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 |
MOL RATIO
1 MOL RATIO (average) |
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structurally unique in that the classical l7-beta two-carbon side chain and the 17-alpha hydrogen of the steroid have been replaced by two alkylthio substituents.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.