Terbogrel

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
CAS Number	149979-74-8 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL281398 ;
ChemSpider	4952549 ;
KEGG	D06077 ;
PubChem CID	6449876;
UNII	5Z4KWQ5OGN ;
	InChI 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+ Key: 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+;
	SMILES N#CN\C(=N/C(C)(C)C)Nc2cccc(C(=C/CCCC(=O)O)\c1cccnc1)c2;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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.

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

References

^ "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.
^ 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.
^ 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.
^ 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.