Nucleosides and Nucleotides

<p>Impurity Ganciclovir EP Impurity I<br>Applications O,O'-Dipropanal Ganciclovir (Ganciclovir EP Impurity I) is derived from Ganciclovir (G235000), which is a nucleoside analog structurally related to Acyclovir (A192400). Ganciclovir is an antiviral.<br>References Halloran, P.J. and Fenton, R.G.: Cancer Res., 58, 3855 (1998), Rubsam, L.Z., et al.: Cancer Res., 59, 669 (1999), Yamasaki, H., et al.: C.R. Acad. Sci. III, 322, 151 (1999)<br></p>

<p>Applications N-​[2-​(Methylthio)​ethyl]​-​2-​[(3,​3,​3-​trifluoropropyl)​thio]​-adenosine is used for developing platelet P2T receptor antagonists, which have potential applications for antithrombotic therapy.<br>References Ingall, A. H., et al.: J. Med. Chem. 42, 213 (1999)<br></p>

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

<p>Applications UDP-3-O[R-3-Hydroxymyristoyl]-N-acetylglucosamine Tris Salt is a lipid A precursor for Escherichia coli.<br>References Anderson, M. S. et al.: Biochem., 27, 1908 (1988);<br></p>

<p>Applications N-[(S)-(4-Nitrophenoxy)phenoxyphosphinyl]-2-ethylbutyl Ester L-Alanine is used for the treatment of ebola and emerging viruses.<br>References Siegel, D., et al.: J. Med. Chem., 60, 1648-1661 (2017)<br></p>

<p>Applications Adenosine is a 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>Stability Hygroscopic<br>Applications 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 Cladribine 5’-Monophosphate Ammonium Salt can be used as an antiviral, antibacterial and antileukemic agent.<br>References Cook, P., et al.: U.S., US 4719295 A 19880112 (1988);<br></p>

<p>Impurity Zidovudine EP Impurity C<br>Applications Thymine (Zidovudine EP Impurity C) is a nitrogenous base component in the nucleic acid of DNA.<br>References Keum, Y., et al.: App. Microbiol. Biotechnol., 80, 863 (2008); Redzic, Z., et al.: Neurochem. Res., 34, 566 (2009); Lanevskij, K., et al.: J. Pharm. Sci., 98, 122 (2009); Rajendar, B., et al.: Bioorg. Med. Chem., 17, 351 (2009);<br></p>

<p>Stability Hygroscopic<br>Applications A synthetic precursor of Zanamivir.<br>References Gonzalez-Diaz, H., et al.: Bioorg. Med. Chem. Lett., 15, 1651 (2005), Bergmann, R., et al.: J. Med. Chem., 50, 2708 (2007), Lue, W., et al.: Eur. J. Med. Chem., 43, 569 (2008),<br></p>

<p>Stability Hygroscopic<br>Applications Metabolite of 6-Mercaptopurine, an immunosuppressive drug used to treat leukemia.<br>References Chou, C., et al.: Biochem. Pharmacol., 75, 1601 (2008), Conejo-Garcia, A., et al.: Eur. J. Med. Chem., 43, 1742 (2008), Hawwa, A., et al.: Brit. J. Clin. Pharmacol., 66, 826 (2008), Askanase, A., et al.: J. Rheumatol., 36, 89 (2009),<br></p>

<p>Stability Hygroscopic, Unstable in Solution<br>Applications A derivative of Cytarabine, a potent cytotoxic-antiviral nucleoside.<br>References Kufe, D., et al.: J. Biol. Chem., 255, 8997 (1980), Ross, D., et al.: Cancer Res., 50, 2658 (1990), Bhalla, K., et al.: Blood, 80, 2883 (1992), Tonetti, D., et al.: J. Biol. Chem., 269, 23230 (1994),<br></p>

<p>Applications 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene is used as a reagent in the synthesis of Dapagliflozin (D185370); a potent, selective renal sodium-dependent glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.<br>References Meng, W., et al.: J. Med. Chem., 51, 1145 (2008);<br></p>

<p>Impurity Methotrexate EP Impurity D N-Desmethyl Impurity<br>Applications Pteroic Acid (Methotrexate EP Impurity D N-Desmethyl Impurity) is a constituent as well as a degradation product of Folic Acid (F680300) formed via enzymatic hydrolysis. has been shown to activate the glutamylation of methotrexate by folylpolyglutamate synthetase.<br>References Vickers, P.J. et al.: Can. J. Biochem. Cell Biol., 63, 777 (1985): Tafolla, W.H. et al.: J. Pharmac. Sci., 70, 1273 (1981); Iwai, K. et al.: J. Butrit. Sci. Vitaminol., 23, 95 (1977);<br></p>

<p>Applications 5-Amino-1-methyl-4-nitroimidazole is a moiety of Azathioprine (A803350); an immunosuppressive antimetabolite that is also active as a 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>Applications Gemcitabine is used for breast cancer treatment. First-line treatment for locally advanced pancreatic cancer.<br>References Hamsici, S., et al.: Bioconjugate Chem., (2017); Peng, T., et al.: J. Cell. Biochem., (2017)<br></p>

<p>Applications 2-Deoxy-D-ribose induces apoptosis by inhibiting the synthesis and increasing the efflux of glutathione.<br>References Fico, A., et al.: Free Radical Biology &amp; Medicine, 45, 211 (2008),<br></p>

<p>Applications Melphalan 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 5’-O-Acetyl Ribavirin is an impurity of Ribavirin (R414475). Ribavirin impurity F.<br>References Zakharieva., et al.: Bioorganic. Medicinal. Chem., 1994, 4, 2831 (1994), Reichard., et al.: The Lancet, 351, 83 (1998),<br></p>

<p>Applications A useful intermediate for chemical modifications of base and sugar moieties in natural nucleosides.<br>References Sashaki, T., et al.: J. Org. Chem., 40(1), 106 (1975)<br></p>

<p>Stability Hygroscopic<br>Applications A metabolite of Lamivudine (L172500).<br>References Burgess, K., et al.: Chem. Rev., 100, 2047 (2000), Gallois-Montbrun, S., et al.: Biochem. Pharmacol., 68, 1749 (2004),<br></p>

<p>Impurity Aciclovir EP Impurity B<br>Applications Guanine is one of the five nucleobases incorporated into biological nucleic acids. Guanine, along with adenine and cytosine, is present in both DNA and RNA, whereas thymine is usually seen only in DNA, and uracil only in RNA. Aciclovir EP Impurity B.<br>References Geslain, R., et al.: J. Biol. Chem., 284, 27760 (2009); Manini, P., et al.: Toxicol. Lett., 190, 41 (2009); Gong, B., et al.: Biochem., 48, 11961 (2009); Sugimoto, M., et al.: J. Agric. Food Chem., 58, 374 (2010);<br></p>

<p>Stability Moisture Sensitive<br>Applications Cytidine 5'-diphosphocholine (cas# 987-78-0) is a useful research chemical.<br></p>

<p>Stability Very Hygroscopic<br>Applications Labelled Emtricitabine. 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 Schinazi, R.F., et al.: Antimicrob. Ag. Chemother., 36, 2423 (1992), Shockeor, J.P., et al.: Xenobioica, 26, 189 (1996), Feng, J.Y., et al.: FASEB J., 13, 1511 (1999), Molina, J.-M., et al.: J. Infec. Dis., 182, 599 (2000)<br></p>

<p>Applications 2-Amino-6-(chloromethyl)-4(3H)-pteridinone is a reagent/intermediate used in the preparation of Folic Acid (F680300) and its derivatives.<br>References Qi, Y., et al.: Faming Zhuanli Shenqing. CN 103755706 A 20140430. Apr 30, 2014;<br></p>

<p>Applications 6-Benzylaminopurine 9-(β-D-glucoside) (cas# 4294-17-1) is a compound useful in organic synthesis.<br></p>

<p>Stability Moisture Sensitive<br>Applications Eye irritant.<br>References Bagley, D. M. et al.; Toxicol. In Vitro 13, 505 (1999); Gilleron, L. et al.; Toxicol. In Vitro 11, 641 (1997)<br></p>

<p>Applications Widespread throughout animal and plant tissues combined with niacinamide, d-ribose, and phosphoric acids; a constituent of nucleic acids and coenzymes, such as codehydrase I and II, adenylic acid, coalaninedehydrase. It is used in microbial determination of niacin; in research on heredity, virus diseases, and cancer.<br>References Philips, et al.: J. Pharmacol. Exp. Ther., 20, 104 (1952), Lambertucci, C., et al.: Bioorg. Med. Chem., 17, 2812 (2009),<br></p>

<p>Applications A metabolite of 5-Fluorouracil. (F596000)<br>References Bocci, G., et al.: Eur. J. Clin. Pharmacol., 58, 593 (2002), Longley, D.B., Nature Rev. Cancer, 3, 330 (2003), Fischel, J., et al.: Anti-Cancer Drugs, 15, 969 (2004)<br></p>

<p>Applications A natural, active form of folic acid used at the cellular level for DNA reproduction, the cysteine cycle and the regulation of homocysteine among other functions. It is a coenzymated form of folic acid. It has been proposed for treatment of cardiovascular disease.<br>References Willems, F. et al.: Br. J. Pharmacol., 145, 823 (2004); Prinz-Langhebohi, R.: et al., Br. J. Pharmacol., 158, 2014 (2009); Wright, A. et al.: Brit, J. Nutrit., 103, 724 (2010)<br></p>

<p>Stability Hygroscopic<br>Applications Labelled Cytarabine, a compound used as an antineoplastic and antiviral. A selective inhibitor of DNA synthesis. Does not inhibit RNA synthesis.<br>References Donehower, R.C., et al.: Cancer Treat. Rep., 70, 1059 (1986)<br></p>

<p>Applications Constituent of deoxyribonucleic acid.<br>References Levene, L., et al.: J. Bil. Chem. 83, 793 (1929), Tollin, et al.: Nature 217, 1148 (1968), Redzic, Z., et al.: Neurochem. Res., 34, 566 (2009), Hazra, S., et al.: Biochem., 48, 1256 (2009), Yang, I., et al.: J. Biol. Chem., 284, 191 (2009),<br></p>

<p>Stability Air Sensitive<br>Applications A labelled Folic acid (F680300) derivative (or folate) found in daily dietary intake that is often used in cancer risk correlation studies.<br>References Keszei, A.P. et al.: Cancer Epidimiol. Biomarker Prev., 18, 1785 (2009); Koning, E.J. et al.: Cancer, 95, 1421 (2002);<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>Applications (2S,3R,4R,5S,6R)-2-(4-Chloro-3-(2-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol is an impurity of Dapagliflozin (D185370), a sodium-glucose transporter 2 inhibitor.<br>References Kasichayanula, S. et al.: Diabetes, Obesity and Metabolism 13, 47 (2011)<br></p>

<p>Stability Hygroscopic<br>Applications Abacavir 5’-β-D-Glucuronide is a metabolite 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>Stability Light Sensitive - Protect from Light Exposure<br>Applications Fenretinide (4-HPR) is a synthetic retinoid deriverative. 4-HBR is shown to exhibit binding to the retinoic acid receptors (RAR) at concentrations necessary to induce cell death.A synthetic analog of Vitamin A.<br>References Marth, C., et al.:J. Nat. Cancer Inst., 75, 871 (1985), Delia, D., et al.: Cancer Res., 53, 6036 (1993), Costa., A., et al.: Cancer Res., 54, Suppl., 2032s (1994), Decensi., A., et al.: Eur. J. Cancer Prev., 3, 377 (1994)<br></p>

<p>Stability Moisture Sensitive<br>Applications 1-(5-O-Acetyl-β-D-ribofuranosyl)-4-amino-1,3,5-triazin-2(1H)-one is an impurity of 5-Azacytidine (A796000), a potent growth inhibitor and cytotoxic agent. It acts as a demethylating agent by inhibiting DNA methyltransferase.<br>References Kusaba, H., et al.: Eur. J. Biochem., 262, 924 (1999), Broday, L., et al.: Mol. Cell Biol., 19, 3198 (1999), Qian, X., et al.: Am. J. Pathol., 153, 1475 (1999), Canova, C., et al.: Mech. Ageing Dev., 101, 153 (1998)<br></p>

<p>Applications Capecitabine is an antineoplastic agent. Capecitabine is a prodrug of Doxifluridine (D556750).<br>References Muss, H., et al.: New Eng. J. Med., 360, 2055 (2009), Takahashi, S., et al.: Drug Metab. Disposition, 37, 956 (2009), Saltz, L., et al.: J. Clin. Oncol., 27, 653 (2009), Sanderson, H., et al.: Toxicol. Lett., 187, 84 (2009),<br></p>