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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
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+
Y Key: XUTLOCQNGLJNSA-RGVLZGJSSA-N
Y 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
Chemical formula
C 23 H 27 N 5 O 2
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).
N (what is Y N ?)
Infobox references
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 [ ]
^ "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 .
Antithrombotics (
thrombolytics ,
anticoagulants and
antiplatelet drugs ) (
B01 )
Antiplatelet drugs
Anticoagulants
Vitamin K antagonists (inhibit II , VII , IX , X )Factor Xa inhibitors (with some II inhibition)
Direct thrombin (IIa) inhibitors
Bivalent : Hirudin
Univalent : Argatroban
Dabigatran
Inogatran §
Melagatran ‡
Ximelagatran ‡
Other
Thrombolytic drugs /fibrinolytics Non-medicinal
# WHO-EM
‡ Withdrawn from market
Clinical trials :
† Phase III
§ Never to phase III
Drugs for
obstructive airway diseases :
asthma /
COPD (
R03 )
Adrenergics , inhalants
Short-acting β2 agonists Long-acting β2 agonists Ultra-long-acting β2 agonists Other
Glucocorticoids Anticholinergics /muscarinic antagonist Mast cell stabilizers Xanthines
Acefylline
Ambuphylline
Aminophylline
Bamifylline
Choline theophyllinate
Doxofylline
Enprofylline
Etamiphylline
Proxyphylline
Theophylline
Eicosanoid inhibition
Leukotriene antagonists Arachidonate 5-lipoxygenase inhibitors Thromboxane receptor antagonists Non-xanthine PDE4 inhibitors
Others/unknown Combination products
# WHO-EM
‡ Withdrawn from market
Clinical trials :
† Phase III
§ Never to phase III
Receptor (ligands )
DP (D2 )
DP1
Agonists: Prostaglandin D2
Treprostinil
DP2
EP (E2 )
EP1 EP2
Agonists:
Misoprostol
Prostaglandin E1 (alprostadil)
Prostaglandin E2 (dinoprostone)
Treprostinil
EP3
Agonists: Beraprost
Enprostil
Iloprost (ciloprost)
Latanoprost
Misoprostol
Prostaglandin D2
Prostaglandin E1 (alprostadil)
Prostaglandin E2 (dinoprostone)
Ricinoleic acid
Sulprostone
EP4
Agonists: Lubiprostone
Misoprostol
Prostaglandin E1 (alprostadil)
Prostaglandin E2 (dinoprostone)
Unsorted
FP (F2α ) IP (I2 )
Agonists:
Beraprost
Iloprost (ciloprost)
Prostacyclin (prostaglandin I2 , epoprostenol)
Prostaglandin E1 (alprostadil)
Selexipag
Treprostinil
TP (TXA2 )
Agonists:
Thromboxane A2
U-46619
Unsorted
Enzyme (inhibitors )
COX (PTGS )PGD2 S
Retinoids
Selenium (selenium tetrachloride , sodium selenite , selenium disulfide )
PGES
PGFS Bimatoprost
PGI2 S TXAS
Others
Precursors: Linoleic acid
γ-Linolenic acid (gamolenic acid)
Dihomo-γ-linolenic acid
Diacylglycerol
Arachidonic acid
Prostaglandin G2
Prostaglandin H2
See also
Receptor/signaling modulators
Leukotriene signaling modulators
Categories :
Antiplatelet drugs Pyridines Guanidines Nitriles Tert-butyl compounds Hidden categories:
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