MedKoo Cat#: 412162 | Name: Brivudine monophosphate

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Brivudine monophosphate is a phosphate ester of Brivudine. Brivudine, also known as bromovinyl-deoxyuridine, 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.

Chemical Structure

Brivudine monophosphate
Brivudine monophosphate
CAS#80860-82-8 (phosphate)

Theoretical Analysis

MedKoo Cat#: 412162

Name: Brivudine monophosphate

CAS#: 80860-82-8 (phosphate)

Chemical Formula: C11H14BrN2O8P

Exact Mass: 0.0000

Molecular Weight: 413.12

Elemental Analysis: C, 31.98; H, 3.42; Br, 19.34; N, 6.78; O, 30.98; P, 7.50

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
Bulk Inquiry
Synonym
Brivudine monophosphate; Bridic; Brivox; Brivudin; Helpin ;Zerpex; Zonavir; and Zostex; BVDU; RP101; RP-101; RP 101;
IUPAC/Chemical Name
5'-Uridylic acid, 5-((1E)-2-bromoethenyl)-2'-deoxy-
InChi Key
LKWCVKAHHUJPQO-PIXDULNESA-N
InChi Code
InChI=1S/C11H14BrN2O8P/c12-2-1-6-4-14(11(17)13-10(6)16)9-3-7(15)8(22-9)5-21-23(18,19)20/h1-2,4,7-9,15H,3,5H2,(H,13,16,17)(H2,18,19,20)/b2-1+/t7-,8+,9+/m0/s1
SMILES Code
O=P(O)(OC[C@@H]1[C@H](C[C@H](N2C(NC(C(/C=C/Br)=C2)=O)=O)O1)O)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 413.12 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Kandil S, Balzarini J, Rat S, Brancale A, Westwell AD, McGuigan C. ProTides of BVdU as potential anticancer agents upon efficient intracellular delivery of their activated metabolites. Bioorg Med Chem Lett. 2016 Dec 1;26(23):5618-5623. doi: 10.1016/j.bmcl.2016.10.077. Epub 2016 Oct 27. PMID: 27818111; PMCID: PMC5131913. 2: Deval J. Antimicrobial strategies: inhibition of viral polymerases by 3'-hydroxyl nucleosides. Drugs. 2009;69(2):151-66. doi: 10.2165/00003495-200969020-00002. PMID: 19228073. 3: Caillat C, Topalis D, Agrofoglio LA, Pochet S, Balzarini J, Deville-Bonne D, Meyer P. Crystal structure of poxvirus thymidylate kinase: an unexpected dimerization has implications for antiviral therapy. Proc Natl Acad Sci U S A. 2008 Nov 4;105(44):16900-5. doi: 10.1073/pnas.0804525105. Epub 2008 Oct 29. PMID: 18971333; PMCID: PMC2579350. 4: Congiatu C, Brancale A, McGuigan C. Molecular modelling studies on the binding of some protides to the putative human phosphoramidase Hint1. Nucleosides Nucleotides Nucleic Acids. 2007;26(8-9):1121-4. doi: 10.1080/15257770701521656. PMID: 18058549. 5: Sauerbrei A, Meier C, Meerbach A, Wutzler P. Inhibitory efficacy of cyclosal- nucleoside monophosphates of aciclovir and brivudin on DNA synthesis of orthopoxvi ruses. Antivir Chem Chemother. 2006;17(1):25-31. doi: 10.1177/095632020601700104. PMID: 16542003. 6: Sauerbrei A, Meier C, Meerbach A, Schiel M, Helbig B, Wutzler P. In vitro activity of cycloSal-nucleoside monophosphates and polyhydroxycarboxylates against orthopoxviruses. Antiviral Res. 2005 Sep;67(3):147-54. doi: 10.1016/j.antiviral.2005.06.001. PMID: 16076502. 7: Meier C, Lomp A, Meerbach A, Wutzler P. cycloSaligenyl-5-[(E)-2-bromovinyl]-2'-deoxyuridine monophosphate (cycloSal- BVDUMP) pronucleotides active against Epstein-Barr virus. Chembiochem. 2001 Apr 2;2(4):283-5. doi: 10.1002/1439-7633(20010401)2:4<283::AID-CBIC283>3.0.CO;2-V. PMID: 11828456. 8: De Clercq E. Hamao Umezawa Memorial Award Lecture: "An Odyssey in the Viral Chemotherapy Field". Int J Antimicrob Agents. 2001 Oct;18(4):309-28. doi: 10.1016/s0924-8579(01)00411-3. PMID: 11691563. 9: Spadari S, Ciarrocchi G, Focher F, Verri A, Maga G, Arcamone F, Iafrate E, Manzini S, Garbesi A, Tondelli L. 5-Iodo-2'-deoxy-L-uridine and (E)-5-(2-bromovinyl)-2'-deoxy-L-uridine: selective phosphorylation by herpes simplex virus type 1 thymidine kinase, antiherpetic activity, and cytotoxicity studies. Mol Pharmacol. 1995 Jun;47(6):1231-8. PMID: 7603465. 10: Kulikowski T. Structure-activity relationships and conformational features of antiherpetic pyrimidine and purine nucleoside analogues. A review. Pharm World Sci. 1994 Apr 15;16(2):127-38. doi: 10.1007/BF01880663. PMID: 8032338. 11: Olofsson S, Sjöblom I, Hellstrand K, Shugar D, Clairmont C, Hirschberg C. 5-Propyl-2-deoxyuridine induced interference with glycosylation in herpes simplex virus infected cells. Nature of PdU-induced modifications of N-linked glycans. Arch Virol. 1993;128(3-4):241-56. doi: 10.1007/BF01309437. PMID: 8382038. 12: Bernaerts R, Desgranges C, De Clercq E. (E)-5-(2-bromovinyl)uridine requires phosphorylation by the herpes simplex virus (type 1)-induced thymidine kinase to express its antiviral activity. Biochem Pharmacol. 1989 Jun 15;38(12):1955-61. doi: 10.1016/0006-2952(89)90494-2. PMID: 2545207. 13: Coen DM, Irmiere AF, Jacobson JG, Kerns KM. Low levels of herpes simplex virus thymidine- thymidylate kinase are not limiting for sensitivity to certain antiviral drugs or for latency in a mouse model. Virology. 1989 Feb;168(2):221-31. doi: 10.1016/0042-6822(89)90261-4. PMID: 2536980. 14: Olofsson S, Milla M, Hirschberg C, De Clercq E, Datema R. Inhibition of terminal N- and O-glycosylation specific for herpesvirus-infected cells: mechanism of an inhibitor of sugar nucleotide transport across Golgi membranes. Virology. 1988 Oct;166(2):440-50. doi: 10.1016/0042-6822(88)90515-6. PMID: 2845656. 15: Bryson YJ. Promising new antiviral drugs. J Am Acad Dermatol. 1988 Jan;18(1 Pt 2):212-8. doi: 10.1016/s0190-9622(88)70031-6. PMID: 2448352. 16: Balzarini J, De Clercq E, Verbruggen A, Ayusawa D, Shimizu K, Seno T. Thymidylate synthase is the principal target enzyme for the cytostatic activity of (E)-5-(2-bromovinyl)-2'-deoxyuridine against murine mammary carcinoma (FM3A) cells transformed with the herpes simplex virus type 1 or type 2 thymidine kinase gene. Mol Pharmacol. 1987 Sep;32(3):410-6. PMID: 2823092. 17: Ayisi NK, Wall RA, Wanklin RJ, Machida H, De Clercq E, Sacks SL. Comparative metabolism of E-5-(2-bromovinyl)-2'-deoxyuridine and 1-beta-D- arabinofuranosyl-E-5-(2-bromovinyl)uracil in herpes simplex virus-infected cells. Mol Pharmacol. 1987 Apr;31(4):422-9. PMID: 3472064. 18: Kit S, Ichimura H, De Clercq E. Phosphorylation of nucleoside analogs by equine herpesvirus type 1 pyrimidine deoxyribonucleoside kinase. Antiviral Res. 1987 Jan;7(1):53-67. doi: 10.1016/0166-3542(87)90039-8. PMID: 3026247. 19: Klein RJ, Friedman-Kien AE. Effect of eight antiviral drugs on the reactivation of herpes simplex virus in explant cultures of latently infected mouse trigeminal ganglia. J Invest Dermatol. 1984 Nov;83(5):344-6. doi: 10.1111/1523-1747.ep12264450. PMID: 6208291. 20: Ayisi NK, De Clercq E, Wall RA, Hughes H, Sacks SL. Metabolic fate of (E)-5-(2-bromovinyl)-2'-deoxyuridine in herpes simplex virus- and mock-infected cells. Antimicrob Agents Chemother. 1984 Nov;26(5):762-5. doi: 10.1128/aac.26.5.762. PMID: 6097176; PMCID: PMC180009.