Antiviraux

<p>Applications (S)-Isopropyl 2-(((R)-(((2R,3R,4R,5R)-3-((tert-Butyldimethylsilyl)oxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluoro-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate is an intermediate in the synthesis of Sofosbuvir (R)-Phosphate (S675615), which is an impurity of PSI-7977 (P839640), a prodrug that is metabolized to the active antiviral agent 2'-deoxy-2'-α-fluoro-β-C-methyluridine-5'-monophosphate and is currently being investigated in phase 3 clinical trials for the treatment of hepatitis C. Studies have profiled PSI-7977 as a nucleotide inhibitor of hepatitis C virus, exerting selective inhibitory effects towards HCV NS5B polymerase.<br>References Lam, A.M.,et al.: Antimicrob. Agents. Chemotherapy., 56, 3359 (2012); Lam, A.M., et al.: J. Virol., 85, 12334 (2011); Sofia, M.J., et al.: J. Medn. Chem., 53, 7202 (2010)<br></p>

<p>Applications (S)-(5S,6S,8S)-5,8-Dibenzyl-12,12-dimethyl-3,10-dioxo-1-(thiazol-5-yl)-2,11-dioxa-4,9-diazatridecan-6-yl 2-(3-((2-Isopropylthiazol-4-yl)methyl)-3-methylureido)-3-methylbutanoate is an protected prodrug of Ritonavir (R535000), which is a selective HIV protease inhibitor.<br></p>

<p>Applications (R)-(((1-(6-Amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonic Acid Methyl Ester Trimethylamine is an intermediate in the synthesis of Tenofovir (T018500), is an acyclic phosphonate nucleotide analogue.<br>References Peng, J., et al.: J. Clin. Pharmacol., 46, 265 (2006), Seminari, E., et al.: J. Antimicrob. Chemother., 60, 831 (2007),<br></p>

<p>Applications 2-Hydroxy-2-methylpropanethioamide is an thioamide compound integrated as an constituent in the synthesis of Ritonavir (R535000) and its derivatives.<br></p>

<p>Applications (S)-2-(3-((2-(2-Hydroxypropan-2-yl)thiazol-4-yl)methyl)-3-methylureido)-3-methylbutanoic Acid is an intermediate in the synthesis of Ritonavir (R535000) derivatives.<br></p>

<p>Applications 1-[2-Deoxy-3,5-O-[1,1,3,3-tetrakis(1-methylethyl)-1,3-disiloxanediyl]-β-D-erythro-pentofuranosyl]-1H-1,2,4-triazole-3-carboxamide is an intermediate in the synthesis of 2’-Deoxyribavirin-5’-triphosphate (D2149940) Triethylamine Salt, a potential new inhibitor for HIV-1 replication.<br>References Vivet-Boudou, V., et al.: Nucleos. Nucleot. Nucl., 26, 743 (2007);<br></p>

<p>Applications T-705RMP TEA Salt is a metabolite of T-705RMP (CAS# 356783-08-9), which is a reagent used for the preparation of pyrazine-ribofuranose derivatives as antiviral agents that are useful in the treatment of viral infections. T-705 (Favipiravir) [F103350] gets converted to T-705RMP by host cells, but T-705RMP has little inhibitory effect on the replication of the host cells based on biological studies.<br>References Zhong, B., et al.: Faming Zhuanli Shenqing, 2014:924257 (2014); Yousuke, F., et al.: Antimicrob Agent Chemother., 49, 981 (2005)<br></p>

<p>Applications 1-[2-O-(Phenoxythioxomethyl)-3,5-O-[1,1,3,3-tetrakis(1-methylethyl)-1,3-disiloxanediyl]-β-D-ribofuranosyl]-1H-1,2,4-triazole-3-carboxamide is an intermediate in the synthesis of 2’-Deoxyribavirin-5’-triphosphate (D2149940) Triethylamine Salt, a potential new inhibitor for HIV-1 replication.<br>References Vivet-Boudou, V., et al.: Nucleos. Nucleot. Nucl., 26, 743 (2007);<br></p>

<p>Applications Used in the synthesis of enantioselective synthesis of carbocyclic ribavirin, its analogs and other antiviral agents.<br>References Kuang, R. et al.; Tetrahedron Lett. 41, 9575 (2000)<br></p>

<p>Applications Intermediate in the preparation of α-Ribavirin.<br></p>

<p>Applications A highly reactive thiol-specific spin-label. A specific conformational probe of thiol site structure by virtue of its minimal rotational freedom and distance from the covalent disulfide linkage to the macromolecule under study.<br></p>

<p>Applications Intermediate in the preparation of Ribavirin.<br></p>

<p>Applications (S)-2-(3-((2-(2-Hydroxypropan-2-yl)thiazol-4-yl)methyl)-3-methylureido)-3-methylbutanoic Acid Methyl Ester is an intermediate in the synthesis of Ritonavir (R535000) derivatives.<br></p>

<p>Tenofovir diphosphate is an antiviral compound, which is a key active metabolite derived from the prodrugs tenofovir disoproxil fumarate and tenofovir alafenamide, both originating from chemical synthesis. Its mode of action involves inhibiting the activity of HIV-1 reverse transcriptase by competing with the natural substrate, deoxyadenosine 5’-triphosphate, and causing chain termination after incorporation into viral DNA. This mechanism effectively prevents the replication of retroviral DNA, thus halting the progression of the infection.</p>

<p>Vidarabine monohydrate is an antiviral agent with action on viral DNA polymerase to inhibit replication and is used for treating herpes simplex virus infections and varicella-zoster virus infections.</p>

<p>Foscarnet sodium is a pyrophosphate analog antiviral agent with action on viral DNA polymerase and is used for treating cytomegalovirus and herpes simplex virus infections.</p>

<p>Acetyl daclatasvir is a direct-acting antiviral agent, which is chemically derived from a series of small-molecule inhibitors. The source of this compound lies in rational drug design, focusing on targeting specific viral proteins involved in the replication of hepatitis C virus (HCV). Its mode of action involves inhibiting the NS5A protein, a non-structural protein essential for HCV RNA replication and virion assembly. By binding to NS5A, acetyl daclatasvir disrupts the replication complex, effectively halting the virus's ability to multiply within the host cells.</p>

<p>HCV-IN-30 is an HCV NS5A replication complex inhibitor (IC50s: 901 and 102 nM for genotypes 1a and 1b replicons).</p>

<p>Impurity Nelfinavir Sulphone Impurity<br>Applications Nelfinavir Sulfone is an impurity of Nelfinavir Mesylate (N389750). It is a COVID19-related research product.<br>References Aymard, G., et al.: J. Chromatogr. B, 744, 227 (2000), Jing, Q., et al.: J. Pharm. Biomed. Anal., 41, 1065 (2006),<br></p>

<p>Impurity Ribavirin EP Impurity C<br>Applications 1,2,4-Triazole-3-carboxylic Acid (Ribavirin EP Impurity C) is a major metabolite of the antiviral agent Ribavirin (R414475).<br>References Miller, J.P. et al.: Ann. N.Y. Acad. Sci., 284, 211 (1977); Catlin, D. et al.: Ribavirin: Broad Spec. Antivir. Ag., 83 (1980); Lin, C.C. et al.: Antimicrob. Ag. Chemother., 50, 2368 (2006);<br></p>

<p>Applications 3,4-Difluoroaniline-2,6-d2 (CAS# 1061566-62-8) can be used in its derivative form as an antiviral agent for Hepatitis B.<br>References Qiu, Y.L., et.al., U.S. Pat. Appl. Publ., 187,(2019);<br></p>

<p>Applications 2'-Fluoro-2'-deoxyuridine-5,6-d2 (CAS# 362049-50-1) is a useful isotopically labeled research compound.<br></p>

<p>Applications An intermediate in the synthesis of Ritonavir.<br>References Sham, H., et al.: Bioorg. Med. Chem. Lett., 12, 3101 (2002),<br></p>

<p>Applications Darunavir intermediate.<br>References Ghosh, A., et al.: J. Med. Chem., 39, 3278 (1996), Ghosh, A., et al.: Bioorg. Med. Chem. Lett., 1998, 8, 687 (1998), Richman, D., et al.: Nature, 410, 995 (2001), Koh, Y., et al.: Antimicrob. Agents Chemother., 47, 3123 (2003),<br></p>

<p>Impurity Atazanavir Impurity (Pyridinyl Benzaldehyde)<br>Applications Reactive metabolite of atazanavir. Atazanavir Impurity; Pyridinyl Benzaldehyde impurity<br>References F. Li et al., Drug Metabolism and Disposition 39, 294 (2011)<br></p>

<p>Applications 5,6,7,8-Tetrahydro-1-naphthalenol was used as a reagent in the synthesis of phosphonamidate and phosphonodiamidate prodrugs of adefovir and tenofovir which are used in the treatment of HIV infections. Also used in the synthesis of tetrahydronaphthalene-1-ol derivatives which were found to be promising potent antitumor agents.<br>References Pertusati, F., et al.: Eur. J. Med. Chem., 78, 259 (2014); Dong, Y., et al.: Bioorg. Med. Chem. Lett., 19, 6289 (2009);<br></p>

<p>Applications Stavudine-alpha,alpha,alpha,6-d4 (CAS# 1219803-67-4) is a useful isotopically labeled research compound.<br></p>

<p>Applications Darunavir intermediate.<br>References Ghosh, A., et al.: J. Med. Chem., 39, 3278 (1996), Ghosh, A., et al.: Bioorg. Med. Chem. Lett., 1998, 8, 687 (1998), Richman, D., et al.: Nature, 410, 995 (2001), Koh, Y., et al.: Antimicrob. Agents Chemother., 47, 3123 (2003),<br></p>

<p>Applications R 77975 is used to modulate lipophilicity in human rhinovirus capsid binders. It also is used in order to identify potential ativiral agents.<br>References Morley, A. et al.: Bioorg. Med. Chem. Lett., 21, 6031 (2011); Tomkinson, N. et al.: Bioorg. Med. Chem. Lett., 22, 7494 (2012);<br></p>

<p>Applications Levovirin is a monocyclic L-nucleosides with type 1 cytokine-inducing activity. Levovirin is the L-enantiomer of Ribavirin (R414475) with similar immunomodulatory activity but does not have direct antiviral activity or hemolytic anemia.<br>References Ramasamy, K.S. et al.: J. Med. Chem., 43, 1019 (2000); Fang, C. et al.: J. Appl. Toxicol., 23, 453 (2003):<br></p>

<p>Applications An intermediate used in the preparation of Zanamivir derivatives.<br>References Andrews, D., et al.: Eur. J. Med. Chem., 34, 563 (1999), Altamore, T., et al.: Bioorg. Med. Chem., 14, 1126 (2006),<br></p>

<p>Stability Hygroscopic<br>Applications (2'R)​-2'-​Deoxy-​2'-​fluoro-​2'-​methyl-uridine 5'-​Triphosphate Tetrasodium Salt is an impurity of Sofosbuvir (P839640) which is a prodrug that is metabolized to the active antiviral agent 2'-deoxy-2'-α-fluoro-β-C-methyluridine-5'-monophosphate.<br>References Lam, A.M.,et al.: Antimicrob. Agents. Chemotherapy., 56, 3359 (2012); Lam, A.M., et al.: J. Virol., 85, 12334 (2011); Sofia, M.J., et al.: J. Medn. Chem., 53, 7202 (2010);<br></p>

<p>Impurity Atazanavir Impurity B<br>Applications An intermediate for the preparation of antiviral protease inhibitors. Atazanavir Impurity B<br>References Fassler, A., et al.: J. Med. Chem., 39, 3203 (1996), Bold, G., et al.: J. Med. Chem., 41, 3387 (1998).<br></p>

<p>Ganciclovir is an antiviral agent specifically designed for culture media use. It is a synthetic analogue of 2'-deoxy-guanosine, derived from nucleoside compounds, and operates primarily by inhibiting the replication of viral DNA. Its mode of action involves selective phosphorylation by viral kinases, which converts it into ganciclovir triphosphate, a potent inhibitor of viral DNA polymerase, ultimately preventing viral DNA synthesis.</p>

<p>Tromantadine hydrochloride is a synthetic antiviral compound, which is a derivative of adamantane. It originates from chemical synthesis, tailored specifically to target viral processes. Tromantadine hydrochloride primarily exerts its effects by inhibiting the penetration of virus particles into host cells and impeding the subsequent stages of viral replication. This mode of action effectively reduces the viral load and hinders the progression of the infection.</p>

<p>Vicriviroc malate is a CCR5 antagonist with action on blocking HIV entry into cells by targeting the CCR5 receptor and is used for research on HIV treatment.</p>

<p>Alamifovir is an antiviral agent, which is synthetically derived. The mode of action of Alamifovir involves the inhibition of viral replication within host cells by targeting specific viral enzymes crucial for the replication process. This interference with the viral life cycle diminishes the ability of the virus to propagate and spread within the host organism.</p>

<p>Viramidine hydrochloride is an antiviral prodrug with action as a precursor to ribavirin, targeting viral RNA synthesis and is used for research on hepatitis C and other viral infections.</p>

<p>Equisetin is a secondary metabolite, which is produced by the fungus *Fusarium equiseti*. It operates predominantly through the inhibition of protein synthesis and interference with cellular processes within target organisms. Equisetin exhibits potent antibacterial and antifungal activities primarily by interfering with cell wall synthesis in bacteria and disrupting key pathways in fungi.</p>

<p>Selective and potent inhibitor of sialidases (neuraminidases) in influenza A and B viruses. The compound binds tightly to the viral neuraminidase active site in late stages of viral life-cycle. It inhibits shedding sialic acids from host cell surface glycans, which interact with viral hemagglutinin, and consequently prevents release of new viral particles from the host cell surface.</p>

<p>Darunavir-D9 is a prodrug of darunavir, which is an HIV protease inhibitor. Darunavir-D9 has been shown to be bioequivalent in pharmacokinetic parameters to darunavir given as a tablet. The drug exhibits a low plasma concentration profile and high clearance values. This may be due to rapid absorption and distribution of the drug, with a short elimination half-life. Darunavir-D9 also has little effect on the matrix effect and reproducibility of the reaction monitoring assay, making it an ideal candidate for use in clinical trials.</p>

<p>8-epiAtazanavir is a stereoisomer of the antiretroviral drug Atazanavir, which is derived from synthetic sources. It acts as an HIV-1 protease inhibitor, where it binds to the active site of the viral protease enzyme, thereby preventing the cleavage of precursor proteins required for the maturation of infectious viral particles. This interference with viral replication is achieved by the structural mimicry of the natural substrate of the protease, allowing it to competitively inhibit the enzyme's activity.</p>

<p>Carbovir triphosphate triethylamine is a nucleotide analog, which is a derivative of nucleoside analogs designed for antiviral applications. It is synthesized through chemical modification of guanosine analogs, resulting in its active triphosphate form. This compound functions as a potent antiretroviral agent by mimicking natural nucleotides and interfering with viral DNA synthesis. The active triphosphate impedes the action of viral reverse transcriptase by incorporating itself into the viral DNA chain, causing premature termination and effectively halting viral replication.</p>