
View Scheme
C22H28O4

C22H28O4

fluorometholone
426-13-1

fluorometholone

Conditions
ConditionsYield
Stage #1: C22H28O4 With hydrogen fluoride In N,N-dimethyl-formamide at -4 - 0℃; for 3h;
Stage #2: With ammonium hydroxide In N,N-dimethyl-formamide for 3h; pH=7; Temperature; pH-value;
C24H30O4

C24H30O4

fluorometholone
426-13-1

fluorometholone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: perchloric acid; 5,5-dibromohydantoin / water; acetone / 4 h / 0 - 5 °C
1.2: 3 h / 0 - 5 °C
2.1: hydrogen fluoride / water / 4 h / -25 - -20 °C
3.1: sodium hydroxide; methanol / 5 h / 0 - 5 °C
View Scheme
fluorometholone
426-13-1

fluorometholone

C22H29FO4

C22H29FO4

Conditions
ConditionsYield
With acetic acid In acetone at 50 - 80℃; for 4h; pH=4 - 5; Reagent/catalyst; pH-value; Temperature;

426-13-1Downstream Products

426-13-1Relevant articles and documents

Fluorometholone, fluorometholone acetate, and preparation method thereof

-

Paragraph 0069-0075, (2020/03/12)

The invention discloses fluorometholone, fluorometholone acetate, and a preparation method thereof. According to the preparation method, a compound represented by a formula (II) is taken as a raw material, the compound carries out de-chlorination reaction, esterification reaction, methenylation reaction, hydrogenation reaction, fermentation de-hydrogenation reaction, epoxidation reaction, and ring-opening reaction in sequence to obtain derivatives of fluorometholone; and fluorometholone derivatives carry out hydrolysis to obtain fluorometholone. The preparation method has the advantages of short synthesis route, high yield, low raw material cost, easily available raw materials, simple and convenient purification, high product purity, and strong technological operability, is suitable for industrial production, and has a high industrialization value.

Sterides ring expanding compound and preparation method thereof

-

Paragraph 0034; 0039; 0044; 0048; 0052, (2019/10/15)

The invention provides a sterides ring expanding compound which is characterized by having a structure shown as a formula I shown in the accompanying drawing or being enantiomers, or solvates or aquo-complexes of the compound with the formula I. The sterides ring expanding compound has the advantages and positive effects that the compound with the formula I can be effectively combined with glucocorticoid receptors; the pharmacological effects identical to glucocorticoid can be generated; the toxicity is lower than that of the glucocorticoid.

Chemoselective hydrogenation of 17α-hydroxy-6-methylen-pregna-4,9(11)-diene-3,20-dione. Synthesis of fluorometholone

Marcos-Escribano, Andrés,Bermejo, Francisco A.,Bonde-Larsen, Antonio Lorente,Retuerto, Jesús Iglesias

experimental part, p. 8493 - 8496 (2010/01/06)

The development of an efficient hydrogenation method of 17α-hydroxy-6-methylen-pregna-4,9(11)-diene-3,20-dione by using wet (10%) Pd on carbon and triethylamine led us to the corresponding 6α-methyl-pregnane in good yield. This chemoselective process allo

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