Nucleosides and Nucleotides

<p>Applications 5-Amino-1-methyl-4-nitroimidazole is a moiety of Azathioprine (A803350); an immunosuppressive antimetabolite that is also active as a 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>Stability Hygroscopic, Light Sensitive, Temperature Sensitive<br>Applications 10-Formyl-5,6,7,8-tetrahydro Folic Acid Disodium Salt is the disodium salt of F701085, which is a Folic Acid (F680300) derivative. Folic Acid is a vitamin needed to synthesize DNA, conduct DNA repair and methylate DNA, it also acts as a cofactor in biological reactions involving folate.10-Formyl-5,6,7,8-tetrahydro Folic Acid Disodium Salt is also used in the diagnosis and prevention and therapy of cerebral folate dificiency in relation to formation of folate receptor autoantibodies and treatment with reduced folate and antioxidants.<br>References Slieker, L.J., et al.: Mol. Pharmacol., 25, 294-302 (1984); 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)Ramaekers, WO 2006119589, (2006)<br></p>

<p>Stability Hygroscopic<br>Applications A tryptamine derivative, a neurotransmitter agonist.<br>References Creveling, C. R., et al.: Mol. Pharmacol., 11, 211 (1975),<br></p>

<p>Applications Gemcitabine is used for breast cancer treatment. First-line treatment for locally advanced pancreatic cancer.<br>References Hamsici, S., et al.: Bioconjugate Chem., (2017); Peng, T., et al.: J. Cell. Biochem., (2017)<br></p>

<p>Applications 2-Deoxy-D-ribose induces apoptosis by inhibiting the synthesis and increasing the efflux of glutathione.<br>References Fico, A., et al.: Free Radical Biology &amp; Medicine, 45, 211 (2008),<br></p>

<p>Applications Melphalan is an antineoplastic.<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 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 D-Menthol is used for oral gel patch or film containing herb extracts or Chinese medicine, fruit extract, spearmint, and menthol for smoking cessation.<br>References Ikaheimo, I., et al.: J. Antimicrob. Chemother., 46, 287 (2000), Gillet, Y., et al.: Lancet, 359, 753 (2002), Turos, E., et al.: Bioorg. Med. Chem. Lett., 2002, 12, 2229 (2002),<br></p>

<p>Applications 5’-O-Acetyl Ribavirin is an impurity of Ribavirin (R414475). Ribavirin impurity F.<br>References Zakharieva., et al.: Bioorganic. Medicinal. Chem., 1994, 4, 2831 (1994), Reichard., et al.: The Lancet, 351, 83 (1998),<br></p>

<p>Applications A useful intermediate for chemical modifications of base and sugar moieties in natural nucleosides.<br>References Sashaki, T., et al.: J. Org. Chem., 40(1), 106 (1975)<br></p>

<p>Stability Hygroscopic<br>Applications A metabolite of Lamivudine (L172500).<br>References Burgess, K., et al.: Chem. Rev., 100, 2047 (2000), Gallois-Montbrun, S., et al.: Biochem. Pharmacol., 68, 1749 (2004),<br></p>

<p>Impurity Aciclovir EP Impurity B<br>Applications Guanine is one of the five nucleobases incorporated into biological nucleic acids. Guanine, along with adenine and cytosine, is present in both DNA and RNA, whereas thymine is usually seen only in DNA, and uracil only in RNA. Aciclovir EP Impurity B.<br>References Geslain, R., et al.: J. Biol. Chem., 284, 27760 (2009); Manini, P., et al.: Toxicol. Lett., 190, 41 (2009); Gong, B., et al.: Biochem., 48, 11961 (2009); Sugimoto, M., et al.: J. Agric. Food Chem., 58, 374 (2010);<br></p>

<p>Stability Moisture Sensitive<br>Applications Cytidine 5'-diphosphocholine (cas# 987-78-0) is a useful research chemical.<br></p>

<p>Stability Very Hygroscopic<br>Applications Labelled Emtricitabine. A reverse transcriptase inhibitor. It is an effective antiviral agent against HIV, HBV, and other viruses replicating in a similar manner. A nucleoside analog structurally related to Lamivudine (L172500).<br>References Schinazi, R.F., et al.: Antimicrob. Ag. Chemother., 36, 2423 (1992), Shockeor, J.P., et al.: Xenobioica, 26, 189 (1996), Feng, J.Y., et al.: FASEB J., 13, 1511 (1999), Molina, J.-M., et al.: J. Infec. Dis., 182, 599 (2000)<br></p>

<p>Applications 2-Amino-6-(chloromethyl)-4(3H)-pteridinone is a reagent/intermediate used in the preparation of Folic Acid (F680300) and its derivatives.<br>References Qi, Y., et al.: Faming Zhuanli Shenqing. CN 103755706 A 20140430. Apr 30, 2014;<br></p>

<p>Impurity Valaciclovir EP Impurity C<br>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.<br>References Pu, T., et al.: Faming Zhuanli Shenqing, (2013);<br></p>

<p>Applications 6-Benzylaminopurine 9-(β-D-glucoside) (cas# 4294-17-1) is a compound useful in organic synthesis.<br></p>

<p>Stability Moisture Sensitive<br>Applications Eye irritant.<br>References Bagley, D. M. et al.; Toxicol. In Vitro 13, 505 (1999); Gilleron, L. et al.; Toxicol. In Vitro 11, 641 (1997)<br></p>

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

<p>Applications A metabolite of 5-Fluorouracil. (F596000)<br>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)<br></p>

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

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

<p>Applications Constituent of deoxyribonucleic acid.<br>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),<br></p>

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

<p>Applications Influenza viral neuraminidase inhibitor; structural analog of the sialic acid. Antiviral.<br>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),<br></p>

<p>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.<br>References Kasichayanula, S. et al.: Diabetes, Obesity and Metabolism 13, 47 (2011)<br></p>

<p>Stability Hygroscopic<br>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.<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>Stability Light Sensitive - Protect from Light Exposure<br>Applications Fenretinide (4-HPR) is a synthetic retinoid deriverative. 4-HBR is shown to exhibit binding to the retinoic acid receptors (RAR) at concentrations necessary to induce cell death.A synthetic analog of Vitamin A.<br>References Marth, C., et al.:J. Nat. Cancer Inst., 75, 871 (1985), Delia, D., et al.: Cancer Res., 53, 6036 (1993), Costa., A., et al.: Cancer Res., 54, Suppl., 2032s (1994), Decensi., A., et al.: Eur. J. Cancer Prev., 3, 377 (1994)<br></p>

<p>Stability Moisture Sensitive<br>Applications 1-(5-O-Acetyl-β-D-ribofuranosyl)-4-amino-1,3,5-triazin-2(1H)-one is an impurity of 5-Azacytidine (A796000), 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 Capecitabine is an antineoplastic agent. Capecitabine is a prodrug of Doxifluridine (D556750).<br>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),<br></p>

<p>Impurity Aciclovir EP Impurity M<br>Applications An impurity of Acyclovir. Aciclovir EP Impurity M<br>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),<br></p>

<p>Stability Hygroscopic<br>Applications A potent adenosine receptor agonist. Inhibits platelet aggregation and is centrally active in vivo.<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 Cusack and Hourani: Br. J. Pharmacol., 72, 433 (1981), Knapp, et al.: Pharmacol. Biochem. Behav., 68, 797 (2001)<br></p>

<p>Applications Cidofovir Diphosphate Trisodium Salt has antiviral activity, which is used against herpes viruses. Cidofovir Diphosphate is a metabolite in human cells.<br>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)<br></p>

<p>Applications A primary degradation product of tRNA, an urinary nucleoside as biological marker for patients with colorectal cancer.<br>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),<br></p>

<p>Applications Adenosine 5'-Monophosphate is a natural occurring nucleotide and a useful ligand determinant that facilitate the binding of APS reductase inhibitors and activates adenosine receptor agonists.<br>References Hong, J.A. et al.: J. Med. Chem., 52, 5485 (2009); Korboukh I. et al.: J. Med. Chem., 55, 6467 (2012)<br></p>

<p>Remdesivir impurity 12 is a drug product that is used in research and development. It is a synthetic impurity standard for HPLC analytical methods. Remdesivir impurity 12 is an impurity of the drug, remdesivir, which has antiviral activity against HIV-1. Metabolism studies have been conducted to investigate how this impurity affects the pharmacokinetics of remdesivir. The use of synthetic material ensures high purity and quality for this product.</p>

<p>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.</p>

<p>2-Acetamido-9-[2-(acetyloxy)ethoxy]methyl-6,9-dihydro-1H-purin-6-one (ademetionine) is a prodrug that is metabolized in the liver to form ademetionine. Ademetionine is a potent inhibitor of guanosine deaminase, which is an enzyme that breaks down guanosine into guanine and ammonia. Ademetionine has shown efficacy in cancer treatment and may also be used to treat tuberculosis. The metabolism of this drug takes place in the liver, where it undergoes oxidation by cytochrome P450 enzymes to form the active metabolite ademetionine. Metabolism of this drug can be inhibited by drugs such as trifluoromethanesulfonic acid (TFMS), which are used for the treatment of malaria. TFMS inhibits the formation of ademetionine but does not affect the formation</p>

<p>Remdesivir impurity 10 is a synthetic chemical compound that has been synthesized for research and development. It is an impurity standard of remdesivir, which is not present in any drug product. The purity of this product is high, and it can be used as a pharmacopoeia or drug development standard. It can also be used as an analytical standard to measure the concentration of metabolites in animal studies or metabolism studies.</p>

<p>4-Amino-7-iodopyrrolo[2,1-f][1,2,4]triazine is an impurity standard of the drug product. It is a high purity synthetic compound with a niche in pharmacopoeia and drug development. 4-Amino-7-iodopyrrolo[2,1-f][1,2,4]triazine has been shown to be a metabolite of the natural product.</p>

<p>3,9-Dihydro-9-[(2-hydroxyethoxy)methyl]-1H-Purine-2,6-dione is an impurity found in the synthesis of a drug product. It is also used as an analytical standard for HPLC methods and as a pharmacopoeia standard. 3,9-Dihydro-9-[(2-hydroxyethoxy)methyl]-1H-Purine-2,6-dione has been shown to be produced by the metabolism of other drugs such as caffeine. This impurity is not expected to have any therapeutic effects when administered to humans.</p>

<p>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 &gt; 99%.</p>