Ribavirin

Ribavirin

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Ribavirin
Category Enzyme inhibitors
Catalog number BBF-04058
CAS 36791-04-5
Molecular Weight 244.20
Molecular Formula C8H12N4O5
Purity ≥95%

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Description

Ribavirin is a guanosine (ribonucleic) analog used to stop viral RNA synthesis and viral mRNA capping, thus, it is a nucleoside inhibitor.

Specification

Synonyms 1-b-D-ribafuranosyl-1H-1,2,4-triazole-3-carboxamide; MegaRibavirin; NSC 163039; Ravanex; Rebetol; Ribamide; Ribamidil; Ribasphere; Ribavarin; Tribavirin; Vilona; Viramid; Virazole; Virizadole; 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-1,2,4-triazole-3-carboxamide
Storage Store at -20°C
IUPAC Name 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide
Canonical SMILES C1=NC(=NN1C2C(C(C(O2)CO)O)O)C(=O)N
InChI 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

Properties

Appearance White Crystalline Powder
Antibiotic Activity Spectrum viruses
Boiling Point 639.8°C at 760 mmHg
Melting Point 174-176°C
Flash Point 340.7±34.3 °C
Density 2.08 g/cm3
Solubility Soluble in DMF, DMSO

Reference Reading

1.New treatment for hepatitis C in chronic kidney disease, dialysis, and transplant.
Fabrizi F1, Martin P2, Messa P3. Kidney Int. 2016 May;89(5):988-94. doi: 10.1016/j.kint.2016.01.011. Epub 2016 Mar 11.
The evidence that chronic hepatitis C plays a detrimental role in survival among patients on maintenance dialysis or renal transplant recipients promotes the antiviral treatment of hepatitis C virus (HCV) among chronic kidney disease patients. Also, it seems that HCV infection is associated with an increased risk of developing chronic kidney disease in the adult general population. Interferon-based regimens have provided limited efficacy and safety among chronic kidney disease patients, whereas the advent of the new direct-acting antivirals for the treatment of hepatitis C (launched over the past 5 years) has given the opportunity to reach sustained virologic response rates of 90% for many patient groups. Unfortunately, poor information exists regarding the antiviral treatment of hepatitis C in the chronic kidney disease population. The first published data on the treatment of hepatitis C among patients with chronic kidney disease (stage 4-5) and HCV genotype 1 regard the grazoprevir (NS3/4A protease inhibitor) and elbasvir (NS5A inhibitor) combination; excellent efficacy (sustained viral response, 94.
2.Reverse Genetics Approaches to Control Arenavirus.
Martínez-Sobrido L1, Cheng BY2, de la Torre JC3. Methods Mol Biol. 2016;1403:313-51. doi: 10.1007/978-1-4939-3387-7_17.
Several arenavirus cause hemorrhagic fever disease in humans and pose a significant public health problem in their endemic regions. To date, no licensed vaccines are available to combat human arenavirus infections, and anti-arenaviral drug therapy is limited to an off-label use of ribavirin that is only partially effective. The development of arenavirus reverse genetics approaches provides investigators with a novel and powerful approach for the investigation of the arenavirus molecular and cell biology. The use of cell-based minigenome systems has allowed examining the cis- and trans-acting factors involved in arenavirus replication and transcription and the identification of novel anti-arenaviral drug targets without requiring the use of live forms of arenaviruses. Likewise, it is now feasible to rescue infectious arenaviruses entirely from cloned cDNAs containing predetermined mutations in their genomes to investigate virus-host interactions and mechanisms of pathogenesis, as well as to facilitate screens to identify anti-arenaviral drugs and development of novel live-attenuated arenavirus vaccines.
3.Toll-Like Receptor 2 Modulates the Balance of Regulatory T Cells and T Helper 17 Cells in Chronic Hepatitis C.
Liu X1, Guan JH2, Jiang BC1, Li ZS3, Zhu GZ1. Viral Immunol. 2016 Apr 15. [Epub ahead of print]
Regulatory T cells (Tregs) and interleukin-17-producing T helper (Th17) cells were mutually antagonistic in the pathogenesis of chronic hepatitis C virus (HCV) infection. However, the regulation of imbalance between Tregs and Th17 cells was poorly understood in HCV infection. A recent report revealed the immunomodulatory role of Toll-like receptor (TLR) 2 in regulating the balance of Tregs/Th17 functions in multiple sclerosis. Thus, the aim of the current study was to assess the effect of TLR2 stimulation on the suppressive function of Tregs and Th17 differentiation in chronic hepatitis C. A total of 65 patients with chronic hepatitis C receiving pegylated interferon-a2a and ribavirin therapy for 48 weeks, as well as 20 of normal controls (NCs) were enrolled. Cellular proliferation and cytokine production was tested in purified CD4+CD25+CD127dim/- Tregs in response to the stimulation of Pam3Csk4, an agonist of TLR2. In treatment-naive patients, Tregs, but not Th17 cells, from chronic hepatitis C patients expressed higher levels of TLR2 compared with NCs.
4.Sustained Virologic Response at 24 Weeks after the End of Treatment Is a Better Predictor for Treatment Outcome in Real-World HCV-Infected Patients Treated by HCV NS3/4A Protease Inhibitors with Peginterferon plus Ribavirin.
Kanda T1, Nakamoto S2, Sasaki R1, Nakamura M1, Yasui S1, Haga Y1, Ogasawara S1, Tawada A1, Arai M1, Mikami S3, Imazeki F4, Yokosuka O1. Int J Med Sci. 2016 Apr 10;13(4):310-5. doi: 10.7150/ijms.14953. eCollection 2016.
Background. Direct-acting antiviral agents against HCV with or without peginterferon plus ribavirin result in higher eradication rates of HCV and shorter treatment duration. We examined which is better for predicting persistent virologic response, the assessment of serum HCV RNA at 12 or 24 weeks after the end of treatment for predicting sustained virologic response (SVR12 or SVR24, respectively) in patients treated by HCV NS3/4A protease inhibitors with peginterferon plus ribavirin. Methods. In all, 149 Japanese patients infected with HCV genotype 1b treated by peginterferon plus ribavirin with telaprevir or simeprevir were retrospectively analyzed: 59 and 90 patients were treated with telaprevir- and simeprevir-including regimens, respectively. HCV RNA was measured by TaqMan HCV Test, version 2.0, real-time PCR assay. SVR12 or SVR24, respectively, was defined as HCV RNA negativity at 12 or 24 weeks after ending treatment. Results. Total SVR rates were 78.

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