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Fluocinolone Acetonide

HCID 6215
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Basic information

CAS
67-73-2
Standard SMILES
CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(=O)C=C[C@]5(C)[C@@]4(F)[C@@H](O)C[C@]3(C)[C@]2(C(=O)CO)O1
InChIKey
FEBLZLNTKCEFIT-VSXGLTOVSA-N
Molecular formula
C24H30F2O6
Average molar mass
452.5 g/mol
Monoisotopic mass
452.201045

Overview

Fluocinolone acetonide is a fluorinated steroid that is flunisolide in which the hydrogen at position 9 is replaced by fluorine. A corticosteroid with glucocorticoid activity, it is used (both as the anhydrous form and as the dihydrate) in creams, gels and ointments for the treatment of various skin disorders. It has a role as an anti-inflammatory drug and an antipruritic drug. It is a primary alpha-hydroxy ketone, a glucocorticoid, a 21-hydroxy steroid, an 11beta-hydroxy steroid, a 20-oxo steroid, an organic heteropentacyclic compound, a fluorinated steroid, a cyclic ketal and a 3-oxo-Delta(1),Delta(4)-steroid.

Names & identifiers

Preferred name
Fluocinolone Acetonide
IUPAC
(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
English name
Fluocinolone Acetonide
Molecular formula
C24H30F2O6
Molecular weight
452.49

Names & synonyms

FLUOCINOLONE ACETONIDE67-73-2SynalarFluonidFlucinarFlupollonSynamolSynandoneJellinCoriphateDermalarFluovitif
Show more names
Fluocinolone acetonide for system suitability6-alpha,9-alpha-difluoro-16-alpha-hydroxyprednisolone16,17-acetonidesynsacFluzon
PercutinaRadiocinRetisertSynandroneTefunoteLocalynSinalarSynotic

Database identifiers

CAS
67-73-2
PubChem CID
6215
DTXSID
DTXSID0040674
ChEMBL
CHEMBL989
ChEBI
CHEBI:31623
UNII
0CD5FD6S2M
EC Number
200-668-5
Nikkaji
J1.414A

Properties

Computed structural properties

XLogP
2.5
Topological polar surface area
93.1 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
8
Rotatable bonds
2
Heavy atoms
32
Formal charge
0
Complexity
960

Experimental & physicochemical properties

Drugs · 4 items

Pharmaceuticals -> Dermatologicals -> Corticosteroids, dermatological preparations

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Analgesics and anti-inflammatories

LogP2.48
OdorODORLESS
Color/Form · 2 items

CRYSTALS FROM ACETONE & HEXANE

WHITE, CRYSTALLINE POWDER

Solubility · 2 items

Insoluble

SOL IN ALC, ACETONE, & METHANOL; INSOL IN WATER; SLIGHTLY SOL IN CHLOROFORM

Human Drugs · 4 items

Breast Feeding; Lactation; Milk, Human; Corticosteroids, Topical; Glucocorticoids; Anti-Inflammatory Agents

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Pharmaceuticals

Animal DrugsFDA approved animal drugs -> Active ingredient
Melting Point · 2 items

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H315 (40.8%): Causes skin irritation [Warning Skin corrosion/irritation]

P203, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 98 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Other Safety InformationIMAP assessments - 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.)-: Environment tier I assessment
Hazard Classes and CategoriesSkin Irrit. 2 (40.8%)

Toxicology

InteractionsREVERSAL OF CORTICOSTEROID-INDUCED IMPAIRMENT OF WOUND HEALING HAS BEEN REPORTED AFTER TOPICAL APPLICATION OF VITAMIN /VITAMIN A/. /CORTICOSTEROIDS/
Human Toxicity Excerpts · 5 items

...FOLLICULITIS OR STRIAE IS FREQUENT COMPLICATION, ESP IF OCCLUSIVE DRESSINGS ARE USED.

PHARMACOLOGICAL DOSES OF GLUCOCORTICOIDS RETARD OR INTERRUPT GROWTH OF CHILDREN, INDICATING ADVERSE EFFECT ON EPIPHYSEAL CARTILAGE. INHIBITION OF GROWTH IS RATHER WIDESPREAD EFFECT... /GLUCOCORTICOIDS/

PROLONGED THERAPY WITH CORTICOSTEROIDS MAY RESULT IN SUPPRESSION OF PITUITARY-ADRENAL FUNCTION THAT CAN BE SLOW IN RETURNING TO NORMAL. /CORTICOSTEROIDS/

...PRINCIPAL COMPLICATIONS RESULTING FROM PROLONGED THERAPY...ARE FLUID & ELECTROLYTE DISTURBANCES; HYPERGLYCEMIA & GLYCOSURIA; INCR SUSCEPTIBILITY TO INFECTIONS, INCL TUBERCULOSIS; PEPTIC ULCERS, WHICH MAY BLEED OR PERFORATE; OSTEOPOROSIS; CHARACTERISTIC MYOPATHY; BEHAVIORAL DISTURBANCES... /CORTICOSTEROIDS/

Chemistry & industry

Pharmacology

ATC Code · 6 items

C - Cardiovascular system

S - Sensory organs

S - Sensory organs

D - Dermatologicals

QS - Sensory organs

QC - Cardiovascular system

Protein BindingThis pharmacokinetic parameter is not relevant as the systemic absorption of fluocinolone acetonide is very minimal.
Pharmacodynamics · 1 item

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.

Mechanism of Action · 3 items

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/

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

266-268

266 °C

Optical RotationSPECIFIC OPTICAL ROTATION: +95 DEG @ 25 °C/D (CHLOROFORM); MAX ABSORPTION: 238 NM (LOG E= 4.21)
Stability/Shelf LifeSTABLE IN LIGHT
Dissociation Constants13.9
Collision Cross Section · 2 items

226.8 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID0040674]

199.7 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
267 · 267-269 °C(lit.)
alpha
95 ° · D +95° (chloroform)
Boiling point
578.5 · 578.5±50.0 °C(Predicted)
Density
1.1826 · 1.1826 (estimate)
refractive index
103 ° · 103 ° (C=1, MeOH)
storage temp.
Refrigerator
solubility
Practically insoluble in water, soluble in acetone and in ethanol
form
Solid
pka
12.78 · 12.78±0.70(Predicted)
color
White to Off-White
Water Solubility
Soluble in water (partly), DMSO, alcohol, chloroform and methanol.
Merck
14 · 14,4150
Major Application
forensics and toxicologyveterinary
InChIKey
FEBLZLNTKCEFIT-VSXGLTOVSA-N
SMILES
CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(=O)C=C[C@]5(C)[C@@]4(F)[C@@H](O)C[C@]3(C)[C@@]2(O1)C(=O)CO
CAS DataBase Reference
67 · 67-73-2(CAS DataBase Reference)
FDA UNII
0 CD5FD6S2M · 0CD5FD6S2M
ATC code
5 AA10,D07AC04,S01BA15,S02BA08 · C05AA10,D07AC04,S01BA15,S02BA08
EPA Substance Registry System
Fluocinolone acetonide (67-73-2)
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319-H335
Precautionary statements
261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
target organs
Respiratory system
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xi,Xn
Risk Statements
36 · 36/37/38-40-20/21/22
Safety Statements
26 · 26-36-22
WGK Germany
3 · 3
RTECS
3830000 · TU3830000
HS Code
2937220000 · 2937220000
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
Hazardous Substances Data
67 · 67-73-2(Hazardous Substances Data)
Toxicity
50 oral · LD50 oral in rat: > 4gm/kg

...PRINCIPAL COMPLICATIONS...POSTERIOR SUBCAPSULAR CATARACTS; & CUSHING'S HABITUS, CONSISTING OF "MOON FACE," "BUFFALO HUMP," SUPRACLAVICULAR FAT PADS, "CENTRAL OBESITY," STRIAE, ECCHYMOSES, ACNE, & HIRSUTISM. /CORTICOSTEROIDS/

Non-Human Toxicity Excerpts · 4 items

IN YOUNG GROWING ANIMALS THERE IS...ADVERSE EFFECT UPON GROWTH APPARATUS, RESULTING IN SLOWING OF GROWTH. RETARDATION OF HEALING OF EXPTL FRACTURES IN ANIMALS FROM ADMIN OF GLUCOCORTICOIDS IS ATTRIBUTED TO DEPRESSION OF OSTEOBLASTIC ACTIVITY. /ADRENOCORTICOSTEROIDS/

SINGLE DOSES OF GLUCOCORTICOIDS (0.5-8.0 G/KG) CAN SUPPRESS IMMUNE RESPONSE IN MICE TO EXTENT THAT HIGH MORTALITY OCCURS AS RESULT OF INTERCURRENT INFECTIONS OVER 1-3 WK. RATS ARE 10-20 TIMES MORE SENSITIVE THAN MICE TO THIS EFFECT. /CORTICOSTEROIDS/

LARGE SINGLE DOSES OF SOME STEROIDS GIVEN PARENTERALLY TO ANIMALS PRODUCE SEDATION, WHEREAS OTHERS INDUCE SIGNS OF CENTRAL STIMULATION. TO SOME EXTENT THESE PHENOMENA MAY BE DOSE-RELATED. /CORTICOSTEROIDS/

Fifteen pregnant New Zealand rabbits were given 125 ug/kg fluocinolone acetonide subcutaneously on days 6-18 of gestation. The same number of controls were given the vehicle. Fluocinolone acetonide decreased the body weight of dams compared with controls and caused 100% abortions before day 29 of gestation.

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
rtecs
TU3830000
hs_code
2937220000
Toxicity
LD50 oral in rat: > 4gm/kg
risk_code
36/37/38-40-20/21/22
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi,Xn
safety_code
26-36-22
Storage Class
11 - Combustible Solids
target organs
Respiratory system
Hazard statements
H315-H319-H335
Hazard Classifications
Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements
P261-P264-P271-P280-P302+P352-P305+P351+P338
Hazardous Substances Data
67-73-2(Hazardous Substances Data)

...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/

Biological Half-LifeThe reported half-life of fluocinolone acetonide ranges between 1.3-1.7 hours.
Metabolism/Metabolites · 2 items

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/

FDA Pharmacological Classification · 6 items

0CD5FD6S2M

FLUOCINOLONE ACETONIDE

Established Pharmacologic Class [EPC] - Corticosteroid

Mechanisms of Action [MoA] - Corticosteroid Hormone Receptor Agonists

Fluocinolone acetonide is a Corticosteroid. The mechanism of action of fluocinolone acetonide is as a Corticosteroid Hormone Receptor Agonist.

FLUOCINOLONE ACETONIDE

MeSH Pharmacological Classification · 2 items

Substances that reduce or suppress INFLAMMATION.

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.

Absorption, Distribution and Excretion · 6 items

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.

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

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

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/

(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.

Uses & manufacturing

Uses · 2 items

MEDICATION (VET)

MEDICATION

Methods of ManufacturingMILLS ET AL, J AM CHEM SOC 82, 3399 (1960); MILLS, BOWERS, US PATENT 3,014,938 (1961 TO SYNTEX).
Formulations/Preparations · 2 items

FLUOCINOLONE ACETONIDE, USP (FLUONID, SYNALAR); TOPICAL FORMS: 0.01, 0.025, 0.2% CREAM; 0.025% OINTMENT; 0.01% TOPICAL SOLN. /FROM TABLE/

NEOMYCIN IS OFTEN INCL IN TOPICAL PREPN OF FLUOCINOLONE ACETONIDE TO SUPPRESS INFECTIONS SECONDARY TO INFLAMMATORY PROCESS OR WHICH RESULT FROM USE OF THE GLUCOCORTICOID.

Use ClassificationPharmaceuticals
Applications · 5 items

UsesIt is suitable in the treatment of eczema, neurodermatitis, skin pruritus, contact dermatitis, psoriasis, dermatitis and other diseases

UsesA synthetic glucocorticoid VEGF inhibitor; anti-inflammatory.

UsesFluocinolone acetonide is primarily used in dermatology to reduce skin inflammation and relieve itching. It acts as an inhibitor of tumor cells and it can regulate lipid metabolism by modulating gene expression. It can also inhibit the expression of VEGF (vascular endothelial growth factor) in the retinal pigment epithelial cell line due to its high glucocorticoid receptor affinity. Furthermore, it can inhibit TNF-α angiogenesis.

UsesFluocinolone acetonide (Derma-Smoothe/FS, Flurosyn, Capex, Synalar) is a synthetic fluorinated corticosteroid.

General DescriptionFluocinolone acetonide,6α,9-difluoro-11β,21-dihydroxy-16α,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione, also known as6α-fluorotriamcinolone acetonide, is the 21-acetate derivativeof fluocinolone acetonide and is about 5 times morepotent than fluocinolone acetonide in at least one topicalactivity assay.

Upstream & downstream products

Upstream raw materials

hydrogen fluorideSelenium dioxideN-BromoacetamideMethanesulfonyl chloridePotassium hydroxideAcetic anhydrideHydrogen fluoride
Additional notes · 1 item

DefinitionChEBI: Fluocinolone acetonide is a fluorinated steroid that is flunisolide in which the hydrogen at position 9 is replaced by fluorine. A corticosteroid with glucocorticoid activity, it is used (both as the anhydrous form and as the dihydrate) in creams, gels and ointments for the treatment of various skin disorders. It has a role as an anti-inflammatory drug and an antipruritic drug. It is an 11beta-hydroxy steroid, a 21-hydroxy steroid, a 20-oxo steroid, a cyclic ketal, a glucocorticoid, a fluorinated steroid, a 3-oxo-Delta(1),Delta(4)-steroid, an organic heteropentacyclic compound and a primary alpha-hydroxy ketone.