Nucleosides and Nucleotides

Applications A constituent of nucleic acids. It was isolated from yeast nucleic acid.
References Parrou, J., et al.: Anal. Biochem., 248, 186 (1997), Phipps, A., et al.: Xenobiotica, 28, 527 (1998), Mohler, R., et al.: Anal. Chem., 78, 2700 (2006),

Stability We have observed that this material decomposes steadily over time. Use immediate
Applications L-Tetrahydrofolic Acid is a folic acid derivative and coenzyme involved in the metabolism of amino and nucleic acids. We have observed that this material decomposes steadily over time. Use immediately upon receipt.
References Prinz-Langenohl, R., et al.: Brit. J. Pharmacol., 158, 2014 (2009), Martin, H., et al.: Anal. Biochem., 402, 137 (2010), Dasarathy, J., et al.: Am. J. Clin. Nut., 91, 357 (2010), Karas-Kuzelicki, N., et al.: Clin. Biochem., 43, 37 (2010),

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

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.
References Dantola, M.L. et al.: Photochem Photobiol Sci., 9, 1604 (2010);

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

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).
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),

Applications A Lamivudine (L172500) intermediate.
Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package
References Chang, C., et al.: J. Biol. Chem., 267, 13938 (1992), Jeong, L., et al.: J. Med. Chem., 36, 181 (1993).

Applications Acetoguanide is a degradation product of the sulfonylurea herbicide Iodosulfuron.
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);

Applications 1R-Dapagliflozin is an isomer of Dapagliflozin (D185370), which is a sodium-glucose transporter 2 inhibitor.
References Kasichayanula, S. et al.: Diabetes, Obesity and Metabolism 13, 47 (2011)

Applications A metabolite of Famciclovir, an antiviral.
References Harnden, M.R., et al.: J. Med. Chem., 32, 1738 (1989)

Applications N-Methyltetrahydrofolic acid (cas# 134-35-0) 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),

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);

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 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);

Applications A labelled metabolite of Capecitabine.

Applications A metabolite of Capecitabine.
References Arellano, M., ET AL.: Br. J. Cancer, 77, 79 (1998), Budman, D., ET AL.: J. Clin. Oncol., 16, 1795 (1998), Khanna, R., et al.: Cancer Res., 60, 4725 (2000), Charasson, V., et al.: Drug Metab. Dispos., 30, 731 (2002),

Applications Canagliflozin 2-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.
References Devineni, D., et al.: Diab. Obes. Metab., 14, 539 (2012); Nicolle, L., et al.: Curr. Med. Res. Opin., 28, 1167 (2012)

Applications An oral antiviral drug used in the treatment of hepatitis B infection. A guanine analogue that inhhibits all three steps in the viral replication process.
References Innaimo, S.F., et al.: Antimicrob. Agents Chemother., 41, 1444 (1997), Honkoop, P., et al.: Expert Opin. Invest. Drugs, 12, 683 (2003), Chang, T.-T., et al.: N. Engl. J. Med., 354, 1001 (2006),

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),

Folinic acid (Leucovorin) is a biofolic acid that can be used in the treatment of methotrexate, often in combination with Methotrexate (MTX) to reduce MTX-

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

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),

2'-Deoxy-2',2'-difluorocytidine 5'-triphosphate sodium, 10 mM aqueous solution is an analytical standard that is used in metabolism studies and as an impurity in some pharmaceuticals. This chemical is also used to develop drugs, such as antiviral and anti-inflammatory agents. 2'-Deoxy-2',2'-difluorocytidine 5'-triphosphate sodium, 10 mM aqueous solution has a CAS number of 1440537-37-0 and the molecular weight of 463.88 g/mol. This compound is soluble in water, ethanol, DMSO, acetone and acetonitrile at room temperature. The purity for this compound is > 99%.

Acyclovir is an antiviral agent that prevents the growth of herpes simplex virus. Acyclovir is a prodrug, which is converted to acycloguanosine 5'-triphosphate (ACV-TP) in vivo. ACV-TP inhibits viral DNA polymerase and thereby prevents viral genome replication, replication. The molecular structure of Acyclovir was determined by X-ray crystallography at 3.2 Å resolution. It has been shown that ACV-TP can be activated by chloride ions and it has been suggested that this activation may be the result of an interaction with a ligand.
ACV-TP binds to guanine residues in the DNA chain and prevents the formation of hydrogen bonds between guanine and adenine or cytosine residues in the same chain, preventing DNA replication.

Acyclovir is an antiviral drug that inhibits the replication of herpes viruses by selectively inhibiting viral DNA polymerase. The drug is active against a broad range of herpes viruses, including both types of herpes simplex virus (HSV-1 and HSV-2) and varicella zoster virus. Acyclovir has also been shown to be effective against aciclovir-resistant mutants. This drug can be used as a prophylaxis or in combination with other antiviral agents for the treatment of active infections. Acyclovir can cause headaches, nausea, vomiting, and diarrhea when taken orally. It should not be taken with certain medicines such as aminoglycosides or high doses of aspirin because this may increase the risk for kidney problems.

Impurity Capecitabine 3-O-BDR Impurity (USP)
Applications Capecitabine (C175650) impurity. Capecitabine 3-O-BDR Impurity (USP).

Applications 2,3,5-Tri-O-acetyl-6-chloropurine-9-β-D-ribofuranoside is a nucleoside compound with inhibitory activity on a rho-GTPase cell protein.
References Mounetou., et al.: J. Med. Chem., 40, 2902 (1997), Panero, J., et al.: Biotech. Lett., 28, 1077 (2006),

Applications Lamivudine intermediate.
References Chang, C., et al.: J. Biol. Chem., 267, 13938 (1992), Jeong, L., et al.: J. Med. Chem., 36, 181 (1993).

Applications Used in the synthesis of 3-(β-D-ribofuranosyl)-2,3-dihydro-6H-1,3-oxazine-2,6-dione, a new pyrimidine nucleoside analog related to uridine.
References Chwang, T.-L., et al.: J. Med. Chem., 19, 643 (1976),

Stability Hygroscopic
Applications Stavudine Triphosphate Trisodium Salt has a free acid of Stavudine Triphosphate. Stavudine Triphosphate inhibits HIV-1 RT (reverse transcriptase). Stavudine Triphosphate Trisodium Salt is a metabolite of Stavudine.
References Vaccaro, J.A., Parnell K.M., Terezakis S.A., Anderson, K.S.: Antimicrob. Agents Ch., 44, 217 (2000)

Stability Moisture Sensitive, Unstable in Solution
Applications 2-Deoxy-3,5-di-O-p-toluoyl-α-L-ribofuranosyl Chloride (cas# 141846-57-3) is a compound useful in organic synthesis.

Stability Hygroscopic
Applications A cell-permeable DNA-binding dye. Binds preferentially to DNA rich in adenine and thymine. Used in flow cytometry for measuring nuclear DNA content or for sorting isolated chromosomes.
References Jpeeesen, C, and Nielsen, P.E.: Eur. J. Biochem., 182, 437 (1989), Li,J., et al.: J. Exp. Biol., 200, 1499 (1997), Zaitsev, E.N., and Kowalczykowsi, S.C.: Nucl. Acids Res., 26(2), 650 (1998), Germ, M., et al.: Biochem. Biophys. Res. Commun., 261, 452 (1999),

Impurity USP Ribavirin Related Compound A
Applications Ribavirin Carboxylic acid is an impurity of Ribavirin (R414475). Ribavirin impurity A.
References Lertora, J., et al.: Clin. Pharmacol. Ther., 50, 442 (1991), Connor, E., et al.: Antimicrob. Agents Chemother., 37, 532 (1993), Manns, M., et al.: Lancet, 358, 958 (2001),

Applications Dopamine labeled biotin (LB) was used as a bifunctional compound to mediate the oxidation of β-nicotinamide adenine dinucleotide (NADH).
References Anderson, L., et al.: Clin. Microbiol., 19, 934 (1984), Bayer, E., et al.: Anal. Biochem., 161, 262 (1987), Harmon, F., et al.: J. Biol. Chem., 255, 9458 (1980),

Impurity Fluorouracil EP Impurity E
Applications Used for the experimental and clinical treatment of neoplastic and viral diseases. Fluorouracil EP Impurity E.
References Yu, H., et al.: J. Biol. Chem., 268, 15935 (1993), Staleva, L., et al.: Mutat. Res., 370, 81(1996), Harris, V., et al.: J. Mol. Biol., 326, 1389 (2003)

Applications 5’-O-Benzoyl Ribavirin is an impurity of Ribavirin (R414475). Ribavirin impurity E.
References Zakharieva., et al.: Bioorganic. Medicinal. Chem., 1994, 4, 2831 (1994), Reichard., et al.: The Lancet, 351, 83 (1998),

Impurity Ganciclovir EP Impurity A
Applications 9-[[2-chloroprop-2-en-1-yl)oxy]methyl]guanine (Ganciclovir EP Impurity A) is an impurity of Ganciclovir (G235000).

Applications Ganciclovir derivative.

Applications Labelled 5-Methyl Uridine. A primary degradation product of tRNA, an urinary nucleoside as biological marker for patients with colorectal cancer.
References Borek, E., et al.: Cancer Res., 37, 3362 (1977), Sander, G., et al.: Clin. Sci.,71, 367 (1986), Sander, G., et al.: Ann. Nutr. Metab., 30, 137 (1986), Rasmuson, T., et al.: Acta Oncol., 34, 61 (1995),

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.
References Siegel, D., et al.: J. Med. Chem., 60, 1648-1661 (2017)

Applications Labelled Azathioprine (A803350). An immunosuppressive antimetabolite. Also active as disease modifying antirheumatic drug (DMARD).
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,)

Impurity Valganociclovir EP Impurity J
Applications Ganciclovir Mono-O-propionate is a potential prodrug of Ganciclovir (G235000). Ganciclovir Mono-O-propionate was also found to exhibit anti-viral activity through experimental studies.
References Dias, C.S., et al.: J. Pharma. Sci., 91, 660 (2002);

Applications Sofosbuvir (R)-Phosphate is an impurity of PSI-7977 (P839640), a prodrug that is metabolized to the active antiviral agent 2'-deoxy-2'-α-fluoro-β-C-methyluridine-5'-monophosphate and is currently being investigated in phase 3 clinical trials for the treatment of hepatitis C. Studies have profiled PSI-7977 as a nucleotide inhibitor of hepatitis C virus, exerting selective inhibitory effects towards HCV NS5B polymerase.
References Lam, A.M.,et al.: Antimicrob. Agents. Chemotherapy., 56, 3359 (2012); Lam, A.M., et al.: J. Virol., 85, 12334 (2011); Sofia, M.J., et al.: J. Medn. Chem., 53, 7202 (2010)

Stability Hygroscopic
Applications A metabolite of 5-Azacytidine. This compound contains sodium chloride and water.
References Lee, T., et al.: Cancer Res., 34, 2482 ( (1974), Drake, J.C., et al.: Biochem. Pharmacol., 29, 807 (1980),