Terbogrel

Terbogrel (INN[1]) is an experimental drug that has been studied for its potential to prevent the vasoconstricting and platelet-aggregating action of thromboxanes. Terbogrel is an orally available thromboxane A2 receptor antagonist and a thromboxane A synthase inhibitor.[2][3] The drug was developed by Boehringer Ingelheim.

Terbogrel
Names
IUPAC name
(5E)-6-{3-[tert-Butyl(cyano)carbamimidamido]phenyl}-6-pyridin-3-ylhex-5-enoic acid
Other names
(5E)-6-[m-(3-tert-Butyl-2-cyanoguanidino)phenyl]-6-(3-pyridyl)-5-hexenoic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
UNII
  • 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+ checkY
    Key: XUTLOCQNGLJNSA-RGVLZGJSSA-N checkY
  • 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+
  • N#CN\C(=N/C(C)(C)C)Nc2cccc(C(=C/CCCC(=O)O)\c1cccnc1)c2
Properties
C23H27N5O2
Molar mass 405.502 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

A phase 2 clinical trial of terbogrel was discontinued due to its induction of leg pain.[4]

See also

References
  1. "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names (Rec. INN): List 37" (PDF). WHO Drug Information. 11 (1): 49. 1997. Archived from the original (PDF) on December 20, 2016. Retrieved 3 December 2016.
  2. Guth, BD; Narjes, H; Schubert, HD; Tanswell, P; Riedel, A; Nehmiz, G (July 2004). "Pharmacokinetics and Pharmacodynamics of Terbogrel, a Combined Thromboxane A2 Receptor and Synthase Inhibitor, in Healthy Subjects". British Journal of Clinical Pharmacology. 58 (1): 40–51. doi:10.1111/j.1365-2125.2004.02083.x. PMC 1884538. PMID 15206991.
  3. Michaux, C; Norberg, B; Dogné, JM; Durant, F; Masereel, B; Delarge, J; Wouters, J (October 2000). "Terbogrel, a Dual-Acting Agent for Thromboxane Receptor Antagonism and Thromboxane Synthase Inhibition". Acta Crystallographica. 56 (Pt 10): 1265–6. doi:10.1107/s0108270100009872. PMID 11025320.
  4. Capra V, Bäck M, Angiolillo DJ, Cattaneo M, Sakariassen KS (2014). "Impact of vascular thromboxane prostanoid receptor activation on hemostasis, thrombosis, oxidative stress, and inflammation". Journal of Thrombosis and Haemostasis. 12 (2): 126–37. doi:10.1111/jth.12472. PMID 24298905.
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