Nucleosides and Nucleotides

Stability Light Sensitive
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.
References Lorine, P., et al.: J. Biol. Chem., 178, 439 (1949); Funamizu, N., PLoS One, 37424 (2012);

Stability Hygroscopic
Applications Adenine Hemisulfate can be one of the factors that influence in vitro growth and shoot multiplication of pomegranate. It can be used in biological study along with varied levels of sucrose, light intensity, and MS medium hydrogen ion concentration where those factors can all significantly influence multiplication and growth of Punica granatum shoots.
References Singh, P., & Patel, R., M.: Bioscan, 9, 1031-1035 (2014)

Applications A tryptamine derivative, a neurotransmitter agonist.
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),

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

Stability Unstable in Solution
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.
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),

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

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);

Stability Hygroscopic
Applications A sodium-glucose transporter 2 inhibitor.
References Kasichayanula, S. et al.: Diabetes, Obesity and Metabolism 13, 47 (2011)

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

Stability Hygroscopic
Applications A metabolite of 6-Mercaptopurine.
References Parker, W., et al.: Cancer Res., 51, 2386 (1991) , Munagala, N., et al.: J. Biol. Chem., 275, 37072 (2000), Guddat, L., et al.: Protein Sci., 11, 1626 (2002), Pinkel, D., et al.: J. Clin. Oncol., 11, 1826 (1993), Tripathy, D., et al.: Oncologist, 12, 375 (2007),

Applications A new antiviral agent for influenza treatment; it can be used as neuraminidase inhibitor for treating human and avian influenza.
References Whitley, R., et al.: Pediatr. Infect. Dis. J., 20, 127 (2001), Bright, R., et al.: Lancet., 366, 1175 (2005), Deyde, V., et al.: J. Infect. Dis., 196, 249 (2007), Lee, N., et al.: Clin. Infect. Dis., 46, 1323 (2008),

Applications A labelled metabolite of Capecitabine.

Applications A novel labelled HIV reverse transcriptase inhibitor useful in treatment of HIV infection.
References Scholler-Gyure, M., et al.: J. Clin. Pharmacol., 48, 322 (2008), Thakur, A., et al.: Eur. J. Med. Chem., 43, 471 (2008),

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 Dihydroxy Melphatalan is an analogue of Melphalan (M216900), an antineoplastic.
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);

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

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.
References Zhang, Q., et al.: Journal of Radioanalytical and Nuclear Chemistry, 320, 823 (2019);

Applications A receptor adenine derivative binding membrane brain animal cell line.
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),

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

Applications A vitamin needed to synthesize DNA, conduct DNA repair and methylate DNA, it 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),

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)

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

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),

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 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 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 A vitamin needed to synthesize DNA, conduct DNA repair and methylate DNA, it 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),

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);

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

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 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),

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

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),

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);

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

Stability Hygroscopic
Applications A cofactor in enzymatic acetyl transfer reactions. It is the source of the phosphopantetheine group that is added as a prosthetic group to proteins such as acyl carrier protein and formyltetrahydrofolate dehydrogenase.
References Strickland K.C. et al.: J. Biol. Chem., 285, 1627 (2010); Elovson J. et al.: J. Biol. Chem., 243, 3603 (1968);

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

Impurity Fluorouracil EP Impurity A
Applications Barbituric Acid (Fluorouracil EP Impurity A) is a parent compound of barbiturate drugs. Unsubstituted barbituric acid has no hypnotic properties.
References Luo, Y., et al.: J. Med. Chem., 53, 3846 (2010), Tomasic, T., et al.: Eur. J. Med. Chem., 45, 1667 (2010), Gilbert, A., et al.: Bioorg. Med. Chem. Lett., 20, 636 (2010),