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Brivudine

Synopsis, Chemistry

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Also known as: 69304-47-8, Bvdu, (e)-5-(2-bromovinyl)-2'-deoxyuridine, Brivudin, Helpin, Zostex

Molecular Formula

C₁₁H₁₃BrN₂O₅

Molecular Weight

333.13 g/mol

InChI Key

ODZBBRURCPAEIQ-PIXDULNESA-N

FDA UNII

2M3055079H

Brivudine is a uridine derivative and nucleoside analog with pro-apoptotic and chemosensitizing properties. In vitro, bromovinyl-deoxyuridine (BVDU) has been shown to downregulate the multifunctional DNA repair enzyme APEX nuclease 1, resulting in the inhibition of DNA repair and the induction of apoptosis. In addition, this agent may inhibit the expression of STAT3 (signal transducer and activator of transcription 3), which may result in the downregulation of vascular endothelial growth factor (VEGF). BVDU has also been found to inhibit the upregulation of chemoresistance genes (Mdr1 and DHFR) during chemotherapy. Overall, the gene expression changes associated with BVDU treatment result in the decrease or prevention of chemoresistance. In addition, this agent has been shown to enhance the cytolytic activity of NK-92 natural killer cells towards a pancreatic cancer cell line in vitro.

1 2D Structure

Brivudine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-[(E)-2-bromoethenyl]-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione

2.1.2 InChI

InChI=1S/C11H13BrN2O5/c12-2-1-6-4-14(11(18)13-10(6)17)9-3-7(16)8(5-15)19-9/h1-2,4,7-9,15-16H,3,5H2,(H,13,17,18)/b2-1+/t7-,8+,9+/m0/s1

2.1.3 InChI Key

ODZBBRURCPAEIQ-PIXDULNESA-N

2.1.4 Canonical SMILES

C1C(C(OC1N2C=C(C(=O)NC2=O)C=CBr)CO)O

2.1.5 Isomeric SMILES

C1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)/C=C/Br)CO)O

2.2 Other Identifiers

2.2.1 UNII

2M3055079H

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (e)-5-(2-bromovinyl)-2'-deoxyuridine

2. (z)-5-(2-bromovinyl)-2'-deoxyuridine

3. 5-(2-bromoethenyl)-2'-deoxyuridine

4. 5-(2-bromovinyl)-2'-deoxyuridine

5. 5-bvdu

6. Brivudin

7. E-5-(2-bromovinyl)-durd

8. Z-5-(2-bromovinyl)-durd

9. Zostex

2.3.2 Depositor-Supplied Synonyms

1. 69304-47-8

2. Bvdu

3. (e)-5-(2-bromovinyl)-2'-deoxyuridine

4. Brivudin

5. Helpin

6. Zostex

7. Bromovinyldeoxyuridine

8. Brivudine [inn]

9. 5-bromovinyldeoxyuridine

10. (e)-5-(2-bromovinyl)-deoxyuridine

11. Rp101

12. Rp-101

13. Uridine, 5-[(1e)-2-bromoethenyl]-2'-deoxy-

14. Uridine, 5-(2-bromovinyl)-2'-deoxy-, (e)-

15. Brivudine (inn)

16. Nsc-633770

17. Ncgc00093656-01

18. 2m3055079h

19. 5-((e)-2-bromovinyl)-1-((2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1h,3h)-dione

20. Brivudinum

21. Brivudina

22. Brivudinum [inn-latin]

23. Brivudina [inn-spanish]

24. Mfcd00058585

25. 5-[(e)-2-bromoethenyl]-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

26. Bvd

27. Ccris 2831

28. 5-(2-bromovinyl)-2'-deoxyuridine

29. Nsc 633770

30. Trans-5-(2-bromovinyl)-2'-deoxyuridine

31. Bridic

32. Brivox

33. Zerpex

34. Brvdurd

35. Nsc633770

36. Unii-2m3055079h

37. Uridine, 5-(2-bromoethenyl)-2'-deoxy-, (e)-

38. Bv-durd

39. Zostex (tn)

40. (e)-5-(2-bromovinyl)-2-deoxyuridine

41. Brivudine [mi]

42. Brivudine [mart.]

43. Brivudine [who-dd]

44. Dsstox_cid_25755

45. Dsstox_rid_81098

46. Dsstox_gsid_45755

47. Lopac0_000175

48. Schembl99350

49. Chembl31634

50. Schembl141408

51. (e)-5-(2-bromovinyl)-durd

52. Dtxsid0045755

53. Zinc3653378

54. Tox21_111213

55. Bdbm50366681

56. S5009

57. Ua-618

58. Zb0745

59. E-5-(2-bromovinyl)-2'-deoxyuridine

60. Akos015833980

61. Ccg-204270

62. Cs-6292

63. Db03312

64. Lp00175

65. Sdccgsbi-0050163.p002

66. Ncgc00093656-02

67. 5-[(e)-2-bromoethenyl]-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione

68. 5-[(e)-2-bromovinyl]-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione

69. As-35234

70. Hy-13578

71. 5-[(e)-2-bromoethenyl]-2'-deoxyuridine

72. Cas-69304-47-8

73. A-176

74. B3404

75. Eu-0100175

76. B 9647

77. D07249

78. 5-((e)-2-bromovinyl)-2'-deoxyuridine

79. Q904107

80. Sr-01000075726

81. J-700153

82. Sr-01000075726-1

83. Bromovinyldeoxyuridine; 5-[(e)-2-bromoethenyl]-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₁H₁₃BrN₂O₅
Molecular Weight	333.13 g/mol
XLogP3	-0.4
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	3
Exact Mass	332.00078 g/mol
Monoisotopic Mass	332.00078 g/mol
Topological Polar Surface Area	99.1 Å²
Heavy Atom Count	19
Formal Charge	0
Complexity	450
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

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.)

4.2 ATC Code

J - Antiinfectives for systemic use

J05 - Antivirals for systemic use

J05A - Direct acting antivirals

J05AB - Nucleosides and nucleotides excl. reverse transcriptase inhibitors

J05AB15 - Brivudine