(1S,2S,4R,8S,9S,11S,12S,13R)-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: 1128
• Molecular Formular: C24H32O6
• Molecular Mass: 416.50728
• Monoisotopic Mass: 416.21988874
• SMILES: O1[C@]2([C@@]3([C@H]([C@H]4[C@H]([C@@H](O)C3)[C@@]3(C(=CC(=O)C=C3)CC4)C)C[C@H]2OC1(C)C)C)C(=O)CO
• Canonical SMILES: OCC(=O)[C@@]12OC(O[C@@H]1C[C@@H]1[C@]2(C)C[C@H](O)[C@H]2[C@H]1CCC1=CC(=O)C=C[C@]21C)(C)C
• InChI: InChI=1S/C24H32O6/c1-21(2)29-19-10-16-15-6-5-13-9-14(26)7-8-22(13,3)20(15)17(27)11-23(16,4)24(19,30-21)18(28)12-25/h7-9,15-17,19-20,25,27H,5-6,10-12H2,1-4H3/t15-,16-,17-,19+,20+,22-,23-,24+/m0/s1
• InChIKey: WBGKWQHBNHJJPZ-LECWWXJVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,4R,8S,9S,11S,12S,13R)-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,12S,13R)-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
• IUPAC Traditional name: desonide
• Brand Name: Desocort; Desowen; Tridesilon; Desilux
• Synonyms: Desonide; Locapred; Topifug; Tridesilon; (11β,16α)-11,21-Dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione; 16α-Hydroxyprednisolone Acetonide

Database IDs

• CAS Number: 638-94-8
• PubChem SID: 46506186; 160964591
• PubChem CID: 5311066

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.7431
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 1.9005109
• LogD (pH = 7.4): 1.9005108
• Log P: 1.9005109
• Molar Refractivity: 112.0618 cm^3
• Polarizability: 43.61315 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.31
• LOG S: -3.85
• Solubility (Water): 5.94e-02 g/l

PROPERTIES

Physical Property

• Solubility: DMF; DMSO; Practically insoluble
• Apperance: Off-White Solid
• Melting Point: 272-274°C
• Hydrophobicity(logP): 1.4

Safety Information

• Storage Condition: -20°C; Refrigerator

Product Information

• Salt Data: Free Base

DETAILS

DrugBank - DB01260

• Drug Groups: approved; investigational
• Description: A nonfluorinated corticosteroid anti-inflammatory agent used topically for dermatoses. [PubChem]
• Indication: For the relief of the inflammatory and pruritic manifestations of corticosteroid responsive dermatose.
• Pharmacology: Desonide is a synthetic nonfluorinated corticosteroid for topical dermatologic use. The corticosteroids constitute a class of primarily synthetic steroids used topically as anti-inflammatory and antipruritic agents.
• Affected Organisms: Humans and other mammals
• Absorption: Topical corticosteroids can be absorbed from normal intact skin, inflammation and/or other disease processes in the skin may increase percutaneous absorption.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S1701

Research Area: Inflammation
Biological Activity:
Desonide is a low potency topical corticosteroid. It is primarily used to treat atopic dermatitis (eczema), seborrheic dermatitis, psoriasis and contact dermatitis in both adults and children and has a fairly good safety profile. [1]

Toronto Research Chemicals - D296940

Anti-inflammatory.

REFERENCES

• http://en.wikipedia.org/wiki/Desonide
• Phillips, et al.: Toxicol. Appl. Pharmacol., 20, 522 (1971)
• Sanen, F.J., et al.: Int. J. Clin. Pharmacol. Biopharm., 12, 174 (1971)
• Tarayre, J.P., et al.: Pharmacol., 19, 323 (1979).