Nucleosides and Nucleotides

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.
References Philips, et al.: J. Pharmacol. Exp. Ther., 20, 104 (1952), Lambertucci, C., et al.: Bioorg. Med. Chem., 17, 2812 (2009),

Applications A metabolite of 5-Fluorouracil. (F596000)
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)

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.
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)

Impurity Fluorouracil EP Impurity B; Fluorouracil USP Related Compound B
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
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);

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

Applications Constituent of deoxyribonucleic acid.
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),

Stability Air Sensitive
Applications A labelled Folic acid (F680300) derivative (or folate) found in daily dietary intake that is often used in cancer risk correlation studies.
References Keszei, A.P. et al.: Cancer Epidimiol. Biomarker Prev., 18, 1785 (2009); Koning, E.J. et al.: Cancer, 95, 1421 (2002);

Applications Influenza viral neuraminidase inhibitor; structural analog of the sialic acid. Antiviral.
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),

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.
References Kasichayanula, S. et al.: Diabetes, Obesity and Metabolism 13, 47 (2011)

Impurity Famciclovir USP Related Compound F
Applications Famciclovir USP Related Compound F

Stability Hygroscopic
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.
References (1) Jackson, A., et al.: Antivir Ther. 17, 19 (2012) (2) Yuen, G. J., et al.: Clin Pharmacokinet. 47, 351 (2008)

Applications An impurity of Levomefolate (L375720), the natural form of folic acid.
References Verlinde, P.H.C.., et al.: J. Agr. Food. Chem., 57, 6803 (2009); Whiteley, J.M., et al.: Biochem. Biophy. Res. Comm., 101, 1259 (1981);

Applications Capecitabine is an antineoplastic agent. Capecitabine is a prodrug of Doxifluridine (D556750).
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),

Impurity Aciclovir EP Impurity M
Applications An impurity of Acyclovir. Aciclovir EP Impurity M
References Laskin, O., et al.: Clin. Pharmacok., 8, 187 (1983), Grass, G., et al.: Pharm. Res., 5, 372 (1988), Mahony, W., et al.: J. Biol. Chem., 263, 9285 (1988), Merino, V., et al.: J. Pharm. Sci., 84, 777 (1995),

Applications Cidofovir Diphosphate Trisodium Salt has antiviral activity, which is used against herpes viruses. Cidofovir Diphosphate is a metabolite in human cells.
References Hitchcock, M. J. M., et al.: Antivir. Chem. Chemoth., 7, 115-127 (1996); Cihlar, T., et al.: Collect. Czech. Chem. C., 57, 661-72 (1992)

Stability Hygroscopic
Applications Dapagliflozin-D5 is a labelled analogue of Dapagliflozin (D185370), a selective sodium-glucose cotransporter-2 inhibitor that reduces renal glucose reabsorption and is used to treat patients with type 2 diabetes.
References List, J., et al.: Diabetes Care, 32, 650 (2009); Meng, W., et al.: J. Med. Chem., 51, 1145 (2008); Wilding, J., et al.: Diabetes Care, 32, 1656 (2009)

Applications Gemcitabine Monophosphate is a gemcitabine derivative. It is an antineoplastic agent.
References Balzarini, J., et al.: Biochem. Pharmacol., 37, 897 (1988), Abbruzzese, J., et al.: Investig. New Drugs, 7, 195 (1989), Balzarini, J., et al.: J. Biol. Chem., 264, 6127 (1989), Chu, C., et al.: Antimicrob. Agents Chemother., 39, 979 (1995)