Nucleosides and Nucleotides

<p>Applications Emtricitabine N,N’-Methylene Dimer is a derivative compound of Emtricitabine (E525000), a reverse transcriptase inhibitor. It is effective antiviral agent against HIV, and other viruses replicating in a similiar manner. A nucleoside analog structurally related to Lamivudine (L172500).<br>References FASEB J., 13, 1511 (1999), Molina, J.-M., et al.: J. InfecSchinazi, R.F., et al.: Antimicrob. Ag. Chemother., 36, 2423 (1992), Shockeor, J.P., et al.: Xenobioica, 26, 189 (1996), Feng, J.Y., et al.: . Dis., 182, 599 (2000)<br></p>

<p>Applications Capecitabine (C175650) impurity.<br></p>

<p>Applications The 2-epi-enantiomer analogue of (-)-Emtricitabine (E525000) evaluated against HIV-1 in human peripheral blood mononuclear (PBM) cells.<br>References Jeong, L.S., et al.: J. Med. Chem., 36, 2627 (1993),<br></p>

<p>Stability Hygroscopic<br>Applications Emtricitabine Triphosphate Triethylammonium Salt is a metabolite of (-)-Emtricitabine (E525000).<br>References Barditch-Crovo, P., et al.: Antimicrob. Agents Chemother., 45, 2733 (2001); Ray, A., et al.: Antivir .Ther., 10, 451 (2005); Borroto-Esoda, K., et al.: Antivir. Ther., 11, 377 (2006)<br></p>

<p>Impurity Capecitabine 2-O-BDR Impurity (USP)<br>Stability Hygroscopic<br>Applications Capecitabine (C175650) impurity. Capecitabine 2-O-BDR Impurity (USP).<br></p>

<p>Applications 2'-Deoxy-2'-fluorocytidine is a potent inhibitor of the subgenomic hepatitis C virus replicon in Huh-7 cells. 2'-Deoxy-2'-fluorocytidine has been shown to inhibit Borna Disease virus replication and spread.<br>References Stuyver, L.J. et al.: Antimicrob. Agents Chemother., 48, 651 (2004); Bajramovic, J.J. et al.: Antiomicrob. Agents Chemother., 48, 1422 (2004);<br></p>

<p>Stability Freezer<br>Applications An intermediate used for the synthesis of 6-substituted purine ribosides.<br></p>

<p>Applications Labelled Azathioprine (A803350). An immunosuppressive antimetabolite. Also active as disease modifying antirheumatic drug (DMARD).<br>References Mitrou, P.S., et al.: Arzneim.-Forsch., 29, 483, 662 (1979), Ding, T.L., et al.: Drug. Metab. Dispos., 7, 373 (1979), Chan, G.L.C., et al.: Pharmacotherapy, 7, 165 (1987), Sandborn, W.J., et al.: : Scand. J. Gastroenterol., 33, Suppl. 225, 92 (1998,)<br></p>

<p>Impurity Aciclovir EP Impurity P<br>Applications 9-(2-Hydroxyethyl)guanine (Aciclovir EP Impurity P) is an impurity of the antiviral agent Acyclovir (A192400). 9-(2-Hydroxyethyl)guanine is a nucleoside phosphotransferase acceptor.<br>References Kamimura, A. et al.: Agric. Biol. Chem., 37, 2037 (1973);<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>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>Applications 5'-Deoxy-5'-chloroadenosine is an intermediate in the synthesis of 5'-Deoxy-5'-(methylthio)adenosine (D242600), a substrate to study the specificity and kinetics of 5′-methylthioadenosinephosphorylase (MTAP) (EC2.4.2.28), a tumor suppressor gene expressed enzyme that supports the S-adenosylmethionine (AdoMet) and methionine salvage pathways.<br>References Olopade, O., et al.: Cancer Res., 53, 2410 (1993), Hartmann, S., et al.: Clin. Chem., 52, 1127 (2006), Penner, N., et al.: J. Pharm. Biomed. Anal., 52, 534 (2010),<br></p>

<p>Applications A new antiviral agent for influenza treatment; it can be used as neuraminidase inhibitor for treating human and avian influenza.<br>References Whitley, R., et al.: Pediatr. Infect. Dis. J., 20, 127 (2001), Bright, R., et al.: Lancet., 366, 1175 (2005), Deyde, V., et al.: J. Infect. Dis., 196, 249 (2007), Lee, N., et al.: Clin. Infect. Dis., 46, 1323 (2008),<br></p>

<p>Impurity Emtricitabine Carboxylic Acid Impurity<br>Applications Emtricitabine Carboxylic Acid is an impurity of the antiviral agent Emtricitabine (E525035).<br>References Pendela, M. et al.: Talanta, 82, 125 (2010);<br></p>

<p>Stability Moisture Sensitive<br>Applications 2,3-Dichloropropionyl Chloride is used as a reagent in the synthesis of 6-chloro-5-cyclohexyl-1-indancarboxylic acid, a potent analgesic, antipyretic, and antiinflammatory agent, and its related compounds.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Sawa, Y., et al.: Yakugaku Zasshi, 96, 653 (1976)<br></p>

<p>Stability Moisture Sensitive<br>Applications 1,2-bis(Chloromethoxy)ethane is a carcinogenic compound.<br>References Kar, S., Roy, K.: Chemoshpere, 87, 339 (2012)<br></p>

<p>Applications Methyl 4-Chlorobenzoate is a reactant used in the synthesis of ataxia-telangiectasia mutated (ATM) kinase, a target for novel radiosensitizing agents. As well, used as a reactant in the synthesis of aminopyridine functionalized polyacrylonitrile fibers.<br>References Min, J. et al.: J. Med. Chem., 59, 559 (2016);<br></p>

<p>Impurity Abacavir EP Impurity E<br>Applications (1R,3S)-3-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopentanemethanol (Abacavir EP Impurity E) is an impurity of Abacavir (A104990). Abacavir is a carbocyclic 2'-deoxyguanosine nucleoside reverse transcriptase inhibitor and an anti-HIV drug used to treat HIV infection (1). Intracellular enzymes convert Abacavir to its active form, carbovir-triphosphate (CBV-TP), which then selectively inhibits HIV reverse transcriptase by incorporating into viral DNA (2). Abacavir is metabolized in the liver by uridine diphosphate glucuronyltransferase and alcohol dehydrogenase resulting in inactive glucuronide and carboxylate metabolites, respectively.<br>References (1) Jackson, A., et al.: Antivir Ther. 17, 19 (2012) (2) Yuen, G. J., et al.: Clin Pharmacokinet. 47, 351 (2008)<br></p>

<p>Applications A novel labelled HIV reverse transcriptase inhibitor useful in treatment of HIV infection.<br>References Scholler-Gyure, M., et al.: J. Clin. Pharmacol., 48, 322 (2008), Thakur, A., et al.: Eur. J. Med. Chem., 43, 471 (2008),<br></p>

<p>Impurity Entecavir EP Impurity D<br>Applications 4’-epi-Entecavir is an epimeric impurity of the antiviral drug Entecavir (E558900).<br></p>

<p>Applications A labelled metabolite of Capecitabine.<br>References Arellano, M., ET AL.: Br. J. Cancer, 77, 79 (1998), Budman, D., ET AL.: J. Clin. Oncol., 16, 1795 (1998), Khanna, R., et al.: Cancer Res., 60, 4725 (2000), Charasson, V., et al.: Drug Metab. Dispos., 30, 731 (2002),<br></p>

<p>Impurity Abacavir EP Impurity C; Abacavir USP Related Compound A<br>Applications Descyclopropyl Abacavir (Abacavir EP Impurity C; Abacavir Related Compound A) is an intermediate of Abacavir (A105000). Abacavir is a carbocyclic 2'-deoxyguanosine nucleoside reverse transcriptase inhibitor and an anti-HIV drug used to treat HIV infection (1). Intracellular enzymes convert Abacavir to its active form, carbovir-triphosphate (CBV-TP), which then selectively inhibits HIV reverse transcriptase by incorporating into viral DNA (2). Abacavir is metabolized in the liver by uridine diphosphate glucuronyltransferase and alcohol dehydrogenase resulting in inactive glucuronide and carboxylate metabolites, respectively.<br>References (1) Jackson, A., et al.: Antivir Ther. 17, 19 (2012) (2) Yuen, G. J., et al.: Clin Pharmacokinet. 47, 351 (2008)<br></p>

<p>Impurity Fluorouracil EP Impurity B; Fluorouracil USP Related Compound B<br>Applications A 5-hydroxy derivative of the nucleobase Uracil (U801000) and an isomer of Barbituric Acid (B118650). Studies show that it can form stable base pairs with all four bases in a DNA duplex. It has been used as oxidative DNA damage biomarker in tissue engineered skin. Fluorouracil EP Impurity B. Fluorouracil USP Related Compound B<br>References Varatharasa T. et al.: Chem. Comm., 3, 400 (2005); Jaruga, P. et al.: Nucleic Acid Res., 24, 1389 (1996); Rodriguez, H. et al.: Adv. Exp. Med. Biol., 534, 129 (2003);<br></p>

<p>Applications A vitamin needed to synthesize DNA, conduct DNA repair and methylate DNA, it also acts as a cofactor in biological reactions involving folate.<br>References Xu, L., et al.: Mol. Pharm., 7, 1311 (2010), Everette, J., et al.: J. Agric. Food Chem., 58, 8139 (2010), Alshatwi, A., et al.: Food, Chem., Toxicol., 48, 1881 (2010), McKay, D., et al.: Nut. J., 9 (2010),<br></p>

<p>Stability Hygroscopic<br>Applications Acyclovir L-Leucinate is an amino acid ester of the antiherpetic agent, Acyclovir (A192400). It is the Leucine analogue of Valacyclovir (V085000).<br>References Burnette, T. et al.: J. Biol. Chem., 270, 15827 (1995);<br></p>

<p>Stability Hygroscopic<br>Applications D-Melphalan is an isomer of melphalan (M216900), which is an antineoplastic.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Ross, W.C.J., et al.: Biochem. Pharmacol., 13, 969 (1964); Donelli, M.G., et al.: J. Pharm. Pharmacol., 18, 760 (1966), Furner, R.L., et al.: Cancer Treat. Rep., 64, 559 (1980),<br></p>

<p>Applications L-Tetrahydrofolic Acid-d4 (Major) is a folic acid derivative and coenzyme involved in the metabolism of amino and nucleic acids.<br>References Prinz-Langenohl, R., et al.: Brit. J. Pharmacol., 158, 2014 (2009), Martin, H., et al.: Anal. Biochem., 402, 137 (2010), Dasarathy, J., et al.: Am. J. Clin. Nut., 91, 357 (2010), Karas-Kuzelicki, N., et al.: Clin. Biochem., 43, 37 (2010),<br></p>

<p>Stability Hygroscopic<br>Applications A reverse transcriptase inhibitor. It is an effective antiviral agent against HIV, HBV, and other viruses replicating in a similar manner. A nucleoside analog structurally related to Lamivudine (L172500).<br>References Mellors, J., et al.: Science, 72, 1167 (1996), Reimann, K., et al.: J. Virol., 79, 8878 (2005), Rose, J., et al.: J. Biol. Chem., 280, 7413 (2005), Acierno, P., et al.: J. Immunol., 176, 5338 (2006),<br></p>

<p>Applications An intermediate in the preparation of Oxiracetam (O846905).<br>References Kondepudi, D., et al.: Science, 250 975 (1990), Di Silvestro, G., et al.: J. Pharm. Sci., 82, 758 (1993),<br></p>

<p>Applications Ethylene Glycol Monobenzoate, is a reagent that can be used as an intermediate in a variety of chemical and biochemical reactions. It is used as an intermediate in the preparation of 1,2-Ethanediol Disodium Salt (E890125), which is the result of the nucleophilic attack on its carbonyl group.<br>References Khouri, F. et al.: J. Am. Chem. Soc., 108, 6683 (1986);<br></p>

<p>Stability Hygroscopic<br>Applications Labelled Adenosine 5’-Monophosphate (A281790), a naturally occurring nucleotide. A useful ligand determinant that facilitate the binding of APS reductase inhibitors and activates adenosine receptor agonists.<br>References Hong, J.A. et al.: J. Med. Chem., 52, 5485 (2009); Korboukh I. et al.: J. Med. Chem., 55, 6467 (2012)<br></p>

<p>Applications Des-(3-Oxo-3,4-dihydrogen) 3,6-Difluoro Favipiravir is a building block related to Favipiravir(F103350). Favipiravir is used for the treatment of advanced Ebola virus infection in a small animal model. Favipiravir suppressed the replication of Zaire Ebola virus and prevented a lethal outcome in 100% of the animals. Based on the studies, Favipiravir can be a candidate for the treatment of Ebola hemorrhagic fever.<br>References Oestereich, L., et al.: Antiviral Res., 105, 17 (2014); Baranovich, T., et al.: J. Virol. 87, 3741 (2013); Chem. and Eng. News p.8, Dec. 1 (2014)<br></p>

<p>Impurity Capecitabine EP Impurity E<br>Applications 5'-Deoxy-5-fluoro-N-[(3-methylbutoxy)carbonyl]cytidine (Capecitabine EP Impurity E) is a 5'-Desoxycytidine derivative and is used as an antitumor agent.<br></p>

<p>Applications 5-O-Trityl-2,3’-anhydrothymidine (cas# 25442-42-6) is a compound useful in organic synthesis.<br></p>

<p>Impurity Valaciclovir EP Impurity P<br>Stability Light Sensitive, Temperature Sensitive<br>Applications Bis Valacyclovir (~90%) (Valaciclovir EP Impurity P) is an impurity is listed in Ph. Eur. monograph for Valaciclovir HCl as impurity P and Bis-valaciclovir in USP monograph (impurity K).<br></p>

<p>Impurity Ganciclovir EP Impurity C<br>Applications 2’-Monodehydroxy-2’-chloro Ganciclovir is an Impurity of Ganciclovir (G235000). 2’-Monodehydroxy-2’-chloro Ganciclovir is a sugar modified acyclic analogue of guanosine (G837900). Studies have shown 2’-Monodehydroxy-2’-chloro Ganciclovir has potential to exhibit virucidal activity. Iso mono chloro ganciclovir<br>References Martin, J.C., et al.: J. Med. Chem., 29, 1384 (1986);<br></p>

<p>Impurity Lamivudine EP Impurity J<br>Applications (2R-cis)-1-[2-(Hydroxymethyl)-1,3-oxathiolan-5-yl]-2,4(1H,3H)-pyrimidinedione (Lamivudine EP Impurity J) is an impurity of Lamivudine (L172500). (2R-cis)-1-[2-(Hydroxymethyl)-1,3-oxathiolan-5-yl]-2,4(1H,3H)-pyrimidinedione is also being further studied to determine its potential as an anti-HIV agent.<br>References Jeong, L., et al.: J. Med. Chem., 36, 181 (1993)<br></p>

<p>Impurity Capecitabine EP Impurity D<br>Applications 5'-Deoxy-5-fluoro-N-[(2-methylbutoxy)carbonyl]cytidine (Capecitabine EP Impurity D) is a Capecitabine analog which shows antitumor activity.<br></p>