Nucleosides and Nucleotides

<p>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.<br>References Folin, et al.: J. Biol. Chem., 17, 463 (1914),<br></p>

<p>Applications Adenosine-3'-monophosphate (cas# 84-21-9) is a useful research chemical.<br></p>

<p>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<br>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);<br></p>

<p>Impurity Entecavir EP Impurity A<br>Applications An epimeric impurity of the antiviral drug Entecavir (E558900).<br></p>

<p>Applications 6-Hydroxy-2,4,5-triaminopyrimidine, Sulfate (cas# 35011-47-3) is a compound useful in organic synthesis.<br></p>

<p>Applications D-Ribose is produced by microorganism fermentation of glucose in a fermentation culture medium without adding calcium carbonate.<br>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),<br></p>

<p>Applications A selective A2-adenosine receptor agonist. Coronary vasodilator, antihypertensive and antipsychotic following systemic administration in vivo.<br>References Martin, et al.: Pharmacol. Biochem. Behav., 45, 951 (1993<br></p>

<p>Applications A 2',3'-cyclic nucleotide phosphodiester.<br>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),<br></p>

<p>Stability Hygroscopic<br>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 DPCPX is a potent and very selective A1-adenosine receptor antagonist, with a Ki of 0.46 nM for A1 receptors in rat whole-brain membranes. Its 740-fold A1-selectivity is the highest reported for an adenosine antagonist.<br>References Gessi, S., et al.: Mol. Pharmacol., 67, 2137 (2005), Minor, T.R., et al.: Behav. Neurosci., 122, 1236 (2008), Gracia, E., et al.: J. Neurochem., 107, 161 (2008), Gessi, S., et al.: Biochem. Pharmacol., 75, 562 (2008),<br></p>

<p>Applications Labelled AMP mixture<br>References Jackson, E.K. et al.: Hypertension, 56, 151 (2010); Jackson, E.K. et al: J. Bio. Chem., 284, 33097 (2009);<br></p>

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

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

<p>Impurity Didanosine EP Impurity E<br>Applications 2',3'-Anhydroinosine (Didanosine EP Impurity E) is an impurity of the antiviral drug 2’,3’-Dideoxyinosine (D440950).<br>References Rao, D.V.N. et al.: J. Pharmac. Biomed.Anal., 45, 516 (2007);<br></p>

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

<p>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.<br>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),<br></p>

<p>Stability Hygroscopic<br>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.<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>Impurity Valaciclovir EP Impurity I/ Aciclovir USP Related Compound A<br>Applications Acyclovir Acetate (Valaciclovir EP Impurity I) is an Acyclovir (A192400) impurity, Aciclovir EP Impurity A<br>References Goskonda, V., et al.: J. Pharm. Sci., 88, 180 (1999); Chang, J., et al.: Pharm. Res., 17, 670 (2000),<br></p>

<p>Impurity Famciclovir USP Related Compound F<br>Applications Famciclovir USP Related Compound F<br></p>

<p>Applications An impurity of Levomefolate (L375720), the natural form of folic acid.<br>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);<br></p>

<p>Stability Hygroscopic<br>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.<br>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)<br></p>

<p>Applications Gemcitabine Monophosphate is a gemcitabine derivative. It is an antineoplastic agent.<br>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)<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 Dihydroxy Melphatalan is an analogue 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 T-705 Ribofuranose is a reagent used for the preparation of pyrazine-ribofuranose derivatives as antiviral agents that are useful in the treatment of viral infections.<br>References Zhong, B., et al.: Faming Zhuanli Shenqing, 2014:924257 (2014)<br></p>

<p>Applications 6-Mercaptopurine Disulfide is an impurity of 6-Mercaptopurine (M225450, monohydrate) which is an immunosuppressive drug used to treat leukemia. It is also used for pediatric non-Hodgkin’s lymphoma, polycythemia vera, and psoriatic arthritis.<br>References Zeng, H., et al.: Biochem. Pharmacol., 68, 911 (2004)<br></p>

<p>Impurity Zidovudine USP Related Compound G<br>Stability Light Sensitive<br>Applications 3'-[3-(3-Azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-3,6-dihydro-5-methyl-2,6-dioxo-1(2H)-pyrimidinyl]-3'-deoxy-thymidine (Zidovudine USP Related Compound G) is used in the biological studies and in the preparation of N-3-substituted thymidine nucleosides as virucides as it has anti-HIV activity.<br>References Adams, D.R., et al.: J. Med. Chem., 40, 1550 (1997), Mainardes, R., et al.: J. Pharm. Sci., 98, 257 (2009),<br></p>

<p>Stability Very Hygroscopic<br>Applications A metabolite of the pesticide Glyphosphate (G765000).<br>References Siehl, D.L. et al.: J. Biol. Chem., 282, 11446 (2007); Env. Prot. Agen. EPA: Fed. Reg., 74, 67129 (2009);<br></p>

<p>Stability Hygroscopic, Temperature Sensitive<br>Applications Gemcitabine Triphosphate is a phosphorylated metabolite of Gemcitabine (G305000), an antineoplastic agent.<br>References Kennedy., E.P., et al.: J. Biol. Chem., 222, 193 (1956),<br></p>

<p>Applications Canagliflozin 3-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>Stability Hygroscopic<br>Applications Isotope labelled analogue of (-)-Inosine (I661000), compound that exhibits neuroprotective properties by improving axonal wiring and has also been used to treat stroke patients to restore neural function.<br>References Vandemeulebroucke, A., et al.: Biochem., 49, 8999 (2010), Nestor, G., et al.: J. Agric. Food Chem., 58, 10799 (2010),<br></p>

<p>Applications Isotope labelled analogue of Adenosine 5’-Monophosphate (A281790), a nucleotide that is used as a monomer in RNA.<br>References Watanabe, M., et al.: Arch. Dermatol., 127, 1689 (1991); Engelke, M., et al.: Br. J. Dermatol., 137, 219 (1997)<br></p>

<p>Stability Hygroscopic<br>Applications Cytidine 2':3'-cyclic Monophosphate Monosodium Salt is a key compound in the enzymic synthesis of short oligoribonucleotides. Reagent in the amine catalyzed solid-phase synthesis of oligonucleotides.<br>References Gusenkova, N. M., et al.: Zhurnal Obshchei Khimii, 46, 939 (1976); Tomasz, J., et al.: Nucleic Acid Chem., 2, 875 (1978)<br></p>

<p>Applications (+)-Isomenthol is a reagent that has been used in the preparation of a phosphine activator.<br>References Rajendran., K.V., et. al.: Tetrahedron Lett., 54, 7009 (2013)<br></p>

<p>Applications Acetoguanide is a degradation product of the sulfonylurea herbicide Iodosulfuron.<br>References Pramauro, E., et al.: Environ. Sci. Technol., 27, 1790 (1993); Rouchard, J., et al.: Toxicol. Environ. Chem., 85, 103 (2003); Brigante, M., et al.: J. Agric. Food Chem., 53, 5347 (2005);<br></p>

<p>Impurity Acicclovir EP Impurity L<br>Applications N2,9-Diacetylguanine (Acicclovir EP Impurity L) is used to synthesize acyclic analogues of deoxyguanosine.<br>References Martin, J. C., et al.: J Med Chem. 26, 759 (1983)<br></p>

<p>Impurity 6-Chloro Famciclovir Impurity<br>Applications 9-[4-Acetoxy-3-(acetoxymethyl)butyl]-2-amino-6-chloropurine is an impurity of Famciclovir (F101125), an antiviral agent and a prodrug of Penciclovir (P221500).<br>References Raman, N., et al.: J. Pharma. Biomed. Anal., 50, 797 (2009); Hodge, V.R.A., et al.: Antimicrob. Ag. Chemother., 33, 1765 (1989),<br></p>

<p>Applications A Lamivudine (L172500) intermediate.<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 Chang, C., et al.: J. Biol. Chem., 267, 13938 (1992), Jeong, L., et al.: J. Med. Chem., 36, 181 (1993).<br></p>

<p>Impurity Lamivudine EP Impurity A<br>Stability Hygroscopic<br>Applications Lamivudine Acid (Lamivudine EP Impurity A) is an impurity of Lamivudine (L172500). Impurity A per European Pharmacopoeia.<br>References Dwyer, O., et al.: Synlett, 11, 1163 (1995),<br></p>

<p>Impurity Abacavir API<br>Applications Abacavir (Abacavir API) 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 Acyclovir (A192400) is the parent compound for 8-Hydroxyacyclovir. Acyclovir (ACV), an anti-virus drug, was widely detected in natural water at concns. . ranging from ng L-1 to μg L-1 due to inefficient biol. treatments in sewage treatment plant.<br>References Zhang, Q., et al.: Journal of Radioanalytical and Nuclear Chemistry, 320, 823 (2019);<br></p>

<p>Applications A tryptamine derivative, a neurotransmitter agonist.<br>References Dalton, T., et al.: Br. J. Pharmacol., 65, 579 (1979), Kang, S., et al.: Mol. Pharmacol., 16, 1031 (1979), Wallis, D., et al.: Eur. J. Pharmacol., 70, 381 (1981),<br></p>

<p>Stability Hygroscopic<br>Applications A metabolite of (-)-Emtricitabine (E525000).<br>References Paff, M. et al.; Antimicrob. Agents Ch. 38, 1230 (1994)<br></p>

<p>Applications A receptor adenine derivative binding membrane brain animal cell line.<br>References Camaioni, E., et al.: Bioorg. Med. Chem., 6, 523 (1998), Kelly, M., et al.: Br. J. Pharmacol., 125, 979 (1998), Redzic, Z., et al.: Brain Res., 888, 66 (2001), Levy, D., et al.: J. Med. Chem., 46, 2177 (2003),<br></p>

<p>Stability Light Sensitive<br>Applications 3,4,5,6-Tetrahydrouridine, is a derivative of Uridine (U829910). Tetrahydrouridine (THU), is a potent inhibitor of cytidine. It inhibits cell proliferation through cell cycle regulation regardless of cytidine deaminase expression levels deaminase (CDA), and thus can be used as a potential and promising treatment for tumors with highly expressed CDA.<br>References Lorine, P., et al.: J. Biol. Chem., 178, 439 (1949); Funamizu, N., PLoS One, 37424 (2012);<br></p>

<p>Impurity Abacavir EP Impurity F<br>Applications N6-Cyclopropyl-9-[(1R,4S)-4-[(1,1-dimethylethoxy)methyl]-2-cyclopenten-1-yl]-9H-purine-2,6-diamine (Abacavir EP Impurity F) is an impurity of Abacavir (A104990), a guanosine analog that inhibits reverse transcriptase (NRTI) (1,2).<br>References (1) Hanumegowda, U., et al.: Chem. Res. Toxicol., 23, 749 (2010) (2) Prasse, C., et al.: Environ. Sci. Technol., 44, 1728 (2010)<br></p>

<p>Stability Hygroscopic<br>Applications Labelled Adenosine-3’,5’-cyclic Monophosphate (A280455). 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>Stability Very Very Hygroscopic<br>Applications Nicotinamide (N407750) analog. Nicotinamide riboside (β-NAR) is an intermediate in one biosynthetic pathway by which Nicotamide is converted into NAD (Nicotinamide Adenine Dinucleotide)<br>References Friedlos, F., et al.: J. Biochem. Pharmacol., 44, 25 (1992), Ong, S., et al.: Biochemistry, 11210 (1992), Zhang, X., et al.: J. Biol. Chem., 278, 13503 (2003),<br></p>

<p>Applications Pterine-6-carboxylic Acid is a degradation product of Folic acid (F680300).<br>References Akhtar, M., et al.: J. Pharm. Biomed. Anal., 19, 269 (1999), Andrisano, V., et al.: J. Pharm. Biomed. Anal., 32, 983 (2003), Patro, B., et al.: Bioorg. Med. Chem. Lett., 15, 67 (2005),<br></p>

<p>Stability Hygroscopic<br>Applications Adenosine 5'-diphosphate monosodium salt (cas# 20398-34-9) is a useful research chemical.<br></p>

<p>Stability Hygroscopic<br>Applications A deoxyribonucleoside as Eg5 kinesin modulator with antiproliferative and apoptosis-inducing activity.<br>References Hecht, S., et al.: Chem. Res. Toxicol., 17, 588 (2004); Choi, J., et al.: J. Biol. Chem., 281, 38244 (2006); Lao, Y., et al.: Chem. Res. Toxicol., 20, 246 (2007);<br></p>

<p>Applications (1R,3R,4R)-Entecavir is an isomeric impurity of Entecavir (E558900).<br></p>

<p>Applications A labelled 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>Applications 5′-Deoxy-5′-(methylthio)adenosine (Methylthioadenosine) may be used as 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. Methylthioadenosine is used in studies on bacterial quorum sensing pathways that envolve enzymes such as 5′-Methylthioadenosine/S-adenosylhomocysteine nucleosidase (MTAN).<br>References Pegg, A., et al.: Biochem. J., 115, 241 (1969), 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 Cytarabine is used as an antineoplastic and antiviral. It is a selective inhibitor of DNA synthesis. Does not inhibit RNA synthesis.Cytarabine, or cytosine arabinoside, is a chemotherapy agent used mainly in the treatment of cancers of white blood cells such as acute myeloid leukemia (AML) and non-Hodgkin lymphoma. It is also known as Ara-C (Arabinofuranosyl Cytidine). It destroys cancer cells by interfering with DNA synthesis.<br>References Donehower, R.C., et al.: Cancer Treat. Rep., 70, 1059 (1986);<br></p>

<p>Stability Hygroscopic<br>Applications A labelled 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>Impurity Lamivudine EP Impurity H<br>Stability Hygroscopic<br>Applications Lamivudine (R)-Sulfoxide (Lamivudine EP Impurity H) is a metabolite of Lamivudine (L172500); a potent nucleoside reverse transcriptase inhibitor and antiviral agent. Lamivudine has been used for treatment of chronic hepatitis B.<br>References Morris, D.M., J. Pharm. Biomed. Anal., 12, 255 (1944); Nevens, B.F., et al.: Gastroenterology, 113, 1258 (1997); Perry, C.M., et al.: Drugs, 53, 657 (1977)<br></p>

<p>Applications 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>Applications 2-Amino-7-(chloromethyl)pteridin-4(1H)-one is the impurity F of Folic acid (F680300) as per EP monograph.<br></p>

<p>Stability Hygroscopic<br>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 9-Carboxymethoxymethylguanine is a metabolite of Acyclovir (A192400) which is an antiviral, orally active acyclic nucleoside with inhibitory activity towards several herpes viruses.<br>References Gunness, P., et al.: Transl. Res., 158, 290 (2011); 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),<br></p>

<p>Applications 2-Hydroxytetrahydrofuran (cas# 5371-52-8) is a compound useful in organic synthesis.<br></p>

<p>Applications Cabotegravir is a long acting HIV-1 integrase inhibitor with action against a broad range of HIV subtypes.<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 Yoshinaga, T. et al.: Antimicrob, Agents Chemother., 59, 397 (2015); Andrews, C. et al.: Sci. Transl. Med., 7, 270 (2015);<br></p>

<p>Impurity USP Capecitabine Related Compound B / Capecitabine EP Impurity B<br>Applications A prodrug of 5-Flurouridine. A fluorinated pyrimidine nucleoside with cytostatic activity.<br>References De Cesare, M., et al.: Cancer Res., 49, 5969 (1994), Di Bartolomeo, M., et al.: Tumori, 81, 147 (1995)<br></p>

<p>Stability Hygroscopic<br>Applications A nucleotide of nicotinic acid which is produced from quinolinic acid by quinolinate phosphoribosyltransferase via transfer of a phosphoribose group. It is an intermediate of nicotinic acid adenine dinucleotide (NaAD) which is then converted to NAD via amidation and in turn converted to NADPH.<br>References Petrelli, R. et al.: Curr. Med. Chem., 18, 1973 (2011); Shibata, K. et al.: J. Chrom. B Biomed. Sci. Appl., 749, 281 (2000); Evans, C. et al.: BMC Chem. Biol., 10, 2 (2010);<br></p>

<p>Applications 2-Hydroxy-2,3-tetrahydrofuranyl Entecavir is an impurity of Entecavir (E558900).<br></p>

<p>Applications 6-Methylpterin is a derivative of Folic Acid (F680300) which is a precursor of coenzymes involved in metabolism of various nucleotides and nucleic acids.<br>References Dantola, M.L. et al.: Photochem Photobiol Sci., 9, 1604 (2010);<br></p>

<p>Impurity Zidovudine EP Impurity B<br>Applications 3'-Chloro-3'-deoxythymidine (Zidovudine EP Impurity B) is an impurity of 3'-Azido-3'-deoxythymidine (A825000), a potent and selective inhibitor of HIV-1 replication and a potential antiviral agent.<br>References Navaneethan, G., et al.: J. Food. Drug Anal., 20, 446 (2012); Srivastav, N.C., et al.: Bioorg. Med. Chem., 18, 7542 (2010); Shakya, N., et al.: J. Med. Chem., 53, 4130 (2010); Fukushima, M., et al.: BIochem. Pharmacol., 59, 1227 (2000);<br></p>

<p>Applications Used in the synthesis of labelled 5'-modified 2'-deoxyadenosine analogues as anti-hepatitis C virus agents.<br>References Gordon, C., et al.: J. Med. Chem., 48, 1 (2005), Ikejiri, M., et al.: Bioorg. Med. Chem., 15, 6882 (2007),<br></p>

<p>Impurity Abacavir - In House Impurity<br>Applications Abacavir Sulfate (Abacavir - In House Impurity) 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 6,7-Dimethylpterin, a derivative of Folic Acid (F680300) is used as a biomarker for a non-invasive cancer diagnosis. Also can function as chromophores in light sensitive proteins allowing for analysis of target cells.<br>References Kritskii, M.S. et al.: Dokl. Akad. Nauk., 380, 408 (2001); Gamagedara, S. et al.: Clin. Chim. Acta., 412, 128 (2011);<br></p>

<p>Applications Intermediate in the preparation of Citicoline (C508050), a naturally occurring nucleotide.<br></p>

<p>Applications 2,6-Diaminopurine-2’-deoxyriboside is a nucleoside analogs synthesized to interfere with DNA metabolism. A derivative of 2,6-Diaminopurine (D416580), which can be used as analyte for biological and analytical studies of incorporation of unnatural nucleotides into mutant tRNA and proteins.<br>References Kaminski, P. A., et al.: J. Biol. Chem., 288, 6534-6541 (2013); Ptacin, J., et al.: PCT Int. Appl., WO 2016115168 A1 20160721 (2016);<br></p>

<p>Applications Azathioprine-d3, is the labeled analogue of 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>Canagliflozin hemihydrate (TA 7284) treats type 2 diabetes by blocking SGLT2, leading to glucose excretion in urine.</p>

<p>Applications Gemcitabine Diphosphate is a phosphorylated metabolite of Gemcitabine (G305000), an antineoplastic agent.<br>References Baker, C., et al.: J. Med. Chem., 34, 1879 (1991), Huang, P., et al.: Cancer Res., 51, 6110 (1991), Plunkett, W., et al.: Nucleosides Nucleotides, 16, 1261 (1997),<br></p>

<p>Applications 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 L-Alanine 2-Ethylbutyl Ester Hydrochloride is used in the synthesis of phosphoramidate prodrug of a pyrrolo[2,1-f][triazin-4-amino] adenine C-nucleoside (GS-5734) for the treatment of ebola and emerging viruses.<br>References Siegel, D., et al.: J. Med. Chem., 60, 1648-1661 (2017)<br></p>

<p>Stability Unstable in Solution<br>Applications Methyl p-toluate is an impurity of 3-Toluoyl Decitabine (T536260), which is an intermediate of decitabine (A796950 for β-Decitabine). It is used as cancer treatment, in particular to inhibit the growth of pancreatic endocrine tumor cell lines.<br>References Deng, T., et al.: Life Sci., 84, 311 (2009), Horne, H., et al.: Mol. Cancer Res., 7, 199 (2009), Zinner, R., et al.: Mol. Cancer Ther., 8, 521 (2009),<br></p>

<p>Applications N-Nitroso-N-(phosphonomethyl)glycine is used as herbicide.<br>References Khan, S.U., et al.: J. Agr. Food Chem., 27, 1398 (1979), Ambrus, A., et al.: Pure Appl. Chem., 75, 937 (2003),<br></p>