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Chemistry

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Also known as: 1629869-44-8, Vx-787, Pimodivir [usan], Jnj872, Jnj-63623872, Vx-787 anhydrous base
Molecular Formula
C20H19F2N5O2
Molecular Weight
399.4  g/mol
InChI Key
JGPXDNKSIXAZEQ-SBBZOCNPSA-N
FDA UNII
DFC121MXC3

Pimodivir
Pimodivir is an orally bioavailable non-nucleoside inhibitor of the polymerase basic protein 2 (PB2) subunit of the influenza A virus polymerase complex with potential antiviral activity. Upon administration, pimodivir occupies the 7-methyl GTP (m7GTP) binding site of PB2, thereby blocking the cap-snatching activity of the influenza polymerase complex and inhibiting the synthesis of viral mRNA. PB2 is one of three subunits that make up the influenza A viral polymerase complex, which is responsible for replication and transcription of the viral RNA (vRNA) genome in the nuclei of infected cells.
1 2D Structure

Pimodivir

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S,3S)-3-[[5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino]bicyclo[2.2.2]octane-2-carboxylic acid
2.1.2 InChI
InChI=1S/C20H19F2N5O2/c21-11-5-12-13(7-24-17(12)23-6-11)18-25-8-14(22)19(27-18)26-16-10-3-1-9(2-4-10)15(16)20(28)29/h5-10,15-16H,1-4H2,(H,23,24)(H,28,29)(H,25,26,27)/t9?,10?,15-,16-/m0/s1
2.1.3 InChI Key
JGPXDNKSIXAZEQ-SBBZOCNPSA-N
2.1.4 Canonical SMILES
C1CC2CCC1C(C2NC3=NC(=NC=C3F)C4=CNC5=C4C=C(C=N5)F)C(=O)O
2.1.5 Isomeric SMILES
C1CC2CCC1[C@@H]([C@H]2NC3=NC(=NC=C3F)C4=CNC5=C4C=C(C=N5)F)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
DFC121MXC3
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (2s,3s)-3-((5-fluoro-2-(5-fluoro-1h-pyrrolo(2,3-b)pyridin-3-yl)-4-pyrimidinyl)amino)bicyclo(2.2.2)octane-2-carboxylic Acid

2. Bicyclo(2.2.2)octane-2-carboxylic Acid, 3-((5-fluoro-2-(5-fluoro-1h-pyrrolo(2,3-b)pyridin-3-yl)-4-pyrimidinyl)amino)-, (2s,3s)-

3. Jnj-63623872

4. Vx-787

2.3.2 Depositor-Supplied Synonyms

1. 1629869-44-8

2. Vx-787

3. Pimodivir [usan]

4. Jnj872

5. Jnj-63623872

6. Vx-787 Anhydrous Base

7. Jnj-63623872-zcd

8. Jnj63623872

9. Dfc121mxc3

10. Chembl3318007

11. Jnj-872

12. (2s,3s)-3-((5-fluoro-2-(5-fluoro-1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)amino)bicyclo[2.2.2]octane-2-carboxylic Acid

13. (2s,3s)-3-[[5-fluoranyl-2-(5-fluoranyl-1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino]bicyclo[2.2.2]octane-2-carboxylic Acid

14. Bicyclo(2.2.2)octane-2-carboxylic Acid, 3-((5-fluoro-2-(5-fluoro-1h-pyrrolo(2,3-b)pyridin-3-yl)-4-pyrimidinyl)amino)-, (2s,3s)-

15. (2s,3s)-3-[[5-fluoro-2-(5-fluoro-1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino]bicyclo[2.2.2]octane-2-carboxylic Acid

16. 21g

17. Pimodivir(vx-787

18. 4p1u

19. Pimodivir [inn]

20. Pimodivir (usan/inn)

21. Pimodivir (vx-787)

22. Unii-dfc121mxc3

23. Pimodivir [who-dd]

24. Schembl2128140

25. Schembl16728380

26. Schembl20150447

27. Dtxsid801028095

28. Ex-a1387

29. Bdbm50050712

30. Hy-12353a

31. Zinc98208077

32. At13207

33. Cs-6423

34. Db14974

35. Vx -787

36. Ncgc00510523-01

37. Ac-30922

38. Jnj - 63623872 - Zcd

39. D11287

40. Q27276370

41. (1r,2s,3s,4r)-3-{[5-fluoro-2-(5-fluoro-1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino}bicyclo[2.2.2]octane-2-carboxylic Acid

42. (2s,3s)-3-((5-fluoro-2-(5-fluoro-1h-pyrrolo(2,3-b)pyridin- 3-yl)pyrimidin-4-yl)amino)bicyclo(2.2.2)octane-2-carboxylic Acid

43. (2s,3s)-3-(5-fluoro-2-(5-fluoro-1h-pyrrolo(2,3-b)pyridin-3-yl)pyrimidin-4-ylamino)bicyclo(2.2.2)octane-2-carboxylic Acid

44. 1259366-34-1

45. 3-[[5-fluoro-2-(5-fluoro-1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino]bicyclo[2.2.2]octane-2-carboxylic Acid; Vx787; (2s,3s)-3-((5-fluoro-2-(5-fluoro-1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)amino)bicyclo[2.2.2]octane-2-carboxylic Acid

2.4 Create Date
2012-11-30
3 Chemical and Physical Properties
Molecular Weight 399.4 g/mol
Molecular Formula C20H19F2N5O2
XLogP33.8
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count8
Rotatable Bond Count4
Exact Mass399.15068119 g/mol
Monoisotopic Mass399.15068119 g/mol
Topological Polar Surface Area104 Ų
Heavy Atom Count29
Formal Charge0
Complexity620
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Treatment of influenza


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