Nucléosides et Nucléotides

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 Cytidine derivative.
References Ueda, T., et al.: Chem. Pharmaceut. Bull., 22, 2377 (1974),

Impurity Zidovudine EP Impurity A
Applications Stavudine (Zidovudine EP Impurity A) is used as an antiviral. A reverse transcriptase inhibitor.
References Mansuri, M.M., et al.: Antimicrob. Ag. Chemother., 34, 637 (1990), Cretton, E.M., et al.: Antimicrob. Ag. Chemother., 37, 1816 (1993), Browne, M.J., et al.: J. Infec. Dis., 167, 21 (1993)

Applications Isotope labelled Melamine (M208703), which forms synthetic resins with formaldehyde. It remains largely non-metabolized in male Wistar rats with 90% of the administered dose excreted in the urine (1,2) and thus acts as a non-protein nitrogen food additive found in milk (3). Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA), environmental, and food contaminants.
References 1. Mast, R. et al.: Food Chem Toxicol. 1983 Dec;21(6):807-10.2. Smith, J. et al.: Toxicol Appl Pharmacol. 1994 Apr;125(2):296-308.3. Anirudhan, T. et al.: Food Chem. 2017 Jul 15;227:85-92.

Applications A metabolite of Lamivudine (L172500).
References Soudeyns, H., et al.: Antimicrob. Agents Chemother., 35, 1386 (1991), Denapoli, L., et al.: Nucleosides Nucleotides, 12, 21 (1993),

Impurity Gemcitabine EP Impurity B
Applications 1’-Epi Gemcitabine Hydrochloride (Gemcitabine EP Impurity B) is an α-Anomer of Gemcitabine.
References Hertel, L.W., et al.: Cancer Res., 50, 4417 (1990), Abbruzzese, J.L., et al.: J. Clin. Oncol., 9, 491 (1991), Ruiz, V.W.T., et al.: Biochem. Pharmacol., 46, 762 (1993),

Stability Hygroscopic
Applications 9-Carboxymethoxymethylguanine-13C2,15N is the labelled analog of 9-Carboxymethoxymethylguanine (C179990) which is a metabolite of Acyclovir (A192400-an antiviral, orally active acyclic nucleoside with inhibitory activity towards several herpes viruses).
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); Gunness, P., et al.: Transl. Res., 158, 290 (2011);

Applications Floxuridine is an antiviral; antineoplastic.
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 Harris, M., et al.: Biophys. J., 4, 203 (1964),

Applications A metabolite of the potent and selective inhibitor of HIV-1 replication, AZT.
References Brehm, J., et al.: Biochem., 47, 14020 (2008), von Kleist, M., et al.: Eur. J. Pharm. Sci., 36, 532 (2009),

Applications A nucleoside analog used in the treatment of viral infections, including those caused by human immunodeficiency virus, cytomegalovirus, and herpes virus.
References Faulds, D., et al.: Drugs, 39, 597 (1990), Greene, J., et al.: Fundam. Appl. Toxicol., 32, 140 (1996), Poirier, M., et al.: Toxicol. Appl. Pharmacol., 199, 151 (2004),

Applications An intermediate in the preparation of thymidine derivatives
References el Kouni, M., et al.: Biochem. Pharmacol., 51, 1687 (1996),

Impurity Ganciclovir EP Impurity I
Applications O,O'-Dipropanal Ganciclovir (Ganciclovir EP Impurity I) is derived from Ganciclovir (G235000), which is a nucleoside analog structurally related to Acyclovir (A192400). Ganciclovir is an antiviral.
References Halloran, P.J. and Fenton, R.G.: Cancer Res., 58, 3855 (1998), Rubsam, L.Z., et al.: Cancer Res., 59, 669 (1999), Yamasaki, H., et al.: C.R. Acad. Sci. III, 322, 151 (1999)

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

Applications UDP-3-O[R-3-Hydroxymyristoyl]-N-acetylglucosamine Tris Salt is a lipid A precursor for Escherichia coli.
References Anderson, M. S. et al.: Biochem., 27, 1908 (1988);

Applications N-[(S)-(4-Nitrophenoxy)phenoxyphosphinyl]-2-ethylbutyl Ester L-Alanine is used for the treatment of ebola and emerging viruses.
References Siegel, D., et al.: J. Med. Chem., 60, 1648-1661 (2017)

Applications Adenosine is a nucleotide.
References Long, X., et al.: J. Pharmacol. Exper. Ther., 335, 781 (2010); Ham, M., et al.: J. Pharmacol. Exper. Ther., 335, 607 (2010);

Stability Hygroscopic
Applications Antineoplastic.
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 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),

Impurity Zidovudine EP Impurity C
Applications Thymine (Zidovudine EP Impurity C) is a nitrogenous base component in the nucleic acid of DNA.
References Keum, Y., et al.: App. Microbiol. Biotechnol., 80, 863 (2008); Redzic, Z., et al.: Neurochem. Res., 34, 566 (2009); Lanevskij, K., et al.: J. Pharm. Sci., 98, 122 (2009); Rajendar, B., et al.: Bioorg. Med. Chem., 17, 351 (2009);

Stability Hygroscopic
Applications A synthetic precursor of Zanamivir.
References Gonzalez-Diaz, H., et al.: Bioorg. Med. Chem. Lett., 15, 1651 (2005), Bergmann, R., et al.: J. Med. Chem., 50, 2708 (2007), Lue, W., et al.: Eur. J. Med. Chem., 43, 569 (2008),

Stability Hygroscopic
Applications Metabolite of 6-Mercaptopurine, an immunosuppressive drug used to treat leukemia.
References Chou, C., et al.: Biochem. Pharmacol., 75, 1601 (2008), Conejo-Garcia, A., et al.: Eur. J. Med. Chem., 43, 1742 (2008), Hawwa, A., et al.: Brit. J. Clin. Pharmacol., 66, 826 (2008), Askanase, A., et al.: J. Rheumatol., 36, 89 (2009),

Stability Hygroscopic, Unstable in Solution
Applications A derivative of Cytarabine, a potent cytotoxic-antiviral nucleoside.
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),

Applications 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene is used as a reagent in the synthesis of Dapagliflozin (D185370); a potent, selective renal sodium-dependent glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.
References Meng, W., et al.: J. Med. Chem., 51, 1145 (2008);

Impurity Methotrexate EP Impurity D N-Desmethyl Impurity
Applications Pteroic Acid (Methotrexate EP Impurity D N-Desmethyl Impurity) is a constituent as well as a degradation product of Folic Acid (F680300) formed via enzymatic hydrolysis. has been shown to activate the glutamylation of methotrexate by folylpolyglutamate synthetase.
References Vickers, P.J. et al.: Can. J. Biochem. Cell Biol., 63, 777 (1985): Tafolla, W.H. et al.: J. Pharmac. Sci., 70, 1273 (1981); Iwai, K. et al.: J. Butrit. Sci. Vitaminol., 23, 95 (1977);

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).
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 Abacavir EP Impurity E
Applications (1R,3S)-3-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopentanemethanol (Abacavir EP Impurity E) is an impurity of Abacavir (A104990). 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.
References (1) Jackson, A., et al.: Antivir Ther. 17, 19 (2012) (2) Yuen, G. J., et al.: Clin Pharmacokinet. 47, 351 (2008)

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

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

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

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

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.

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.

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),

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).

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

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)

Applications The 2-epi-enantiomer analogue of (-)-Emtricitabine (E525000) evaluated against HIV-1 in human peripheral blood mononuclear (PBM) cells.
References Jeong, L.S., et al.: J. Med. Chem., 36, 2627 (1993),

Impurity Capecitabine EP Impurity E
Applications 5'-Deoxy-5-fluoro-N-[(3-methylbutoxy)carbonyl]cytidine (Capecitabine EP Impurity E) is a 5'-Desoxycytidine derivative and is used as an antitumor agent.

Applications 2,5,6-Triamino-4(3H)-pyrimidinone Sulfate is used in the preparation of guanines and other purine derivatives with antiviral activities.
References Hemmati, S. et al.: Int. J. Chem. Sci., 2, 9 (2004); Chetsanga, C.J. et al.: Chem.-Biol. inter., 58, 117 (1986);

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 L-Glucono-1,5-lactone is the lactone derivative of L-gluconic acid.
References Fuhrhop, J. H., et al.: J. Am. Chem. Soc., 113, 7437 (1991); Szarek, W.A., et al.: Canadian. J. Chem., 62, 671 (1984);

Impurity Penciclovir Impurity F
Applications 6-Chloro Desacetyl Famciclovir is a prodrug of Penciclovir (P221500); an antiviral.
References Weinberg, A., et al.: Antimicrob. Ag. Chemother., 36, 2037 (1992); McMeekin, J.R., et al.: Anal. Proc., 29, 178 (1992)

Applications 5'-Deoxy-5'-chloroadenosine is an intermediate in the synthesis of 5'-Deoxy-5'-(methylthio)adenosine (D242600), 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.
References 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 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),

Stability Moisture Sensitive
Applications Adenosine 5’-Diphosphate-13C5 Ammonium Salt Hydrate is the isotope labelled analog of Adenosine 5’-Diphosphate Ammonium Salt Hydrate (A281700); a nucleoside diphosphate that interacts with a family of ADP receptors found on platelets (P2Y1, P2Y12 and P2X1), to induce platelet activation. ADP in the blood is converted to adenosine by the action of ecto-ADPases, inhibiting further platelet activation via adenosine receptors.
References Gamba, G. et al.: Haematologia, 58, 1215 (1973); Dejana, E. et al.: Thromb. Haemost., 39, 135 (1978)

Impurity Capecitabine 2-O-BDR Impurity (USP)
Stability Hygroscopic
Applications Capecitabine (C175650) impurity. Capecitabine 2-O-BDR Impurity (USP).

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 Ethylene Glycol Monobenzoate, is a reagent that can be used as an intermediate in a variety of chemical and biochemical reactions. It is used as an intermediate in the preparation of 1,2-Ethanediol Disodium Salt (E890125), which is the result of the nucleophilic attack on its carbonyl group.
References Khouri, F. et al.: J. Am. Chem. Soc., 108, 6683 (1986);

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),

Impurity Lamivudine EP Impurity D
Stability Hygroscopic
Applications ent-Lamivudine (Lamivudine EP Impurity D) is an enantiomer of Lamivudine (L172500); an antiviral that inhibits HIV-reverse transcriptase.
References Pepe, G. et al.: Eur. J. Med. Chem., 31, 775 (1996); Marr, E. et al.: Antiviral Res., 28, 1 (1995); Parikh, U.M. et al.: Antimicrob. Agents Chemother., 49, 1139 (2005);

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),