| Stereochemistry | ACHIRAL |
| Molecular Formula | C23H32N2O2S |
| Molecular Weight | 400.577 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)CCOC1=CC=C(NC(=S)NC2=CC=C(OCCC(C)C)C=C2)C=C1
InChI
InChIKey=BWBONKHPVHMQHE-UHFFFAOYSA-N
InChI=1S/C23H32N2O2S/c1-17(2)13-15-26-21-9-5-19(6-10-21)24-23(28)25-20-7-11-22(12-8-20)27-16-14-18(3)4/h5-12,17-18H,13-16H2,1-4H3,(H2,24,25,28)
| Molecular Formula | C23H32N2O2S |
| Molecular Weight | 400.577 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Thiocarlide (or tiocarlide or isoxyl) is a drug which was used in the treatment of tuberculosis. In addition was preclinical experiments, which showed, that it purely bacteriostatic against M. leprae. The precise mechanism is still unknown but was shown, that Delta9-desaturase could be a target for it. The more recent experiments have revealed, that Thiocarlide inhibits the dehydration step by the (3R)-hydroxyacyl dehydratases HadAB and HadBC.
Originator
Approval Year
PubMed
Sample Use Guides
3 g in tablet form (6 tablets of 0.5 g) repeated after six hours.
Route of Administration:
Oral
The specific inhibition of oleic acid synthesis by thiocarlide (ISO) suggested that the drug target is the aerobic desaturation system responsible for the synthesis of oleic acid from stearoyl-CoA in mycobacteria. To test this hypothesis Mycobacterium bovis BCG strain was grown in iron-supplemented medium, sonicated, and centrifuged at low speed, and both the cell wall pellet and the supernatant containing both cytosol and plasma membrane were assayed for Δ9 fatty acid desaturase activity. The assay was performed as originally described by Fulco and Bloch with minor modifications. Consistent with the findings of Fulco and Bloch in the absence of NADPH in the assay mixture, no oleic acid was detected. ISO consistently inhibited the incorporation of radioactivity into the oleic acid, but not into stearic acid, by 7% at 0.1 μg/ml and 61% at a concentration of 1.0 μg of ISO/ml in one typical experiment.
