| Stereochemistry | ACHIRAL |
| Molecular Formula | C23H21F6NO3 |
| Molecular Weight | 473.4082 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)C1=CCCN(CCOC(C2=CC=C(C=C2)C(F)(F)F)C3=CC=C(C=C3)C(F)(F)F)C1
InChI
InChIKey=CMHQDSBIBSKHFP-UHFFFAOYSA-N
InChI=1S/C23H21F6NO3/c24-22(25,26)18-7-3-15(4-8-18)20(16-5-9-19(10-6-16)23(27,28)29)33-13-12-30-11-1-2-17(14-30)21(31)32/h2-10,20H,1,11-14H2,(H,31,32)
| Molecular Formula | C23H21F6NO3 |
| Molecular Weight | 473.4082 |
| 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 |
CI-966 is a GABA reuptake inhibitor, acting as an indirect and nonselective GABA agonist by blocking GABA transporter protein GAT-1. CI-966 was investigated in phase I clinical study for treatment of epilepsy, but its development was discontinued due to physical and mental disturbances at high doses.
CNS Activity
Originator
Approval Year
Doses
AEs
PubMed
Patents
Sample Use Guides
In phase 1 clinical trial CI-966 was administered orally. Doses 1-10 mg were well tolerated. A volunteer who received 25 mg of CI-966 developed transient short- and long-term memory deficits. Both volunteers following administration of 50 mg drug doses presented with a constellation of physical and mental disturbances.
Route of Administration:
Oral
The ability of CI-966 to block GABA transport was measured using human cells, stably transfected with GAT-1 transporter. Cells were grown in 25 well plates, washed with Hepes-buffered saline and allowed to equilibrate at 37°C for 10 min. The medium was removed and the drug was added. Transport was initiated by adding 50 uL of a concentrated [3H]GABA solution at a final concentration of 50 nM. Plates were incubated for 10 min, then washed, solubilized, and radioactivity was determined by scintillation counting. CI-966 inhibited [3H]GABA transport with IC50 of 0.26 uM.
