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Fluocinonide
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Name

Fluocinonide

 EINECS 206-597-6
CAS No. 356-12-7 Density 1.34 g/cm3
PSA 99.13000 LogP 2.93760
Solubility 0.53mg/L(25 oC) Melting Point 309 °C
Formula C26H32F2O7 Boiling Point 591.1 °C at 760 mmHg
Molecular Weight 494.533 Flash Point 311.3 °C
Transport Information UN 2811 6.1/PG 2 Appearance white crystalline powder
Safety 22-25-28-36/37/39-45 Risk Codes 28-63
Molecular Structure Molecular Structure of 356-12-7 (Fluocinonide) Hazard Symbols VeryT+
Synonyms

Pregna-1,4-diene-3,20-dione,6a,9-difluoro-11b,16a,17,21-tetrahydroxy-, cyclic 16,17-acetal withacetone, 21-acetate (7CI,8CI);Biscosal;Dermaplus;Flucinar;Fluocinolide acetate;Fluocinolone acetonide 21-acetate;Fluocinolone acetonide acetate;Lidex;Lidex E;Metosyn;NSC101791;Straderm;Topsym;Topsymin;Topsyn;Vanos;

Article Data 12

Fluocinonide Synthetic route

67-73-2

fluocinolone Acetonide

108-24-7

acetic anhydride

356-12-7

fluocinonide

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 0.0833333h;100%
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 1.16667h;59%
With trimethylsilyl trifluoromethanesulfonate In dichloromethane

C26H31FO7

356-12-7

fluocinonide

Conditions
ConditionsYield
With 1-ethyl-3-methylimidazole hydrogen fluoride at 25℃; Reagent/catalyst; Temperature;98.2%
4306-83-6

21-acetyloxy-11β,16α,17α-trihydroxy-6α,9α-difluoro-1,4-diene-3,20-dione

67-64-1

acetone

356-12-7

fluocinonide

Conditions
ConditionsYield
With perchloric acid at 25 - 30℃;87.3%
With toluene-4-sulfonic acid at 35℃; Reagent/catalyst; Temperature; Inert atmosphere;6.9 g
With methanesulfonic acid at 50℃; for 1.5h; Temperature;
3932-49-8

21-acetoxy-6α,9α-difluoro-11β-hydroxy-16α,17-[(1-methylethylidene)bis(oxy)]pregn-4-ene-3,20-dione

356-12-7

fluocinonide

Conditions
ConditionsYield
With pyridine; selenium(IV) oxide In tert-butyl alcohol Reflux;
With selenium(IV) oxide In pyridine; tert-butyl alcohol at 95℃;
67-73-2

fluocinolone Acetonide

108-24-7

acetic anhydride

A

356-12-7

fluocinonide

B

11β,21-diacetoxy-6α,9α-difluoro-16α,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione

Conditions
ConditionsYield
With pyridine; dmap at 20℃; for 4h; Inert atmosphere; Heating;
7753-60-8

anecortave

356-12-7

fluocinonide

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: D-glucose / aq. phosphate buffer
2.1: perchloric acid / acetone; water / 0.17 h / 0 - 5 °C
2.2: 1 h / 0 - 5 °C
2.3: 2 h / 0 - 35 °C
3.1: pyridine; toluene-4-sulfonic acid; Isopropenyl acetate / acetonitrile; methanol / 3 h / 80 °C / Inert atmosphere
4.1: SelectfluorTM / acetonitrile / 8.5 h
5.1: toluene-4-sulfonic acid / 12 h / 70 °C
6.1: hydrogen fluoride; N,N-dimethyl acetamide / water / -15 °C
7.1: potassium acetate / N,N-dimethyl-formamide / 8 h / 90 - 100 °C / Inert atmosphere
8.1: formic acid; potassium permanganate / acetone / 0.33 h / -5 - 0 °C
9.1: perchloric acid / 25 - 30 °C
View Scheme
4380-55-6

pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 21-acetate

356-12-7

fluocinonide

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: perchloric acid / acetone; water / 0.17 h / 0 - 5 °C
1.2: 1 h / 0 - 5 °C
1.3: 2 h / 0 - 35 °C
2.1: pyridine; toluene-4-sulfonic acid; Isopropenyl acetate / acetonitrile; methanol / 3 h / 80 °C / Inert atmosphere
3.1: SelectfluorTM / acetonitrile / 8.5 h
4.1: toluene-4-sulfonic acid / 12 h / 70 °C
5.1: hydrogen fluoride; N,N-dimethyl acetamide / water / -15 °C
6.1: potassium acetate / N,N-dimethyl-formamide / 8 h / 90 - 100 °C / Inert atmosphere
7.1: formic acid; potassium permanganate / acetone / 0.33 h / -5 - 0 °C
8.1: perchloric acid / 25 - 30 °C
View Scheme
38680-83-0

21-acetyloxy-9β,11β-epoxy-17α-hydroxy-1,4-diene-3,20-dione

356-12-7

fluocinonide

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: pyridine; toluene-4-sulfonic acid; Isopropenyl acetate / acetonitrile; methanol / 3 h / 80 °C / Inert atmosphere
2: SelectfluorTM / acetonitrile / 8.5 h
3: toluene-4-sulfonic acid / 12 h / 70 °C
4: hydrogen fluoride; N,N-dimethyl acetamide / water / -15 °C
5: potassium acetate / N,N-dimethyl-formamide / 8 h / 90 - 100 °C / Inert atmosphere
6: formic acid; potassium permanganate / acetone / 0.33 h / -5 - 0 °C
7: perchloric acid / 25 - 30 °C
View Scheme

C30H33NO9

356-12-7

fluocinonide

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: SelectfluorTM / acetonitrile / 8.5 h
2: toluene-4-sulfonic acid / 12 h / 70 °C
3: hydrogen fluoride; N,N-dimethyl acetamide / water / -15 °C
4: potassium acetate / N,N-dimethyl-formamide / 8 h / 90 - 100 °C / Inert atmosphere
5: formic acid; potassium permanganate / acetone / 0.33 h / -5 - 0 °C
6: perchloric acid / 25 - 30 °C
View Scheme
3802-45-7

21-acetyloxy-9β,11β-epoxy-6α-fluoro-17α-hydroxy-1,4-diene-3,20-dione

356-12-7

fluocinonide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: toluene-4-sulfonic acid / 12 h / 70 °C
2: hydrogen fluoride; N,N-dimethyl acetamide / water / -15 °C
3: potassium acetate / N,N-dimethyl-formamide / 8 h / 90 - 100 °C / Inert atmosphere
4: formic acid; potassium permanganate / acetone / 0.33 h / -5 - 0 °C
5: perchloric acid / 25 - 30 °C
View Scheme

Fluocinonide Specification

The Fluocinolide with CAS registry number of 356-12-7 is also known as Topsymin. The systematic name is 2-[(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-Difluoro-5-hydroxy-4a,6a,8,8-tetramethyl-2-oxo-2,4a,4b,5,6,6a,9a,10,10a,10b,11,12-dodecahydro-6bH-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-6b-yl]-2-ox oethyl acetate. It belongs to product categories of Steroids. Its EINECS registry number is 206-597-6 . In addition, the formula is C26H32F2O7 and the molecular weight is 494.52. This chemical is a white crystalline powder and used for atopic dermatitis, eczema and so on.

Physical properties about Fluocinolide are: (1)ACD/LogP: 3.36; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.36; (4)ACD/LogD (pH 7.4): 3.36; (5)ACD/BCF (pH 5.5): 209.69; (6)ACD/BCF (pH 7.4): 209.69; (7)ACD/KOC (pH 5.5): 1597.31; (8)ACD/KOC (pH 7.4): 1597.3; (9)#H bond acceptors: 7; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Index of Refraction: 1.56; (13)Molar Refractivity: 119.09 cm3; (14)Molar Volume: 368 cm3; (15)Surface Tension: 49.9 dyne/cm; (16)Density: 1.34 g/cm3; (17)Flash Point: 311.3 °C; (18)Enthalpy of Vaporization: 101.2 kJ/mol; (19)Boiling Point: 591.1 °C at 760 mmHg; (20)Vapour Pressure: 1.97E-16 mmHg at 25 °C.

Preparation of Fluocinolide: it is prepared by reaction of acetic acid anhydride with fluocinolon-acetonid. The reaction needs reagent trimethylsilyl trifluoromethanesulfonate and solvent CH2Cl2 at the temperature of 20 °C for 5 minutes. The yield is about 100%.

Fluocinolide is prepared by reaction of acetic acid anhydride with fluocinolon-acetonid.

When you are using this chemical, please be cautious about it. As a chemical, it is very toxic if swallowed and has possible risk of harm to the unborn child. During using it, wear suitable protective clothing, gloves and eye/face protection. Besides, do not breathe dust and avoid contact with eyes. In case of accident or if you feel unwell seek medical advice immediately.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: CC(=O)OCC(=O)C12C(CC3C1(CC(C4(C3CC(C5=CC(=O)C=CC54C)F)F)O)C)OC(O2)(C)C
2. Isomeric SMILES: CC(=O)OCC(=O)[C@@]12[C@@H](C[C@@H]3[C@@]1(C[C@@H]([C@]4([C@H]3C[C@@H](C5=CC(=O)C=C[C@@]54C)F)F)O)C)OC(O2)(C)C
3. InChI: InChI=1S/C26H32F2O7/c1-13(29)33-12-20(32)26-21(34-22(2,3)35-26)10-15-16-9-18(27)17-8-14(30)6-7-23(17,4)25(16,28)19(31)11-24(15,
26)5/h6-8,15-16,18-19,21,31H,9-12H2,1-5H3/t15-,16-,18-,19-,21+,23-,24-,25-,26+/m0/s1
4. InChIKey: WJOHZNCJWYWUJD-IUGZLZTKSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 subcutaneous > 3170mg/kg (3170mg/kg)   Drugs in Japan Vol. 6, Pg. 694, 1982.
mouse LD50 intraperitoneal 160mg/kg (160mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 17, Pg. 849, 1975.
mouse LD50 oral > 6gm/kg (6000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 6, Pg. 386, 1975.
mouse LD50 subcutaneous 165mg/kg (165mg/kg)   Yakkyoku. Pharmacy. Vol. 26, Pg. 741, 1975.
rat LD50 intraperitoneal 300ug/kg (0.3mg/kg)   Drugs in Japan Vol. 6, Pg. 694, 1982.
rat LD50 oral 14mg/kg (14mg/kg)   Drugs in Japan Vol. 6, Pg. 694, 1982.
rat LD50 subcutaneous 720ug/kg (0.72mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 6, Pg. 386, 1975.

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