Stereochemistry | ABSOLUTE |
Molecular Formula | C19H17NO4S2 |
Molecular Weight | 387.473 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@@H]1CS[C@@H](SC2=CC=C(C=C2)C(=O)C3=CC=C(C=C3)C#N)[C@H](O)[C@H]1O
InChI
InChIKey=IMAFEPKOGMHYNH-LULLPPNCSA-N
InChI=1S/C19H17NO4S2/c20-9-11-1-3-12(4-2-11)16(22)13-5-7-14(8-6-13)26-19-18(24)17(23)15(21)10-25-19/h1-8,15,17-19,21,23-24H,10H2/t15-,17+,18-,19+/m1/s1
Naroparcil [LF 90055], the lead compound in a series of orally-active antithrombotics, is an analogue of LF 1351, a compound shown to have antithrombotic action. Antithrombotic activity of naroparcil is dependent on modification in the plasma GAG profile which inactivates thrombin via heparin cofactor II (HCII).
Originator
Approval Year
PubMed
Patents
Sample Use Guides
The venous antithrombotic profile of naroparcil or (4-[4-cyanobenzoyl]-phenyl)-1.5-dithio-beta-D-xylopyranoside was investigated in the rabbit following single i.v. and oral administration. Naroparcil attenuated thrombus development in a Wessler stasis model of venous thrombosis (jugular vein) employing bovine factor Xa as a thrombogenic stimulus giving ED50 values of 21.9 mg/kg and 36.0 mg/kg after respectively i.v. and oral administration. Venous antithrombotic activity was maximal 2-3 h after i.v. administration and 4-8 h after oral administration. Four hours after the oral administration of maximal antithrombotic (Wessler model, factor Xa) doses (100 and 400 mg/kg), naroparcil had no significant effect on bleeding time. In platelet poor plasma obtained from animals treated 4 h previously with various doses. A sensitized thrombin time (to about 35 s) was modestly but significantly increased following oral administration of the compound at 400 mg/kg.
Route of Administration:
Other