Nucleosides and Nucleotides

<p>Applications Adenosine 5'-Monophosphate is a natural occurring nucleotide and 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 A Cytidine (C998300) analog and also an isostere of Thymidine (T412000).<br>References Sabini, E., et al.: J. Med. Chem., 51, 4219 (2008), Sabini, E., et al.: J. Mol. Biol., 378, 607 (2008),<br></p>

<p>Impurity Zidovudine Impurity;<br>Stability Hygroscopic, Moisture Sensitive<br>Applications A metabolite of Zidovudine (3'-Azido-3'-deoxythymidine; AZT).<br>References Qian, M., et al.: Biochem. Pharmacol., 48, 383 (1994), Diwan, B., et al.: Toxicol. Appl. Pharmacol., 161, 82 (1999) , Lim, S., et al.: J. Biol. Chem., 276, 23616 (2001), Von Tungeln, L., et al.: Carcinogenesis, 23, 1427 (2002),<br></p>

<p>Applications Labelled Entecavir. An oral antiviral drug used in the treatment of hepatitis B infection. A guanine analogue that inhhibits all three steps in the viral replication process.<br>References Innaimo, S.F., et al.: Antimicrob. Agents Chemother., 41, 1444 (1997), Honkoop, P., et al.: Expert Opin. Invest. Drugs, 12, 683 (2003), Chang, T.-T., et al.: N. Engl. J. Med., 354, 1001 (2006),<br></p>

<p>Applications Lamivudine epimer.<br>References Chang, C., et al.: J. Biol. Chem., 267, 13938 (1992), Jeong, L., et al.: J. Med. Chem., 36, 181 (1993),<br></p>

<p>Impurity Sofosbuvir Metabolite GS331007<br>Applications RO 2433 is the deaminated metabolite of β-D-2'-Deoxy-2'-fluoro-2'-C-methylcytidine, an effective inhibitor of hepatitis C virus (HCV) replication in vitro.<br>References Asif, G., et. al.: Antimicrob. Agents Ch., 51, 2877 (2007)<br></p>

<p>Applications 3’,5’-Di-O-benzyl Entecavir is an intermediate in the preparation of the hepatitis B antiviral agent, Entecavir (E558900).<br>References Li, R. et al.: Zhong. Yao., 6, 292 (2008); Bisacchi, G.S. et al.: Bioorg. Med. Chem. Lett., 7, 127 (1997);<br></p>

<p>Applications Antiviral nucleoside analog, also an impurity found in emtricitabine (E525000).<br>References Jeong, L., et al.: J. Med. Chem., 36, 181 (1993),<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>Applications trans-Abacavir Dihydrochloride is an impurity of Abacavir. Abacavir (A104990) 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>Stability Hygroscopic<br>Applications Used in the characterization and elucidation of coordination requirements of adenine nucleotides complexes with Fe(II) ions.<br>References Richter, Y., et al.: Nucleos. Nucleot. Nucleic Acids, 22, 1757 (2003),<br></p>

<p>Impurity Aciclovir EP Impurity F<br>Applications N2-Acetyl Acyclovir (Aciclovir EP Impurity F) is an impurity of Acyclovir (A192400).<br>References Balon, K., et al.: Pharm. Res., 16, 882 (1999),<br></p>

<p>Applications Intermediate in the synthesis of ent-Emtricitabine (E525005).<br></p>

<p>Applications A metabolite of Famciclovir, an antiviral.<br>References Harnden, M.R., et al.: J. Med. Chem., 32, 1738 (1989)<br></p>

<p>Applications 1R-Dapagliflozin is an isomer of Dapagliflozin (D185370), which is a sodium-glucose transporter 2 inhibitor.<br>References Kasichayanula, S. et al.: Diabetes, Obesity and Metabolism 13, 47 (2011)<br></p>

<p>Impurity Didanosine EP Impurity D<br>Applications 3'-Deoxyinosine (Didanosine EP Impurity D) is an Inosine (I661000) analog with potential use as an antileishmanial drug. Used as an inhibiting agent in studies of Trypanosoma cruzi growth inside host cells in vitro. An impurity of the antiviral drug 2’,3’-Dideoxyinosine (D440950).<br>References Morishige, K. et al.: Exp. Parasitol., 80, 665 (1995); Aoki, T. et al.: Adv. Exp. Med. Biol., 370, 499 (1994);<br></p>

<p>Applications α-Decitabine is shown to inhibit DNA methylation resulting in an effective anticancer agent.<br>References Hajek, M. et al.: Biochem. Pharm., 75, 965 (2008); Rogstad, D. et al.: Chem. Res. Toxicol., 22, 1194 (2009);<br></p>

<p>Applications 2,4-Diamino-6-hydroxypyrimidine (cas# 56-06-4) is a compound useful in organic synthesis.<br></p>

<p>Stability Very Hygroscopic<br>Applications Abacavir-d4 is deuterium labeled 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 1’-epi-Cladribine is an impurity of Cladribine (C557500), a substituted purine nucleoside with antileukemic activity.<br>References Seto, S., et al.: J. Clin. Invest., 75, 377 (1985), Piro, L.D., et al.: N. Engl. J. Med., 322, 1117 (1990),<br></p>

<p>Applications Labelled Floxuridine. Antiviral; 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 Harris, M., et al.: Biophys. J., 4, 203 (1964),<br></p>

<p>Applications Isotope labelled Melamine (M208703), which forms synthetic resins with formaldehyde. It remains largely non-metabolized in male Wistar rats with 90% of the administered dose excreted in the urine (1,2) and thus acts as a non-protein nitrogen food additive found in milk (3). Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA), environmental, and food contaminants.<br>References 1. Mast, R. et al.: Food Chem Toxicol. 1983 Dec;21(6):807-10.2. Smith, J. et al.: Toxicol Appl Pharmacol. 1994 Apr;125(2):296-308.3. Anirudhan, T. et al.: Food Chem. 2017 Jul 15;227:85-92.<br></p>

<p>Applications (1S)-1,5-anhydro-1-C-[4-Chloro-3-[(4-ethoxyphenyl)hydroxymethyl]phenyl]-D-glucitol is an impurity of the drug Dapagliflozin (D185370), a sodium-glucose transporter 2 inhibitor.<br>References Kasichayanula, S. et al.: Diabetes, Obesity and Metabolism 13, 47 (2011)<br></p>

<p>Applications Influenza viral neuraminidase inhibitor; structural analog of the sialic acid. Antiviral.<br>References Woods, J.M., et al.: Antimicrob. Agents Chemother., 37, 1473 (1993), Pegg, M.S., et al.: Biochem. Mol. Biol. Int., 32, 851 (1994), Monto, A.S., et al.: J. Am. Med. Assoc., 282, 31 (1999),<br></p>

<p>Stability Hygroscopic<br>Applications Adenosine-3’,5’-cyclic Monophosphate is an Adenosine (A280400) derivative useful as anticancer agent.<br>References Keast, R., et al.: Pharma. Res., 19, 1019 (2002),<br></p>

<p>Applications Labelled Uridine, a nucleoside; widely distributed in nature. Uridine is one of the four basic components of ribonucleic acid (RNA)<br>References Lorine, P., et al.: J. Biol. Chem., 178, 439 (1949); Grakoui, A., et al.: J. Virol., 63, 5216 (1989); Strauss, J., et al.: Microbiol. Rev., 58, 491 (1994); Lin, Y., et al.: Virology, 292, 78 (2002);<br></p>

<p>Applications Etravirine is a novel 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>Stability Hygroscopic<br>Applications Baquiloprim is an amiopyrimidine antibacterial synergist with high activity and slow elimination. Baquiloprim has a better half-life than trimethoprim.<br>References Zhi-hui, H., et al.: Anhui Nongye Kexue, 41, 2503 (2013)<br></p>

<p>Applications A phosphorylated metabolite of the deoxyribonucleoside 2’-Deoxycytidine. A constituent of Deoxyribonucleic acid. Studies show that it increases influenza virus antigen-induced immune cell proliferation.<br>References Holen, E. et al.: Nutrition, 21, 1003 (2005); Alexandre, J.A. et al.: Nucleosides Nucleotides Nucelic Acids, 26, 1375 (2007);<br></p>

<p>Stability Hygroscopic<br>Applications Labelled Gemcitabine, an antineoplastic.<br>References Hertel, L.W., et al.: Cancer Res., 50, 4417 (1990), Abbruzzese, J.L., et al.: J. Clin. Oncol., 9, 491 (1991), Ruiz, V.W.T., et al.: Biochem. Pharmacol., 46, 762 (1993),<br></p>

<p>Applications A lactone (cyclic ester) of D-gluconic acid used as a used as a sequestrant, an acidifier, or a curing, pickling, or leavening agent.<br>References Jacob, M. et al.: Food Hydrocoll., 25, 928 (2011); Li, J. et al.: J. Sci. Food Agric., 91, 38, 2011;<br></p>

<p>Stability Hygroscopic<br>Applications 4-[(2-Chloroethyl)amino]-L-phenylalanine is a metabolite of Melphalan (M216900); an antineoplastic.<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 Dapagliflozin Tetraacetate is a derivative of Dapagliflozin [D226255], a sodium-glucose transporter 2 inhibitor.<br>References Kasichayanula, S. et al.: Diabetes, Obesity and Metabolism 13, 47 (2011); Bernhardson, D. et al.: Org. Proc. Res. Dev., 18, 57 (2014);<br></p>

<p>Applications ent-Entecavir is an enantiomeric impurity of the antiviral drug Entecavir (E558900).<br>References Ruediger, E. et al.: Tetrahed. Lett., 45, 739 (2004): Bisacchi, G.S. et al.: Bioorg. Med. Chem. Lett., 7, 127 (1997);<br></p>

<p>Applications A 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>Applications Viaminate is a pharmaceutical used to treat severe acne and other keratinization disorders. Viaminate can be taken orally, or topically in prepared gels and creams.<br>References Zhang, H.; et al.: Am. J. Med. Sci., 356, 84 (2018); Lu, J.; et al.: Zhongguo Yaofang, 22, 155 (2011); Li, G.: Zhonghua Yiyao Zazhi, 7, 536 (2007).<br></p>

<p>Applications Canagliflozin 2-glucuronide is a derivative of Canagliflozin (C175190). Canagliflozin is a sodium-glucose cotransporter 2 inhibitor that is used to treat patients with type 2 diabetes. Canagliflozin lowers blood glucose by increasing the amount of glucose that exits the body through urinary excretion.<br>References Devineni, D., et al.: Diab. Obes. Metab., 14, 539 (2012); Nicolle, L., et al.: Curr. Med. Res. Opin., 28, 1167 (2012)<br></p>

<p>Applications An antiviral.<br>References Weinberg, A., et al.: Antimicrob. Ag. Chemother., 36, 2037 (1992), McMeekin, J.R., et al.: Anal. Proc., 29, 178 (1992),<br></p>

<p>Applications 5-FC is a toxic antifungal/antimicrobial agent.<br>References Gopinath, P., et al.: Biotechnol. Lett., 30, 1913 (2008), Kalkanci, A., et al.: Microbiol Immunol., 52, 435 (2008), Dubeau, M., et al.: App. Env. Microbiol., 75, 1211 (2009),<br></p>

<p>Stability Hygroscopic<br>Applications Labelled nucleotide.<br>References Long, X., et al.: J. Pharmacol. Exper. Ther., 335, 781 (2010), Ham, M., et al.: J. Pharmacol. Exper. Ther., 335, 607 (2010),<br></p>

<p>Impurity Ribavirin EP Impurity D<br>Applications N-Des-1-β-D-ribofuranosyl Ribavirin (Ribavirin EP Impurity D) is an impurity in the synthesis of Ribavirin (R414475), a purine nucleoside analog; inhibits inosine monophosphate dehydrogenase (IMPDH). Used as an antiviral agent.This compound is suitable for pyruvate dehydrogenase (PDH) related research.<br>References Fernandez, H., et al.: Eur. J. Epidemiol., 2, 1 (1986), Liao, H.J. and Stollar, V.: Antiviral Res., 22, 285 (1993), Honda, Y., et al.: Antimicrob. Agents Chemother., 38, 653 (1994), Reichard, O., et al.: Lancet, 351, 83 (1998)<br></p>

<p>Stability Hygroscopic<br>Applications Decarboxylated S-Adenosylmethionine Sulfate Salt, is a substrate that is involved in the biosynthesis of polyamines including spermidine, spermine, and thermospermine.<br>References Takahashi,T., et al.: Ann. Bot., 105, 1 (2009); Wu, H., et al.: Biochem., 46, 8331 (2007); Pegg, A., et al.: Biochem., 28, 8446 (1989);<br></p>

<p>Applications Ammeline is a metabolite of Melamine (1) (M208700), which acts as a non-protein nitrogen food additive (2). Also present in pet foods as well (3).Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA). Environmental contaminants; Food contaminants.<br>References 1. Mast RW. et al.: Food Chem Toxicol. 1983 Dec;21(6):807-10.2. Ehling S. et al.: Food Addit Contam. 2007 Dec;24(12):1319-25.3. Vail T. et al.: J Anal Toxicol. 2007 Jul-Aug;31(6):304-12.<br></p>

<p>Applications A labelled metabolite of Capecitabine.<br></p>

<p>Impurity Cytarabine EP Impurity A<br>Applications Antiviral agent. Used for the treatment of severe acute respiratory syndrome (SARS).<br>References Weber, G., et al.: Cancer Res., 43, 3466 (1983), Broet, P., et al.: J. Clin. Oncol., 19, 2778 (2001), Galmarini, C., et al.: Leukemia, 15, 875 (2001), Barth, R., et al.: Cancer Res., 64, 6287 (2004), Song, M., et al.: Bioorg. Med. Chem., 12, 489 (2004),<br></p>