CAS 69304-47-8|Brivudine
| Common Name | Brivudine | ||
|---|---|---|---|
| CAS Number | 69304-47-8 | Molecular Weight | 333.135 |
| Density | 1.9±0.1 g/cm3 | Boiling Point | 382.9ºC at 760 mmHg |
| Molecular Formula | C11H13BrN2O5 | Melting Point | 165ºC |
| MSDS | USA | Flash Point | 185.4ºC |
Names
| Name | Brivudine |
|---|---|
| Synonym | More Synonyms |
Brivudine BiologicalActivity
| Description | Brivudine is a thymidine analogue with antiviral activity, indicated for the early treatment of acute herpes zoster. |
|---|---|
| Related Catalog | Signaling Pathways >>Anti-infection >>CMVResearch 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. |
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 |
| InChIKey | ODZBBRURCPAEIQ-PIXDULNESA-N |
| SMILES | O=c1[nH]c(=O)n(C2CC(O)C(CO)O2)cc1C=CBr |
| Water Solubility | Soluble in water and methanol. |
Toxicological Information
CHEMICAL IDENTIFICATION |
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
- 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 |
Articles27
More 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 ... |
Synonyms
| 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 |
