From Wikipedia, the free encyclopedia
Terbogrel
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Names
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IUPAC name
(5E)-6-{3-[tert-Butyl(cyano)carbamimidamido]phenyl}-6-pyridin-3-ylhex-5-enoic acid
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Other names
(5E)-6-[m-(3-tert-Butyl-2-cyanoguanidino)phenyl]-6-(3-pyridyl)-5-hexenoic acid
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Identifiers
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ChEMBL
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ChemSpider
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KEGG
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UNII
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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+ YKey: XUTLOCQNGLJNSA-RGVLZGJSSA-N YInChI=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+
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N#CN\C(=N/C(C)(C)C)Nc2cccc(C(=C/CCCC(=O)O)\c1cccnc1)c2
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Properties
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C23H27N5O2
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Molar mass
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405.502 g·mol−1
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Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
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]
See also
References
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^
"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.
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^ 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.
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^ 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.
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^ 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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Receptor (
ligands) |
DP (D2)Tooltip Prostaglandin D2 receptor |
DP1Tooltip Prostaglandin D2 receptor 1 | |
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DP2Tooltip Prostaglandin D2 receptor 2 | |
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EP (E2)Tooltip Prostaglandin E2 receptor |
EP1Tooltip Prostaglandin EP1 receptor | |
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EP2Tooltip Prostaglandin EP2 receptor | |
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EP3Tooltip Prostaglandin EP3 receptor | |
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EP4Tooltip Prostaglandin EP4 receptor | |
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Unsorted | |
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FP (F2α)Tooltip Prostaglandin F receptor | |
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IP (I2)Tooltip Prostacyclin receptor | |
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TP (TXA2)Tooltip Thromboxane receptor | |
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Unsorted | |
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Enzyme (
inhibitors) |
COX (
PTGS) | |
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PGD2STooltip Prostaglandin D synthase | |
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PGESTooltip Prostaglandin E synthase | |
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PGFSTooltip Prostaglandin F synthase | |
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PGI2STooltip Prostacyclin synthase | |
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TXASTooltip Thromboxane A synthase | |
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Others | |
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