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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
Structure of TIPREDANE

SMILES

CCS[C@@]1(CC[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]12C)SC

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

HIDE SMILES / InChI
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structurally unique in that the classical l7-beta two-carbon side chain and the 17-alpha hydrogen of the steroid have been replaced by two alkylthio substituents.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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Ligand-induced differentiation of glucocorticoid receptor (GR) trans-repression and transactivation: preferential targetting of NF-kappaB and lack of I-kappaB involvement.
1999-06
Interleukin-2 and -4 induce resistance of granulocyte-macrophage colony-stimulating factor to corticosteroids.
1997-09-10
Determination of the two major human metabolites of tipredane in human urine by high-performance liquid chromatography with column switching.
1997-06-20
Determination of a major metabolite of tipredane in rat urine by high-performance liquid chromatography with column switching.
1997-06-20
The S-oxidative degradation of a novel corticosteroid tipredane (INN) Part III. Detailed investigations into the disulphoxidation of tipredane.
1996-12
A radioimmunoassay for the determination of tipredane in human plasma.
1996-10
Excretion and metabolism of tipredane, a novel glucocorticoid, in the rat, mouse, monkey, and human.
1996-10
The S-oxidative degradation of a novel corticosteroid tipredane (INN). Part II--Detailed investigations into the primary S-oxidation of tipredane using achiral oxidants.
1994-06
Liquid chromatographic resolution of the isomers of tipredane and phenylthioproline using urea-solubilized beta-cyclodextrin in the mobile phase.
1992-06
The S-oxidative degradation of a novel corticosteroid tipredane (INN). Part I: Preliminary investigations into the hydrogen peroxide S-oxidation of tipredane.
1992-04
Optimization of cosolvent concentration and excipient composition in a topical corticosteroid solution.
1991-09
[Results of a preliminary study of 50 patients treated with a new corticosteroid: tipredane cream 0.1%].
1990-04
Method validation in pharmaceutical analysis.
1990
Biotransformation of tipredane, a novel topical steroid, in mouse, rat, and human liver homogenates.
1989-09-01
Rapid metabolic inactivation of tipredane, a structurally novel topical steroid.
1988-11
[Double-blind evaluation of the effectiveness and tolerance of tipredane cream and betamethasone valerate cream in patients with psoriasis].
1988-09
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.
1986-12
Androstene-17-thioketals. 1st communication: glucocorticoid receptor binding, antiproliferative and antiinflammatory activities of some novel 20-thiasteroids (androstene-17-thioketals).
1986-12
Name Type Language
TIPREDANE
INN   USAN  
USAN   INN  
Official Name English
SQ 27,239
Preferred Name English
TIPREDANE [USAN]
Common Name English
SQ-27239
Code English
ANDROSTA-1,4-DIEN-3-ONE, 17-(ETHYLTHIO)-9-FLUORO-11-HYDROXY-17-(METHYLTHIO)-, (11.BETA.,17.ALPHA.)-
Common Name English
tipredane [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C521
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Code System Code Type Description
MESH
C051756
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FDA UNII
169D68E13P
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SMS_ID
100000077242
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CAS
85197-77-9
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USAN
W-121
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NCI_THESAURUS
C152649
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PUBCHEM
6917939
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EVMPD
SUB11105MIG
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INN
5834
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ChEMBL
CHEMBL1908322
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EPA CompTox
DTXSID101318657
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