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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

[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

HIDE SMILES / InChI

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structurally unique in that the classical l7-beta two-carbon side chain and the 17-alpha hydrogen of the steroid have been replaced by two alkylthio substituents.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

Approval Year

PubMed

PubMed

TitleDatePubMed
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
Androstene-17-thioketals. 1st communication: glucocorticoid receptor binding, antiproliferative and antiinflammatory activities of some novel 20-thiasteroids (androstene-17-thioketals).
1986 Dec
Rapid metabolic inactivation of tipredane, a structurally novel topical steroid.
1988 Nov
[Double-blind evaluation of the effectiveness and tolerance of tipredane cream and betamethasone valerate cream in patients with psoriasis].
1988 Sep
Biotransformation of tipredane, a novel topical steroid, in mouse, rat, and human liver homogenates.
1989 Sep-Oct
Method validation in pharmaceutical analysis.
1990
[Results of a preliminary study of 50 patients treated with a new corticosteroid: tipredane cream 0.1%].
1990 Apr
Optimization of cosolvent concentration and excipient composition in a topical corticosteroid solution.
1991 Sep
The S-oxidative degradation of a novel corticosteroid tipredane (INN). Part I: Preliminary investigations into the hydrogen peroxide S-oxidation of tipredane.
1992 Apr
Liquid chromatographic resolution of the isomers of tipredane and phenylthioproline using urea-solubilized beta-cyclodextrin in the mobile phase.
1992 Jun
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
The S-oxidative degradation of a novel corticosteroid tipredane (INN) Part III. Detailed investigations into the disulphoxidation of tipredane.
1996 Dec
A radioimmunoassay for the determination of tipredane in human plasma.
1996 Oct
Excretion and metabolism of tipredane, a novel glucocorticoid, in the rat, mouse, monkey, and human.
1996 Oct
Determination of the two major human metabolites of tipredane in human urine by high-performance liquid chromatography with column switching.
1997 Jun 20
Determination of a major metabolite of tipredane in rat urine by high-performance liquid chromatography with column switching.
1997 Jun 20
Interleukin-2 and -4 induce resistance of granulocyte-macrophage colony-stimulating factor to corticosteroids.
1997 Sep 10
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 Sat Dec 16 05:15:19 GMT 2023
Edited
by admin
on Sat Dec 16 05:15:19 GMT 2023
Record UNII
169D68E13P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TIPREDANE
INN   USAN  
USAN   INN  
Official 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
SQ 27,239
Code English
Classification Tree Code System Code
NCI_THESAURUS C521
Created by admin on Sat Dec 16 05:15:19 GMT 2023 , Edited by admin on Sat Dec 16 05:15:19 GMT 2023
Code System Code Type Description
MESH
C051756
Created by admin on Sat Dec 16 05:15:19 GMT 2023 , Edited by admin on Sat Dec 16 05:15:19 GMT 2023
PRIMARY
FDA UNII
169D68E13P
Created by admin on Sat Dec 16 05:15:19 GMT 2023 , Edited by admin on Sat Dec 16 05:15:19 GMT 2023
PRIMARY
SMS_ID
100000077242
Created by admin on Sat Dec 16 05:15:19 GMT 2023 , Edited by admin on Sat Dec 16 05:15:19 GMT 2023
PRIMARY
CAS
85197-77-9
Created by admin on Sat Dec 16 05:15:19 GMT 2023 , Edited by admin on Sat Dec 16 05:15:19 GMT 2023
PRIMARY
USAN
W-121
Created by admin on Sat Dec 16 05:15:19 GMT 2023 , Edited by admin on Sat Dec 16 05:15:19 GMT 2023
PRIMARY
NCI_THESAURUS
C152649
Created by admin on Sat Dec 16 05:15:19 GMT 2023 , Edited by admin on Sat Dec 16 05:15:19 GMT 2023
PRIMARY
PUBCHEM
6917939
Created by admin on Sat Dec 16 05:15:19 GMT 2023 , Edited by admin on Sat Dec 16 05:15:19 GMT 2023
PRIMARY
EVMPD
SUB11105MIG
Created by admin on Sat Dec 16 05:15:19 GMT 2023 , Edited by admin on Sat Dec 16 05:15:19 GMT 2023
PRIMARY
INN
5834
Created by admin on Sat Dec 16 05:15:19 GMT 2023 , Edited by admin on Sat Dec 16 05:15:19 GMT 2023
PRIMARY
ChEMBL
CHEMBL1908322
Created by admin on Sat Dec 16 05:15:19 GMT 2023 , Edited by admin on Sat Dec 16 05:15:19 GMT 2023
PRIMARY
EPA CompTox
DTXSID101318657
Created by admin on Sat Dec 16 05:15:19 GMT 2023 , Edited by admin on Sat Dec 16 05:15:19 GMT 2023
PRIMARY
Related Record Type Details
EXCRETED UNCHANGED
Unchanged tipredane was not detected in any urine extracts.
URINE
Related Record Type Details
METABOLITE -> PARENT
MINOR
URINE
METABOLITE -> PARENT
MAJOR
URINE
METABOLITE -> PARENT
MAJOR
URINE
METABOLITE -> PARENT
MAJOR
URINE
Related Record Type Details
ACTIVE MOIETY