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Fluocinolone acetonide

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Name

Fluocinolone acetonide

EINECS 200-668-5
CAS No. 67-73-2 Density 1.36 g/cm3
PSA 93.06000 LogP 2.36680
Solubility Soluble in water (partly), DMSO, alcohol, chloroform and methanol. Melting Point 267-269 °C(lit.)
Formula C24H30F2O6 Boiling Point 578.5 °C at 760 mmHg
Molecular Weight 452.495 Flash Point 303.7 °C
Transport Information N/A Appearance Crystalline Solid
Safety 26-36-22 Risk Codes 20/21/22-36/37/38-40
Molecular Structure Molecular Structure of 67-73-2 (Fluocinolone acetonide) Hazard Symbols IrritantXi; HarmfulXn
Synonyms

Pregna-1,4-diene-3,20-dione,6a,9-difluoro-11b,16a,17,21-tetrahydroxy-, cyclic 16,17-acetal with acetone(6CI,8CI);16a,17a-Isopropylidene-6a,9a-difluoro-1,4-pregnadiene-11b,16a,17a,21-tetrol-3,20-dione;6a,9-Difluoro-11b,21-dihydroxy-16a,17a-(isopropylidenedioxy)pregna-1,4-diene-3,20-dione;6a,9a-Difluoro-16a,17a-isopropylidenedioxy-D1-hydrocortisone;6a,9a-Difluoro-16a-hydroxyprednisolone16,17-acetonide;6a-Fluorotriamcinolone acetonide;Coriphate;Cortiplastol;Dermalar;Dermatin;Dermatin (steroid);Fluocinolone 16,17-acetonide;Fluovitef;Fluvean;Jellin;Localyn;NSC 92339;Percutina;Sinaflan;Sinalar;Synaflan;Synamol;Synandrone;Synemol;Synsac;Pregna-1,4-diene-3,20-dione,6,9-difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-, (6a,11b,16a)-;

Article Data 15

Fluocinolone acetonide Synthetic route

356-12-7

fluocinonide

67-73-2

fluocinolone Acetonide

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane; water at 0 - 5℃; Inert atmosphere;99.4%
With sodium hydroxide; sodium sulfite In dichloromethane; water at 5 - 15℃; for 1.5h; Reagent/catalyst; Temperature; Inert atmosphere;91%
With sodium methylate; sodium hydroxide In dichloromethane Inert atmosphere;83.6%

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

67-73-2

fluocinolone Acetonide

Conditions
ConditionsYield
With water; potassium carbonate In methanol80%
With potassium carbonate In methanol; water
64-17-5

ethanol

1217194-25-6

(6α,11β,16α)-6,9-difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione-21-(2'-phenoxypropionate)

A

67-73-2

fluocinolone Acetonide

B

42412-84-0

ethyl 2-phenoxypropionate

Conditions
ConditionsYield
With sodium hydrogencarbonate In water
3932-49-8

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

67-73-2

fluocinolone Acetonide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: pyridine; dmap
2: benzeneseleninic anhydride / toluene / 7 h / Reflux
3: potassium carbonate / methanol; water
View Scheme

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

67-73-2

fluocinolone Acetonide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: benzeneseleninic anhydride / toluene / 7 h / Reflux
2: potassium carbonate / methanol; water
View Scheme
1217194-25-6

(6α,11β,16α)-6,9-difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione-21-(2'-phenoxypropionate)

67-73-2

fluocinolone Acetonide

Conditions
ConditionsYield
With ethanol; sodium hydrogencarbonate In water Kinetics;
1269666-11-6

(6α,11β,16α)-6,9-difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione-21-(2'-ethoxypropionate)

67-73-2

fluocinolone Acetonide

Conditions
ConditionsYield
With ethanol; sodium hydrogencarbonate In water Kinetics;
1269666-13-8

(6α,11β,16α)-6,9-difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione-21-(2'-ethoxybutyrate)

67-73-2

fluocinolone Acetonide

Conditions
ConditionsYield
With ethanol; sodium hydrogencarbonate In water Kinetics;
1269666-10-5

(6α,11β,16α)-6,9-difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione-21-(2'-methoxypropionate)

67-73-2

fluocinolone Acetonide

Conditions
ConditionsYield
With ethanol; sodium hydrogencarbonate In water Kinetics;
1269666-12-7

(6α,11β,16α)-6,9-difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione-21-(2'-methoxybutyrate)

67-73-2

fluocinolone Acetonide

Conditions
ConditionsYield
With ethanol; sodium hydrogencarbonate In water Kinetics;

Fluocinolone acetonide Consensus Reports

EPA Genetic Toxicology Program.

Fluocinolone acetonide Specification

1. Introduction of Fluocinolone acetonide

The Fluocinolone acetonide is a kind of crystalline solid, and it belongs to the following product categories which include Organics; Alkaloids; Biochemistry; Quinoline Alkaloids; Intermediates & Fine Chemicals; Pharmaceuticals; Steroids. What's more, it is a corticosteroid primarily used in dermatology to reduce skin inflammation and relieve itching. And it is a synthetic hydrocortisone derivative.

2. Properties of Fluocinolone acetonide

The physical properties of Fluocinolone acetonide are as followings: (1)ACD/LogP: 2.24; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.24; (4)ACD/LogD (pH 7.4): 2.24; (5)ACD/BCF (pH 5.5): 29.91; (6)ACD/BCF (pH 7.4): 29.91; (7)ACD/KOC (pH 5.5): 396.28; (8)ACD/KOC (pH 7.4): 396.28; (9)#H bond acceptors: 6; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 71.06 Å2; (13)Index of Refraction: 1.577; (14)Molar Refractivity: 109.5 cm3; (15)Molar Volume: 330.3 cm3; (16)Polarizability: 43.41×10-24cm3; (17)Surface Tension: 52.7 dyne/cm; (18)Density: 1.36 g/cm3; (19)Flash Point: 303.7 °C; (20)Enthalpy of Vaporization: 99.42 kJ/mol; (21)Boiling Point: 578.5 °C at 760 mmHg; (22)Vapour Pressure: 8.57E-16 mmHg at 25°C.

3. Structure Descriptors of Fluocinolone acetonide

You could convert the following datas into the molecular structure:
(1)SMILES: O=C\1\C=C5/[C@@](/C=C/1)(C)[C@]2(F)[C@H]([C@H]3[C@](C[C@@H]2O)([C@@]4(OC(O[C@@H]4C3)(C)C)C(=O)CO)C)C[C@@H]5F
(2)InChI: InChI=1/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
(3)InChIKey: FEBLZLNTKCEFIT-VSXGLTOVBO

4. Toxicity of Fluocinolone acetonide

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 103mg/kg (103mg/kg)   Drugs in Japan Vol. 6, Pg. 694, 1982.
mouse LD50 oral > 4gm/kg (4000mg/kg)   Drugs in Japan Vol. 6, Pg. 694, 1982.
mouse LD50 subcutaneous 200mg/kg (200mg/kg)   Drugs in Japan Vol. 6, Pg. 694, 1982.
rat LD50 intraperitoneal 42mg/kg (42mg/kg)   Drugs in Japan Vol. 6, Pg. 694, 1982.
rat LD50 oral > 4gm/kg (4000mg/kg)   Drugs in Japan Vol. 6, Pg. 694, 1982.
rat LD50 subcutaneous 108mg/kg (108mg/kg)   Drugs in Japan Vol. 6, Pg. 694, 1982.

5. Safety Information of Fluocinolone acetonide

You should be cautious while dealing with this chemical. It irritates to eyes, respiratory system and skin, and it is also harmful by inhalation, in contact with skin and if swallowed. What's more, there's limited evidence of a carcinogenic effect. Therefore, you had better take the following instructions: Do not breathe the dust; Wear suitable protective clothing, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

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