426-13-1 Usage
Uses
Used in Ophthalmology:
Fluorometholone is used as an anti-inflammatory agent for the treatment of corticosteroid-responsive inflammation of the palpebral and bulbar conjunctiva, cornea, and anterior segment of the globe. Its exclusive use in ophthalmic products makes it a valuable asset in managing eye-related inflammation and conditions.
Used in Dermatology:
Fluorometholone is used topically for the local treatment of skin allergy, pruritus, rash, and other diseases related to allergy. Its potent anti-inflammatory properties make it an effective treatment option for various skin conditions.
Used in Oncology:
Oral administration of fluorometholone is also used for the treatment of breast cancer, childhood leukemia, and connective tissue disease. Its anti-inflammatory and immunosuppressive effects contribute to its utility in managing these conditions.
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.
Originator
Oxylone, Upjohn, US,1959
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
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
426-13-1Relevant articles and documents
Synthesis method and application of 9-fluorosteroid compound
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Paragraph 0089-0096; 0125-0127, (2021/01/15)
The invention provides a synthesis method and application of a 9-fluorosteroid compound, and relates to the technical field of chemical synthesis. The synthesis method of the 9-fluorosteroid compoundcomprises the following step: reacting a compound II in an ionic liquid containing hydrogen fluoride salt to obtain a 9-fluorosteroid compound III. According to the synthesis method of the 9-fluorosteroid compound, the ionic liquid containing the hydrogen fluoride salt is used as a fluorinating agent to replace a traditional hydrogen fluoride aqueous solution, volatilization of hydrogen fluoride gas is avoided, corrosivity is small, toxicity is greatly reduced, reaction conditions are mild, reaction can be completed at the room temperature, operability is high, the safety coefficient is high,and production applicability is improved. The synthesis method of the 9-fluorosteroid compound is used for preparing corticosteroid drugs, highly toxic chemical reagents are not used in the synthesisroute, the operability is high, the safety coefficient is high, and the production applicability is improved.
Fluorometholone, fluorometholone acetate, and preparation method thereof
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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
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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.
PROCESS FOR OBTAINING FLUOROMETHOLONE AND INTERMEDIATES THEREFOR
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Page/Page column 29, (2010/11/05)
The present invention relates to a process for obtaining compounds of formula (I) and (V), wherein R1 is C1-C6 alkyl; and R2 is OR3, OC(=O)R4 or O-(HPG), wherein R3 is H, C1-C6 alkyl or C6-C14 aryl; R4 is H or C1-C6 alkyl; and HPG is a hydro xyl protecting group, intermediates useful in the synthesis of some steroids, for example, fluorometholone and derivatives thereof. The invention also relates to other intermediates useful in synthesis.
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
Method for reducing or preventing transplant rejection in the eye and intraocular implants for use therefor
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, (2008/06/13)
Methods for reducing or preventing transplant rejection in the eye of an individual are described, comprising: a) performing an ocular transplant procedure; and b) implanting in the eye a bioerodible drug delivery system comprising an immunosuppressive agent and a bioerodible polymer.
Water-soluble steroid compounds
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, (2008/06/13)
Beta-cyclodextrin forms a water-soluble complex or inclusion compound with steroid compounds having a molecular structure smaller than the interior cavity in the doughnut-shaped molecular structure of beta-cyclodextrin. The resulting inclusion compounds can be used for a variety of applications including aqueous topical ophthalmic preparations and topical dermatological ointments.
Base catalyzed acylation with enol esters
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, (2008/06/13)
This invention relates to processes for base catalyzed acylations using enol esters, for example, isopropenyl acetate. Particularly, the processes are useful for acylating acid sensitive alcohols including hydroxy steroids.
