Identification

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

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). It is also being investigated by Sivida and Alimera, under the brand name Medidur, as a sustained release intraocular implant for the treatment of diabetic macular edema.

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
  • 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.1988-02-032013-07-08Us
Derma-Smoothe/FSOil0.11 mg/1mLTopicalRoyal Pharmaceuticals1995-02-16Not applicableUs
Derma-Smoothe/FSOil0.11 mg/1mLTopicalHill Dermaceuticals, Inc.1995-02-162013-07-08Us
Derma-Smoothe/FSOil0.11 mg/1mLTopicalPhysicians Total Care, Inc.2009-09-03Not applicableUs
Derma-Smoothe/FSOil0.11 mg/1mLTopicalRoyal Pharmaceuticals1995-02-16Not applicableUs
Derma-Smoothe/FSOil0.11 mg/1mLTopicalPhysicians Total Care, Inc.1988-02-032012-06-30Us
DermOticOil0.11 mg/1mLAuricular (otic)Royal Pharmaceuticals2005-11-09Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Flac Otic OilOil0.11 mg/1mLAuricular (otic)Patrin Pharma2018-04-12Not applicableUs
Fluocinolone AcetonideCream0.1 mg/1gTopicalPhysicians Total Care, Inc.1982-12-162012-06-30Us
Fluocinolone AcetonideOil0.11 mg/1mLAuricular (otic)Versa Pharm Incorporated2016-09-13Not applicableUs
Fluocinolone AcetonideOil0.11 mg/20mLAuricular (otic)Av Kare, Inc.2013-12-18Not applicableUs
Fluocinolone AcetonideSolution0.1 mg/1mLTopicalPhysicians Total Care, Inc.1996-04-03Not applicableUs
Fluocinolone AcetonideCream0.1 mg/1gTopicalGw Pharmaceuticals Ltd.1988-07-26Not applicableUs
Fluocinolone AcetonideOil0.11 mg/20mLAuricular (otic)Amneal Pharmaceuticals2015-09-22Not applicableUs
Fluocinolone AcetonideCream0.1 mg/1gTopicalE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.1982-12-16Not applicableUs
Fluocinolone AcetonideOil0.11 mg/118.28mLTopicalAv Kare, Inc.2013-12-17Not applicableUs
Fluocinolone AcetonideSolution0.1 mg/1mLTopicalLupin Pharmaceuticals2015-09-02Not 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
Coriphate / Cortiplastol / Dermalar (Teva) / Flucinar (Jelfa) / Flucort / Fluocet / Fluonid (Biolab) / Fluotrex / Fluovitif / Flupollon (Mayado Seiyaku) / Fluzon / Futocan (Shinlon) / Jellin (Grünenthal) / Locafluo (Recordati) / Localyn / Mecloderm (ICI) / Omniderm / Percutina / Prodermin / Radiocin / Sinalar / Synamol / Synandone / Synandrone / Synemol / Synotic / Synsac / Tefunote
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[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]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

For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses. Also for the treatment of chronic non-infectious uveitis affecting the posterior segment of the eye (Retisert).

Associated Conditions
Pharmacodynamics
Not Available
Mechanism of action

Fluocinolone Acetonide is a corticosteroid that binds to 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. The anti-inflammatory actions of corticosteroids are thought to involve lipocortins, phospholipase A2 inhibitory proteins which, through inhibition arachidonic acid, control the biosynthesis of prostaglandins and leukotrienes. Specifically glucocorticoids induce lipocortin-1 (annexin-1) synthesis, which then binds to cell membranes preventing the phospholipase A2 from coming into contact with its substrate arachidonic acid. This leads to diminished eicosanoid production. Cyclooxygenase (both COX-1 and COX-2) expression is also suppressed, potentiating the effect. In another words, the two main products in inflammation Prostaglandins and Leukotrienes are inhibited by the action of Glucocorticoids. Glucocorticoids also stimulate the lipocortin-1 escaping to the extracellular space, where it binds to the leukocyte membrane receptors and inhibits various inflammatory events: epithelial adhesion, emigration, chemotaxis, phagocytosis, respiratory burst and the release of various inflammatory mediators (lysosomal enzymes, cytokines, tissue plasminogen activator, chemokines etc.) from neutrophils, macrophages and mastocytes. Additionally the immune system is suppressed by corticosteroids due to a decrease in the function of the lymphatic system, a reduction in immunoglobulin and complement concentrations, the precipitation of lymphocytopenia, and interference with antigen-antibody binding. Like other glucocorticoid agents Fluocinolone acetonide acts as a physiological antagonist to insulin by decreasing glycogenesis (formation of glycogen). It also promotes the breakdown of lipids (lipolysis), and proteins, leading to the mobilization of extrahepatic amino acids and ketone bodies. This leads to increased circulating glucose concentrations (in the blood). There is also decreased glycogen formation in the liver.

TargetActionsOrganism
AGlucocorticoid receptor
agonist
Human
Absorption

Rapidly absorbed (15 minutes)

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Primarily hepatic, corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys.

Route of elimination

Corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys. Some of the topical corticosteroids and their metabolites are also excreted into the bile.

Half life

1.3-1.7 hours

Clearance
Not Available
Toxicity
Not Available
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 2-Methoxyethanol is combined with Fluocinolone Acetonide.
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]
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 antiinfectivesD07CC02 — Fluocinolone acetonide and antibioticsD07BC02 — Fluocinolone acetonide and antisepticsC05AA10 — Fluocinolone acetonideD07AC04 — 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
CreamTopical
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 %
Kit0.1 mg/1mL
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)
US8247395No2002-10-222022-10-22Us
US8653053No2002-10-252022-10-25Us
US7939516No2005-05-042025-05-04Us
US7915243No2006-03-222026-03-22Us
US6217895No1999-03-222019-03-22Us
US6548078No1999-03-222019-03-22Us
US6375972No2000-04-262020-04-26Us
US8252307No1999-06-272019-06-27Us
US8871241No2007-08-122027-08-12Us
US8932610No2010-03-242030-03-24Us

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.
logP2.48HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0547 mg/mLALOGPS
logP2.47ALOGPS
logP1.6ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)13.35ChemAxon
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
Polarizability44.97 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]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Phospholipase a2 activity
Specific Function
Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory...
Gene Name
PLA2G4A
Uniprot ID
P47712
Uniprot Name
Cytosolic phospholipase A2
Molecular Weight
85238.2 Da
References
  1. Norris JF, Ilderton E, Yardley HJ, Summerly R, Forster S: Utilization of epidermal phospholipase A2 inhibition to monitor topical steroid action. Br J Dermatol. 1984 Jul;111 Suppl 27:195-203. [PubMed:6743552]
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 September 22, 2018 22:24