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    Chemistry

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    Also known as: 426-13-1, Fluoromethalone, Oxylone, Flumetholon, Fluor-op, Fluormetholone
    Molecular Formula
    C22H29FO4
    Molecular Weight
    376.5  g/mol
    InChI Key
    FAOZLTXFLGPHNG-KNAQIMQKSA-N
    FDA UNII
    SV0CSG527L
    Fluorometholone
    A glucocorticoid employed, usually as eye drops, in the treatment of allergic and inflammatory conditions of the eye. It has also been used topically in the treatment of various skin disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p732)
    Fluorometholone is a Corticosteroid. The mechanism of action of fluorometholone is as a Corticosteroid Hormone Receptor Agonist.
    1 2D Structure

    Fluorometholone

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (6S,8S,9R,10S,11S,13S,14S,17R)-17-acetyl-9-fluoro-11,17-dihydroxy-6,10,13-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
    2.1.2 InChI
    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
    2.1.3 InChI Key
    FAOZLTXFLGPHNG-KNAQIMQKSA-N
    2.1.4 Canonical SMILES
    CC1CC2C3CCC(C3(CC(C2(C4(C1=CC(=O)C=C4)C)F)O)C)(C(=O)C)O
    2.1.5 Isomeric SMILES
    C[C@H]1C[C@H]2[C@@H]3CC[C@@]([C@]3(C[C@@H]([C@@]2([C@@]4(C1=CC(=O)C=C4)C)F)O)C)(C(=O)C)O
    2.2 Other Identifiers
    2.2.1 UNII
    SV0CSG527L
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Cortisdin

    2. Efflumidex

    3. Flucon

    4. Flucon, Isopto

    5. Fluor Op

    6. Fluor-op

    7. Fluoro Ophtal

    8. Fluoro-ophtal

    9. Fluoropos

    10. Fml

    11. Fml Forte

    12. Fml Liquifilm

    13. Isopto Flucon

    14. Pms Fluorometholone

    15. Pms-fluorometholone

    2.3.2 Depositor-Supplied Synonyms

    1. 426-13-1

    2. Fluoromethalone

    3. Oxylone

    4. Flumetholon

    5. Fluor-op

    6. Fluormetholone

    7. Cortilet

    8. Delmeson

    9. Fml Liquifilm

    10. Trilcin

    11. Fml Forte

    12. Fluorometolona

    13. Fluorometholonum

    14. Fluormetholon

    15. Nsc 33001

    16. Fml

    17. Component Of Neo-oxylone

    18. U 8614

    19. Chebi:31625

    20. 9-fluoro-11beta,17-dihydroxy-6alpha-methylpregna-1,4-diene-3,20-dione

    21. Nsc-33001

    22. (6s,8s,9r,10s,11s,13s,14s,17r)-17-acetyl-9-fluoro-11,17-dihydroxy-6,10,13-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one

    23. Sv0csg527l

    24. Mls000069537

    25. Mls001076157

    26. Fluormetholonum

    27. 9-fluoro-11,17-dihydroxy-6-methylpregna-1,4-diene-3,20-dione

    28. Nsc33001

    29. Fluorometolone

    30. Smr000058598

    31. Fluorometolone [dcit]

    32. Neo-oxylone

    33. Fml-s Liquifilm

    34. Dsstox_cid_27435

    35. Dsstox_rid_82345

    36. Fml S.o.p.

    37. Dsstox_gsid_47435

    38. Fluorometholonum [inn-latin]

    39. Fluorometolona [inn-spanish]

    40. Pregna-1,4-diene-3,20-dione, 9-fluoro-11,17-dihydroxy-6-methyl-, (6.alpha.,11.beta.)-

    41. Oxylone (tn)

    42. Fluor-op (tn)

    43. Fml (tn)

    44. Einecs 207-041-5

    45. Unii-sv0csg527l

    46. Fluorometholon

    47. Ai3-52813

    48. Ncgc00016442-01

    49. Cas-426-13-1

    50. Prestwick_227

    51. 9-fluoro-11-beta,17-dihydroxy-6-alpha-methylpregna-1,4-diene-3,20-dione

    52. Fluorometholone [usp:inn:ban:jan]

    53. Mfcd00056461

    54. Opera_id_341

    55. Prestwick0_000718

    56. Prestwick1_000718

    57. Prestwick2_000718

    58. Prestwick3_000718

    59. F0414

    60. 11beta,17alpha-dihydroxy-9-fluoro-6-methyl-1,4-pregnadiene-3,20-dione

    61. Fluorometholone, >=98%

    62. Pregna-1,4-diene-3,20-dione, 9-fluoro-11-beta,17-dihydroxy-6-alpha-methyl-

    63. Schembl5051

    64. Fluorometholone [mi]

    65. Pregna-1,4-diene-3,20-dione, 9-fluoro-11,17-dihydroxy-6-methyl-, (6alpha,11beta)-

    66. Bspbio_000935

    67. Fluorometholone [inn]

    68. Fluorometholone [jan]

    69. Spbio_002856

    70. Fluorometholone [vandf]

    71. Bpbio1_001029

    72. Gtpl7079

    73. Fluorometholone [mart.]

    74. Chembl1200600

    75. Dtxsid7047435

    76. Fluorometholone [usp-rs]

    77. Fluorometholone [who-dd]

    78. 9-fluoro-11.beta.,17-dihydroxy-6.alpha.-methylpregna-1,4-diene-3,20-dione

    79. Pregna-1,4-diene-3,20-dione, 9-fluoro-11.beta.,17-dihydroxy-6.alpha.-methyl-

    80. Fluorometholone (jp17/usp/inn)

    81. Hms1570o17

    82. Hms2097o17

    83. Hms2234f16

    84. Hms3714o17

    85. Hy-b1893

    86. Tox21_110440

    87. Tox21_302593

    88. Bdbm50103631

    89. Fluorometholone [orange Book]

    90. S5486

    91. Akos015895108

    92. Fml-s Component Fluorometholone

    93. Pregna-1,4-diene-3,20-dione, 9-fluoro-11beta,17-dihydroxy-6alpha-methyl-

    94. Tox21_110440_1

    95. Zinc118912517

    96. Ac-3520

    97. Ccg-220718

    98. Db00324

    99. Fluorometholone [usp Monograph]

    100. (6alpha,11beta)-9-fluoro-11,17-dihydroxy-6-methylpregna-1,4-diene-3,20-dione

    101. Ncgc00021575-03

    102. Ncgc00021575-05

    103. Ncgc00256631-01

    104. As-12363

    105. Fluorometholone Component Of Fml-s

    106. Nci60_002886

    107. Cs-0013955

    108. Progesterone, 17-dihydroxy-6.alpha.-methyl-

    109. D01367

    110. 426f131

    111. Q607349

    112. Sr-01000003019

    113. Sr-01000003019-2

    114. Brd-k64862097-001-03-9

    115. Brd-k64862097-001-12-0

    116. Fluorometholone, British Pharmacopoeia (bp) Reference Standard

    117. Fluorometholone, United States Pharmacopeia (usp) Reference Standard

    118. Pregna-1,20-dione, 9-fluoro-11.beta.,17-dihydroxy-6.alpha.-methyl-

    119. Progesterone, 1-dehydro-9-fluoro-11.beta., 17-dihydroxy-6.alpha.-methyl-

    120. Pregna-1,20-dione, 9-fluoro-11,17-dihydroxy-6-methyl-, (6.alpha.,11.beta.)-

    121. Pregna-1,4-diene-3,20-dione, 9-fluoro-11,17-dihydroxy-6-methyl-, (6i+/-,11i(2))-

    122. (1r,2s,8s,10s,11s,14r,15s,17s)-14-acetyl-1-fluoro-14,17-dihydroxy-2,8,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one

    123. (1r,2s,8s,10s,11s,14r,15s,17s)-14-acetyl-1-fluoro-14,17-dihydroxy-2,8,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

    124. Pregna-1, 4-diene-3,20-dione, 9-fluoro-11,17-dihydroxy-6-methyl-, (6.alpha., 11.beta.)-

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 376.5 g/mol
    Molecular Formula C22H29FO4
    XLogP32
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count1
    Exact Mass376.20498756 g/mol
    Monoisotopic Mass376.20498756 g/mol
    Topological Polar Surface Area74.6 Ų
    Heavy Atom Count27
    Formal Charge0
    Complexity787
    Isotope Atom Count0
    Defined Atom Stereocenter Count8
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameFml
    PubMed HealthFluorometholone (Into the eye)
    Drug ClassesOphthalmologic Agent
    Drug LabelFML (fluorometholone ophthalmic ointment) 0.1% is a sterile, topical anti-inflammatory agent for ophthalmic use....
    Active IngredientFluorometholone
    Dosage FormOintment; Suspension/drops
    RouteOphthalmic
    Strength0.1%
    Market StatusPrescription
    CompanyAllergan

    2 of 4  
    Drug NameFml forte
    PubMed HealthFluorometholone (Into the eye)
    Drug ClassesOphthalmologic Agent
    Drug LabelFML FORTE (fluorometholone ophthalmic suspension, USP) 0.25% is a sterile, topical anti-inflammatory agent for ophthalmic use. Chemical NameFluorometholone: 9-Fluoro-11, 17-dihydroxy-6-methylpregna-1,4-diene-3,20-dione. Structural FormulaContai...
    Active IngredientFluorometholone
    Dosage FormSuspension/drops
    RouteOphthalmic
    Strength0.25%
    Market StatusPrescription
    CompanyAllergan

    3 of 4  
    Drug NameFml
    PubMed HealthFluorometholone (Into the eye)
    Drug ClassesOphthalmologic Agent
    Drug LabelFML (fluorometholone ophthalmic ointment) 0.1% is a sterile, topical anti-inflammatory agent for ophthalmic use....
    Active IngredientFluorometholone
    Dosage FormOintment; Suspension/drops
    RouteOphthalmic
    Strength0.1%
    Market StatusPrescription
    CompanyAllergan

    4 of 4  
    Drug NameFml forte
    PubMed HealthFluorometholone (Into the eye)
    Drug ClassesOphthalmologic Agent
    Drug LabelFML FORTE (fluorometholone ophthalmic suspension, USP) 0.25% is a sterile, topical anti-inflammatory agent for ophthalmic use. Chemical NameFluorometholone: 9-Fluoro-11, 17-dihydroxy-6-methylpregna-1,4-diene-3,20-dione. Structural FormulaContai...
    Active IngredientFluorometholone
    Dosage FormSuspension/drops
    RouteOphthalmic
    Strength0.25%
    Market StatusPrescription
    CompanyAllergan

    4.2 Drug Indication

    For the ophthalmic treatment of corticosteroid-responsive inflammation of the palpebral and bulbar conjunctiva, cornea and anterior segment of the globe.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Corticosteroids such as fluorometholone inhibit the inflammatory response to a variety of inciting agents and probably delay or slow healing. They inhibit the edema, fibrin deposition, capillary dilation, leukocyte migration, capillary proliferation, fibroblast proliferation, deposition of collagen, and scar formation associated with inflammation.

    5.2 MeSH Pharmacological Classification

    Anti-Inflammatory Agents

    Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)

    Glucocorticoids

    A group of CORTICOSTEROIDS that affect carbohydrate metabolism (GLUCONEOGENESIS, liver glycogen deposition, elevation of BLOOD SUGAR), inhibit ADRENOCORTICOTROPIC HORMONE secretion, and possess pronounced anti-inflammatory activity. They also play a role in fat and protein metabolism, maintenance of arterial blood pressure, alteration of the connective tissue response to injury, reduction in the number of circulating lymphocytes, and functioning of the central nervous system. (See all compounds classified as Glucocorticoids.)

    Anti-Allergic Agents

    Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475) (See all compounds classified as Anti-Allergic Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    FLUOROMETHOLONE
    5.3.2 FDA UNII
    SV0CSG527L
    5.3.3 Pharmacological Classes
    Corticosteroid [EPC]; Corticosteroid Hormone Receptor Agonists [MoA]
    5.4 ATC Code

    S01BA07

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    C - Cardiovascular system

    C05 - Vasoprotectives

    C05A - Agents for treatment of hemorrhoids and anal fissures for topical use

    C05AA - Corticosteroids

    C05AA06 - Fluorometholone

    D - Dermatologicals

    D07 - Corticosteroids, dermatological preparations

    D07A - Corticosteroids, plain

    D07AB - Corticosteroids, moderately potent (group ii)

    D07AB06 - Fluorometholone

    D - Dermatologicals

    D07 - Corticosteroids, dermatological preparations

    D07X - Corticosteroids, other combinations

    D07XB - Corticosteroids, moderately potent, other combinations

    D07XB04 - Fluorometholone

    D - Dermatologicals

    D10 - Anti-acne preparations

    D10A - Anti-acne preparations for topical use

    D10AA - Corticosteroids, combinations for treatment of acne

    D10AA01 - Fluorometholone

    S - Sensory organs

    S01 - Ophthalmologicals

    S01B - Antiinflammatory agents

    S01BA - Corticosteroids, plain

    S01BA07 - Fluorometholone

    S - Sensory organs

    S01 - Ophthalmologicals

    S01C - Antiinflammatory agents and antiinfectives in combination

    S01CB - Corticosteroids/antiinfectives/mydriatics in combination

    S01CB05 - Fluorometholone

    5.5 Mechanism of Action

    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. Their primary target is the cytosolic glucocorticoid receptor. After binding the receptor the newly formed receptor-ligand complex translocates itself into the cell nucleus, where it binds to many glucocorticoid response elements (GRE) in the promoter region of the target genes. The DNA bound receptor then interacts with basic transcription factors, causing the increase in expression of specific target genes.

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    Registration Number : 303MF10110

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    Fluorometholone "Teva"

    Registration Number : 218MF10820

    Registrant's Address : Piazzale Luigi Cadorna, 4 - 20123 MILANO, Italy

    Initial Date of Registration : 2006-10-06

    Latest Date of Registration : 2006-10-06

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    Axplora

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    Fluorometholone

    Registrant Name : Samoh Pharmaceutical Co., Ltd.

    Registration Date : 2021-02-18

    Registration Number : 20210218-211-J-842

    Manufacturer Name : Farmabios SpA@IMS srl

    Manufacturer Address : Via Pavia 1, 27027 Gropello Cairoli (PV), Italy@Via Venezia Giulia 23, 20157 Milano

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    EUROAPI

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    Virtual BoothEUROAPI, the leading small molecules API player, provides both API sales & CDMO services.

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    Fluorometholone

    Registrant Name : Samoh Pharmaceutical Co., Ltd.

    Registration Date : 2021-05-06

    Registration Number : 20210506-211-J-808

    Manufacturer Name : EUROAPI France

    Manufacturer Address : 4 La Paterie, VERTOLAYE, 63480, France

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    NEWCHEM SPA

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    Fluorometholone

    Registrant Name : Sungjin Exim Co., Ltd.

    Registration Date : 2021-05-27

    Registration Number : 20210527-211-J-1001

    Manufacturer Name : NEWCHEM SpA@Microchem Srl

    Manufacturer Address : Via Roveggia, 47-37136 VERONA (VR), Italy@Via Turati, 2-29017 Fiorenzuola D'arda (PC)...

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    Tianjin Tianyao Pharmaceuticals Co....

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    Fluorometholone

    Registrant Name : Ace Biopharm Co., Ltd.

    Registration Date : 2021-08-17

    Registration Number : 20210817-211-J-1091

    Manufacturer Name : Tianjin Tianyao Pharmaceutic...

    Manufacturer Address : No.19 Xinye 9th Street, west Area of ​​Tianjin Economic-Technological Development...

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    API Reference Price

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ROAD,","city":"HYDERABAD-A.P.","supplier":"M\/S. THE U.S PHARMACOPEIAL CONVENTION","supplierCountry":"ITALY","foreign_port":"#N\/A","customer":"UNITED STATES PHARMACOPEIA - INDIA PRIVATE LIMITED","customerCountry":"INDIA","quantity":"0.00","actualQuantity":"0.002","unit":"KGS","unitRateFc":"86660","totalValueFC":"179.5","currency":"USD","unitRateINR":"6600140","date":"20-Sep-2021","totalValueINR":"13200.28","totalValueInUsd":"179.5","indian_port":"HYDERABAD AIR","hs_no":"29372200","bill_no":"5507657","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Pharma Grade","supplierPort":"#N\/A","supplierAddress":"","customerAddress":"106, FIRST FLOOR , ASHOKA BHOOPALCHAMBERS BEGUMPET, S.P. ROAD,"},{"dataSource":"API Import","activeIngredients":"","year":"2021","qtr":"Q3","strtotime":1632767400,"product":"FLUOROMETHOLONE MICRONISED USP BP JP","address":"","city":"","supplier":"SANOFI","supplierCountry":"FRANCE","foreign_port":"PLAYA SAMARA","customer":"PIRAMAL PHARMA SOLUTIONS","customerCountry":"INDIA","quantity":"3.00","actualQuantity":"3","unit":"KGS","unitRateFc":"13500","totalValueFC":"40964.5","currency":"USD","unitRateINR":"1004400","date":"28-Sep-2021","totalValueINR":"3013200","totalValueInUsd":"40964.5","indian_port":"BOMBAY AIR","hs_no":"29372200","bill_no":"5617290","productDescription":"API","marketType":"REGULATED MARKET","country":"FRANCE","selfForZScoreResived":"Micronized","supplierPort":"PLAYA SAMARA","supplierAddress":"","customerAddress":""},{"dataSource":"API Import","activeIngredients":"","year":"2021","qtr":"Q4","strtotime":1636482600,"product":"FLUOROMETHOLONE 17-ACETATE MICR.","address":"212 ASHIRWAD COMMERCIAL COMPLEX,D- 1 GREEN 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    09-Mar-2021
    08-Aug-2024
    KGS
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    Average Price (USD/KGS)

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    (USD/KGS)    		 Number of Transactions

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    DOSAGE - SUSPENSION/DROPS;OPHTHALMIC - 0.1%

    USFDA APPLICATION NUMBER - 16851

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    DOSAGE - OINTMENT;OPHTHALMIC - 0.1%

    USFDA APPLICATION NUMBER - 17760

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