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Chemistry

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Also known as: 110140-89-1, Ridogrelum [inn-latin], R-68070, R 68070, Qts5qoo42o, 5-[(e)-[pyridin-3-yl-[3-(trifluoromethyl)phenyl]methylidene]amino]oxypentanoic acid
Molecular Formula
C18H17F3N2O3
Molecular Weight
366.3  g/mol
InChI Key
GLLPUTYLZIKEGF-HAVVHWLPSA-N
FDA UNII
QTS5QOO42O

Ridogrel
Ridogrel is a dual action drug useful for the prevention of systemic thrombo-embolism and as an adjunctive agent to thrombolytic therapy in acute myocardial infarction. However, there currently are no clinical indications for preferential use of ridogrel over aspirin.
1 2D Structure

Ridogrel

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
5-[(E)-[pyridin-3-yl-[3-(trifluoromethyl)phenyl]methylidene]amino]oxypentanoic acid
2.1.2 InChI
InChI=1S/C18H17F3N2O3/c19-18(20,21)15-7-3-5-13(11-15)17(14-6-4-9-22-12-14)23-26-10-2-1-8-16(24)25/h3-7,9,11-12H,1-2,8,10H2,(H,24,25)/b23-17+
2.1.3 InChI Key
GLLPUTYLZIKEGF-HAVVHWLPSA-N
2.1.4 Canonical SMILES
C1=CC(=CC(=C1)C(F)(F)F)C(=NOCCCCC(=O)O)C2=CN=CC=C2
2.1.5 Isomeric SMILES
C1=CC(=CC(=C1)C(F)(F)F)/C(=N\OCCCCC(=O)O)/C2=CN=CC=C2
2.2 Other Identifiers
2.2.1 UNII
QTS5QOO42O
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 5-((((3-pyridinyl)(3-(trifluoromethyl)phenyl)methylene)amino)oxy)pentanoic Acid

2. R 68,070

3. R 68070

4. R 70416

5. R-68070

6. R-70416

2.3.2 Depositor-Supplied Synonyms

1. 110140-89-1

2. Ridogrelum [inn-latin]

3. R-68070

4. R 68070

5. Qts5qoo42o

6. 5-[(e)-[pyridin-3-yl-[3-(trifluoromethyl)phenyl]methylidene]amino]oxypentanoic Acid

7. Chembl280728

8. Ridogrelum

9. Pentanoic Acid, 5-(((3-pyridinyl(3-(trifluoromethyl)phenyl)methylene)amino)oxy)-, (e)-

10. Ibidel

11. 5-[[pyridin-3-yl-[3-(trifluoromethyl)phenyl]methylidene]amino]oxypenta Noic Acid

12. Ridogrel (usan/inn)

13. Unii-qts5qoo42o

14. Ridogrel [usan:inn:ban]

15. Ridogrel [usan]

16. Ridogrel [inn]

17. Ridogrel [mi]

18. Schembl11709

19. Dtxsid90872935

20. Chebi:135542

21. Hy-a0221

22. Bdbm50003795

23. Akos015951347

24. Db01207

25. (e)-5-(((alpha-3-pyridyl-m-(trifluoromethyl)benzylidene)amino)oxy)valeric Acid

26. Cs-0017567

27. Ec-000.2105

28. D05727

29. L001350

30. (e)-5-(((.alpha.-3-pyridyl-m-(trifluoromethyl)benzylidene)amino)oxy)valeric Acid

31. (e)-5-(pyridin-3-yl(3-(trifluoromethyl)phenyl)methyleneaminooxy)pentanoic Acid

32. 5-[1-pyridin-3-yl-1-(3-trifluoromethyl-phenyl)-meth-(e)-ylideneaminooxy]-pentanoic Acid

33. 5-[pyridin-3-yl-(3-trifluoromethyl-phenyl)-methyleneaminooxy]-pentanoic Acid

34. 5-{[(e)-{pyridin-3-yl[3-(trifluoromethyl)phenyl]methylidene}amino]oxy}pentanoic Acid

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 366.3 g/mol
Molecular Formula C18H17F3N2O3
XLogP33.9
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count8
Rotatable Bond Count8
Exact Mass366.11912689 g/mol
Monoisotopic Mass366.11912689 g/mol
Topological Polar Surface Area71.8 Ų
Heavy Atom Count26
Formal Charge0
Complexity483
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Used as an adjunctive therapy to induce thrombolysis in patients suffering acute myocardial infarction.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Ridogrel, a combined thromboxane synthase inhibitor and receptor antagonist, is used with streptokinase as an adjunctive therapy to reduce the formation and size of blood clots. Blood clots can cause ischemic cardiac events (heart attacks). Ridogrel has the dual property of inhibiting the synthesis of thromboxane and blocking the receptors of thromboxane/prostaglandin/endoperoxides. It has been shown to accelerate the speed of recanalization and to delay or prevent reocclusion during systemic thrombolysis with tissue plasminogen activator (streptokinase). Ridogrel is a more potent antiplatelet agent than aspirin and might offer an advantage over aspirin as an adjunct to thrombolysis in patients suffering from acute myocardial infarction. While aspirin inhibits cyclooxygenase, the enzyme responsible for producing thromboxane, ridogrel inhibits thromboxane synthesis directly. A recent comparison between aspirin and ridogrel in as adjunct to thrombolysis in patients with acute myocardial infarction demonstrated that ridogrel is not superior to aspirin in enhancing the fibrinolytic efficacy of streptokinase but might be more effective in preventing new ischemic events. Clinical experience with this drug is still relatively limited.


5.2 MeSH Pharmacological Classification

Enzyme Inhibitors

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)


Platelet Aggregation Inhibitors

Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system. (See all compounds classified as Platelet Aggregation Inhibitors.)


Gastrointestinal Agents

Drugs used for their effects on the gastrointestinal system, as to control gastric acidity, regulate gastrointestinal motility and water flow, and improve digestion. (See all compounds classified as Gastrointestinal Agents.)


5.3 Absorption, Distribution and Excretion

Absorption

Rapidly absorbed after oral administration (30-60 min)


5.4 Mechanism of Action

Ridogrel inhibits thromboxane A2 synthase and also blocks the thromboxane A2/prostaglandin endoperoxide receptors. Thromboxane synthetase produces thromboxane in platelets. Thromboxane is a vasoconstrictor and facilitates the clumping of platelets. Therefore by inhibiting the production and promotion of thromboxane, thrombolysis is enhanced.


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