Fluocinolone acetonide

CAS No.: 67-73-2

Molecular Weight：452.495

Modify Date.: 2022-10-30 19:34

Introduction: It is suitable in the treatment of eczema, neurodermatitis, skin pruritus, contact dermatitis, psoriasis, dermatitis and other diseases View more+

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1. Names and Identifiers

1.1 Name: Fluocinolone acetonide
1.2 Synonyms: (4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-Difluor-5-hydroxy-6b-(hydroxyacetyl)-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2- (4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-Difluor-5-hydroxy-6b-(hydroxyacetyl)-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-on (4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-difluoro-5-hydroxy-6b-(hydroxyacétyl)-4a,6a,8,8-tétraméthyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodécahydro-2H-naphto[2',1':4,5]indéno[1,2-d][1,3]dioxol-2- (4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-difluoro-5-hydroxy-6b-(hydroxyacétyl)-4a,6a,8,8-tétraméthyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodécahydro-2H-naphto[2',1':4,5]indéno[1,2-d][1,3]dioxol-2-one (4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-difluoro-5-hydroxy-6b-(hydroxyacetyl)-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2 (4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-difluoro-5-hydroxy-6b-(hydroxyacetyl)-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one (4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-Difluoro-6b-glycoloyl-5-hydroxy-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one (6a,11b,16a)-6,9-Difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-pregna-1,4-diene-3,20-dione (6-alpha,11-beta,16-alpha)-idene)bis(oxy)) (6alpha,11beta,16alpha)-idene)bis(oxy)) 20-dione,6,9-difluoro-11,12-dihydroxy-16,17-((1-methylethylidene)bis(oxy))-,(6-alpha,11-bpregna-4-diene-3 2H-Naphth[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one, 4b,12-difluoro-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-5-hydroxy-6b-(2-hydroxyacetyl)-4a,6a,8,8-tetramethyl-, (4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)- 2H-naphth[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one, 4b,12-difluoro-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-5-hydroxy-6b-(hydroxyacetyl)-4a,6a,8,8-tetramethyl-, (4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)- 4b,12-difluoro-6b-glycoloyl-5-hydroxy-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one 6a,9a-Difluoro-11b,16a,17,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with acetone 6a,9a-Difluoro-16a,17a-isopropylidenedioxy-1,4-pregnadiene-3,20-dione 6a,9a-Difluoro-16a-hydroxyprednisolone 16,17-acetonide 6-alpha,9-alpha-difluoro-16-alpha-hydroxyprednisolone16,17-acetonide 6alpha,9alpha-difluoro-16alpha-hydroxyprednisolone16,17-acetonide 6α,9α-Difluoro-11Β,16α,17α,21-tetrahydroxy-1,4-pregnadiene-3,20-dione dermalar EINECS 200-668-5 Fluocinolone (Acetonide) fluocinolone16,17-acetonide MFCD00010525

1.3 CAS No.: 67-73-2

1.4 CID: 6215

1.5 EINECS(EC#): 200-668-5

1.6 Molecular Formula: C24H30F2O6 (isomer)

1.7 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

1.8 InChkey: FEBLZLNTKCEFIT-VSXGLTOVSA-N

1.9 Canonical Smiles: CC1(OC2CC3C4CC(C5=CC(=O)C=CC5(C4(C(CC3(C2(O1)C(=O)CO)C)O)F)C)F)C

1.10 Isomers Smiles: C[C@]12C[C@@H]([C@]3([C@H]([C@@H]1C[C@@H]4[C@]2(OC(O4)(C)C)C(=O)CO)C[C@@H](C5=CC(=O)C=C[C@@]53C)F)F)O

2. Properties

2.1 Density: 1.36

2.1 Melting point: 267-269℃

2.1 Boiling point: 579

2.1 Refractive index: 103 ° (C=1, MeOH)

2.1 Flash Point: 304

2.1 Precise Quality: 452.20100

2.1 PSA: 93.06000

2.1 logP: 2.36680

2.1 AnalyticLaboratory Methods: CHROMATOGRAPHY PROCEDURE FOR STEROID IDENTIFICATION INVOLVED SPOTTING STEROID ON FLUORESCENT SILICA GEL PLATE WITHOUT BINDER, HEATING PLATE FOR 18 HR @ 110 DEG, DEVELOPING RESULTANT DECOMP PRODUCTS TO FORM PATTERN CHARACTERISTIC OF STEROID.

2.2 Appearance: Crystalline powder

2.3 Storage: Refrigerator

2.4 Color/Form: CRYSTALS FROM ACETONE & HEXANE
WHITE, CRYSTALLINE POWDER

2.5 Odor: ODORLESS

2.6 Physical: Solid

2.7 pKa: 12.78±0.70(Predicted)

2.8 Water Solubility: Insoluble

2.9 Spectral Properties: SPECIFIC OPTICAL ROTATION: +95 DEG @ 25 DEG C/D (CHLOROFORM); MAX ABSORPTION: 238 NM (LOG E= 4.21)

2.10 Stability: STABLE IN LIGHT

2.11 StorageTemp: Refrigerator

3. Use and Manufacturing

3.1 Definition: ChEBI: 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 treatmet of various skin disorders.

3.2 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 65 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H315 (38.46%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (38.46%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (36.92%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
H361 (63.08%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P201, P202, P261, P264, P271, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501

3.3 Methods of Manufacturing: MILLS ET AL, J AM CHEM SOC 82, 3399 (1960); MILLS, BOWERS, US PATENT 3,014,938 (1961 TO SYNTEX).

3.4 Usage: It is suitable in the treatment of eczema, neurodermatitis, skin pruritus, contact dermatitis, psoriasis, dermatitis and other diseases

4. Safety and Handling

4.1 Symbol: GHS07

4.1 Hazard Codes: Xn

4.1 Signal Word: Warning

4.1 Risk Statements: R20/21/22;R36/37/38;R40

4.1 Safety Statements: S22;S26;S36

4.1 Hazard Declaration: H315-H319-H335

4.1 RIDADR: NONH for all modes of transport

4.1 Caution Statement: P261-P305 + P351 + P338

4.1 Formulations/Preparations: 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.

4.2 WGK Germany: 3

4.2 RTECS: TU3830000

4.2 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TU3830000

CHEMICAL NAME :: Pregna-1,4-diene-3,20-dione, 6,9-difluoro-11,12-dihydroxy-16,17-((1-methylethylide ne) bis(oxy))-, (6-alpha,11-beta,16-alpha)-

CAS REGISTRY NUMBER :: 67-73-2

LAST UPDATED :: 199710

DATA ITEMS CITED :: 21

MOLECULAR FORMULA :: C24-H30-F2-O6

MOLECULAR WEIGHT :: 452.54

WISWESSER LINE NOTATION :: T F5 E5 B666 GO IO RV AHTTTT&J A BF CQ E FVIQ H H OF -A&BHO -B&ACEF

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >4 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 42 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 108 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >4 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 103 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 200 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: >3170 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1750 ug/kg/35D-I

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 1 mg/kg

SEX/DURATION :: female 1-20 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 1200 ug/kg

SEX/DURATION :: female 8-31 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - stillbirth

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 1625 ug/kg

SEX/DURATION :: female 6-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - abortion

TYPE OF TEST :: Mutation test systems - not otherwise specified

TYPE OF TEST :: DNA inhibition

MUTATION DATA

TYPE OF TEST :: Morphological transformation

TEST SYSTEM :: Rodent - hamster Embryo

DOSE/DURATION :: 620 ug/L

REFERENCE :: AETODY Advances in Modern Environmental Toxicology. (Senate Press, Inc., P.O. Box 252, Princeton Junction, NJ 08550) V.1- 1980- Volume(issue)/page/year: 1,241,1980 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 83287 No. of Facilities: 100 (estimated) No. of Industries: 2 No. of Occupations: 3 No. of Employees: 1551 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 83287 No. of Facilities: 72 (estimated) No. of Industries: 1 No. of Occupations: 5 No. of Employees: 4106 (estimated) No. of Female Employees: 3249 (estimated)

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Reproductive toxicity, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H361 Suspected of damaging fertility or the unborn child
Precautionary statement(s)
Prevention	P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood. P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	P308+P313 IF exposed or concerned: Get medical advice/ attention.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. Synthesis Route

67-73-2Total: 8 Synthesis Route

356-12-7 150 Suppliers

67-73-2 221 Suppliers

Literatures:
Journal of Labelled Compounds and Radiopharmaceuticals, , vol. 52, # 4 p. 103 - 109
Yield: null

3932-49-8 2 Suppliers

67-73-2 221 Suppliers

Literatures:
Journal of Labelled Compounds and Radiopharmaceuticals, , vol. 53, # 5-6 p. 260 - 265
Yield: null

1269666-11-6

67-73-2 221 Suppliers

Literatures:
Molecules, , vol. 16, # 3 p. 2658 - 2671
Yield: null

View all

7. Precursor and Product

precursor:

64-17-5

1269666-13-8

1269666-11-6

356-12-7

1269666-12-7

1217194-25-6

1269666-10-5

3932-49-8

product :

356-12-7

106931-78-6

8. Other Information

8.0 Merck: 14,4150

8.1 Target: Value

8.2 Corticosteroid drug: Fluocinolone acetonide is a kind of topical corticosteroids of the most significant effect and the least side effect in current china, and can cause the contraction of dermal capillary, inhibit cell proliferation or regeneration of connective tissue; it can also stabilize the intracellular lysosomal membrane and prevent the release of histamine from the intracellular lysosomal enzyme and the further tissue damage. The anti-inflammatory effects of Fluocinolone is 100 times as great s that of hydrocortisone. It has significant efficacy even at the lowest concentration (0.025%) with rapid onset rate and can significantly reduce or cure the symptoms in a few days with a relative excellent itching relief effect.

Fluocinolone acetonide is mainly used for the treatment of skin diseases to which glucocorticoid is effective such as contact dermatitis, atopic dermatitis, seborrheic dermatitis, neurodermatitis, dermatitis, eczema (especially infant eczema), pruritus disease, psoriasis, discoid lupus erythematosus, lichen planus, otitis externa and so on. Its combination with neomycin and other antibiotics can be used for the treatment of suppurative skin disease. Apply 0.025-0.05% ointment, lotion for scrubbing the affected area with 2-3 times per day. You can gently knead and make it be incorporated into the skin.

8.3 Physical and Chemical Properties: It appears as white or white-like crystalline powder and is odorless and tasteless. [α] D20+80-+88° (dioxane). It is soluble in acetone, slightly soluble in ethanol, dioxane but insoluble in water and petroleum ether. It is obtained through the sulfonic esterfication, ring-opening reaction and further 16-steps reactions starting from the 11α-hydroxy-16α, 17α-epoxy pregnane-4-ene-3, 20-dione. It can be applied to atopic dermatitis, contact dermatitis, eczema and other skin diseases.

8.4 Fluocinolone acetonide: Fluocinolone acetonide is a synthetic, fluorine-containing potent steroid. Topical administration of it can cause dermal capillary contraction and can inhibit epidermal cell proliferation or regeneration, inhibit the newborn of the fibroblast cells inside the connective tissue and stabilize the intracellular lysosomal membrane with anti-inflammatory and anti-itching effect. After topical administration, it can be absorbed through intact skin. After its absorption, similar as the metabolism of corticosteroid after systemic administration, it is mainly metabolized in the liver and can be excreted by the kidneys. Fluocinolone acetonide is suitable for treating the skin disease to which corticosteroid is effective skin such as eczema (especially eczema), neurodermatitis, skin pruritus, contact dermatitis, psoriasis, discoid lupus erythematosus, lichen planus, otitis externa, and solar dermatitis. However, it should be note that long-term or large-scale application can cause skin atrophy, telangiectasia and the occurrence of acne-like dermatitis, perioral dermatitis, folliculitis, and increased susceptibility to infection and so on. Allergic contact dermatitis can also occur in some cases.
This information is edited by Xiongfeng Dai from .

8.5 Uses: It is suitable in the treatment of eczema, neurodermatitis, skin pruritus, contact dermatitis, psoriasis, dermatitis and other diseases

8.6 Chemical Properties: Crystalline Solid

8.7 Originator: Synalar,Syntex,US,1961

8.8 Uses: A synthetic glucocorticoid VEGF inhibitor; anti-inflammatory.

8.9 Uses: Fluocinolone acetonide (Derma-Smoothe/FS, Flurosyn, Capex, Synalar) is a synthetic fluorinated corticosteroid.

8.10 Uses: Fluocinolone 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.

8.11 Definition: ChEBI: 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 treatme t of various skin disorders.

8.12 Manufacturing Process: A mixture of 1.2 grams of 6α-fluoro-16α-hydroxy-hydrocortisone, 4 cc of acetic anhydride and 8 cc of pyridine was heated at 60°C for 2 hours and then kept at room temperature for 2 hours. Ice and water were added and the solid was collected, washed with water, dried and recrystallized from methylene chloride-methanol, thus giving 1.05 grams of the 16,21-diacetate of 6α-fluoro-16α-hydroxy-hydrocortisone (solvated) of MP 182° to 187°C;concentration of the mother liquors afforded an additional 130 mg of the same compound, MP 184° to 187°C. By recrystallization from the same solvents there was obtained the compound with a lower constant melting point of 175° to 177°C.
2.94 grams of the 16,21-diacetate of 6α-fluoro-16α-hydroxy-hydrocortisone was mixed with 60 cc of dimethylformamide, 3.6 cc of pyridine and 2.4 cc of methane-sulfonyl chloride was heated on the steam bath for 2 hours. The diacetate of 6α-fluoro-16α-hydroxy-hydrocortisone had been prepared as set forth above, and further dried by azeotropic distillation with benzene; the dimethylformamide had been previously distilled. After the 2 hours on the steam bath the mixture was cooled and poured into saturated aqueous sodium bicarbonate solution; the product was extracted with methylene chloride, the extract was washed with water, dried over anhydrous sodium sulfate and the solvent was evaporated.
The residue was chromatographed on 90 grams of silica gel eluting the product with methylene chloride-acetone (9:1) and then recrystallizing from methylene chloride-methanol. There was thus obtained 1.6 grams of the 16,21-diacetate of 6α-fluoro-δ4,9(11)-pregnadiene-16α,-17α,21-triol-3,20-dione with MP 110° to 114°C; the analytical sample melted at 115° to 117°C, [α]D+23.5° (chloroform), λ max. 234 to 236 nm, log ε 4.18.
A mixture of 1.38 grams of the above compound and 15 cc of dioxane was treated with 1.9 cc of a 0.5 N aqueous solution of perchloric acid and 600 mg of N-bromoacetamide, adding the latter in the dark, in three portions, in the course of half an hour and under continuous stirring, It was then stirred for a further 1% hours in the dark, then the excess of reagent was decomposed by the addition of aqueous sodium bisulfite solution and ice water was added; the product was extracted with methylene chloride, washed with water, dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure, thus giving a yellow oil consisting of the 16,21-diacetate of 6α- fluoro-9α-bromo-16α-hydroxy-hydrocortisone which was used for the next step without further purification.
The above crude bromohydrin was mixed with 2.5 grams of potassium acetate and 60 cc of acetone and refluxed for 6 hours, at the end of which the acetone was distilled, water was added to the residue and the product was extracted with methylene chloride. The extract was washed with water, dried over anhydrous sodium sulfate and the solvent was evaporated. Recrystallization of the residue from methanol furnished 800 mg of the 16,21- diacetate of 6α-fluoro-9β,11β-oxido-δ4-pregnene-16α,17α,21-triol-3,20-dione with MP 120° to 124°C; by chromatography of the mother liquors on silica gel there was obtained 180 milligrams more of the same compound with MP 117° to 119°C. The analytical sample was obtained by recrystallization from methanol; it showed MP 125° to 127°C.
To a solution of 1.6 grams of anhydrous hydrogen fluoride in 2.85 grams of tetrahydrofurane and 10 cc of methylene chloride cooled to -60°C was added a solution of 650 mg of the 16,21-diacetate of 6α-fluoro-9β,11β-oxido-δ4- pregnene-16α,17α,21-triol-3,20-dione in 20 cc of methylene chloride and the mixture was kept at -10°C for 72 hours. It was then poured into saturated aqueous sodium bicarbonate solution and the organic layer was separated, washed with water, dried over anhydrous sodium sulfate and evaporated. The residue was reacetylated by heating with 3 cc of acetic anhydride and 6 cc of pyridine for 1 hour on the steam bath. The reagents were evaporated under reduced pressure and the residue was chromatographed on 30 grams of silica gel. Upon elution with methylene chloride-acetone (9:1) and recrystallization of the residue from methylene chloride-methanol there was obtained 290 mg of the 16,21-diacetate of 6α,9α-difluoro-16α-hydroxy-hydrocortisone which melted with loss of solvent at 140° to 150°C. Recrystallization from acetonehexane afforded the analytical sample which was dried at 130°C; it then showed a MP of 182° to 185°C.

8.13 Brand name: Fluonid (Allergan); Fluotrex (Savage); FS Shampoo (Galderma); Retisert (Bausch & Lomb); Synalar (Medicis).

8.14 Therapeutic Function: Glucocorticoid, Antiinflammatory

8.15 General Description: Fluocinolone 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.

8.16 Usage: Fluocinolone 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.

9. Computational chemical data

Molecular Weight: 452.495g/mol
Molecular Formula: C₂₄H₃₀F₂O₆
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 452.20104500
Monoisotopic Mass: 452.20104500
Complexity: 960
Rotatable Bond Count: 2
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 8
Topological Polar Surface Area: 93.1
Heavy Atom Count: 32
Defined Atom Stereocenter Count: 9
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceB4OYAAAAAAAAAAAAAAAAAAAaIAAAAwYIAAAAASAGDAAAAAGwAACAAAD1SggAICCAAABgCIAqBSAAIAAAAgAAAICAFAAEgREBYAAQQiQAAFoAAOAYPI7PzPgAAAAAAAAADAAAYAADAAAYAADCAAAA==

10. Question & Answer

Fluocinolone acetonide-Application Nov 17 2020
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 ski...

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12. Realated Product Infomation

13242-30-3 Fluocinolone Acetonide-21-aldehyde

106931-78-6 Fluocinolone Acetonide-21-carboxylic Acid

76-25-5 Triamcinolone acetonide

4968-09-6 Alphasone acetonide

64790-68-7 Heraclel acetonide

581772-29-4 Atorvastatin Acetonide

320624-68-8 MarMin acetonide

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