Brivudine

Category	Cytomegalovirus (CMV)
CAS	69304-47-8
Description	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. 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.

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Product Information

Synonyms	(E)-5-(2-Bromovinyl)-2'-deoxyuridine; (E)-5-(2-Bromovinyl)deoxyuridine; (E)-5-O-(2-bromoethenyl)-2'-deoxyuridine; 5-[(1E)-2-Bromoethenyl]-2'-deoxyuridine; 5-[(E)-2-Bromoethenyl]-2'-deoxyuridine; BVDU; Brivudin; Bromovinyldeoxyuridine; Helpin
IUPAC Name	5-[(E)-2-bromoethenyl]-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
Molecular Weight	333.14
Molecular Formula	C11H13BrN2O5
Canonical SMILES	C1C(C(OC1N2C=C(C(=O)NC2=O)C=CBr)CO)O
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
InChIKey	ODZBBRURCPAEIQ-PIXDULNESA-N
Boiling Point	382.9°C at 760 mmHg
Melting Point	157-160°C
Flash Point	185.4°C
Purity	≥98% by HPLC
Density	1.9±0.1 g/cm3
Solubility	Soluble in DMSO (Slightly), Methanol (Slightly)
Appearance	White or yellow crystalline powder
Storage	Store at -20°C under inert atmosphere
Complexity	450
Exact Mass	332.00078
Index Of Refraction	1.709
In Vitro	Brivudine blocks the action of DNA polymerases, thereby inhibiting viral replication. It has a strong antiviral effect against the varicella-zoster virus. It has high, selective activity against varicella zoster virus (VZV), inhibiting VZV replication, possibly through competitive inhibition of viral DNA polymerase, or by acting as an alternative substrate to deoxythymidine triphosphate, causing viral DNA strand breakage.
In Vivo	At a dose of 125 mg once daily, brivudine can reduce the period of new blister production, and has shortened the duration of post-herpetic neuralgia.
PSA	104.55000
Target	CMV
XLogP3-AA	-0.4