40925-28-8

Usage

Uses

Used in Antiviral Applications:
Ribavirin-5'-phosphate is used as an antiviral agent for its ability to inhibit the replication of various viruses, including respiratory syncytial virus (RSV), influenza A and B, and hepatitis C virus (HCV). Its mechanism of action involves the disruption of the viral replication process by depleting the viral nucleotide pool and causing mutations in the viral genome.
Used in Respiratory Syncytial Virus (RSV) Treatment:
In the healthcare industry, ribavirin-5'-phosphate is used as a therapeutic agent for the treatment of severe RSV infections in infants and young children. It helps to reduce the severity and duration of the illness, as well as the risk of complications associated with RSV infection.
Used in Influenza Treatment:
Ribavirin-5'-phosphate is also used in the treatment of influenza A and B infections, particularly in cases where other antiviral medications are not effective or well-tolerated. Its antiviral activity helps to alleviate symptoms and shorten the duration of the illness.
Used in Hepatitis C Virus (HCV) Treatment:
In the field of hepatology, ribavirin-5'-phosphate is used in combination with other antiviral agents for the treatment of chronic hepatitis C infection. The combination therapy helps to improve the response rate and reduce the risk of viral resistance.
Overall, ribavirin-5'-phosphate is a versatile antiviral agent with applications in various medical fields, making it an essential component in the fight against viral infections.

InChI:InChI=1/C8H13N4O8P/c9-6(15)7-10-2-12(11-7)8-5(14)4(13)3(20-8)1-19-21(16,17)18/h2-5,8,13-14H,1H2,(H2,9,15)(H2,16,17,18)/t3-,4-,5-,8-/m1/s1

Upstream product

• 512-56-1 trimethyl phosphite 
• 7440-44-0 pyrographite 
• 36791-04-5 ribavirin 
• 594860-49-8 1-(5-iodo-5-deoxy-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide 
• 594860-57-8 1-(2,3-di-O-benzoyl-5-deoxy-5-iodo-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide 

Relevant academic research and scientific papers

Synthesis and antiviral acticity of some phosphates of the broad-spectrum antiviral nucleoside, 1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamide (ribavirin).

1-beta-D-Ribofuranosyl-1,2,4-triazole-3-carboxamide 5'-phosphate (2) was prepared and converted into the following derivatives: the 5'-phosphoramidate 3, the 5'-diphosphate 4, the 5'-triphosphate 5, and the cyclic 3',5'-phosphate 6. The cyclic 2',3'-phosp

Phosphorylation of ribavirin and viramidine by adenosine kinase and cytosolic 5′-nucleotidase II: Implications for ribavirin metabolism in erythrocytes

Many nucleoside analog drugs, such as ribavirin and viramidine, are activated or metabolized in vivo through 5′-phosphorylation. In this report, we determined the steady-state kinetic parameters for 5′-monophosphorylation of ribavirin and viramidine by adenosine kinase. The apparent Km for ribavirin is 540 μM, and kcat is 1.8 min-1. Its catalytic efficiency of 3.3 × 10-3 min-1 is 1,200-fold lower than that of adenosine. In contrast to the common belief that ribavirin is exclusively phosphorylated by adenosine kinase, cytosolic 5′-nucleotidase II was found to catalyze ribavirin phosphorylation in vitro. The reaction is optimally stimulated by the physiological concentration of ATP or 2,3-bisphosphoglycerate. In phosphate-buffered saline plus ATP and 2,3-bisphosphoglycerate, the apparent Km for ribavirin is 88 μM, and kcat is 4.0 min -1. These findings suggest that cytosolic 5′-nucleotidase II may be involved in ribavirin phosphorylation in vivo. Like ribavirin, viramidine was found to be phosphorylated by either adenosine kinase or cytosolic 5′-nucleotidase II, albeit with a much lower activity. The catalytic efficiency for viramidine phosphorylation is 10- to 330-fold lower than that of ribavirin, suggesting that other nucleoside kinase(s) may be involved in viramidine phosphorylation in vivo. Both ribavirin and viramidine are not phosphorylated by deoxycytidine kinase and uridine-cytidine kinase. The coincidence of presence of high concentrated 2,3-bisphosphoglycerate in erythrocytes suggests that cytosolic 5′-nucleotidase II could play an important role in phosphorylating ribavirin and contribute to anabolism of ribavirin triphosphate in erythrocytes. Elucidation of ribavirin and viramidine phosphorylation mechanism should shed light on their in vivo metabolism, especially the ribavirin-induced hemolytic anemia in erythrocytes. Copyright

Synthesis of Azole Nucleoside 5′-Monophosphate Mimics (P1Ms) and Their Inhibitory Properties of IMP Dehydrogenases

IMPDH inhibitors have potential antimicrobial, anticancer and immunomodulatory effects. Nucleoside inhibitors of IMPDH exert their inhibitory effects via nucleoside 5′-MPs. Conversion of nucleoside analogs to NMPs by cellular nucleoside kinases is not ass

Polymeric carriers linked to nucleotide analogues via a phosphoramide bond

Novel compositions of nucleotide analog prodrugs for the treatment of viral infections and cancer are herein disclosed. The prodrugs have a biocompatible polymeric carrier conjugated to the nucleotide analog via an amino-phosphate linkage. The amino group is provided by the carrier, which either inherently possesses a primary amine, or is modified with reactive groups that incorporate the primary amine onto the carrier. The carrier can be a polyamino acid, a polyvinylic polymer, a polysaccharide or combinations thereof, such as polylysine, HPMA, dextran, hydroxyethyl starch, or polyethylene glycol; the nucleotide analog can be ribavirin araA, AZT, acyclovir, 5-FUDR, araC or ddI. Methods of treating a viral infection of cancer using these prodrugs are also disclosed. The prodrugs endow the nucleotide analogs with substantially enhanced therapeutic efficacy and reduces toxicity in comparison to the nucleotide analog alone.