Terbogrel

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 470602217

| ImageFile = Terbogrel.svg

| ImageSize =

| IUPACName = (5E)-6-{3-[tert-Butyl(cyano)carbamimidamido]phenyl}-6-pyridin-3-ylhex-5-enoic acid

| OtherNames = (5E)-6-[m-(3-tert-Butyl-2-cyanoguanidino)phenyl]-6-(3-pyridyl)-5-hexenoic acid

| Section1 = {{Chembox Identifiers

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 5Z4KWQ5OGN

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 149979-74-8

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 281398

| PubChem = 6449876

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4952549

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D06077

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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+

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = XUTLOCQNGLJNSA-RGVLZGJSSA-N

| SMILES = N#CN\C(=N/C(C)(C)C)Nc2cccc(C(=C/CCCC(=O)O)\c1cccnc1)c2

| 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+

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| Section2 = {{Chembox Properties

| C=23 | H=27 | N=5 | O=2

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| Section3 = {{Chembox Hazards

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Terbogrel (INN{{cite journal | title = International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names (Rec. INN): List 37 | journal = WHO Drug Information | date = 1997 | volume = 11 | issue = 1 | page = 49 | url = http://apps.who.int/medicinedocs/index/assoc/s14162e/s14162e.pdf | archive-url = https://web.archive.org/web/20161220045248/http://apps.who.int/medicinedocs/index/assoc/s14162e/s14162e.pdf | url-status = dead | archive-date = December 20, 2016 | access-date = 3 December 2016}}) 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.{{cite journal | last1 = Guth | first1 = BD | last2 = Narjes | first2 = H | last3 = Schubert | first3 = HD | last4 = Tanswell | first4 = P | last5 = Riedel | first5 = A | last6 = Nehmiz | first6 = G | title = Pharmacokinetics and Pharmacodynamics of Terbogrel, a Combined Thromboxane A₂ Receptor and Synthase Inhibitor, in Healthy Subjects | journal = British Journal of Clinical Pharmacology | date = July 2004 | volume = 58 | issue = 1 | pages = 40–51 | doi = 10.1111/j.1365-2125.2004.02083.x | pmid = 15206991 | pmc = 1884538}}{{cite journal | last1 = Michaux | first1 = C | last2 = Norberg | first2 = B | last3 = Dogné | first3 = JM | last4 = Durant | first4 = F | last5 = Masereel | first5 = B | last6 = Delarge | first6 = J | last7 = Wouters | first7 = J | title = Terbogrel, a Dual-Acting Agent for Thromboxane Receptor Antagonism and Thromboxane Synthase Inhibition | journal = Acta Crystallographica | date = October 2000 | volume = 56 | issue = Pt 10 | pages = 1265–6 | pmid = 11025320 | doi=10.1107/s0108270100009872}} The drug was developed by Boehringer Ingelheim.

A phase 2 clinical trial of terbogrel was discontinued due to its induction of leg pain.{{cite journal | vauthors = Capra V, Bäck M, Angiolillo DJ, Cattaneo M, Sakariassen KS | title = Impact of vascular thromboxane prostanoid receptor activation on hemostasis, thrombosis, oxidative stress, and inflammation | journal = Journal of Thrombosis and Haemostasis | volume = 12 | issue = 2 | pages = 126–37 | year = 2014 | pmid = 24298905 | doi = 10.1111/jth.12472 | doi-access = free }}