2-[(1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-14,17-dien-8-yl]-2-oxoethyl acetate

• ChemBase ID: 919
• Molecular Formular: C26H32F2O7
• Molecular Mass: 494.5248864
• Monoisotopic Mass: 494.2116098
• SMILES: F[C@@]12[C@H]([C@H]3[C@@]([C@@]4(OC(O[C@@H]4C3)(C)C)C(=O)COC(=O)C)(C[C@@H]1O)C)C[C@H](F)C1=CC(=O)C=C[C@]21C
• Canonical SMILES: CC(=O)OCC(=O)[C@@]12OC(O[C@@H]1C[C@@H]1[C@]2(C)C[C@H](O)[C@]2([C@H]1C[C@@H](C1=CC(=O)C=C[C@]21C)F)F)(C)C
• 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
• InChIKey: WJOHZNCJWYWUJD-IUGZLZTKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-14,17-dien-8-yl]-2-oxoethyl acetate; 2-[(1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-14,17-dien-8-yl]-2-oxoethyl acetate; 2-[(1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.0?,?.0?,?.0??,??]icosa-14,17-dien-8-yl]-2-oxoethyl acetate
• IUPAC Traditional name: fluocinonide
• Brand Name: Bestasone; Biscosal; Cortalar; Fluzon; Lidex; Lidex E; Metosyn; Straderm; Synalar acetate; Topsymin; Topsyn; Vanos; Fluonex; Lidex-E; Lonide; Lyderm
• Synonyms: (6α,11β,16α)-21-(Acetyloxy)-6,9-difluoro-11-hydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione; Biscosal; Dermaplus; Flucetonide; Flucinar; Lidex E; Metosyn; NSC 101791; Straderm; Topsym; Topsymin; Topsyn; Topsyne; Vanos; Fluocinolone Acetonide Acetate; Fluonex; Lidex; Lidex-E; Lonide; Lyderm; Fluocinolide acetate; Fluocinolide; Fluocinolone acetonide acetate; Fluocinonide Emulsified Base; Fluocinonide [USAN:BAN:INN:JAN]; Fluocinonido [INN-Spanish]; Fluocinonidum [INN-Latin]; fluocinonide; Fluocinonide; Fluocinomide; FLUOCINOLONE ACETONIDE 21-ACETATE; (6α,11β,16α)-21-(acetyloxy)-6,9-difluoro-11-hydroxy-16,17-[(1-methylethylidene)bis(oxy)]-pregna-1,4-diene-3,20-dione; Fluocinonide

Database IDs

• CAS Number: 356-12-7; 56-12-7
• EC Number: 206-597-6
• MDL Number: MFCD00079302
• PubChem SID: 46504523; 160964382
• PubChem CID: 9642
• ATC CODE: C05AA11; D07AC08
• CHEMBL: 1501
• Chemspider ID: 9265
• DrugBank ID: DB01047
• KEGG ID: D00325
• Unique Ingredient Identifier: 2W4A77YPAN
• Wikipedia Title: Fluocinonide
• Medline Plus: a601054

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.551528
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 2.045524
• LogD (pH = 7.4): 2.0455236
• Log P: 2.045524
• Molar Refractivity: 120.5647 cm^3
• Polarizability: 47.012203 Å^3
• Polar Surface Area: 99.13 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.93
• LOG S: -4.47
• Solubility (Water): 1.68e-02 g/l

PROPERTIES

Physical Property

• Solubility: 4.74 mg/L; DMSO; DMSO: ≥19 mg/mL; Methanol
• Apperance: White Solid; white to tan powder
• Melting Point: 296-297°C (dec.)
• Optical Rotation: [α]/D +75 to +90°, c = 1 in dichloromethane
• Hydrophobicity(logP): 1.9

Safety Information

• Storage Condition: -20°C; Refrigerator; Room Temperature (15-30°C)
• RTECS: TU3831000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• Hazard Class: 6.1
• Packing Group: II
• Australian Hazchem: 2XE
• Risk Statements: R:28
• Safety Statements: S:28-29-36/37/39-45
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• Storage Temperature: 2-8°C

Pharmacology Properties

• Admin Routes: topical
• Metabolism: hepatic
• Legal Status: POM (UK); Rx-only (US); S4 (Australia)
• Pregnancy Category: C

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C26H32F2O7
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

MP Biomedicals - 02158060

(Fluocinomide)

DrugBank - DB01047

• Drug Groups: approved; investigational
• Description: A topical glucocorticoid used in the treatment of eczema. [PubChem]
• Indication: A topical anti-inflammatory product for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.
• Pharmacology: Fluocinonide is a potent glucocorticoid steroid used topically as anti-inflammatory agent for the treatment of skin disorders such as eczema. It relieves itching, redness, dryness, crusting, scaling, inflammation, and discomfort. [Wikipedia]
• Toxicity: Side effects may include acne-like eruptions, burning, dryness, excessive hair growth, infection of the skin, irritation, itching, lack of skin color, prickly heat, skin inflammation, skin loss or softening, stretch marks
• Affected Organisms: Humans and other mammals
• Absorption: The extent of percutaneous absorption of topical corticosteroids is determined by many factors including the vehicle, the integrity of the epidermal barrier, and the use of occlusive dressings. In general, percutaneous absorption is minimal.
• Elimination: Corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys. Corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S2608

Research Area: Inflammation
Biological Activity:
Fluocinonide(Vanos) is a potent glucocorticoid steroid used topically as anti-inflammatory agent for the treatment of skin disorders such as eczema. It relieves itching, redness, dryness, crusting, scaling, inflammation, and discomfort. [1]

Sigma Aldrich - SML0099

Biochem/physiol Actions
Flucinonide is a fluorinated glucocorticid that is used as a topical anti-inflammatory agent. Recently, flucinonide and other fluorinated glucocorticolids were identified as smoothend agonists. Flucinonide induces expression of Gli-reporter luciferase in Shh-LIGHT2 cells.

Toronto Research Chemicals - F455805

Glucocorticoid; anti-inflammatory.

REFERENCES

• http://en.wikipedia.org/wiki/Fluocinonide
• Sammul, et al.: J. Assoc. Off. Agric. Chem., 47, 952 (1964)
• Brunmair, B., et al.: J. Pharmacol. Exp. Therap., 311, 109 (1964)
• Emerson, M.V., et al.: BioDrugs, 21, 245 (1964)