Brivudine

Names

[ Name ]:
Brivudine

[Synonym ]:
5-[(E)-2-bromoethenyl]-2'-deoxyuridine
Brivudine
BrVDU
Bromovinyldeoxyuridine
MFCD00058585
5-[(E)-2-Bromovinyl]-2'-deoxyuridine
Zostrex
BVDU
Uridine, 5-[(E)-2-bromoethenyl]-2'-deoxy-
(E)-5-(2-Bromovinyl)-2'-deoxyuridine
BVDR

Biological Activity

[Description]:

Brivudine is a thymidine analogue with antiviral activity, indicated for the early treatment of acute herpes zoster.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> CMV

Research Areas >> Infection

[In Vitro]

Brivudine is an analog of thymidine, and is incorporated into the viral DNA. It blocks the action of DNA polymerases, thus inhibiting viral replication. It has a stronger antiviral effect against the varicella-zoster virus compared with reference compounds such as aciclovir or penciclovir[1]. 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[2].

[In Vivo]

At a dose of 125 mg once daily, brivudine has proved to be superior to aciclovir with respect to reducing the period of new blister production, and has shortened the duration of post-herpetic neuralgia[1].

[References]

[1]. Rabasseda X, et al. Brivudine: a herpes virostatic with rapid antiviral activity and once-daily dosing. Drugs Today (Barc). 2003 May;39(5):359-71.

[2]. Keam SJ, et al. Brivudin (bromovinyl deoxyuridine). Drugs. 2004;64(18):2091-7; discussion 2098-9.

[Related Small Molecules]

Letermovir | Maribavir | B220 | Tomeglovir

Chemical & Physical Properties

[ Density]:
1.9±0.1 g/cm3

[ Boiling Point ]:
382.9ºC at 760 mmHg

[ Melting Point ]:
165ºC

[ Molecular Formula ]:
C₁₁H₁₃BrN₂O₅

[ Molecular Weight ]:
333.135

[ Flash Point ]:
185.4ºC

[ Exact Mass ]:
332.000763

[ PSA ]:
104.55000

[ LogP ]:
-0.80

[ Index of Refraction ]:
1.709

[ Water Solubility ]:
Soluble in water and methanol.

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YU7355000

CHEMICAL NAME :: Uridine, 5-(2-bromovinyl)-2'-deoxy-, (E)-

CAS REGISTRY NUMBER :: 69304-47-8

LAST UPDATED :: 199509

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C11-H13-Br-N2-O5

MOLECULAR WEIGHT :: 333.17

WISWESSER LINE NOTATION :: T6NVMVJ E1U1E A- ET5OTJ B1Q CQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1420 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 10920 mg/kg/52W-I

TOXIC EFFECTS :: Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Liver - other changes Nutritional and Gross Metabolic - changes in chlorine

MUTATION DATA

TYPE OF TEST :: Mutation in mammalian somatic cells

TEST SYSTEM :: Human HeLa cell

DOSE/DURATION :: 4 mg/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 267,125,1992

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Safety Phrases ]:
24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
YU7355000

Synthetic Route

Click to get detail synthetic route

Articles

Characterization of pyrimidine nucleoside phosphorylase of Mycoplasma hyorhinis: implications for the clinical efficacy of nucleoside analogues.

Biochem. J. 445(1) , 113-23, (2012)

In the present paper we demonstrate that the cytostatic and antiviral activity of pyrimidine nucleoside analogues is markedly decreased by a Mycoplasma hyorhinis infection and show that the phosphorol...

Synthesis of nucleoside-based antiviral drugs in ionic liquids.

Bioorg. Med. Chem. Lett. 18(20) , 5640-2, (2008)

Nucleoside-based antiviral drugs have been synthesized using imidazolium-based ionic liquids as reaction medium. The ionic liquids were proved to be better solvents for all the nucleoside in terms of ...

Retained sensitivity to cytotoxic pyrimidine nucleoside analogs in thymidine kinase 2 deficient human fibroblasts.

Nucleosides Nucleotides Nucleic Acids 29(1) , 1-13, (2010)

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 ...