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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 | Hazard Symbols | Xi; Xn | |
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 |
Conditions | Yield |
---|---|
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% |
fluocinolone Acetonide
Conditions | Yield |
---|---|
With water; potassium carbonate In methanol | 80% |
With potassium carbonate In methanol; water |
ethanol
(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
fluocinolone Acetonide
B
ethyl 2-phenoxypropionate
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water |
21-acetoxy-6α,9α-difluoro-11β-hydroxy-16α,17-[(1-methylethylidene)bis(oxy)]pregn-4-ene-3,20-dione
fluocinolone Acetonide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: pyridine; dmap 2: benzeneseleninic anhydride / toluene / 7 h / Reflux 3: potassium carbonate / methanol; water View Scheme |
fluocinolone Acetonide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: benzeneseleninic anhydride / toluene / 7 h / Reflux 2: potassium carbonate / methanol; water View Scheme |
(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)
fluocinolone Acetonide
Conditions | Yield |
---|---|
With ethanol; sodium hydrogencarbonate In water Kinetics; |
(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)
fluocinolone Acetonide
Conditions | Yield |
---|---|
With ethanol; sodium hydrogencarbonate In water Kinetics; |
(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)
fluocinolone Acetonide
Conditions | Yield |
---|---|
With ethanol; sodium hydrogencarbonate In water Kinetics; |
(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)
fluocinolone Acetonide
Conditions | Yield |
---|---|
With ethanol; sodium hydrogencarbonate In water Kinetics; |
(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)
fluocinolone Acetonide
Conditions | Yield |
---|---|
With ethanol; sodium hydrogencarbonate In water Kinetics; |
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. |