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2D Structure
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

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

2D Structure

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.