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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
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 Weight 333.13 g/mol
Molecular Formula C11H13BrN2O5
XLogP3-0.4
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Exact Mass332.00078 g/mol
Monoisotopic Mass332.00078 g/mol
Topological Polar Surface Area99.1 Ų
Heavy Atom Count19
Formal Charge0
Complexity450
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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


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ABOUT THIS PAGE

Brivudine Manufacturers

A Brivudine manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Brivudine, including repackagers and relabelers. The FDA regulates Brivudine manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Brivudine API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Brivudine manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Brivudine Suppliers

A Brivudine supplier is an individual or a company that provides Brivudine active pharmaceutical ingredient (API) or Brivudine finished formulations upon request. The Brivudine suppliers may include Brivudine API manufacturers, exporters, distributors and traders.

click here to find a list of Brivudine suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Brivudine WC

A Brivudine written confirmation (Brivudine WC) is an official document issued by a regulatory agency to a Brivudine manufacturer, verifying that the manufacturing facility of a Brivudine active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting Brivudine APIs or Brivudine finished pharmaceutical products to another nation, regulatory agencies frequently require a Brivudine WC (written confirmation) as part of the regulatory process.

click here to find a list of Brivudine suppliers with Written Confirmation (WC) on PharmaCompass.

Brivudine GMP

Brivudine Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Brivudine GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Brivudine GMP manufacturer or Brivudine GMP API supplier for your needs.

Brivudine CoA

A Brivudine CoA (Certificate of Analysis) is a formal document that attests to Brivudine's compliance with Brivudine specifications and serves as a tool for batch-level quality control.

Brivudine CoA mostly includes findings from lab analyses of a specific batch. For each Brivudine CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Brivudine may be tested according to a variety of international standards, such as European Pharmacopoeia (Brivudine EP), Brivudine JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Brivudine USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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