B9647
(E)-5-(2-Bromovinyl)-2′-deoxyuridine
Synonym(s):
BVdU
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About This Item
Empirical Formula (Hill Notation):
C11H13BrN2O5
CAS Number:
Molecular Weight:
333.14
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
form
powder
Quality Level
storage temp.
2-8°C
SMILES string
O=C(C(/C=C/Br)=CN1[C@H]2C[C@H](O)[C@@H](CO)O2)NC1=O
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
InChI key
ODZBBRURCPAEIQ-PIXDULNESA-N
Gene Information
human ... HV1S(3365)
Application
(E)-5-(2-Bromovinyl)-2′-deoxyuridine (BVdU) has been used:
- as a substrate for thymidine kinase 1 to study its effects on cancer cells by a dual-promoter integrator approach
- as a bromovinyl nucleoside analog to study its effects on varicella-zoster virus replication in a mouse model
- as a nucleoside analog prodrug to study its effects on transduced cells
Biochem/physiol Actions
(E)-5-(2-Bromovinyl)-2′-deoxyuridine(BVdU) is a thymidine analog and a well-known inhibitor of Herpes simplex virus type 1 (HSV-1) and Varicella zoster virus (VZV) infections. It shows a minimal effect on HSV-2. BVdU shows therapeutic effects against herpetic keratitis, recurrent herpes labialis, and herpes zoster. BVdU undergoes phosphorylation at its 5’-diphosphate and further to 5’-triphosphate by the virus-encoded thymidine kinase, this results in BVdU acting as a competitive inhibitor to the viral DNA polymerase.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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Alexandre Mottu et al.
Journal of hepatology, 51(5), 967-969 (2009-08-21)
Brivudin is licensed in several European countries for the treatment of herpetic infections, and is considered safe (approximately 1% of patients with transient elevation of liver enzymes) in large multicenter trials. We report a case of acute brivudin hepatitis documented
Mia Bjerke et al.
Nucleosides, nucleotides & nucleic acids, 29(1), 1-13 (2010-04-15)
Thymidine kinase 2 (TK2) is a mitochondrial deoxyribonucleoside kinase that phosphorylates several nucleoside analogs used in anti-viral and anti-cancer therapy. A fibroblast cell line with decreased TK2 activity was investigated in order to obtain insights in the effects of TK2
Determination of (E)-5-(2-bromovinyl)-2?-deoxyuridine in plasma and urine by capillary electrophoresis
Jan Olgemoller, et al.
Journal of Chromatography. B, Biomedical Sciences and Applications, 726, 261-268 (1999)
Leonardo D'Aiuto et al.
Schizophrenia bulletin, 41(1), 123-132 (2014-03-14)
Herpes simplex virus, type 1 (HSV-1) commonly produces lytic mucosal lesions. It invariably initiates latent infection in sensory ganglia enabling persistent, lifelong infection. Acute HSV-1 encephalitis is rare and definitive evidence of latent infection in the brain is lacking. However
Jörg-Christian Heinrich et al.
Journal of cancer research and clinical oncology, 137(9), 1349-1361 (2011-08-13)
Several reports describe the importance of the chaperone HSP27 (HSPB1) in cancer progression, and the demand for drugs that modulate HSPB1-activity is increasing rapidly. We reported earlier that RP101 (Bromovinyldeoxyuridine, BVDU, Brivudine) improves the efficacy of chemotherapy in pancreatic cancer.
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