Nucleosides and Nucleotides

Applications Antibacterial and antioxidant for preventing and treating cancer.
References Itoh, K., et al.: J. Immunol., 170, 3688 (2003), Liu, A., et al.: J. Biol. Chem., 279, 53196 (2004), Wullaert, A., et al.: Biochem. Pharmacol., 72, 1090 (2006),

Impurity Valaciclovir EP Impurity C
Applications 2-[(2-Amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]ethylester N-Methyl-L-Valine (Valaciclovir EP Impurity C) is a useful building block in the synthesis of various pharmaceuticals. Is used in preparation of N-Alkyl Valaciclovir compounds and intermediates thereof.
References Pu, T., et al.: Faming Zhuanli Shenqing, (2013);

Stability Hygroscopic
Applications 5-Methylcytidine is a derivative of Cytidine (C998300), found in ribonucleic acids of animals, plants and bacteria. 5-Methylcytidine is a nucleoside found in liver emulsion that can inhibit the growth of spontaneous tumors of mammary gland origin in mice. 5-Methylcytidine is one of many nucleosides that can be used as biomedical marker using liquid chromatography and ion trap mass spectrometry coupling.
References Kammerer, B., et al.: Anal. Biol. Chem., 382, 1017 (2005); Strong, L. and Matsunaga, H.: J. Surg. Oncol., 4, 528 (1972)

Applications Triethyl Methanetricarboxylate is used in the synthesis of novel inhibitors of Hsp90. It is also used in the preparation of novel dihydroquinoline-3-carboxylic acids that function as HIV-1 integrase inhibitors.
References Day, J. et al.: Chem. A Eur. J., 16, 2758 (2010); Sechi, M. et al.: Bioorg. Med. Chem., 17, 2925 (2009);

Stability Hygroscopic
Applications Isotope labelled Ammeline (A633660), which s 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.
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.

Applications Carbon 13 Labelled analogue of Adenosine (A280400), a purine nucleoside that plays an important role in various biochemical processes.
References Long, X., et al.: J. Pharmacol. Exper. Ther., 335, 781 (2010); Ham, M., et al.: J. Pharmacol. Exper. Ther., 335, 607 (2010)

Applications A new potent neuraminidase (NA) inhibitor, shows long-acting anti-influenza virus activity.
References Bantia, S., et al.: Antimicrob. Agents Chemother., 42, 801 (1998), Honda, T., et al.: Bioorg. Med. Chem. Lett., 12, 1925 (2002), Kiso, M., et al.: Lancet, 364, 759 (2004), Macdonald, S., et al.: J. Med. Chem., 48, 2964 (2005),

Applications Labelled analogue of Adenosine (A280400), a purine nucleoside that plays an important role in various biochemical processes.
References Long, X., et al.: J. Pharmacol. Exper. Ther., 335, 781 (2010); Ham, M., et al.: J. Pharmacol. Exper. Ther., 335, 607 (2010)

Impurity Abacavir - In House Impurity
Stability Hygroscopic
Applications Abacavir Carboxylate (Abacavir - In House Impurity) is a major metabolite of Abacavir (A105000) in human urine and cerebrospinal fluid (1,2,3).
References (1) Hoetelmans, R., et al.: Pharm. World Sci., 19, 159 (1997) (2) Beach, J., et al.: Clin. Ther., 20, 2 (1998) (3) McDowell, J., et al.: Antimicrob. Agents Chemother., 43, 2855 (1999)

Applications Dapagliflozin Methyl Acetate is the impurity of Dapagliflozin (D185370), which is a sodium-glucose transporter 2 inhibitor.
References Kasichayanula, S. et al.: Diabetes, Obesity and Metabolism 13, 47 (2011)

Impurity Azacitidine USP Related Compound A
Applications Inhibits the growth of Escherichia coli. Azacitidine USP Related Compound A.
References Shapir, N., et al.: J. Bacteriol., 184, 5376 (2002), Hrdlicka, P., et al.: Bioorg. Med. Chem., 13, 1249 (2005), Krecmerova, M., et al.: J. Med. Chem., 50, 1069 (2007),

Applications (2R,3R,4S,5R)-2-(4-Aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-carbonitrile is a predominant metabolite of remdesivir with great potential for Covid-19 treatment.
References Yan, V. C., et al.: ACS Med. Chem., 11, 1361 (2020)

Applications Ribavirin-13C2 is the labeled analogue 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.
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)

Stability Hygroscopic
Applications Hydrolytic impurity of D226730 and A796950 (decitabine)
References Beisler, Jj.A., et al.: J. Med. Chem., 21, 204 (1978),

Applications N6-Isopentenyladenosine has antiproliferative activity on MCF-7 breast cancer cells.
References Rajabi, M. et al.; DNA Cell Biol.; 29, 687 (2010)

Stability Hygroscopic
Applications A metabolite of the potent and selective inhibitor of HIV-1 replication, AZT.

Impurity Aciclovir EP Impurity R
Applications Acyclovir Formacetal Dimer is a dimer impurity of Acyclovir (A192400); an orally active acyclic nucleoside with inhibitory activity towards several herpes viruses. Also antiviral. (Aciclovir EP Impurity R)
References Collins, P., et al.: J. Antimicrob. Chemother., 5, 431 (1979); Matsumoto, H., et al.: Chem. Pharm. Bull., 36, 1153 (1988); Whitley, R.J., et al.: N. Engl. J. Med., 327, 782 (1992)

Applications 2prime-Deoxyadenosine is a nucleoside adenosine derivative with mutagenic properties.

Applications A deuterated prodrug of Penciclovir (P221500), which is used as an antiviral.
References Hodge, V.R.A., et al.: Antimicrob. Ag. Chemother., 33, 1765 (1989),

Applications Acyclovir (A192400) impurity. The L-Valine ester prodrug of Acyclovir.
References Beauchamp, L.M., et al.: Antiviral Chem. Chemother., 3, 157 (1992), Weller, S., et al.: Clin. Pharmacol. Ther., 54, 595 (1996), Lowance, D., et al.: N. Engl. J. Med., 340, 1462 (1999),

Applications Used as an antiviral. Prodrug of Penciclovir (P221500).
References Hodge, V.R.A., et al.: Antimicrob. Ag. Chemother., 33, 1765 (1989),

Applications Canagliflozin is a sodium/glucose cotransporter 2 (SGLT2) inhibitor. Canagliflozin has been shown to dose dependently reduce calculated renal threshold for glucose excretion and increase urinary glucose excretion. Canagliflozin is a candidate for the treatment of type 2 diabetes and obesity.
References Chao, E. et al.: Drug Fut., 36, 351 (2011); Sha, S. et al.: Diab. Obes. Metab., 13, 669 (2011); Kipnes, M.S.: Clin. Invest., 1, 145 (2011);

Stability Hygroscopic
Applications Labelled Ribavirin (R414475). Purine nucleoside analog; inhibits inosine monophosphate dehydrogenase (IMPDH). Used as an antiviral agent.This compound is suitable for pyruvate dehydrogenase (PDH) related research.
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)

Stability Hygroscopic
Applications The prosthetic group of certain flavoproteins including D-amino acid oxidase, glucose oxidase, glycine oxidase, fumaric hydrogenase, histaminase, and xanthine oxidase. Riboflavin kinase tumor necrosis factor receptor 1 NADPH oxidase.
References DeLuca, K., et al.: J. Biol. Chem., 223, 569 (1956), Yagi, K., et al.: Biochemistry, 19, 1553 (1980), Li, G., et al.: J. Phys. Chem., 112, 4573 (2008),

Applications 6,6'-Thiobis-9H-purine is used in the study of the activity of topoisomerase IIα.
References Jensen, L.H., et al.: Molecular Pharmacology, 70, 1503 (2006);

Stability Hygroscopic, Temperature Sensitive
Applications A metabolite of Adenosine (A280400), a multifunctional nucleoside triphosphate used in cells as a coenzyme of intracellular energy transfer. It transports chemical energy within cells for metabolism.
References Knowles, J., et al.: Annu. Rev. Biochem., 49, 877 (1980),

Applications A metabolite of Ribavirin.
References Allen, L.B., et al.: J. Med. Chem., 21, 742 (1978), Zimmerman, T., et al.: Biochem. Pharmacol., 27, 709 (1978), Page, T., et al.: Int. J. Biochem., 22, 379 (1990), Lin, C., et al.: Antimicrob. Agents Chemother., 47, 1395 (2003),

Applications A naturally occurring purine derivative. Pharmaceuticals, Intermediates & Fine Chemicals
References Jansen, R., et al.: Clin. Biochem., 38, 362 (2005), Vorst, O., et al.: Metabolomics, 1, 169 (2005), Want, E., et al.: ChemBioChem., 6, 1941 (2005), van der Werf, M., et al.: Anal. Biochem., 370, 17 (2007),

Stability Hygroscopic
Applications Ademethionine 1,4-Butanedisulfonate is used in the synthesis of sulfonio-adenosyl-L-methionine (SAMe) salts.

Applications (1R,​2R,​5R)​-​2-​Isopropyl-​5-​methylcyclohexanol is used in the tetrahydropyranylation of alcohols.
References Magyar, A. et al.: Catal. Lett., 145, 1876 (2015);

Applications Labelled Creatinine. The end product of creatine catabolism. Normal constituent of urine. Also found together with creatine in muscle tissues and blood. Occurs in all soils and in grain seeds and other vegetable matter. Has been found in certain fish and in crab meat extract.
References Folin, et al.: J. Biol. Chem., 17, 463 (1914),

Applications Adenosine-3'-monophosphate (cas# 84-21-9) is a useful research chemical.

Applications 4-(Hydroxymethyl)-2’-deoxycytidine is a modified pyrimidine that is capable of producing interstrand cross-links in duplex DNA. 4-(Hydroxymethyl)-2’-deoxycytidine can be analyzed to quantify DNA hydroxymethylation levels in biological samples
References Peng, X. et al.: J. Am. Chem. Soc., 130, 10299 (2008); Berkner, K. et al.: J. Biol. Chem., 252, 3185 (1977); Le, T. et al.: Anal. Biochem., 412, 203 (2011);

Impurity Entecavir EP Impurity A
Applications An epimeric impurity of the antiviral drug Entecavir (E558900).

Applications 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. It is a COVID19-related research product.
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)

Applications D-Ribose is produced by microorganism fermentation of glucose in a fermentation culture medium without adding calcium carbonate.
References Ostrowski, S., et al.: Science, 305, 71 (2004), Vavilin, D., et al.: Biochim. Biophys. Acta, 1708, 91 (2005), Fletcher, J., et al.: Anal. Chem., 79, 2199 (2007), Weissleder, R., et al.: Nature, 452, 580 (2008),

Applications A 2',3'-cyclic nucleotide phosphodiester.
References Voegtli, W., et al.: Biochemistry, 39, 15365 (2000), Bernstein, N., et al.: Mol. Cell, 17, 657 (2005), Blondal, T., et al.: J. Biol. Chem., 280, 5188 (2005), Shenoy, A., et al.: J. Mol. Biol., 365, 211 (2007),

Applications Cabotegravir O-β-D-Glucuronide is a metabolite of Cabotegravir (C050100), a long acting HIV-1 integrase inhibitor with action against a broad range of HIV subtypes.
References Yoshinaga, T. et al.: Antimicrob, Agents Chemother., 59, 397 (2015); Andrews, C. et al.: Sci. Transl. Med., 7, 270 (2015)

Applications The epimer of the degradation product of Gemcitabine (G305000), a new antitumor agent.
References Anliker, S.L., et al.: J. Pharmaceut. Sci., 83, 716 (1994),

Applications An effective agent for increasing nicotinamide adenine dinucleotide (NAD) concentrations in mammalian cells.
References Yang, T. et al.: J. Med. Chem., 50, 6458 (2007);

Stability Hygroscopic
Applications 9-Oxofolic Acid is a derivative of Folic Acid (F680300) which is a vitamin needed to synthesize DNA, conduct DNA repair and methylate DNA. Folic Acid also acts as a cofactor in biological reactions involving folate.
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),

Impurity Fluorouracil EP Impurity D
Applications 5-Methoxyuracil (Fluorouracil EP Impurity D) is methoxylated uracil, a component of nucleid acid. 5-Methoxyuracil is used in the preparation of nucleosides.
References Vorbrueggen, H. et al.: Chem. Ber., 114, 1279 (1981); Novacek, A. et al.: Coll. Czech. Chem. Comm., 32, 1045 (1967);

Applications Hypocholesterolemic isolated from shiitake mushrooms, effecting phospholipid and linoleic acid metabolisms. Specifically, Eritadenine is a potent inhibitor of S-adenosyl-L-homocysteine hydrolase (SAHH), decreasing total cholesterol levels in plasma.
References Fukada, S., et al.: J. Nut., 136, 2797 (2006), Vilar, S., et al.: J. Med. Chem., 49, 1118 (2006), Yamada, T., et al.: Biochem. Pharmacol., 73, 981 (2007), Enman, J., et al.; J. Agric. Food Chem., 56, 2609 (2008),