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Viramidine

Viramidine structure

Viramidine 

structure
  • CAS No:

    119567-79-2

  • Formula:

    C8H13N5O4

  • Chemical Name:

    Viramidine

  • Synonyms:

    1H-1,2,4-Triazole-3-carboximidamide,1-β-D-ribofuranosyl-;1-β-D-Ribofuranosyl-1H-1,2,4-triazole-3-carboximidamide;Ribamidine;Viramidine;Taribavirin;132425-32-2

  • Categories:

    Biochemical Engineering  >  Saccharides

Description

Taribavirin is a nucleobase-containing molecular entity.|Taribavirin is an orally available prodrug of ribavirin, a synthetic nucleoside analog of ribofuranose with activity against a wide range of viruses, especially the hepatitis C virus and influenza virus. Taribavirin is converted into ribavirin, which is incorporated into viral nucleic acid, thereby inhibiting viral RNA synthesis, inducing viral genome mutations, and inhibiting normal viral replication.

Viramidine Basic Attributes

243.22000

243.22

R3B1994K2E

C76499

Characteristics

150.50000

-2.02630

2.08g/cm3

595.5ºC

313.9ºC

1.851

5.01E-15mmHg at 25°C

Drug Information

Investigated for use/treatment in hepatitis (viral, C).

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)

The prodrug taribavirin (1-b-D-ribofuranosyl-1H-1, 2, 4-triazole-3-carboxamidine) is a synthetic nucleoside (guanosine) analog under development for the treatment of patients with chronic hepatitis C. Taribavirin is metabolized by the liver and converted into its active metabolite, ribavirin. This pathway reduces exposure to red blood cells (RBCs) and increases exposure to the liver, the site of HCV replication. [Valeant Website] Ribavirin is readily phosphorylated intracellularly by adenosine kinase to ribavirin mono-, di-, and triphosphate metabolites. Ribavirin triphosphate (RTP) is a potent competitive inhibitor of inosine monophosphate (IMP) dehydrogenase, viral RNA polymerase and messenger RNA (mRNA) guanylyltransferase (viral). Guanylyltranserase inhibition stops the capping of mRNA. These diverse effects result in a marked reduction of intracellular guanosine triphosphate (GTP) pools and inhibition of viral RNA and protein synthesis. Ribavirin is also incorporated into the viral genome causing lethal mutagenesis and a subsequent decrease in specific viral infectivity.

1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamidine

Computed Properties

Molecular Weight:243.22
XLogP3:-1.8
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:3
Exact Mass:243.09675391
Monoisotopic Mass:243.09675391
Topological Polar Surface Area:151
Heavy Atom Count:17
Complexity:304
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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