Identification

Name
Fluocinolone acetonide
Accession Number
DB00591  (APRD00977)
Type
Small Molecule
Groups
Approved, Investigational, Vet approved
Description

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]

Structure
Thumb
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
Active Moieties
NameKindUNIICASInChI Key
FluocinoloneunknownCT1IX58L9S807-38-5UUOUOERPONYGOS-CLCRDYEYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CapexKit1 mg/1mgTopicalGalderma1984-10-12Not applicableUs
CapexShampoo0.01 %TopicalGalderma2001-02-022014-07-15Canada
Derma Smoothe/fs Liq 0.01%Liquid0.01 %TopicalHill Dermaceuticals, Inc.1991-12-31Not applicableCanada
Derma-Smoothe/FSOil0.11 mg/1mLTopicalHill Dermaceuticals, Inc.1995-02-162013-07-08Us
Derma-Smoothe/FSOil0.11 mg/1mLTopicalRoyal Pharmaceuticals1995-02-16Not applicableUs
Derma-Smoothe/FSOil0.11 mg/1mLTopicalHill Dermaceuticals, Inc.1988-02-032013-07-08Us
Derma-Smoothe/FSOil0.11 mg/1mLTopicalPhysicians Total Care, Inc.1988-02-032012-06-30Us
Derma-Smoothe/FSOil0.11 mg/1mLTopicalRoyal Pharmaceuticals1995-02-16Not applicableUs
Derma-Smoothe/FSOil0.11 mg/1mLTopicalPhysicians Total Care, Inc.2009-09-03Not applicableUs
DermOticOil0.11 mg/1mLAuricular (otic)Hill Dermaceuticals, Inc.2005-11-092013-07-08Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Flac Otic OilOil0.11 mg/1mLAuricular (otic)Patrin Pharma2018-04-12Not applicableUs
Fluocinolone AcetonideSolution0.1 mg/1mLTopicalPhysicians Total Care, Inc.1996-04-03Not applicableUs
Fluocinolone AcetonideSolution0.1 mg/1mLTopicalGw Pharmaceuticals Ltd.2016-09-28Not applicableUs
Fluocinolone AcetonideOintment0.25 mg/1gTopicalTeligent Pharma, Inc.2012-12-27Not applicableUs
Fluocinolone AcetonideCream0.25 mg/1gTopicalG&W Laboratories, Inc.2018-11-05Not applicableUs
Fluocinolone AcetonideOil0.11 mg/118.28mLTopicalTaro Pharmaceuticals U.S.A., Inc.2016-05-19Not applicableUs
Fluocinolone AcetonideOil0.11 mg/118.28mLTopicalAv Kare, Inc.2013-12-17Not applicableUs
Fluocinolone AcetonideOil0.11 mg/118.28mLTopicalPhysicians Total Care, Inc.2012-12-07Not applicableUs
Fluocinolone AcetonideOil0.11 mg/1mLTopicalGlenmark Pharmaceuticals Inc., USA2018-10-30Not applicableUs
Fluocinolone AcetonideOil0.11 mg/1mLTopicalVersaPharm Inc - an Akorn Company2015-09-10Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Neo-SynalarFluocinolone acetonide (0.25 mg/1g) + Neomycin sulfate (3.5 mg/1g)CreamTopicalMedimetriks Pharmaceuticals1963-06-11Not applicableUs
Neo-SynalarFluocinolone acetonide (0.25 mg/1g) + Neomycin sulfate (3.5 mg/1g)KitMedimetriks Pharmaceuticals2014-07-15Not applicableUs
NoxipakFluocinolone acetonide (0.1 mg/1mL) + Urea (17 g/85g)KitSolutech Pharmaceuticals Llc2017-11-01Not applicableUs
OtixalFluocinolone acetonide (0.025 %) + Ciprofloxacin (0.3 %)SolutionAuricular (otic)Pediapharm Inc2017-05-08Not applicableCanada
OtovelFluocinolone acetonide (62.5 ug/0.25mL) + Ciprofloxacin (872.5 ug/0.25mL) + Polysorbate 80 (6250 ug/0.25mL)For solutionAuricular (otic)Arbor Pharmaceuticals2016-04-29Not applicableUs
Synalar Bi-otic SolutionFluocinolone acetonide (0.25 mg) + Neomycin (3.5 mg) + Polymyxin B Sulfate (10000 unit)SolutionAuricular (otic)Medicis Pharmaceutical Corporation1986-12-311998-09-25Canada
Tri-lumaFluocinolone acetonide (0.1 mg/1g) + Hydroquinone (40 mg/1g) + Tretinoin (0.5 mg/1g)CreamTopicalGalderma2002-01-18Not applicableUs
International/Other Brands
Alfabios (Iton) / Alvadermo (Alvarez-Gomez) / Benamizol (Mohan Yakuhin) / Biscosal (Onta Seiyaku) / Boniderma (Boniscontro) / Co-FIuosin (Sanchez-Covisa) / Coderma (Biotrading) / Cordes F (Ichthyol) / Cortalar (Bergamon) / Cortiderma (Gazzini) / Cortiespec (Centrum) / Cortiphate (Tokyo Tanabe) / Cortiplastol / Cortoderm (Lennon) / Dermacort (P.S.N) / Dermaisom (Isom) / Dermalar (Teva) / Dermaplus (Ripari-Gero) / Dermil (Cifa) / Dermo Framan (Oftalmiso) / 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) / Flupollon (Mayado Seiyaku, Kaigai and Ohta) / Fluzon (Taisho) / Futocan (Shinlon) / Gelargin (Leciva) / Gelidina (I.F.L.) / 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) / Sterolone (Francia) / Straderm (I.T.A.) / Synalar (Syntex, Cassenne and ICI) / Synandone (I.C.I.) / Synemol (Syntex) / Synotic (Zoetis) / Synsac (MP Biomedicals, LLC) / Tefunote (Taiyo) / Topifluor (Tiber) / Ultraderm (Ecobi) / Ungovac (I.C.N.)
Categories
UNII
0CD5FD6S2M
CAS number
67-73-2
Weight
Average: 452.4882
Monoisotopic: 452.201045102
Chemical Formula
C24H30F2O6
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

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]

Associated Conditions
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
Human
AAnnexin A1
inducer
Human
AAnnexin A2
inducer
Human
AAnnexin A3
inducer
Human
AAnnexin A4
inducer
Human
AAnnexin A5
inducer
Human
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]

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]

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be increased when combined with Fluocinolone acetonide.
(S)-WarfarinThe metabolism of (S)-Warfarin can be increased when combined with Fluocinolone acetonide.
1-TestosteroneThe risk or severity of edema formation can be increased when 1-Testosterone is combined with Fluocinolone acetonide.
1,10-PhenanthrolineThe therapeutic efficacy of 1,10-Phenanthroline can be decreased when used in combination with Fluocinolone acetonide.
16-BromoepiandrosteroneThe risk or severity of edema formation can be increased when 16-Bromoepiandrosterone is combined with Fluocinolone acetonide.
19-norandrostenedioneThe risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Fluocinolone acetonide.
1alpha-Hydroxyvitamin D5The therapeutic efficacy of 1alpha-Hydroxyvitamin D5 can be decreased when used in combination with Fluocinolone acetonide.
2-MethoxyethanolThe risk or severity of adverse effects can be increased when Fluocinolone acetonide is combined with 2-Methoxyethanol.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be increased when combined with Fluocinolone acetonide.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be increased when combined with Fluocinolone acetonide.
Food Interactions
Not Available

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. [PubMed:17923537]
  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. [PubMed:17722513]
  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. [PubMed:11006254]
  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. [PubMed:1582642]
  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. [PubMed:25994877]
  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. [PubMed:19744340]
  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. [PubMed:1874579]
  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]
External Links
Human Metabolome Database
HMDB0014729
KEGG Drug
D01825
PubChem Compound
6215
PubChem Substance
46506244
ChemSpider
5980
ChEBI
31623
ChEMBL
CHEMBL989
Therapeutic Targets Database
DAP000813
PharmGKB
PA164754912
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Fluocinolone_acetonide
ATC Codes
S01CA10 — Fluocinolone acetonide and antiinfectivesS01BA15 — Fluocinolone acetonideS02BA08 — Fluocinolone acetonideS02CA05 — Fluocinolone acetonide and antiinfectivesD07BC02 — Fluocinolone acetonide and antisepticsD07CC02 — Fluocinolone acetonide and antibioticsD07AC04 — Fluocinolone acetonideC05AA10 — Fluocinolone acetonide
AHFS Codes
  • 84:06.00 — Anti-inflammatory Agents
  • 52:08.08 — Corticosteroids
FDA label
Download (49.7 KB)
MSDS
Download (75.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentUveitis Affecting the Posterior Segment1
1CompletedTreatmentPsoriasis Vulgaris (Plaque Psoriasis)1
2CompletedTreatmentDiabetic Macular Edema (DME)1
2CompletedTreatmentBenign facial lentigines1
2TerminatedTreatmentAge-Related Macular Degeneration (ARMD)1
2TerminatedTreatmentMacular Edema (ME) / Retinal Vein Occlusions(RVO)1
2, 3CompletedTreatmentDiabetic Macular Edema (DME)1
2, 3CompletedTreatmentNon-Infectious Uveitis1
2, 3CompletedTreatmentNoninfectious Posterior Uveitis1
2, 3TerminatedTreatmentNon-Infectious Uveitis1
3CompletedTreatmentDiabetic Macular Edema (DME)3
4Active Not RecruitingTreatmentDiabetic Macular Edema (DME)1
4CompletedTreatmentAllergies1
4CompletedTreatmentChronic Diabetic Macular Edema1
4CompletedTreatmentDiabetic Macular Edema (DME)1
4CompletedTreatmentMelasma1
4CompletedTreatmentUveitis1
4TerminatedTreatmentMelasma1
4Unknown StatusTreatmentNon-Infectious Uveitis / Ocular Behcet's Disease / Refractory Uveitis1
4WithdrawnTreatmentDiabetic Macular Edema (DME)1
Not AvailableCompletedNot AvailableDexmedetomidine / Endoscopy, Gastrointestinal / Sedation therapy1
Not AvailableCompletedPreventionSolar Lentigines1

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 %
LiquidTopical0.01 %
OilTopical0.11 mg/1mL
OilAuricular (otic)0.11 mg/1mL
SolutionAuricular (otic)0.01 %
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
SolutionTopical0.1 mg/1mL
Solution / dropsAuricular (otic)0.11 mg/1mL
CreamTopical.01 %
CreamTopical.025 %
OintmentTopical.1 mg
OintmentTopical0.25 mg
ShampooTopical.01 %
ImplantIntravitreal0.19 mg/1
Kit
For solutionAuricular (otic)
ImplantIntravitreal0.59 mg/1
ImplantIntravitreal0.59 mg
CreamTopical0.25 mg/1g
KitTopical0.25 mg/1g
OintmentTopical0.25 mg/1g
SolutionAuricular (otic)
CreamTopical0.025 %
OintmentTopical0.025 %
OintmentTopical0.01 %
OintmentTopical.025 %
SolutionTopical0.01 %
CreamTopical0.01 %
CreamTopical
Kit0.1 mg/1mL
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)
US8247395No2012-08-212022-10-22Us
US8653053No2014-02-182022-10-25Us
US7939516No2011-05-102025-05-04Us
US7915243No2011-03-292026-03-22Us
US6217895No2001-04-172019-03-22Us
US6548078No2003-04-152019-03-22Us
US6375972No2002-04-232020-04-26Us
US8252307No2012-08-282019-06-27Us
US8871241No2014-10-282027-08-12Us
US8932610No2015-01-132030-03-24Us

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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0il9-0496400000-d158ff1b8dbcf078b8ff
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-3981000000-e34007db14fcd7363a09

Taxonomy

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
Progestogin-skeleton / 21-hydroxysteroid / 20-oxosteroid / Pregnane-skeleton / 3-oxo-delta-1,4-steroid / 3-oxosteroid / 9-halo-steroid / 6-halo-steroid / Halo-steroid / Oxosteroid
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)

Targets

Kind
Protein
Organism
Human
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. [PubMed:19744340]
Kind
Protein
Organism
Human
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
Human
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
Human
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
Human
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
Human
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]

Enzymes

Kind
Protein
Organism
Human
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. [PubMed:23143891]

Carriers

Kind
Protein
Organism
Human
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. [PubMed:17139284]
  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. [PubMed:17016423]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Drug created on June 13, 2005 07:24 / Updated on December 14, 2018 17:06