(1R,2S,10S,11S,13R,14S,15S,17S)-1-fluoro-17-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one

• ChemBase ID: 429
• Molecular Formular: C22H29FO4
• Molecular Mass: 376.4616632
• Monoisotopic Mass: 376.20498763
• SMILES: F[C@@]12[C@H]([C@H]3[C@@]([C@H]([C@@H](C3)C)C(=O)CO)(C[C@@H]1O)C)CCC1=CC(=O)C=C[C@]21C
• Canonical SMILES: OCC(=O)[C@H]1[C@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2CCC2=CC(=O)C=C[C@]12C)F
• InChI: InChI=1S/C22H29FO4/c1-12-8-16-15-5-4-13-9-14(25)6-7-21(13,3)22(15,23)18(27)10-20(16,2)19(12)17(26)11-24/h6-7,9,12,15-16,18-19,24,27H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,18+,19-,20+,21+,22+/m1/s1
• InChIKey: VWVSBHGCDBMOOT-IIEHVVJPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,10S,11S,13R,14S,15S,17S)-1-fluoro-17-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one; (1R,2S,10S,11S,13R,14S,15S,17S)-1-fluoro-17-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• IUPAC Traditional name: desoximetasone
• Brand Name: Topicort; Topicort LP
• Synonyms: Desoximetasone; (11β,16α)-9-Fluoro-11,21-dihydroxy-16-methyl-pregna-1,4-diene-3,20-dione; 17-Deoxydexamethasone; 9-Fluoro-16α-methyl-1-corticosterone; Desoximetasone; Stidex; Topicort; Topicorte; Topisolon; Desoxymetasone; Desoximetasone; 9-氟-11β,21-二羟基-16α-甲基孕甾-1,4-二烯-3,20-二酮; 去羟米松

Database IDs

• CAS Number: 382-67-2
• EC Number: 206-845-3
• MDL Number: MFCD00083301
• PubChem SID: 160963892; 24893994; 46506793
• PubChem CID: 5311067

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.440161
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.351041
• LogD (pH = 7.4): 2.3510406
• Log P: 2.351041
• Molar Refractivity: 101.1699 cm^3
• Polarizability: 38.960907 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.13
• LOG S: -4.08
• Solubility (Water): 3.10e-02 g/l

PROPERTIES

Physical Property

• Solubility: 42.1 mg/L; Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 213-215°C
• Hydrophobicity(logP): 2.3

Safety Information

• Storage Condition: Refrigerator
• RTECS: TU3834000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-36/37/38-40-43
• Safety Statements: 22-26-36
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H315-H317-H319-H332-H335-H351
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

DETAILS

DrugBank - DB00547

• Drug Groups: approved
• Description: A topical anti-inflammatory glucocorticoid used in dermatoses, skin allergies, psoriasis, etc. [PubChem]
• Indication: For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.
• Pharmacology: Like other topical corticosteroids, desoximetasone has anti-inflammatory, antipruritic, and vasoconstrictive properties. Once absorbed through the skin, topical corticosteroids are handled through pharmacokinetic pathways similar to systemically administered corticosteroids. Desoximetasone is a potent topical corticosteroid that should not be used with occlusive dressings. It is recommended that treatment should be limited to 2 consecutive weeks and therapy should be discontinued when adequate results have been achieved.
• Toxicity: Topically applied desoximetasone can be absorbed in sufficient amounts to produce systemic effects. Symptoms of overdose include thinning of skin and suppression of adrenal cortex (decreased ability to respond to stress).
• Affected Organisms: Humans and other mammals
• Biotransformation: Metabolized, primarily in the liver, and then excreted by the kidneys.
• Absorption: Topical corticosteroids can be absorbed from intact healthy skin. The extent of percutaneous absorption of topical corticosteroids is determined by many factors, including the vehicle and the integrity of the epidermal barrier. Occlusion, inflammation and/or other disease processes in the skin may also increase percutaneous absorption.
• Half Life: The half-life of the material was 15 ± 2 hours (for urine) and 17 ± 2 hours (for feces) between the third and fifth trial day.
• Protein Binding: Bound to plasma proteins in varying degrees.
• Elimination: Corticosteroids are bound to plasma proteins in varying degrees, are metabolized primarily in the liver and excreted by the kidneys. Some of the topical corticosteroids and their metabolites are also excreted into the bile.Pharmacokinetic studies in men with Desoximetasone Cream USP, 0.25% with tagged desoximetasone showed a total of 5.2% ± 2.9% excretion in urine (4.1% ± 2.3%) and feces (1.1% ± 0.6%)
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Toronto Research Chemicals - D296970

Glucocorticoid anti-inflammatory. It is also found as an impurity in Dexamethasone (D298800).

REFERENCES

• Lee, P., et al.: Bioorg. Med. Chem. Lett., 20, 69 (2010)
• Schriks, M., et al.: Environ. Sci. Technol., 44, 4766 (2010)
• Baeck, M., et al.: Eur. J. Dermatol., 20, 102 (2010)