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

• ChemBase ID: 473
• Molecular Formular: C24H30F2O6
• Molecular Mass: 452.4882064
• Monoisotopic Mass: 452.20104512
• SMILES: F[C@@]12[C@H]([C@H]3[C@@]([C@@]4(OC(O[C@@H]4C3)(C)C)C(=O)CO)(C[C@@H]1O)C)C[C@H](F)C1=CC(=O)C=C[C@]21C
• Canonical SMILES: 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/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
• InChIKey: FEBLZLNTKCEFIT-VSXGLTOVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-14,17-dien-16-one; (1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-14,17-dien-16-one; (1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0?,?.0?,?.0??,??]icosa-14,17-dien-16-one
• IUPAC Traditional name: synalar
• Brand Name: Coriphate; Derma-smoothe/fs; Dermalar; Flucinar; Flucort; Fluocet; Fluonid; Fluotrex; Fluovitif; Flupollon; FS Shampoo; Jellin; Localyn; Localyn Syntex; Neo-Synalar; Omniderm; Percutina; Radiocin; Retisert; Sinalar; Synalar; Synalar-HP; Synamol; Synandone; Synandrone; Synemol; Synotic; Synsac; Tefunote; Medidur
• Synonyms: Fluocinolonacetonidum; Fluocinolone acetonide [DCIT]; Fluocinoloni acetonidum [INN-Latin]; flucinolone; Fluocinolone Acetonide; 6α,9α-Difluoro-11β,16α,17α,21-tetrahydroxy-1,4-pregnadiene-3,20-dione; 6α,9α-Difluoro-16α-hydroxyprednisolone 16,17-acetonide; 6α-Fluorotriamcinolone acetonide; Fluocinolone acetonide; (6α,11β,16α)-6,9-Difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-pregna-1,4-diene-3,20-dione; Fluonid; Fluzon; Radiocin; NSC 92339; Synsac; 6α-Fluorotriamcinolone acetonide; Sinalar; Synandone; 6α,9α-Difluoro-11β,16α,17α,21-tetrahydroxy-1,4-pregnadiene-3,20-dione; 6α,9α-Difluoro-16α-hydroxyprednisolone 16,17-acetonide; 6α,9α-二氟-11β,16α,17α,21-四羟基-1,4-妊娠双烯-3,20-二酮; 6α,9α-二氟-16α-羟基泼尼松龙16,17-缩丙酮; 6α-氟代曲安奈德; 仙乃乐; 醋酸肤轻松; 醋酸氟轻松

Database IDs

• CAS Number: 67-73-2
• EC Number: 200-668-5
• MDL Number: MFCD00010525
• PubChem SID: 24894978; 160963936; 46506244
• PubChem CID: 6215

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.351801
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 1.6043986
• LogD (pH = 7.4): 1.6043981
• Log P: 1.6043986
• Molar Refractivity: 111.4132 cm^3
• Polarizability: 43.155457 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.47
• LOG S: -3.92
• Solubility (Water): 5.47e-02 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: White Solid
• Melting Point: 265-266°C; 267-269 °C(lit.); 267-269°C
• Optical Rotation: [α]25/D +98°, c = 1 in chloroform
• Hydrophobicity(logP): 2.48 [HANSCH,C ET AL. (1995)]

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• RTECS: TU3830000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98%; 97%
• Grade: analytical standard, for drug analysis
• Packaging: 100 mg of vial
• Empirical Formula (Hill Notation): C24H30F2O6
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

MP Biomedicals - 02151131

Crystals from acetone and hexane.
mp 265-266°C

DrugBank - DB00591

• Drug Groups: approved; investigational
• Description: A glucocorticoid derivative used topically in the treatment of various skin disorders. It is usually employed as a cream, gel, lotion, or ointment. It has also been used topically in the treatment of inflammatory eye, ear, and nose disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p732). It is also being investigatied by pSivida and Alimera, under the brand name Medidur, as a sustained release intraocular implant for the treatment of diabetic macular edema.
• Indication: For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses. Also for the treatment of chronic non-infectious uveitis affecting the posterior segment of the eye (Retisert).
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily hepatic, corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys.
• Absorption: Rapidly absorbed (15 minutes)
• Half Life: 1.3-1.7 hours
• Elimination: Corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys. Some of the topical corticosteroids and their metabolites are also excreted into the bile.
• References: Goldstein DA, Godfrey DG, Hall A, Callanan DG, Jaffe GJ, Pearson PA, Usner DW, Comstock TL: Intraocular pressure in patients with uveitis treated with fluocinolone acetonide implants. Arch Ophthalmol. 2007 Nov;125(11):1478-85. Epub 2007 Oct 8. [Pubmed] ; Brumm MV, Nguyen QD: Fluocinolone acetonide intravitreal sustained release device--a new addition to the armamentarium of uveitic management. Int J Nanomedicine. 2007;2(1):55-64. [Pubmed] ; Jaffe GJ, Yang CH, Guo H, Denny JP, Lima C, Ashton P: Safety and pharmacokinetics of an intraocular fluocinolone acetonide sustained delivery device. Invest Ophthalmol Vis Sci. 2000 Oct;41(11):3569-75. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - F455800

Glucocorticoid; anti-inflammatory.

REFERENCES

• Goldstein DA, Godfrey DG, Hall A, Callanan DG, Jaffe GJ, Pearson PA, Usner DW, Comstock TL: Intraocular pressure in patients with uveitis treated with fluocinolone acetonide implants. Arch Ophthalmol. 2007 Nov;125(11):1478-85. Epub 2007 Oct 8. Pubmed
• Brumm MV, Nguyen QD: Fluocinolone acetonide intravitreal sustained release device--a new addition to the armamentarium of uveitic management. Int J Nanomedicine. 2007;2(1):55-64. Pubmed
• Jaffe GJ, Yang CH, Guo H, Denny JP, Lima C, Ashton P: Safety and pharmacokinetics of an intraocular fluocinolone acetonide sustained delivery device. Invest Ophthalmol Vis Sci. 2000 Oct;41(11):3569-75. Pubmed
• Sammul, et al.: J. Assoc. Off. Agric. Chem., 47, 952 (1964)
• Emerson, M.V., et al.: BioDrugs, 21, 245 (1964)