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CHEMISTRY
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ACTIVE PHARMA INGREDIENTS

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Chemistry

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Also known as: 244767-67-7, Tmc-120, Dapivirine (tmc120), Tmc120, Dapivirinum, Tmc 120

Molecular Formula

C₂₀H₁₉N₅

Molecular Weight

329.4 g/mol

InChI Key

ILAYIAGXTHKHNT-UHFFFAOYSA-N

FDA UNII

TCN4MG2VXS

Dapivirine is a diarylpyrimidine non-nucleoside reverse transcriptase inhibitor. Dapivirine has activity against wild-type virus strains and strains harboring different NNRTI resistance-inducing mutations and may have direct virucidal activity.

1 2D Structure

Dapivirine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[[4-(2,4,6-trimethylanilino)pyrimidin-2-yl]amino]benzonitrile

2.1.2 InChI

InChI=1S/C20H19N5/c1-13-10-14(2)19(15(3)11-13)24-18-8-9-22-20(25-18)23-17-6-4-16(12-21)5-7-17/h4-11H,1-3H3,(H2,22,23,24,25)

2.1.3 InChI Key

ILAYIAGXTHKHNT-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=CC(=C(C(=C1)C)NC2=NC(=NC=C2)NC3=CC=C(C=C3)C#N)C

2.2 Other Identifiers

2.2.1 UNII

TCN4MG2VXS

2.3 Synonyms

2.3.1 MeSH Synonyms

1. R 147681

2. R-147681

3. Tmc 120

4. Tmc-120

5. Tmc120-r147681

2.3.2 Depositor-Supplied Synonyms

1. 244767-67-7

2. Tmc-120

3. Dapivirine (tmc120)

4. Tmc120

5. Dapivirinum

6. Tmc 120

7. R 147681

8. R-147681

9. 4-[[4-(2,4,6-trimethylanilino)pyrimidin-2-yl]amino]benzonitrile

10. Tmc120-r147681

11. R147681

12. Dapivirine,tmc-120

13. Benzonitrile, 4-[[4-[(2,4,6-trimethylphenyl)amino]-2-pyrimidinyl]amino]-

14. Tcn4mg2vxs

15. Aids-105293

16. Gel-02

17. 4-({4-[(2,4,6-trimethylphenyl)amino]pyrimidin-2-yl}amino)benzonitrile

18. 4-[[4-[(2,4,6-trimethylphenyl)amino]-2-pyrimidinyl]amino]benzonitrile

19. 4-[4-(2,4,6-trimethyl-phenylamino)-pyrimidin-2-ylamino]-benzonitrile

20. 4-((4-(mesitylamino)pyrimidin-2-yl)amino)benzonitrile

21. Tmc120;r147681

22. 4-((4-((2,4,6-trimethylphenyl)amino)pyrimidin-2-yl)amino)benzonitrile

23. Dapivirine [inn]

24. Unii-tcn4mg2vxs

25. Dapivirine [usan:inn]

26. Gel-002

27. Dapivirine-[d11]

28. Dapivirine(tmc120)

29. Tmc-120/r-147681

30. Ring-004

31. Dapivirine (usan/inn)

32. Dapivirine [usan]

33. 4-({4-[(2,4,6-trimethylphenyl)amino]pyrimidin-2-yl}amino)benzenecarbonitrile

34. Dapivirine Intravaginal Ring

35. Dapivirine [who-dd]

36. Chembl70663

37. Schembl383370

38. Zinc7761

39. Dtxsid40179244

40. Ex-a115

41. Hms3651j10

42. Bcp06491

43. Bdbm50467334

44. Mfcd09833899

45. S2914

46. Akos016513117

47. Ccg-267802

48. Db08639

49. Dt-0051

50. Sb16698

51. Dapivirine,4-[[4-(2,4,6-trimethylphenyl)amino]pyrimidin-2-yl]amino]benzonitrile

52. Ncgc00371120-06

53. Ac-30627

54. Hy-14266

55. Ft-0665472

56. Sw220193-1

57. D11246

58. 4-(4-(mesitylamino)pyrimidin-2-ylamino)benzonitrile

59. J-690269

60. Q27097831

61. 4-[[4-[(2,4,6-trimethylphenyl)-amino]-2-pyrimidinyl]amino]benzonitrile

62. 4-[[4-[(2,4,6trimethylphenyl)amino]-2-pyrimidinyl]amino]benzonitrile

63. 4-[[4[(2,4,6-trimethylphenyl)amino]-2-pyrimidinyl]amino]benzonitrile

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₁₉N₅
Molecular Weight	329.4 g/mol
XLogP3	4.8
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	4
Exact Mass	329.16404563 g/mol
Monoisotopic Mass	329.16404563 g/mol
Topological Polar Surface Area	73.6 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	452
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

Anti-HIV Agents

Agents used to treat AIDS and/or stop the spread of the HIV infection. These do not include drugs used to treat symptoms or opportunistic infections associated with AIDS. (See all compounds classified as Anti-HIV Agents.)

4.2 ATC Code

G - Genito urinary system and sex hormones

G01 - Gynecological antiinfectives and antiseptics

G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids

G01AX - Other antiinfectives and antiseptics

G01AX17 - Dapivirine

NDC API