U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C23H27N5O2
Molecular Weight 405.4928
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of TERBOGREL

SMILES

CC(C)(C)N\C(NC#N)=N\C1=CC(=CC=C1)C(=C/CCCC(O)=O)\C2=CC=CN=C2

InChI

InChIKey=XUTLOCQNGLJNSA-RGVLZGJSSA-N
InChI=1S/C23H27N5O2/c1-23(2,3)28-22(26-16-24)27-19-10-6-8-17(14-19)20(11-4-5-12-21(29)30)18-9-7-13-25-15-18/h6-11,13-15H,4-5,12H2,1-3H3,(H,29,30)(H2,26,27,28)/b20-11+

HIDE SMILES / InChI

Description

Terbogrel, an agent having two pharmacodynamic actions, namely inhibition of thromboxane A2 synthase and antagonism of the thromboxane A2 receptor. The antithrombotic effect of terbogrel was dose-dependent and was associated with enhanced prostacyclin production. The drug was studied for the treatment of peripheral vascular disorders, pulmonary hypertension, and thrombosis. Terbogrel participated in phase II clinical trial to investigate its safety and efficacy in patients with primary pulmonary hypertension, however, this study was discontinued due to terbogrel’s induction of leg pain.

Originator

Approval Year

PubMed

Sample Use Guides

In Vivo Use Guide
Forty-eight healthy male subjects received a single oral dose (10, 25, 50, 100, 150 or 200 mg) of terbogrel or placebo and 32 different subjects received one of the following treatments twice daily for 7 days: 50, 100 or 150 mg terbogrel, placebo, or once-a-day 330 mg acetylsalicylic acid.
Route of Administration: Oral