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
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).
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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

• Ramatroban

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. 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.