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R9644 Sigma-Aldrich

Ribavirin

antiviral

Synonym: 1-β-D-Ribofuranosyl-1,2,4-triazole-3-carboxamide

  • CAS Number 36791-04-5

  • Empirical Formula (Hill Notation) C8H12N4O5

  • Molecular Weight 244.20

  •  MDL number MFCD00058564

  •  PubChem Substance ID 24278685

  •  NACRES NA.77

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Properties

Related Categories AIDS and Viral Research Reagents, Antibiotics, Antibiotics A to Z, Antibiotics N-S, Antiviral,
Quality Level   200
assay   ≥98% (TLC)
form   powder
solubility   water: 19.60-20.40 mg/mL, clear, colorless to faintly yellow
Mode of action   DNA synthesis | interferes
antibiotic activity spectrum   viruses
storage temp.   2-8°C
SMILES string   NC(=O)c1ncn(n1)[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O
InChI   1S/C8H12N4O5/c9-6(16)7-10-2-12(11-7)8-5(15)4(14)3(1-13)17-8/h2-5,8,13-15H,1H2,(H2,9,16)/t3-,4-,5-,8-/m1/s1
InChI key   IWUCXVSUMQZMFG-AFCXAGJDSA-N
Gene Information   human ... IMPDH1(3614), IMPDH2(3615)

Description

General description

Analog of the imidazole nucleotide intermediates in purine nucleotide biosynthesis.

Chemical structure: nucleoside

Packaging

10 mg in poly bottle

50 mg in glass bottle

Biochem/physiol Actions

Antiviral agent used against a wide variety of human viral infections, in particular, chronic hepatitis C, HIV, and adenovirus. Its metabolite, ribavirin 5′-phosphate, is an inhibitor of inosine monophosphate (IMP) dehydrogenase, but many other mechanisms of action are also supported with experimental evidence.

Antiviral agent. Its metabolite, ribavirin 5′-phosphate, is an inhibitor of inosine monophosphate (IMP) dehydrogenase. Used to inhibit purine (GTP pools) biosynthesis at the level of inosine monophosphate (IMP) dehydrogenase and as a precursor to the di- and tri-phosphates which inhibit viral RNA-dependent RNA polymerases.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. R9644.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Symbol 
GHS08  GHS08
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
XZ4250000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Nucleotide Synthesis in Cancer Cells

Neoplastic cells are highly dependent on the de novo synthesis of nucleotides to maintain sufficient pools to support DNA replication and the production of RNA. The metabolic pathways supporting nucl...
BioFiles v7 n4
Keywords: Cancer, Catalysis, Citric Acid Cycle, DNA replication, Gene expression, Glycolysis, Metabolic Pathways, Metabolism, Metabolites, Nucleotide Synthesis, Pentose phosphate pathway, Pyrimidine synthesis

Peer-Reviewed Papers
15

References

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