loader
Please Wait
Applying Filters...

Athena Athena

X

Technical details about Fluocinolone Acetonide, learn more about the structure, uses, toxicity, action, side effects and more

Client Email Product
Menu
2D Structure
Also known as: 67-73-2, Synalar, Fluonid, Flucinar, Synandone, Jellin
Molecular Formula
C24H30F2O6
Molecular Weight
452.5  g/mol
InChI Key
FEBLZLNTKCEFIT-VSXGLTOVSA-N
FDA UNII
0CD5FD6S2M

A glucocorticoid derivative used topically in the treatment of various skin disorders. It is usually employed as a cream, gel, lotion, or ointment. It has also been used topically in the treatment of inflammatory eye, ear, and nose disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p732)
Fluocinolone acetonide is a Corticosteroid. The mechanism of action of fluocinolone acetonide is as a Corticosteroid Hormone Receptor Agonist.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one
2.1.2 InChI
InChI=1S/C24H30F2O6/c1-20(2)31-19-9-13-14-8-16(25)15-7-12(28)5-6-21(15,3)23(14,26)17(29)10-22(13,4)24(19,32-20)18(30)11-27/h5-7,13-14,16-17,19,27,29H,8-11H2,1-4H3/t13-,14-,16-,17-,19+,21-,22-,23-,24+/m0/s1
2.1.3 InChI Key
FEBLZLNTKCEFIT-VSXGLTOVSA-N
2.1.4 Canonical SMILES
CC1(OC2CC3C4CC(C5=CC(=O)C=CC5(C4(C(CC3(C2(O1)C(=O)CO)C)O)F)C)F)C
2.1.5 Isomeric SMILES
C[C@]12C[C@@H]([C@]3([C@H]([C@@H]1C[C@@H]4[C@]2(OC(O4)(C)C)C(=O)CO)C[C@@H](C5=CC(=O)C=C[C@@]53C)F)F)O
2.2 Other Identifiers
2.2.1 UNII
0CD5FD6S2M
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Acetonide, Fluocinolone

2. Acetonide, Fluortriamcinolone

3. Alvadermo

4. Capex

5. Co Fluocin

6. Co-fluocin

7. Cortiespec

8. Derma Smooth Fs

9. Derma-smooth Fs

10. Flucinar

11. Fluocid

12. Fluodermo

13. Fluonid

14. Fluortriamcinolone Acetonide

15. Fluotrex

16. Flurosyn

17. Flusolgen

18. Gelidina

19. Jellin

20. Jellisoft

21. Synalar

22. Synalar Hp

23. Synalar-hp

24. Synamol

25. Synemol

2.3.2 Depositor-Supplied Synonyms

1. 67-73-2

2. Synalar

3. Fluonid

4. Flucinar

5. Synandone

6. Jellin

7. Synamol

8. Synemol

9. Coriphate

10. Fluovitif

11. Flupollon

12. Percutina

13. Synandrone

14. Dermalar

15. Localyn

16. Omniderm

17. Radiocin

18. Retisert

19. Sinalar

20. Synotic

21. Tefunote

22. Synsac

23. Fluotrex

24. Fluocet

25. Derma-smoothe/fs

26. Synalar-hp

27. Localyn Syntex

28. Cortiplastol

29. Iluvien

30. Prodermin

31. Capex

32. Fs Shampoo

33. Fluocinolone 16,17-acetonide

34. 6alpha-fluorotriamcinolone Acetonide

35. Fluocinoloni Acetonidum

36. Rs-1401 At

37. Acetonide De Fluocinolone

38. Component Of Neo-synalar

39. Fluocinolone (acetonide)

40. Oto-synalar

41. Flucort-n

42. Dermatin (steroid)

43. 6alpha,9alpha-difluoro-16alpha-hydroxyprednisolone 16,17-acetonide

44. Nsc-92339

45. Flucinolone Acetonide

46. Fluocinolide (acetate)

47. 0cd5fd6s2m

48. Mls000028545

49. Fluocinolonacetonidum

50. Chebi:31623

51. Fluocinolone Acetonide (flucort-n)

52. Nsc92339

53. Smr000058329

54. Mfcd00010525

55. Fluocinolone Acetonide [dcit]

56. Dsstox_cid_20674

57. Dsstox_rid_79533

58. Dsstox_gsid_40674

59. C24h30f2o6

60. Fluocinoloni Acetonidum [inn-latin]

61. Acetonida De Fluocinolona

62. Rs 1401at

63. 6.alpha.-fluorotriamcinolone Acetonide

64. Cas-67-73-2

65. Retisert (tn)

66. Fluocet (tn)

67. Synalar (tn)

68. Acetonide De Fluocinolone [inn-french]

69. Acetonida De Fluocinolona [inn-spanish]

70. Ccris 3250

71. Hsdb 3083

72. 6.alpha.,9-difluoro

73. Einecs 200-668-5

74. Nsc 92339

75. Unii-0cd5fd6s2m

76. Dermatin

77. Dermotic

78. Fluzon [steroid]

79. Ncgc00021301-04

80. (6alpha,9alpha,11beta,16beta)-6,9-difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione

81. 6-alpha,9-alpha-difluoro-16-alpha-hydroxyprednisolone 16,17-acetonide

82. 6.alpha.,9-difluoro-11.beta.,16.alpha.,17,21-tetrahydroxypregna-1,4-diene-3,20-dione, Cyclic 16,17-acetal With Acetone

83. Fluocinoloneacetonide

84. Fluocinolone-acetonide

85. Yutiq

86. 6alpha,9-difluoro-11beta,16alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione, Cyclic 16,17-acetal With Acetone

87. Pregna-1,4-diene-3,20-dione, 6,9-difluoro-11,21-dihydroxy-16,17-((1-methylethylidene)bis(oxy))-, (6alpha,11beta,16alpha)-

88. Pregna-1,4-diene-3,20-dione, 6alpha,9-difluoro-11beta,16alpha,17,21-tetrahydroxy-, Cyclic 16,17-acetal With Acetone

89. Fluocinolone Acetonide Intravitreal Implant

90. Acetonido De Fluocinolona

91. 6.alpha.,17-acetonide

92. Opera_id_1295

93. F0657

94. Fluocinolone Acetonide [usan:usp:inn:jan]

95. Chembl989

96. Schembl4795

97. Fluocinolone Acetonide - Bp

98. 6alpha,9alpha-difluoro-11beta,16alpha,17alpha,21-tetrahydroxy-1,4-pregnadiene-3,20-dione 16,17-acetonide

99. Mls001076276

100. Gtpl7077

101. Dtxsid0040674

102. Hms2090i14

103. Hms2230d13

104. Hms3259g12

105. Hms3715j11

106. Fluocinolone Acetonide [mi]

107. Hy-b0415

108. Zinc3977981

109. Fluocinolone Acetonide [inn]

110. Fluocinolone Acetonide [jan]

111. Tox21_110869

112. Tox21_302364

113. Ac-429

114. Ac1069

115. Fluocinolone Acetonide [hsdb]

116. Fluocinolone Acetonide [usan]

117. S2470

118. Fluocinolone Acetonide [vandf]

119. Akos015963144

120. Fluocinolone Acetonide [mart.]

121. Tox21_110869_1

122. Ccg-221165

123. Db00591

124. Fluocinolone Acetonide [usp-rs]

125. Fluocinolone Acetonide [who-dd]

126. Nc00562

127. Fluocinolone Acetonide (jp17/usp/inn)

128. Ncgc00021301-06

129. Ncgc00255654-01

130. (4as,4br,5s,6as,6bs,9ar,10as,10bs,12s)-4b,12-difluoro-5-hydroxy-6b-(hydroxyacetyl)-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2h-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one

131. (4as,4br,5s,6as,6bs,9ar,10as,10bs,12s)-4b,12-difluoro-6b-glycoloyl-5-hydroxy-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2h-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one

132. 4b,12-difluoro-6b-glycoloyl-5-hydroxy-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2h-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one

133. As-13690

134. Bf176452

135. Nci60_042042

136. Fluocinolone Acetonide [green Book]

137. Fluocinolone Acetonide, Analytical Standard

138. Fluocinolone Acetonide [orange Book]

139. Fluocinolone Acetonide [ep Monograph]

140. Fluocinolone Acetonide [usp Impurity]

141. Fluocinolone Acetonide For System Suitability

142. Fluocinolone Acetonide [usp Monograph]

143. Otovel Component Fluocinolone Acetonide

144. D01825

145. Iluvien Component Fluocinolone Acetonide

146. Ab00383017-10

147. Ab00383017_11

148. Fluocinolone Acetonide Component Of Otovel

149. Otovel Component Of Fluocinolone Acetonide

150. Tri-luma Component Fluocinolone Acetonide

151. 010f525

152. A853087

153. Fluocinolone Acetonide 100 Microg/ml In Methanol

154. Fluocinolone Acetonide Component Of Iluvien

155. Neo-synalar Component Fluocinolone Acetonide

156. Q924467

157. Sr-01000000109

158. Fluocinolone Acetonide Component Of Tri-luma

159. Sr-01000000109-2

160. W-104704

161. Brd-k94353609-001-21-6

162. Difluoro-hydroxy-(2-hydroxyacetyl)-tetramethyl-[?]one

163. Fluocinolone Acetonide Component Of Neo-synalar

164. 6.alpha., 9.alpha.-difluoro-16.alpha.-hydroxyprednisolone 16,17-acetonide

165. Fluocinolone Acetonide, European Pharmacopoeia (ep) Reference Standard

166. Fluocinolone Acetonide, United States Pharmacopeia (usp) Reference Standard

167. Fluocinolone Acetonide For System Suitability, European Pharmacopoeia (ep) Reference Standard

168. Fluocinolone Acetonide, Pharmaceutical Secondary Standard; Certified Reference Material

169. Wln: T F5 E5 B666 Go Io Rv Ahtttt&j A Bf Cq E Fviq H H Of -a&bho -b&acef

170. (1s,2s,4r,8s,9s,11s,12r,13s,19s)-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-14,17-dien-16-one

171. (2s,6as,6br,7s,8as,8bs,11ar,12as,12bs)-2,6b-difluoro-7-hydroxy-8b-(2-hydroxyacetyl)-6a,8a,10,10-tetramethyl-6a,6b,7,8,8a,8b,11a,12,12a,12b-decahydro-1h-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-4(2h)-one

172. (6a,11b,16a)-6,9-difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-pregna-1,4-diene-3,20-dione

173. (6alpha,11beta,16alpha)-6,9-difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione

174. 6.alpha.,16.alpha.,17,21-tetrahydroxypregna-1,4-diene-3,20-dione, Cyclic 16,17-acetal With Acetone

175. Fluocinolone Acetonide For Peak Identification, European Pharmacopoeia (ep) Reference Standard

176. Pregna-1,20-dione, 6,9-difluoro-11,12-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-, (6.alpha.,11.beta.,16.alpha.)-

177. Pregna-1,20-dione, 6,9-difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)-, (6.alpha.,11.beta.,16.alpha.)-

178. Pregna-1,20-dione, 6,9-difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-, (6.alpha.,11.beta.,16.alpha.)-

179. Pregna-1,20-dione, 6.alpha.,9-difluoro-11.beta.,16.alpha.,17,21-tetrahydroxy-, Cyclic 16,17-acetal With Acetone

180. Pregna-1,4-diene-3,20-dione, 6,9-difluoro-11,21-dihydroxy-16,17-((1-methylethylidene)bis(oxy))-, (6.alpha.,11.beta.,16.alpha.)-

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 452.5 g/mol
Molecular Formula C24H30F2O6
XLogP32.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count8
Rotatable Bond Count2
Exact Mass452.20104500 g/mol
Monoisotopic Mass452.20104500 g/mol
Topological Polar Surface Area93.1 Ų
Heavy Atom Count32
Formal Charge0
Complexity960
Isotope Atom Count0
Defined Atom Stereocenter Count9
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 10  
Drug NameFluocinolone acetonide
PubMed HealthFluocinolone Acetonide (Into the ear)
Drug ClassesOtic Agent
Drug LabelFluocinolone Acetonide 0.01 % Topical Oil contains fluocinolone acetonide {(6, 11, 16)-6,9-difluoro-11,21-dihydroxy-16,17[(1-methylethylidene)bis(oxy)]-pregna-1,4-diene-3,20-dione, cyclic 16,17 acetal with acetone}, a synthetic corticosteroid f...
Active IngredientFluocinolone acetonide
Dosage FormOintment; Cream; Oil; Oil/drops; Solution
RouteTopical; Otic
Strength0.025%; 0.01%
Market StatusPrescription
CompanyTaro; Fougera; Identi Pharms; G And W Labs; Perrigo Israel

2 of 10  
Drug NameIluvien
PubMed HealthFluocinolone
Drug ClassesCorticosteroid, Intermediate, Fluocinolone, Otic Agent
Active IngredientFluocinolone acetonide
Dosage FormInsert
RouteIntravitreal
Strength0.19mg
Market StatusPrescription
CompanyAlimera Sciences

3 of 10  
Drug NameNeo-synalar
PubMed HealthFluocinolone
Drug ClassesCorticosteroid, Intermediate, Fluocinolone, Otic Agent
Drug LabelRETISERT (fluocinolone acetonide intravitreal implant) 0.59 mg is a sterile implant designed to release fluocinolone acetonide locally to the posterior segment of the eye at a nominal initial rate of 0.6 g/day, decreasing over the first month to...
Active IngredientFluocinolone acetonide; neomycin sulfate
Dosage FormCream
RouteTopical
Strength0.025%; eq 3.5mg base/gm
Market StatusPrescription
CompanyMedimetriks Pharms

4 of 10  
Drug NameRetisert
Drug LabelSYNALAR (fluocinolone acetonide) Topical Solution 0.01% is intended for topical administration. The active component is the corticosteroid fluocinolone acetonide, which has the chemical name pregna-1,4-diene-3,20-dione,6,9-difluoro-11,21-dihydroxy-...
Active IngredientFluocinolone acetonide
Dosage FormImplant
RouteIntravitreal
Strength0.59mg
Market StatusPrescription
CompanyBausch And Lomb

5 of 10  
Drug NameSynalar
Active IngredientFluocinolone acetonide
Dosage FormOintment; Cream; Solution
RouteTopical
Strength0.025%; 0.01%
Market StatusPrescription
CompanyMedimetriks Pharms

6 of 10  
Drug NameFluocinolone acetonide
PubMed HealthFluocinolone Acetonide (Into the ear)
Drug ClassesOtic Agent
Drug LabelFluocinolone Acetonide 0.01 % Topical Oil contains fluocinolone acetonide {(6, 11, 16)-6,9-difluoro-11,21-dihydroxy-16,17[(1-methylethylidene)bis(oxy)]-pregna-1,4-diene-3,20-dione, cyclic 16,17 acetal with acetone}, a synthetic corticosteroid f...
Active IngredientFluocinolone acetonide
Dosage FormOintment; Cream; Oil; Oil/drops; Solution
RouteTopical; Otic
Strength0.025%; 0.01%
Market StatusPrescription
CompanyTaro; Fougera; Identi Pharms; G And W Labs; Perrigo Israel

7 of 10  
Drug NameIluvien
PubMed HealthFluocinolone
Drug ClassesCorticosteroid, Intermediate, Fluocinolone, Otic Agent
Active IngredientFluocinolone acetonide
Dosage FormInsert
RouteIntravitreal
Strength0.19mg
Market StatusPrescription
CompanyAlimera Sciences

8 of 10  
Drug NameNeo-synalar
PubMed HealthFluocinolone
Drug ClassesCorticosteroid, Intermediate, Fluocinolone, Otic Agent
Drug LabelRETISERT (fluocinolone acetonide intravitreal implant) 0.59 mg is a sterile implant designed to release fluocinolone acetonide locally to the posterior segment of the eye at a nominal initial rate of 0.6 g/day, decreasing over the first month to...
Active IngredientFluocinolone acetonide; neomycin sulfate
Dosage FormCream
RouteTopical
Strength0.025%; eq 3.5mg base/gm
Market StatusPrescription
CompanyMedimetriks Pharms

9 of 10  
Drug NameRetisert
Drug LabelSYNALAR (fluocinolone acetonide) Topical Solution 0.01% is intended for topical administration. The active component is the corticosteroid fluocinolone acetonide, which has the chemical name pregna-1,4-diene-3,20-dione,6,9-difluoro-11,21-dihydroxy-...
Active IngredientFluocinolone acetonide
Dosage FormImplant
RouteIntravitreal
Strength0.59mg
Market StatusPrescription
CompanyBausch And Lomb

10 of 10  
Drug NameSynalar
Active IngredientFluocinolone acetonide
Dosage FormOintment; Cream; Solution
RouteTopical
Strength0.025%; 0.01%
Market StatusPrescription
CompanyMedimetriks Pharms

4.2 Therapeutic Uses

Glucocorticoids, Synthetic; Glucocorticoids, Topical

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


WITH EXCEPTION OF SUBSTITUTION THERAPY, USE OF CORTICOSTEROIDS & THEIR CONGENERS IN DISEASE IS EMPIRICAL. ...FOR ANY DISEASE, IN ANY PT, APPROPRIATE DOSE TO ACHIEVE GIVEN THERAPEUTIC EFFECT MUST BE DETERMINED BY TRIAL & ERROR & MUST BE REEVALUATED FROM TIME TO TIME AS STAGE & ACTIVITY OF DISEASE ALTER... /CORTICOSTEROID/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1497


GLUCOCORTICOID WITH POTENT ANTI-INFLAMMATORY & METABOLIC ACTIONS & NEGLIGIBLE MINERALOCORTICOID ACTIONS.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 892


IT IS EMPLOYED TOPICALLY IN TREATMENT OF VARIOUS DERMATOSES. IN RESISTANT NUMMULAR DERMATITIS, PSORIASIS, OR CHRONIC NEURODERMATITIS USUALLY USED UNDER OCCLUSIVE DRESSINGS.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 892


For more Therapeutic Uses (Complete) data for FLUOCINOLONE ACETONIDE (7 total), please visit the HSDB record page.


4.3 Drug Warning

...AS CORTICOSTEROID THERAPY IS PROLONGED OVER PERIODS OF MO, & TO EXTENT THAT DOSE EXCEEDS EQUIV OF SUBSTITUTION THERAPY, INCIDENCE OF DISABLING & POTENTIALLY LETHAL EFFECTS INCR; EXCEPT IN ADRENAL INSUFFICIENCY, ADMIN...IS NEITHER ETIOLOGICAL OR CURATIVE THERAPY BUT ONLY PALLIATIVE...ANTI-INFLAMMATORY... /CORTICOSTEROIDS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1497


EVEN IN INSTANCES IN WHICH NEARLY WHOLE BODY HAS BEEN COVERED BY CREAM CONTAINING CORTICOID, EVIDENCES OR SYSTEMIC SIDE EFFECTS ARE RARE. ... TOPICAL FLUOCINOLONE IS CONTRAINDICATED IN PRESENCE OF TUBERCULOSIS, FUNGAL INFECTIONS, & MOST VIRAL LESIONS OF SKIN (VACCINIA, VARICELLA, HERPES SIMPLEX, ETC).

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 892


...CAUTION SHOULD BE EXERCISED IF FLUORINATED PREPN ARE USED ON FACE OR OTHER COSMETICALLY IMPORTANT AREAS, SINCE PARADOXICAL SKIN ERUPTIONS MAY OCCUR WITH LONG-TERM USE.

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 518


VET: SOLN IN PROPYLENE GLYCOL USUALLY PRODUCES FAR MORE THAN "TRANSIENT STINGING SENSATION" DESCRIBED BY MFR & SHOULD BE AVOIDED ESP ON RAW OR DENUDED AREAS.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 224


For more Drug Warnings (Complete) data for FLUOCINOLONE ACETONIDE (7 total), please visit the HSDB record page.


4.4 Drug Indication

Fluocinolone acetonide has been used extensively in different medical areas. -In dermatology, it is extensively used for the relief of inflammatory dermatosis, dermatitis, psoriasis, hypertrophic tissues, keloid tissues and atopic dermatitis. -It has been used in shampoo products as a low to medium potency corticosteroid for the treatment of seborrheic dermatitis of the scalp. -In ear drops, it is used as a low to medium potency corticosteroid for the treatment of chronic eczematous external otitis in adults and pediatric patients 2 years and older. -As an intravitreal implant, it is indicated for the treatment of diabetic macular edema with patients that have been previously treated with a course of corticosteroids and no clinically significant rise in intraocular pressure. -Fluocinolone acetonide was announced on October 15, 2018 to be FDA approved for the treatment of chronic non-infectious uveitis affecting the posterior segment of the eye. -Some reports have indicated the use of fluocinolone acetonide as a vasoprotective agent and for its use in the treatment of first-degree hemorrhoids.


FDA Label


Treatment of dermatitis and eczema


Treatment of diabetic macular oedema


Treatment of chronic non-infectious uveitis


5 Pharmacology and Biochemistry
5.1 Pharmacology

Fluocinolone acetonide is a synthetic anti-inflammatory corticosteroid and thus, the effect of its interaction with the body produces vasoconstriction and suppression of membrane permeability, mitotic activity, immune response and release of inflammatory mediators. For its ophthalmic indications, fluocinolone acetonide is administered as intravitreal micro-insert. This preparation was observed in clinical trials to reduce the recurrence of uveitis flares by 2 fold when compared with the non treated patients even after six months after initial administration. As well the intraocular pressure seemed to increase slightly with the presence of the fluocinolone implant but it is important to monitor intraocular pressure.


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.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
FLUOCINOLONE ACETONIDE
5.3.2 FDA UNII
0CD5FD6S2M
5.3.3 Pharmacological Classes
Corticosteroid [EPC]; Corticosteroid Hormone Receptor Agonists [MoA]
5.4 ATC Code

C - Cardiovascular system

C05 - Vasoprotectives

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

C05AA - Corticosteroids

C05AA10 - Fluocinolone acetonide


D - Dermatologicals

D07 - Corticosteroids, dermatological preparations

D07A - Corticosteroids, plain

D07AC - Corticosteroids, potent (group iii)

D07AC04 - Fluocinolone acetonide


S - Sensory organs

S01 - Ophthalmologicals

S01B - Antiinflammatory agents

S01BA - Corticosteroids, plain

S01BA15 - Fluocinolone acetonide


S - Sensory organs

S02 - Otologicals

S02B - Corticosteroids

S02BA - Corticosteroids

S02BA08 - Fluocinolone acetonide


5.5 Absorption, Distribution and Excretion

Absorption

When administered as an eye implant, fluocinolone acetonide presents a sustained delivery for even 12 months in which there can be observed a sustained release. The concentration of fluocinolone acetonide are generally higher in the vitreous and retina with a little dispersion to the aqueous humor. There are reports indicating that topical administration of fluocinolone acetonide produces a percutaneous absorption which is determined by the vehicle, integrity of the epidermal barrier and the use of occlusive dressing. Independently of the route of administration, the systemic absorption of fluocinolone acetonide is below 0.1 ng/ml which indicates that the systemic distribution is very minimal and the effect of fluocinolone is mainly local.


Route of Elimination

Fluocinolone acetonide is mainly excreted by the kidneys. It is important to mention that the systemically absorbed dose is very minimal.


Volume of Distribution

This pharmacokinetic parameter is not relevant as the systemic absorption of fluocinolone acetonide is very minimal.


Clearance

This pharmacokinetic parameter is not relevant as the systemic absorption of fluocinolone acetonide is very minimal and the concentration in urine is lower than the minimum quantitation limit.


METABOLISM OF CORTICOSTEROIDS IS GREATLY SLOWED BY INTRODUCTION OF THE 1,2 DOUBLE BOND OR A FLUORINE ATOM INTO MOLECULE, & HALF-LIFE IS CORRESPONDINGLY PROLONGED. /CORTICOSTEROIDS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1489


(14)C WAS RAPIDLY & MAINLY EXCRETED IN 48-HR FECES (90%), VIA BILE (70% IN 24 HR), & IN URINE (8%). AFTER DERMAL APPLICATION OF CREAM CONTAINING [(14)C]FLUOCINOLONE ACETONIDE TO MICE, GREATER THAN 7% OF (14)C WAS ABSORBED.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 130


...WITHIN 1 HR OF SC DOSE OF [(14)C]FLUOCINOLONE ACETONIDE TO MICE, LARGE AMT...PRESENT IN LIVER & INJECTION SITE, LOWER AMT IN PANCREAS, KIDNEYS, SALIVARY GLANDS, MYOCARDIUM, PITUITARY, & LACRIMAL GLANDS. TISSUE (14)C DECR FAIRLY RAPIDLY DURING 24 HR, EXCEPT IN LIVER & INTESTINES, BECAUSE OF BILIARY SECRETION...

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 130


PENETRATION OF...FLUOCINOLONE ACETONIDE...TOPICALLY APPLIED, THROUGH HUMAN ABDOMINAL SKIN WAS OPTIMAL WHEN CONCN OF DRUGS WAS MAXIMAL WHILE MAINTAINING FAVORABLE PARTITION COEFFICIENT BETWEEN SKIN BARRIER & VEHICLE.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 426


For more Absorption, Distribution and Excretion (Complete) data for FLUOCINOLONE ACETONIDE (6 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Following absorption, fluocinolone acetonide metabolism is primarily hepatic. It is important to mention that the systemically absorbed dose is very minimal.


...IT IS GENERALLY ASSUMED THAT METAB OF /CORTISOL &/ ITS CONGENERS & SYNTH DERIV IS QUALITATIVELY SIMILAR. ...METABOLIZED PRINCIPALLY BY REDN OF RING A, REDN OF KETONE AT C 20, & CLEAVAGE OF SIDE CHAIN. METABOLITES ARE EXCRETED...AS GLUCURONIDES, SULFATES, & UNCONJUGATED COMPOUNDS. /CORTICOSTEROIDS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1489


5.7 Biological Half-Life

The reported half-life of fluocinolone acetonide ranges between 1.3-1.7 hours.


5.8 Mechanism of Action

Fluocinolone acetonide is a corticosteroid and thus, it can be inferred that it acts by inhibiting the edema, fibrin deposition, capillary dilation, leukocyte migration, capillary proliferation, fibroblast proliferation, collagen deposition, and scar formation. Some reports have indicated that fluocinolone acetonide presents a high binding affinity for the 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 in the promoter region of the target genes. This effect promotes the induction of phospholipase A2 inhibitory proteins (lipocortins). Through this mechanism of action, it is thought that fluocinolone induces mainly one of the lipocortins, annexin 1, which will later mediate the synthesis of inflammatory mediators such as prostaglandins and leukotrienes by inhibiting the release of arachidonic acid which is the precursor of all these inflammatory mediators. Hence, the induction of these proteins will prevent the release of arachidonic acid by phospholipase A2.


CORTICOSTEROIDS...ARE THOUGHT TO ACT BY CONTROLLING RATE OF SYNTH OF PROTEINS. ...CORTICOSTEROIDS REACT WITH RECEPTOR PROTEINS IN CYTOPLASM OF SENSITIVE CELLS TO FORM STEROID-RECEPTOR COMPLEX. ... STEROID HORMONES APPEAR TO STIMULATE TRANSCRIPTION & ULTIMATELY SYNTH OF SPECIFIC PROTEINS. /CORTICOSTEROIDS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1480


...CORTICOSTEROIDS...INFLUENCE CARBOHYDRATE, PROTEIN, FAT, & PURINE METABOLISM; ELECTROLYTE & WATER BALANCE; & FUNCTIONS OF CVS, KIDNEY, SKELETAL MUSCLE, NERVOUS SYSTEM, & OTHER ORGANS & TISSUES. ...CORTICOSTEROIDS ENDOW ORGANISM WITH CAPACITY TO RESIST MANY TYPES OF NOXIOUS STIMULI & ENVIRONMENTAL CHANGE. /CORTICOSTEROIDS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1478


Post Enquiry
POST ENQUIRY