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Also known as: 348086-71-5, Bay 57-1293, Bay-57-1293, Aic316, Pritelivir [inn], N-methyl-n-(4-methyl-5-sulfamoylthiazol-2-yl)-2-(4-(pyridin-2-yl)phenyl)acetamide

Molecular Formula

C₁₈H₁₈N₄O₃S₂

Molecular Weight

402.5 g/mol

InChI Key

IVZKZONQVYTCKC-UHFFFAOYSA-N

FDA UNII

07HQ1TJ4JE

Pritelivir is a thiazolylamide and helicase-primase enzyme inhibitor that is active against herpes simplex virus types 1 and 2 (HSV-1 and HSV-2). Pritelivir inhibits the helicase-primase complex and prevents helicase or primase catalytic cycling of viral DNA, which interferes with DNA replication and growth. This agent does not require activation by HSV thymidine kinase and has a longer plasma half-life than nucleoside analogues.

1 2D Structure

Pritelivir

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-methyl-N-(4-methyl-5-sulfamoyl-1,3-thiazol-2-yl)-2-(4-pyridin-2-ylphenyl)acetamide

2.1.2 InChI

InChI=1S/C18H18N4O3S2/c1-12-17(27(19,24)25)26-18(21-12)22(2)16(23)11-13-6-8-14(9-7-13)15-5-3-4-10-20-15/h3-10H,11H2,1-2H3,(H2,19,24,25)

2.1.3 InChI Key

IVZKZONQVYTCKC-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=C(SC(=N1)N(C)C(=O)CC2=CC=C(C=C2)C3=CC=CC=N3)S(=O)(=O)N

2.2 Other Identifiers

2.2.1 UNII

07HQ1TJ4JE

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Aic316

2. Bay 57-1293

3. N-(5-(aminiosulfonyl)-4-methyl-1,3-thiazol-2-yl)-n-methyl-2-(4-(2-pyridinyl)phenyl)acetamide

2.3.2 Depositor-Supplied Synonyms

1. 348086-71-5

2. Bay 57-1293

3. Bay-57-1293

4. Aic316

5. Pritelivir [inn]

6. N-methyl-n-(4-methyl-5-sulfamoylthiazol-2-yl)-2-(4-(pyridin-2-yl)phenyl)acetamide

7. Bay57-1293

8. Aic-316

9. N-methyl-n-(4-methyl-5-sulfamoyl-1,3-thiazol-2-yl)-2-(4-pyridin-2-ylphenyl)acetamide

10. 07hq1tj4je

11. Pritelivir (bay 57-1293)

12. 348086-71-5 (free Base)

13. Bay 57-1293;aic316

14. Unii-07hq1tj4je

15. Benzeneacetamide, N-(5-(aminosulfonyl)-4-methyl-2-thiazolyl)-n-methyl-4-(2-pyridinyl)-

16. N-(5-(aminosulfonyl)-4-methyl-1,3-thiazol-2-yl)-n-methyl-2-(4-(2-pyridinyl)phenyl)acetamide

17. N-[5-(aminosulfonyl)-4-methyl-1,3-thiazol-2-yl]-n-methyl-2-[4-(2-pyridinyl)phenyl]acetamide

18. N-methyl-n-(4-methyl-5-sulfamoyl-1,3-thiazol-2-yl)-2-(4-(pyridin-2-yl)phenyl)acetamide

19. N-methyl-n-(4-methyl-5-sulfamoyl-1,3-thiazol-2-yl)-2-[4-(pyridin-2-yl)phenyl]acetamide

20. Pritelivir;aic316

21. Pritelivir [who-dd]

22. Pritelivirbay-57-1293

23. Schembl1074614

24. Pritelivir(bay 57-1293)

25. Chembl4069597

26. Aic 316

27. Dtxsid70188344

28. Ex-a247

29. Hms3653b15

30. Hms3744e03

31. Bcp08742

32. Yna08671

33. Zinc3955689

34. Mfcd18633192

35. S7546

36. Akos026750515

37. Ccg-268675

38. Cs-1693

39. Db11844

40. Ks-5353

41. Sb19731

42. Ncgc00378984-02

43. Ac-33065

44. Da-42669

45. Hy-15303

46. Ls-14637

47. N-(5-(aminiosulfonyl)-4-methyl-1,3-thiazol-2-yl)-n-methyl-2-(4-(2-pyridinyl)phenyl)acetamide

48. Ft-0732285

49. Sw219861-1

50. A13324

51. A857450

52. Q15410303

53. N-methyl-n-(4-methyl-5-sulfamoyl-thiazol-2-yl)-2-[4-(2-pyridyl)phenyl]acetamide

54. Bay-571293; Aic-316; Aic 316;n-[5-(aminosulfonyl)-4-methyl-1,3-thiazol-2-yl]-n-methyl-2-[4-(2-pyridinyl)phenyl]acetamide;n-methyl-n-(4-methyl-5-sulfamoylthiazol-2-yl)-2-(4-(pyridin-2-yl)phenyl)acetamide

55. N-[5-(aminosulfonyl)-4-methyl-1,3-thiazol-2-yl]-n-methyl-2-[4-(2-pyridinyl)phenyl] Acetamide

56. N-[5-(aminosulfonyl)-4-methyl-1,3-thiazol-2-yl]-n-methyl-2-[4-(2-pyridyl)phenyl]acetamide

57. N-[5-(aminosulphonyl)-4-methyl-1,3-thiazol-2-yl]-n-methyl-2-[4-(2-pyridinyl)phenyl]acetamide

2.4 Create Date

2005-08-01

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₁₈N₄O₃S₂
Molecular Weight	402.5 g/mol
XLogP3	2.1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	5
Exact Mass	402.08203280 g/mol
Monoisotopic Mass	402.08203280 g/mol
Topological Polar Surface Area	143 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	617
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 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.)

Antiviral Agents

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)

Drugs in Development