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Chemical Structure| 69304-47-8 Chemical Structure| 69304-47-8

Structure of 69304-47-8

Chemical Structure| 69304-47-8

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Brivudine is an antiviral drug acts by inhibiting replication of the target virus, used in the treatment of Herpes Zoster.

Synonyms: Brivudine; Bromovinyldeoxyuridine; BVDU

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Product Details of (E)-5-(2-Bromovinyl)-2'-deoxyuridine

CAS No. :69304-47-8
Formula : C11H13BrN2O5
M.W : 333.14
SMILES Code : OC[C@@H]1[C@H](C[C@H](N2C(NC(C(/C=C/Br)=C2)=O)=O)O1)O
Synonyms :
Brivudine; Bromovinyldeoxyuridine; BVDU
MDL No. :MFCD00058585
InChI Key :ODZBBRURCPAEIQ-PIXDULNESA-N
Pubchem ID :446727

Safety of (E)-5-(2-Bromovinyl)-2'-deoxyuridine

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P261-P305+P351+P338

Related Pathways of (E)-5-(2-Bromovinyl)-2'-deoxyuridine

DNA
PI3K-AKT

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
Vero cells 0.3, 0.6, 1.3 μM 24 h To investigate the effect of BVdU on the synthesis of HSV-1-specific polypeptides, showing marked alterations in the synthesis and processing of HSV-1-infected cell polypeptides. Antimicrob Agents Chemother. 1984 May;25(5):566-70
EBV infected P3HR-1K cells 41 μM To study the inhibitory effect of BVdUrd on EBV DNA polymerase, results showed that EBV DNA polymerase was less sensitive to BVdUrd. Proc Natl Acad Sci U S A. 1981 May;78(5):2698-702
HSV-1 infected KB cells 0.007-0.01 μg/ml To study the inhibitory effect of BVdUrd on HSV-1 replication, results showed that BVdUrd could inhibit HSV-1 replication at very low concentrations. Proc Natl Acad Sci U S A. 1981 May;78(5):2698-702
Vero cells 0.5 μg/ml 7 days To evaluate the inhibitory effect of BVdU on HSV-1 and HSV-2, it was found that the titers of HSV-1 were reduced by more than 3 log10, while the titers of HSV-2 were reduced by less than 2 log10. J Clin Microbiol. 1985 Mar;21(3):459-61
Vero cells 10 μg/ml 8 h To investigate the metabolic differences of BVdU in HSV-1 and HSV-2 infected cells. Results showed that HSV-1 infected cells metabolized BVdU to triphosphate (BVdUTP), while HSV-2 infected cells only metabolized it to monophosphate (BVdUMP). Antimicrob Agents Chemother. 1984 Nov;26(5):762-5
P3HR-1(LS) cells 0.055 μM 14 days Evaluate the inhibitory effect of BVdU on EBV DNA replication. Results showed an ED50 of 0.055 μM and a therapeutic index of 6,500. Antimicrob Agents Chemother. 1988 Jul;32(7):1068-72
Human embryo diploid fibroblast (HEF) cells 0.001 to 0.01 μg/ml 2 to 15 days Evaluate the inhibitory effect of BVDU on varicella-zoster virus (VZV) replication. Results showed that BVDU significantly inhibited VZV replication at very low concentrations without significant toxicity to host cells. Antimicrob Agents Chemother. 1982 Jan;21(1):33-8

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
Wistar rats Wistar rats Intraperitoneal injection 90μmol/rat Single dose To study the metabolism and regeneration of BVdUrd in vivo. Results showed that BVdUrd was cleared from the bloodstream within 2-3 hours after injection, degraded to BVUra, which remained in the bloodstream for a longer time. BVdUrd could be regenerated from BVUra by injecting dThd or other 5-substituted deoxyuridines. Nucleic Acids Res. 1984 Feb 24;12(4):2081-90
NMRI mice 20-day-old mice weighing approximately 10 to 12 g Intraperitoneal, subcutaneous, or oral route 100 mg/kg Single dose, samples taken at 20, 40, 80, 160, or 320 minutes after administration Compared the pharmacokinetics of (E)-5-(2-bromovinyl)-2'-deoxyuridine with 5-iodo-2'-deoxyuridine, found that the active drug concentrations of (E)-5-(2-bromovinyl)-2'-deoxyuridine in serum were significantly higher than those of 5-iodo-2'-deoxyuridine, and active drug levels could still be detected 320 minutes after oral administration Antimicrob Agents Chemother. 1979 Aug;16(2):234-6
Rabbits Experimental herpes simplex keratoconjunctivitis Topical application 0.5% ointment Five times a day for 5 consecutive days Compare the effectiveness of BVDU and IDU in preventing and treating experimental herpes simplex keratoconjunctivitis. Results showed BVDU was significantly better than IDU in suppressing conjunctivitis and promoting healing of keratitis. Antimicrob Agents Chemother. 1980 Jan;17(1):8-12
Hairless (hr/hr) mice Cutaneous herpes simplex virus type 1 (HSV-1) infection model Topical application 0.3%, 1%, 3%, 10% Four times a day for 5 days Suppressed the development of herpetic skin lesions and reduced the associated paralysis and mortality. BVdU was effective even at a concentration as low as 0.3% in 5% Azone-DMSO. Antimicrob Agents Chemother. 1984 Aug;26(2):155-9

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

3.00mL

0.60mL

0.30mL

15.01mL

3.00mL

1.50mL

30.02mL

6.00mL

3.00mL

References

 

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