Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C22H31FO2S2 |
Molecular Weight | 410.609 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 7 / 7 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC[C@@](SC)(SCC)[C@@]1(C)C[C@H](O)[C@@]3(F)[C@@]2([H])CCC4=CC(=O)C=C[C@]34C
InChI
InChIKey=DXEXNWDGDYUITL-FXSSSKFRSA-N
InChI=1S/C22H31FO2S2/c1-5-27-21(26-4)11-9-16-17-7-6-14-12-15(24)8-10-19(14,2)22(17,23)18(25)13-20(16,21)3/h8,10,12,16-18,25H,5-7,9,11,13H2,1-4H3/t16-,17-,18-,19-,20-,21+,22-/m0/s1
Molecular Formula | C22H31FO2S2 |
Molecular Weight | 410.609 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 7 / 7 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Tipredane is one of the compounds of a new series of sulfur-containing steroids synthesized at The Squibb Institute for Medical Research and is being developed for topical treatment of human dermatoses. Tipredane is structurally unique in that the classical l7-beta two-carbon side chain and the 17-alpha hydrogen of the steroid have been replaced by two alkylthio substituents. Tipredane has been shown to possess moderate to potent anti-inflammatory activity in various animal models, and to exhibit favorable separation of local anti-inflammatory activity from adverse systemic effects in both animals and humans. After oral administration, [3H]tipredane was rapidly absorbed, metabolized, and excreted into urine and feces. Metabolism of tipredane was rapid and complex, with significant species differences, although the disposition in rhesus and cynomolgus monkeys seemed to be similar to humans. Tipredane had been investigated as the therapeutic agent for the treatment of allergic rhinitis, asthma and skin disorders. However, this development was discontinued.
Originator
Approval Year
PubMed
Title | Date | PubMed |
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Androstene-17-thioketals. 2nd communication: pharmacological profiles of tipredane and (11 beta, 17 alpha)-17-(ethylthio)-9 alpha-fluoro-17-[2-(fluoroethyl)thio]-11 beta-hydroxy-androsta-1,4-dien-3-one, structurally novel 20-thiasteroids possessing potent and selective topical antiinflammatory activity. | 1986 Dec |
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Androstene-17-thioketals. 1st communication: glucocorticoid receptor binding, antiproliferative and antiinflammatory activities of some novel 20-thiasteroids (androstene-17-thioketals). | 1986 Dec |
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Rapid metabolic inactivation of tipredane, a structurally novel topical steroid. | 1988 Nov |
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[Double-blind evaluation of the effectiveness and tolerance of tipredane cream and betamethasone valerate cream in patients with psoriasis]. | 1988 Sep |
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Biotransformation of tipredane, a novel topical steroid, in mouse, rat, and human liver homogenates. | 1989 Sep-Oct |
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Method validation in pharmaceutical analysis. | 1990 |
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[Results of a preliminary study of 50 patients treated with a new corticosteroid: tipredane cream 0.1%]. | 1990 Apr |
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Optimization of cosolvent concentration and excipient composition in a topical corticosteroid solution. | 1991 Sep |
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The S-oxidative degradation of a novel corticosteroid tipredane (INN). Part I: Preliminary investigations into the hydrogen peroxide S-oxidation of tipredane. | 1992 Apr |
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Liquid chromatographic resolution of the isomers of tipredane and phenylthioproline using urea-solubilized beta-cyclodextrin in the mobile phase. | 1992 Jun |
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The S-oxidative degradation of a novel corticosteroid tipredane (INN). Part II--Detailed investigations into the primary S-oxidation of tipredane using achiral oxidants. | 1994 Jun |
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The S-oxidative degradation of a novel corticosteroid tipredane (INN) Part III. Detailed investigations into the disulphoxidation of tipredane. | 1996 Dec |
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A radioimmunoassay for the determination of tipredane in human plasma. | 1996 Oct |
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Excretion and metabolism of tipredane, a novel glucocorticoid, in the rat, mouse, monkey, and human. | 1996 Oct |
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Determination of the two major human metabolites of tipredane in human urine by high-performance liquid chromatography with column switching. | 1997 Jun 20 |
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Determination of a major metabolite of tipredane in rat urine by high-performance liquid chromatography with column switching. | 1997 Jun 20 |
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Interleukin-2 and -4 induce resistance of granulocyte-macrophage colony-stimulating factor to corticosteroids. | 1997 Sep 10 |
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Ligand-induced differentiation of glucocorticoid receptor (GR) trans-repression and transactivation: preferential targetting of NF-kappaB and lack of I-kappaB involvement. | 1999 Jun |
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 05:15:19 GMT 2023
by
admin
on
Sat Dec 16 05:15:19 GMT 2023
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Record UNII |
169D68E13P
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Record Status |
Validated (UNII)
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Record Version |
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C521
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EXCRETED UNCHANGED |
Unchanged tipredane was not detected in any urine extracts.
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