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Terbogrel

From Wikipedia, the free encyclopedia
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
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+ checkY
    Key: XUTLOCQNGLJNSA-RGVLZGJSSA-N checkY
  • 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
C23H27N5O2
Molar mass405.502 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Terbogrel (INN[1]) is an experimental drug that has been studied for its potential to prevent the vasoconstricting and platelet-aggregating action ofthromboxanes. Terbogrel is an orally availablethromboxane A2 receptor antagonist and athromboxane A synthase inhibitor.[2][3] The drug wasdeveloped byBoehringer Ingelheim.

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

See also

[edit]

References

[edit]
  1. ^"International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names (Rec. INN): List 37"(PDF).WHO Drug Information.11 (1): 49. 1997. Archived fromthe original(PDF) on December 20, 2016. Retrieved3 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.
Antiplatelet drugs
Glycoprotein IIb/IIIa inhibitors
ADP receptor/P2Y12inhibitors
Prostaglandin analogue (PGI2)
COX inhibitors
Thromboxane inhibitors
Phosphodiesterase inhibitors
Other
Anticoagulants
Vitamin K antagonists
(inhibitII,VII,IX,X)
Factor Xa inhibitors
(with some II inhibition)
Heparin group/
glycosaminoglycans/
(bindantithrombin)
Direct Xa inhibitors ("xabans")
Direct thrombin (IIa) inhibitors
Other
Thrombolytic drugs/
fibrinolytics
Non-medicinal
Adrenergics,inhalants
Short-acting β2 agonists
Long-acting β2 agonists
Ultra-long-acting β2 agonists
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Glucocorticoids
Anticholinergics/
muscarinic antagonist
Mast cell stabilizers
Xanthines
Eicosanoid inhibition
Leukotriene antagonists
Arachidonate 5-lipoxygenase inhibitors
Thromboxane receptor antagonists
Non-xanthinePDE4 inhibitors
Others/unknown
Combination products
Receptor
(ligands)
DP (D2)Tooltip Prostaglandin D2 receptor
DP1Tooltip Prostaglandin D2 receptor 1
DP2Tooltip Prostaglandin D2 receptor 2
EP (E2)Tooltip Prostaglandin E2 receptor
EP1Tooltip Prostaglandin EP1 receptor
EP2Tooltip Prostaglandin EP2 receptor
EP3Tooltip Prostaglandin EP3 receptor
EP4Tooltip Prostaglandin EP4 receptor
Unsorted
FP (F)Tooltip Prostaglandin F receptor
IP (I2)Tooltip Prostacyclin receptor
TP (TXA2)Tooltip Thromboxane receptor
Unsorted
Enzyme
(inhibitors)
COX
(
PTGS)
PGD2STooltip Prostaglandin D synthase
PGESTooltip Prostaglandin E synthase
PGFSTooltip Prostaglandin F synthase
PGI2STooltip Prostacyclin synthase
TXASTooltip Thromboxane A synthase
Others
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