(1S,2S,4R,8S,9S,11S,12S,13R,19S)-19-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icos-17-en-16-one

• ChemBase ID: 724
• Molecular Formular: C24H33FO6
• Molecular Mass: 436.5136232
• Monoisotopic Mass: 436.226117
• SMILES: F[C@H]1C[C@H]2[C@H]3[C@@]([C@@]4(OC(O[C@@H]4C3)(C)C)C(=O)CO)(C[C@H](O)[C@@H]2[C@@]2(C1=CC(=O)CC2)C)C
• 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]1C[C@@H](C1=CC(=O)CC[C@]21C)F)(C)C
• InChI: InChI=1S/C24H33FO6/c1-21(2)30-19-9-14-13-8-16(25)15-7-12(27)5-6-22(15,3)20(13)17(28)10-23(14,4)24(19,31-21)18(29)11-26/h7,13-14,16-17,19-20,26,28H,5-6,8-11H2,1-4H3/t13-,14-,16-,17-,19+,20+,22-,23-,24+/m0/s1
• InChIKey: POPFMWWJOGLOIF-XWCQMRHXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,4R,8S,9S,11S,12S,13R,19S)-19-fluoro-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]icos-17-en-16-one; (1S,2S,4R,8S,9S,11S,12S,13R,19S)-19-fluoro-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}]icos-17-en-16-one
• IUPAC Traditional name: flurandrenolide
• Brand Name: Alondra-F; Cordran; Drenison; Drocort; Haelan; Haldrone-F; Sermaka
• Synonyms: (6α,11β,16α)-6-Fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregn-4-ene-3,20-dione; 6α-Fluoro-11β,21-dihydroxy-16α,17α-(isopropylidenedioxy)pregn-4-ene-3,20-dione; 6α-Fluoro-16α-hydroxyhydrocortisone 16,17-Acetonide; Alondra F; Cordran; Drenison; Drocort; Fluadrenolone; Fluoroandrenolone acetonide; Haelan; Haldrone F; L 33379; Sermaka; Fludroxycortidum [INN-Latin]; Fludroxicortida [INN-Spanish]; Fludrossicortide [DCIT]; Flurandrenolone; Flurandrenolone acetonide; Fluorandrenolone acetonide; Fluorandrenolone; Fludroxycortide; Fludroxicortidum; Floudroxycortide; Flurandrenolide

Database IDs

• CAS Number: 1524-88-5
• PubChem SID: 46505159; 160964187
• PubChem CID: 15209

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.73489
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 1.5629681
• LogD (pH = 7.4): 1.5629679
• Log P: 1.5629681
• Molar Refractivity: 110.7919 cm^3
• Polarizability: 43.61583 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.02
• LOG S: -3.88
• Solubility (Water): 5.78e-02 g/l

PROPERTIES

Physical Property

• Solubility: Insoluble
• Hydrophobicity(logP): 0.6

DETAILS

DrugBank - DB00846

• Drug Groups: approved
• Description: A corticosteroid used topically in the treatment of various skin disorders. It is usually employed as a cream or an ointment, and is also used as a polyethylene tape with an adhesive. (From Martindale, The Extra Pharmacopoeia, 30th ed, p733)
• Indication: For relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses, particularly dry, scaling localized lesions
• Pharmacology: Flurandrenolide is primarily effective because of its anti-inflammatory, antipruritic, and vasoconstrictive actions.
• Toxicity: Systemic absorption of topical corticosteroids has produced reversible hypothalamic-pituitary- adrenal (HPA) axis suppression, manifestations of Cushing's syndrome, hyperglycemia, and glucosuria in some patients
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily hepatic
• Absorption: Once absorbed through the skin, topical corticosteroids are handled through pharmacokinetic pathways similar to those of systemically administered corticosteroids
• Protein Binding: Corticosteroids are bound to plasma proteins in varying degrees.
• Elimination: Topical corticosteroids can be absorbed from normal intact skin. They are metabolized primarily in the liver and then excreted in the kidneys. Some of the topical corticosteroids and their metabolites are also excreted into the bile.
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - F598650

Glucocorticoid; antipsoriatic.

REFERENCES

• Pearlman, R., et al.: Int. J. Pharm., 18, 53 (1984)
• Neufeld, E., et al.: J. Chromatogr., 718, 273 (1984)