Fluocinolone acetonide

Identification

Summary

Fluocinolone acetonide is a corticosteroid used to treat skin conditions, eczematous otitis externa, diabetic macular edema, and non-infectious uveitis of the posterior segment of the eye.

Brand Names
Capex, Derma-Smoothe/FS, Derma-smoothe FS, Dermotic, Flac, Iluvien, Neo-synalar, Otixal, Otovel, Retisert, Synalar, Tri-luma, Yutiq
Generic Name
Fluocinolone acetonide
DrugBank Accession Number
DB00591
Background

Fluocinolone acetonide, with the formula 6-alpha, 9-alpha-difluoro-16-alpha, 17 alpha-acetonide, is a corticosteroid that presents a high lipophilicity.8 It has been used extensively in dermatological preparations and it has also been investigated thoroughly for its use in implantable corticosteroid devices.9 This type of device containing fluocinolone acetonide was developed by Taro Pharmaceuticals and approved by FDA in May 2016.11

Type
Small Molecule
Groups
Approved, Investigational, Vet approved
Structure
Weight
Average: 452.4882
Monoisotopic: 452.201045102
Chemical Formula
C24H30F2O6
Synonyms
  • 6alpha-fluorotriamcinolone acetonide
  • 6alpha,9alpha-difluoro-16alpha-hydroxyprednisolone 16,17-acetonide
  • 6α-fluorotriamcinolone acetonide
  • 6α,9α-difluoro-16α-hydroxyprednisolone 16,17-acetonide
  • acétonide de fluocinolone
  • acetónido de fluocinolona
  • fluocinolon acetonid
  • fluocinolone 16,17-acetonide
  • Fluocinolone acetonide
  • fluocinoloni acetonidum
External IDs
  • NSC-92339

Pharmacology

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.17

-It has been used in shampoo products as a low to medium potency corticosteroid for the treatment of seborrheic dermatitis of the scalp.12

-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.13

-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.14

-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.15

-Some reports have indicated the use of fluocinolone acetonide as a vasoprotective agent and for its use in the treatment of first-degree hemorrhoids.4

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatAcute otitis mediaCombination Product in combination with: Ciprofloxacin (DB00537)•••••••••••••••••• ••••• •• •••••••• •••• •••••••••••• •••••••••••••
Used in combination to treatAllergy skinCombination Product in combination with: Gentamicin (DB00798)••• ••••••••
Used in combination to treatAnal fissuresCombination Product in combination with: Ketocaine (DB16020)•••••••••••••••••• •••••••••••
Treatment ofAtopic dermatitis••••••••••••
Used in combination to treatChronic disease of skinCombination Product in combination with: Gentamicin (DB00798)••• ••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

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.18

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.15

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.19

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.6 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 A2.19

TargetActionsOrganism
AGlucocorticoid receptor
agonist
Humans
AAnnexin A1
inducer
Humans
AAnnexin A2
inducer
Humans
AAnnexin A3
inducer
Humans
AAnnexin A4
inducer
Humans
AAnnexin A5
inducer
Humans
UPhospholipase A2
inhibitor
Humans
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.16 The concentration of fluocinolone acetonide are generally higher in the vitreous and retina with a little dispersion to the aqueous humor.10

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.18

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.5

Volume of distribution

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

Protein binding

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

Metabolism

Following absorption, fluocinolone acetonide metabolism is primarily hepatic.18 It is important to mention that the systemically absorbed dose is very minimal.10

Route of elimination

Fluocinolone acetonide is mainly excreted by the kidneys.18 It is important to mention that the systemically absorbed dose is very minimal.10

Half-life

The reported half-life of fluocinolone acetonide ranges between 1.3-1.7 hours.7

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.10

Adverse Effects
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Toxicity

Studies to determine the carcinogenic and its effect in fertility have not been performed. It is important to consider that several corticosteroids have been shown to present genotoxic potential but fluocinolone acetonide was shown to not be genotoxic in the Ames test and mouse lymphoma TK assay.19

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirFluocinolone acetonide may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbametapirThe serum concentration of Fluocinolone acetonide can be increased when it is combined with Abametapir.
AbataceptThe risk or severity of adverse effects can be increased when Fluocinolone acetonide is combined with Abatacept.
AbemaciclibThe metabolism of Abemaciclib can be increased when combined with Fluocinolone acetonide.
AcalabrutinibThe metabolism of Acalabrutinib can be increased when combined with Fluocinolone acetonide.
Food Interactions
No interactions found.

Products

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Active Moieties
NameKindUNIICASInChI Key
FluocinoloneunknownCT1IX58L9S807-38-5UUOUOERPONYGOS-CLCRDYEYSA-N
International/Other Brands
Biscosal (Onta Seiyaku) / Boniderma (Boniscontro) / Co-FIuosin (Sanchez-Covisa) / Coderma (Biotrading) / Cordes F (Ichthyol) / Coriphate / Cortalar (Bergamon) / Cortiderma (Gazzini) / Cortiespec (Centrum) / Cortiphate (Tokyo Tanabe) / Cortiplastol / Cortoderm (Lennon) / Derma-Smoothe/FS / Dermaisom (Isom) / Dermalar (Teva) / Dermaplus (Ripari-Gero) / Dermil (Cifa) / Dermobeta (Amelix) / Dermobiomar (Dermologia Marina) / Dermofil (N.C.S.N.) / Dermolin (Lafare) / Dermomagis (Magis) / Dermophyl (Rougier) / Dermotergol (Wolner) / Doricum (Farmila) / Esacinone (Lisapharma) / Esilon (S.I.T.) / Eskaton (Pharma Farm. Spec) / Fellin (Gruenenthal) / Flucinar (Jelfa and Polfa) / Flucort (Syntex-Tanabe) / Fluocet (Galderma Laboratories) / Fluocinil (Coli) / Fluocinone (Panther-Osfa) / Fluocit (C.T.) / Fluoderm (Unipharm) / Fluodermol (Medosan) / Fluogisol (Washington in Italy) / Fluolar (Riva) / Fluomix (Savoma) / Fluonid (Biolab and Herbert) / Fluonide Dermica (Janus) / Fluordima (Intersint) / Fluoskin (Dessy) / Fluotrex (Savage Labs) / Fluovean (Kowa) / Fluovitef (Italfarmaco) / Fluovitif / Flupollon (Mayado Seiyaku, Kaigai and Ohta) / Fluzon (Taisho) / Futocan (Shinlon) / Gelargin (Leciva) / Gelidina (I.F.L.) / Iluvien / Intradermo (Pental) / Isnaderm (Isnardi) / Isoderma (Isola-Ibi) / Jellin (Grünenthal) / Locafluo (Recordati) / Localyn (Ricordati) / Mecloderm (ICI) / Monoderm (Pharbil) / Omniderm (Face) / Oxidermiol Fuerte (Mazuelos) / Percutina (Mitim) / Prodermin (Eufarma) / Radiocin (Radiopharma) / Roliderm (Neopharmed) / Sinalar / Sterolone (Francia) / Straderm (I.T.A.) / Synalar / Synamol / Synandone (I.C.I.) / Synandrone / Synemol (Syntex) / Synotic (Zoetis) / Synsac (MP Biomedicals, LLC) / Tefunote (Taiyo) / Topifluor (Tiber) / Ultraderm (Ecobi) / Ungovac (I.C.N.)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CapexKit1 mg/1mgTopicalGalderma1984-10-12Not applicableUS flag
CapexShampoo0.01 %TopicalGalderma2001-02-022014-07-15Canada flag
Derma Smoothe/fs Liq 0.01%Emulsion0.01 %TopicalHill Dermaceuticals, Inc.1991-12-31Not applicableCanada flag
Derma-Smoothe/FSOil0.11 mg/1mLTopicalHill Dermaceuticals, Inc.1995-02-162013-07-08US flag
Derma-Smoothe/FSOil0.11 mg/1mLTopicalRoyal Pharmaceuticals1995-02-16Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Flac Otic OilOil0.11 mg/1mLAuricular (otic)Patrin Pharma2018-04-12Not applicableUS flag
Fluocinolone AcetonideCream0.25 mg/1gTopicalCosette Pharmaceuticals, Inc.2018-11-05Not applicableUS flag
Fluocinolone AcetonideOintment0.25 mg/1gTopicalANI Pharmaceuticals, Inc.2023-11-13Not applicableUS flag
Fluocinolone acetonideOil0.01 mg/100mLTopicalPadagis Israel Pharmaceuticals Ltd2017-06-14Not applicableUS flag
Fluocinolone AcetonideOintment0.25 mg/1gTopicalTeligent Pharma, Inc.2012-12-27Not applicableUS flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ฟลูซิเดอร์ม ครีมCream0.025 %w/wบริษัท สหแพทย์เภสัช จำกัด2017-01-232020-08-24Thailand flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ACEOTO PLUS®Fluocinolone acetonide (0.25 mg) + Ciprofloxacin hydrochloride (3 mg)SolutionAuricular (otic)LABORATORIOS SALVAT S.A2013-11-25Not applicableColombia flag
ALBAVANCE FFluocinolone acetonide (4 %) + Hydroquinone (0.05 %) + Tretinoin (0.01 %)CreamImmortal Pharmaceutical Laboratories2017-09-182027-04-19Indonesia flag
BRAVODERM-NFluocinolone acetonide (0.25 mg/g) + Neomycin sulfate (5 mg/g)CreamTopicalBufa Aneka2017-11-212027-01-28Indonesia flag
CETRAXAL PLUS EAR DROPS SOLUTIONFluocinolone acetonide (0.25 mg) + Ciprofloxacin hydrochloride (3 mg)SolutionAuricular (otic)HYPHENS PHARMA PTE. LTD.2014-08-29Not applicableSingapore flag
CEXIDALFluocinolone acetonide (0.25 MG/ML) + Ciprofloxacin (3 MG/ML)Solution / dropsAuricular (otic)Infectopharm Arzneimittel Und Consilium Gmbh2014-07-08Not applicableItaly flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Fluocinolone Acetonide 0.01/ Niacinamide 4Fluocinolone acetonide (0.025 g/100g) + Nicotinamide (4 g/100g)CreamTopicalSincerus Florida LLC2019-05-13Not applicableUS flag
Fluocinolone Acetonide 0.01% / Minoxidil 5% / Tretinoin 0.025%Fluocinolone acetonide (0.01 g/100g) + Minoxidil (5 g/100g) + Tretinoin (0.025 g/100g)SolutionTopicalSincerus Florida, LLC2019-05-09Not applicableUS flag
Fluocinolone Acetonide 0.01% / Minoxidil 7% / Progesterone 0.1%Fluocinolone acetonide (0.01 g/100g) + Minoxidil (7 g/100g) + Progesterone (0.1 g/100g)SolutionTopicalSincerus Florida, LLC2019-05-09Not applicableUS flag
Fluocinolone Acetonide 0.01% / Niacinamide 4%Fluocinolone acetonide (0.01 g/100g) + Nicotinamide (4 g/100g)CreamTopicalSincerus Florida LLC2019-05-13Not applicableUS flag
Fluocinolone Acetonide 0.025% / Lidocaine HCl Monohydrate 1%Fluocinolone acetonide (0.025 g/100g) + Lidocaine hydrochloride (1 g/100g)GelTopicalSincerus Florida, LLC2019-05-20Not applicableUS flag

Categories

ATC Codes
S01CA10 — Fluocinolone acetonide and antiinfectivesD07BC02 — Fluocinolone acetonide and antisepticsS02BA08 — Fluocinolone acetonideC05AA10 — Fluocinolone acetonideS01BA15 — Fluocinolone acetonideD07AC04 — Fluocinolone acetonideS02CA05 — Fluocinolone acetonide and antiinfectivesD07CC02 — Fluocinolone acetonide and antibiotics
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Hydroxysteroids
Direct Parent
21-hydroxysteroids
Alternative Parents
Gluco/mineralocorticoids, progestogins and derivatives / 20-oxosteroids / 11-beta-hydroxysteroids / 3-oxo delta-1,4-steroids / Halogenated steroids / Delta-1,4-steroids / Ketals / 1,3-dioxolanes / Alpha-hydroxy ketones / Secondary alcohols
show 9 more
Substituents
11-beta-hydroxysteroid / 11-hydroxysteroid / 20-oxosteroid / 21-hydroxysteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / 6-halo-steroid / 9-halo-steroid / Acetal / Alcohol
show 27 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
organic heteropentacyclic compound, 11beta-hydroxy steroid, glucocorticoid, cyclic ketal, 20-oxo steroid, fluorinated steroid, 3-oxo-Delta(1),Delta(4)-steroid, 21-hydroxy steroid (CHEBI:31623)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
0CD5FD6S2M
CAS number
67-73-2
InChI Key
FEBLZLNTKCEFIT-VSXGLTOVSA-N
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
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[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-14,17-dien-16-one
SMILES
[H][C@@]12C[C@@]3([H])[C@]4([H])C[C@H](F)C5=CC(=O)C=C[C@]5(C)[C@@]4(F)[C@@H](O)C[C@]3(C)[C@@]1(OC(C)(C)O2)C(=O)CO

References

Synthesis Reference

Mills, J.S. and Bowers, A.; U.S. Patent 3,014,938; December 26, 1961; assigned to Syntex SA, Mexico.

General References
  1. Goldstein DA, Godfrey DG, Hall A, Callanan DG, Jaffe GJ, Pearson PA, Usner DW, Comstock TL: Intraocular pressure in patients with uveitis treated with fluocinolone acetonide implants. Arch Ophthalmol. 2007 Nov;125(11):1478-85. Epub 2007 Oct 8. [Article]
  2. Brumm MV, Nguyen QD: Fluocinolone acetonide intravitreal sustained release device--a new addition to the armamentarium of uveitic management. Int J Nanomedicine. 2007;2(1):55-64. [Article]
  3. Jaffe GJ, Yang CH, Guo H, Denny JP, Lima C, Ashton P: Safety and pharmacokinetics of an intraocular fluocinolone acetonide sustained delivery device. Invest Ophthalmol Vis Sci. 2000 Oct;41(11):3569-75. [Article]
  4. Knoch HG, Klug W, Hubner WD: [Ointment treatment of 1st degree hemorrhoids. Comparison of the effectiveness of a phytogenic preparation with two new ointments containing synthetic drugs]. Fortschr Med. 1992 Mar 20;110(8):135-8. [Article]
  5. Sadiq MA, Agarwal A, Soliman MK, Hanout M, Sarwar S, Do DV, Nguyen QD: Sustained-release fluocinolone acetonide intravitreal insert for macular edema: clinical pharmacology and safety evaluation. Expert Opin Drug Saf. 2015 Jul;14(7):1147-56. doi: 10.1517/14740338.2015.1041916. Epub 2015 May 20. [Article]
  6. Nehme A, Lobenhofer EK, Stamer WD, Edelman JL: Glucocorticoids with different chemical structures but similar glucocorticoid receptor potency regulate subsets of common and unique genes in human trabecular meshwork cells. BMC Med Genomics. 2009 Sep 10;2:58. doi: 10.1186/1755-8794-2-58. [Article]
  7. Broggini M, Benvenuti C, Botta V, Broccali G: Pharmacokinetics of fluocinolone acetonide in patch versus cream formulations. Int J Clin Pharmacol Res. 1991;11(1):17-21. [Article]
  8. Lemke T., Williams D., Roche V. and Zito W. (2008). Foye's Principles of Medicinal Chemistry (6th) (6th ed.). Lippincott Williams & Wilkins. [ISBN:978-0-7817-6879-5]
  9. Becker M., Davis J. (2008). Surgical Management of Inflammatory Eye Disease. Springer. [ISBN:978-3-540-33861-1]
  10. Narayanan R. and Kuppermann B. (2010). Retinal pharmacotherapy. Elsevier.
  11. FDA approvals [Link]
  12. Dailymed [Link]
  13. Dailymed [Link]
  14. Dailymed [Link]
  15. Drugs.com [Link]
  16. Retina today [Link]
  17. Topical Fluocinolone acetonide [File]
  18. Topical Fluocinolone acetonide UK label [File]
  19. Retisert (Fluocinolone acetate) FDA label [File]
Human Metabolome Database
HMDB0014729
KEGG Drug
D01825
PubChem Compound
6215
PubChem Substance
46506244
ChemSpider
5980
RxNav
4461
ChEBI
31623
ChEMBL
CHEMBL989
ZINC
ZINC000003977981
Therapeutic Targets Database
DAP000813
PharmGKB
PA164754912
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Fluocinolone_acetonide
FDA label
Download (49.7 KB)
MSDS
Download (75.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentDiabetic Macular Edema (DME)1
4CompletedTreatmentAllergic Reaction1
4CompletedTreatmentChronic Diabetic Macular Edema1
4CompletedTreatmentDiabetic Macular Edema (DME)2
4CompletedTreatmentMelasma2

Pharmacoeconomics

Manufacturers
  • Alpharma us pharmaceuticals division
  • E fougera div altana inc
  • G and w laboratories inc
  • Perrigo new york inc
  • Pharmaderm div altana inc
  • Pharmafair inc
  • Taro pharmaceuticals inc
  • Taro pharmaceuticals usa inc
  • Usl pharma inc
  • Allergan herbert div allergan inc
  • Savage laboratories inc div altana inc
  • Medicis pharmaceutical corp
  • Bausch and lomb inc
  • Hill dermaceuticals inc
  • Galderma laboratories lp
  • Bausch and lomb pharmaceuticals inc
  • Morton grove pharmaceuticals inc
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Amend
  • Bausch & Lomb Inc.
  • Dispensing Solutions
  • E. Fougera and Co.
  • G & W Labs
  • Galderma Laboratories
  • Hill Dermaceuticals
  • Hill Laboratories Inc.
  • Major Pharmaceuticals
  • Medicis Pharmaceutical Co.
  • Nycomed Inc.
  • Patheon Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Qualitest
  • Taro Pharmaceuticals USA
Dosage Forms
FormRouteStrength
KitTopical1 mg/1mg
ShampooTopical0.01 %
SolutionAuricular (otic)3 mg
Cream
SolutionAuricular (otic)
Cream0.25 mg
OintmentTopical
CreamCutaneous0.010 g
EmulsionTopical0.01 %
OilTopical0.11 mg/1mL
OilAuricular (otic)0.11 mg/1mL
SolutionAuricular (otic)0.01 % w/v
Solution / dropsAuricular (otic)
Solution / dropsAuricular (otic)250 MICROGRAMMI/ML
GelTopical
CreamCutaneous0.0100 g
CreamTopical0.25 mg
OintmentTopical0.25 mg
Cream0.025 %w/w
CreamTopical0.25 mg/g
CreamTopical0.1 mg/1g
OilAuricular (otic)0.11 mg/20mL
OilTopical0.01 mg/100mL
OilTopical0.11 mg/118.28 mL
OilTopical0.11 mg/118.28mL
OintmentTopical
SolutionTopical0.1 mg/1mL
Solution / dropsAuricular (otic)0.11 mg/1mL
SolutionTopical
GelTopical
CreamTopical.01 %
CreamTopical.025 %
OintmentTopical.1 mg / g
OintmentTopical0.25 mg / g
EmulsionTopical
CreamCutaneous0.25 MG/G
ShampooTopical.01 %
GelTopical0.025 g
ImplantIntravitreal0.19 mg
ImplantIntravitreal0.19 mg/1
ImplantIntravitreal190 MICROGRAMMI
ImplantIntravitreal190 ug
EmulsionTopical0.25 mg/g
OintmentTopical0.25 mg/g
OintmentTopical1.667 %
SprayNasal0.01 %
LotionTopical
LotionTopical0.01 %
LotionTopical0025 %
Solution
SprayNasal
Cream15 G
Cream20 G
CreamTopical
KitTopical
InsertVaginal
CreamRectal
SuppositoryRectal
SuppositoryTopical2 G
Cream
ImplantIntravitreal0.59 mg
ImplantIntravitreal0.59 mg/1
CreamTopical0.025 % W/V
CreamTopical0.025 % w/w
CreamTopical0.25 mg/1g
KitTopical0.25 mg/1g
OintmentTopical0.025 %
OintmentTopical0.25 mg/1g
SolutionTopical0.01 %
CreamTopical0.025 %
OintmentTopical0.01 %
OintmentTopical.025 %
CreamTopical0.010 g
Kit; solutionTopical0.1 mg/1mL
CreamTopical0.01 %
CreamCutaneous
CreamTopical0.1 mg/g
KitTopical0.1 mg/1mL
ImplantIntraocular0.18 mg/1
ImplantIntravitreal0.18 mg/1
Prices
Unit descriptionCostUnit
Retisert implant21900.0USD each
Synalar 0.01% Solution 60ml Bottle108.72USD bottle
Synalar 0.025% Cream 60 gm Tube103.1USD tube
Synalar 0.025% Ointment 60 gm Tube103.1USD tube
Fluocinolone Acetonide 0.01% Cream 15 gm Tube76.61USD tube
Fluocinolone Acetonide 0.01% Cream 60 gm Tube73.5USD tube
Fluocinolone Acetonide 0.025% Cream 15 gm Tube46.1USD tube
Fluocinolone Acetonide 0.025% Cream 60 gm Tube38.99USD tube
Fluocinolone Acetonide 0.025% Ointment 60 gm Tube38.99USD tube
Fluocinolone acetonide powder35.28USD g
Fluocinolone Acetonide 0.025% Ointment 15 gm Tube33.47USD tube
Fluocinolone Acetonide 0.01% Solution 60ml Bottle20.45USD bottle
Dermotic oil 0.01% ear drops1.75USD ml
Derma-smoothe-fs scalp oil0.35USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US8247395No2012-08-212022-10-22US flag
US8653053No2014-02-182022-10-25US flag
US7939516No2011-05-102025-05-04US flag
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US6217895No2001-04-172019-03-22US flag
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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)266-268Mills, J.S. and Bowers, A.; U.S. Patent 3,014,938; December 26, 1961; assigned to Syntex SA, Mexico.
water solubilityInsoluble'MSDS'
logP2.48HANSCH,C ET AL. (1995)
pKa13.9Graham P. (2013). An Introduction to Medicinal Chemistry. Fifth ed. Oxford.
Predicted Properties
PropertyValueSource
Water Solubility0.0547 mg/mLALOGPS
logP2.47ALOGPS
logP1.6Chemaxon
logS-3.9ALOGPS
pKa (Strongest Acidic)13.38Chemaxon
pKa (Strongest Basic)-3.3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area93.06 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity111.41 m3·mol-1Chemaxon
Polarizability44.84 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9865
Blood Brain Barrier+0.9683
Caco-2 permeable+0.5
P-glycoprotein substrateSubstrate0.7912
P-glycoprotein inhibitor INon-inhibitor0.5674
P-glycoprotein inhibitor IINon-inhibitor0.8383
Renal organic cation transporterNon-inhibitor0.8304
CYP450 2C9 substrateNon-substrate0.8679
CYP450 2D6 substrateNon-substrate0.8856
CYP450 3A4 substrateSubstrate0.6964
CYP450 1A2 substrateNon-inhibitor0.9327
CYP450 2C9 inhibitorNon-inhibitor0.9394
CYP450 2D6 inhibitorNon-inhibitor0.9559
CYP450 2C19 inhibitorNon-inhibitor0.9311
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8806
Ames testNon AMES toxic0.7682
CarcinogenicityNon-carcinogens0.9174
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7033 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9838
hERG inhibition (predictor II)Non-inhibitor0.671
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0a4u-2790300000-f726c5edd782f086d667
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0il9-0496400000-d158ff1b8dbcf078b8ff
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-00di-3981000000-e34007db14fcd7363a09
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0il9-0496400000-d158ff1b8dbcf078b8ff
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-3981000000-e34007db14fcd7363a09
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f8a-0003900000-4baadbb066235c507f6d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0000900000-e5dcb18d8d3186e6c553
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-1225900000-a125636915974eef1dd3
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01dl-1009600000-dc888016ac3ddcd148c7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052n-4926400000-8582708073f42daab648
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-005a-4398100000-404bff95a4e60bc2bd08
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-209.138121
predicted
DarkChem Lite v0.1.0
[M-H]-205.335921
predicted
DarkChem Lite v0.1.0
[M-H]-206.57959
predicted
DeepCCS 1.0 (2019)
[M+H]+209.168421
predicted
DarkChem Lite v0.1.0
[M+H]+201.7887498
predicted
DarkChem Lite v0.1.0
[M+H]+208.3033
predicted
DeepCCS 1.0 (2019)
[M+Na]+207.768921
predicted
DarkChem Lite v0.1.0
[M+Na]+212.6199073
predicted
DarkChem Lite v0.1.0
[M+Na]+214.63228
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modula...
Gene Name
NR3C1
Uniprot ID
P04150
Uniprot Name
Glucocorticoid receptor
Molecular Weight
85658.57 Da
References
  1. Nehme A, Lobenhofer EK, Stamer WD, Edelman JL: Glucocorticoids with different chemical structures but similar glucocorticoid receptor potency regulate subsets of common and unique genes in human trabecular meshwork cells. BMC Med Genomics. 2009 Sep 10;2:58. doi: 10.1186/1755-8794-2-58. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inducer
General Function
Structural molecule activity
Specific Function
Plays important roles in the innate immune response as effector of glucocorticoid-mediated responses and regulator of the inflammatory process. Has anti-inflammatory activity (PubMed:8425544). Play...
Gene Name
ANXA1
Uniprot ID
P04083
Uniprot Name
Annexin A1
Molecular Weight
38713.855 Da
References
  1. Retisert (Fluocinolone acetate) FDA label [File]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inducer
General Function
S100 protein binding
Specific Function
Calcium-regulated membrane-binding protein whose affinity for calcium is greatly enhanced by anionic phospholipids. It binds two calcium ions with high affinity. May be involved in heat-stress resp...
Gene Name
ANXA2
Uniprot ID
P07355
Uniprot Name
Annexin A2
Molecular Weight
38603.63 Da
References
  1. Retisert (Fluocinolone acetate) FDA label [File]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inducer
General Function
Phospholipase a2 inhibitor activity
Specific Function
Inhibitor of phospholipase A2, also possesses anti-coagulant properties. Also cleaves the cyclic bond of inositol 1,2-cyclic phosphate to form inositol 1-phosphate.
Gene Name
ANXA3
Uniprot ID
P12429
Uniprot Name
Annexin A3
Molecular Weight
36374.85 Da
References
  1. Retisert (Fluocinolone acetate) FDA label [File]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inducer
General Function
Calcium/phospholipid-binding protein which promotes membrane fusion and is involved in exocytosis.
Specific Function
Calcium ion binding
Gene Name
ANXA4
Uniprot ID
P09525
Uniprot Name
Annexin A4
Molecular Weight
35882.36 Da
References
  1. Retisert (Fluocinolone acetate) FDA label [File]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inducer
General Function
Phospholipid binding
Specific Function
This protein is an anticoagulant protein that acts as an indirect inhibitor of the thromboplastin-specific complex, which is involved in the blood coagulation cascade.
Gene Name
ANXA5
Uniprot ID
P08758
Uniprot Name
Annexin A5
Molecular Weight
35936.375 Da
References
  1. Retisert (Fluocinolone acetate) FDA label [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Receptor binding
Specific Function
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides, this releases glycerophospholipids and arachidonic acid that serve as the precursors of signal molecules.
Gene Name
PLA2G1B
Uniprot ID
P04054
Uniprot Name
Phospholipase A2
Molecular Weight
16359.535 Da
References
  1. Emerit I, Levy A, Cerutti P: Suppression of tumor promoter phorbolmyristate acetate-induced chromosome breakage by antioxidants and inhibitors of arachidonic acid metabolism. Mutat Res. 1983 Aug;110(2):327-35. doi: 10.1016/0027-5107(83)90149-5. [Article]
  2. Kaszkin M, Espe U, Furstenberger G, Kinzel V: Dual effect of the phorbol ester TPA on arachidonic acid release from HeLa cells. FEBS Lett. 1988 Jun 20;233(2):244-8. doi: 10.1016/0014-5793(88)80435-6. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Moore CD, Roberts JK, Orton CR, Murai T, Fidler TP, Reilly CA, Ward RM, Yost GS: Metabolic pathways of inhaled glucocorticoids by the CYP3A enzymes. Drug Metab Dispos. 2013 Feb;41(2):379-89. doi: 10.1124/dmd.112.046318. Epub 2012 Nov 9. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Steroid binding
Specific Function
Major transport protein for glucocorticoids and progestins in the blood of almost all vertebrate species.
Gene Name
SERPINA6
Uniprot ID
P08185
Uniprot Name
Corticosteroid-binding globulin
Molecular Weight
45140.49 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48