Nucléosides et Nucléotides

Applications Capecitabine (C175650) impurity.

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

Applications 2'-Deoxy-2'-fluorocytidine is a potent inhibitor of the subgenomic hepatitis C virus replicon in Huh-7 cells. 2'-Deoxy-2'-fluorocytidine has been shown to inhibit Borna Disease virus replication and spread.
References Stuyver, L.J. et al.: Antimicrob. Agents Chemother., 48, 651 (2004); Bajramovic, J.J. et al.: Antiomicrob. Agents Chemother., 48, 1422 (2004);

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

Impurity Abacavir EP Impurity F
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).
References (1) Hanumegowda, U., et al.: Chem. Res. Toxicol., 23, 749 (2010) (2) Prasse, C., et al.: Environ. Sci. Technol., 44, 1728 (2010)

Applications (1R,3R,4R)-Entecavir is an isomeric impurity of Entecavir (E558900).

Impurity Lamivudine EP Impurity H
Stability Hygroscopic
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.
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)

Applications 2-Hydroxy-2,3-tetrahydrofuranyl Entecavir is an impurity of Entecavir (E558900).

Impurity Zidovudine EP Impurity B
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.
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);

Stability Hygroscopic
Applications (2'R)​-2'-​Deoxy-​2'-​fluoro-​2'-​methyl-uridine 5'-​Triphosphate Tetrasodium Salt is an impurity of Sofosbuvir (P839640) which is a prodrug that is metabolized to the active antiviral agent 2'-deoxy-2'-α-fluoro-β-C-methyluridine-5'-monophosphate.
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);

Applications 5-Azacytidine 2’,3’5’-O-triacetate is a useful compound for the treatment and prevention of cancer and disorders related to abnormal cell proliferation, hematological disorders, and myelodysplastic syndromes (MDS). It can be also used to synthesize 2'3'5'triacetyl-5-azacytidine which is a prodrug for azacitidine. Azacitidine is a FDA-appproved DNA metnyltransferase (DNMT) inhibitor.
References Rajendiran, C., et al.: PCT Int. Appl. WO 2012135405 A1 20121004 (2012); Ziemba, A., et al.: Chemother Res Pract 965826, 9 (2011); Beisler, J. A., et al.: J. Carbohyd. Chem 4, 281 (1977)

Impurity Emtricitabine Carboxylic Acid Impurity
Applications Emtricitabine Carboxylic Acid is an impurity of the antiviral agent Emtricitabine (E525035).
References Pendela, M. et al.: Talanta, 82, 125 (2010);

Applications Second generation purine nucleoside analog; antimetabolite that inhibits DNA synthesis and resists deamination by adenosine deaminase. 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 Gandhi, V., et al.: Clin. Cancer Res., 9, 6335 (2003), Kantarjian, H., et al.: Blood, 102, 2379 (2003), Faderl, S., et al.: Cancer, 103, 1985 (2005),

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)

Stability Moisture Sensitive
Applications 2,3-Dichloropropionyl Chloride is used as a reagent in the synthesis of 6-chloro-5-cyclohexyl-1-indancarboxylic acid, a potent analgesic, antipyretic, and antiinflammatory agent, and its related compounds.
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 Sawa, Y., et al.: Yakugaku Zasshi, 96, 653 (1976)

Stability Moisture Sensitive
Applications 1,2-bis(Chloromethoxy)ethane is a carcinogenic compound.
References Kar, S., Roy, K.: Chemoshpere, 87, 339 (2012)

Applications Methyl 4-Chlorobenzoate is a reactant used in the synthesis of ataxia-telangiectasia mutated (ATM) kinase, a target for novel radiosensitizing agents. As well, used as a reactant in the synthesis of aminopyridine functionalized polyacrylonitrile fibers.
References Min, J. et al.: J. Med. Chem., 59, 559 (2016);

Impurity Entecavir EP Impurity D
Applications 4’-epi-Entecavir is an epimeric impurity of the antiviral drug Entecavir (E558900).

Applications A labelled 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),

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

Impurity Abacavir EP Impurity C; Abacavir USP Related Compound A
Applications Descyclopropyl Abacavir (Abacavir EP Impurity C; Abacavir Related Compound A) is an intermediate 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.
References (1) Jackson, A., et al.: Antivir Ther. 17, 19 (2012) (2) Yuen, G. J., et al.: Clin Pharmacokinet. 47, 351 (2008)

Stability Hygroscopic
Applications Acyclovir L-Leucinate is an amino acid ester of the antiherpetic agent, Acyclovir (A192400). It is the Leucine analogue of Valacyclovir (V085000).
References Burnette, T. et al.: J. Biol. Chem., 270, 15827 (1995);

Stability Moisture Sensitive
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.
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)

Stability Hygroscopic
Applications D-Melphalan is an isomer of melphalan (M216900), which 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 L-Tetrahydrofolic Acid-d4 (Major) is a folic acid derivative and coenzyme involved in the metabolism of amino and nucleic acids.
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),

Stability Hygroscopic
Applications 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).
References Mellors, J., et al.: Science, 72, 1167 (1996), Reimann, K., et al.: J. Virol., 79, 8878 (2005), Rose, J., et al.: J. Biol. Chem., 280, 7413 (2005), Acierno, P., et al.: J. Immunol., 176, 5338 (2006),

Stability Hygroscopic
Applications Used in the characterization and elucidation of coordination requirements of adenine nucleotides complexes with Fe(II) ions.
References Richter, Y., et al.: Nucleos. Nucleot. Nucleic Acids, 22, 1757 (2003),

Applications An intermediate in the preparation of Oxiracetam (O846905).
References Kondepudi, D., et al.: Science, 250 975 (1990), Di Silvestro, G., et al.: J. Pharm. Sci., 82, 758 (1993),

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 Des-(3-Oxo-3,4-dihydrogen) 3,6-Difluoro Favipiravir is a building block related to Favipiravir(F103350). 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.
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)

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 5-O-Trityl-2,3’-anhydrothymidine (cas# 25442-42-6) is a compound useful in organic synthesis.

Impurity Valaciclovir EP Impurity P
Stability Light Sensitive, Temperature Sensitive
Applications Bis Valacyclovir (~90%) (Valaciclovir EP Impurity P) is an impurity is listed in Ph. Eur. monograph for Valaciclovir HCl as impurity P and Bis-valaciclovir in USP monograph (impurity K).

Applications Labelled Uridine, a nucleoside; widely distributed in nature. Uridine is one of the four basic components of ribonucleic acid (RNA)
References Lorine, P., et al.: J. Biol. Chem., 178, 439 (1949); Grakoui, A., et al.: J. Virol., 63, 5216 (1989); Strauss, J., et al.: Microbiol. Rev., 58, 491 (1994); Lin, Y., et al.: Virology, 292, 78 (2002);

Impurity Ganciclovir EP Impurity C
Applications 2’-Monodehydroxy-2’-chloro Ganciclovir is an Impurity of Ganciclovir (G235000). 2’-Monodehydroxy-2’-chloro Ganciclovir is a sugar modified acyclic analogue of guanosine (G837900). Studies have shown 2’-Monodehydroxy-2’-chloro Ganciclovir has potential to exhibit virucidal activity. Iso mono chloro ganciclovir
References Martin, J.C., et al.: J. Med. Chem., 29, 1384 (1986);

Impurity Lamivudine EP Impurity J
Applications (2R-cis)-1-[2-(Hydroxymethyl)-1,3-oxathiolan-5-yl]-2,4(1H,3H)-pyrimidinedione (Lamivudine EP Impurity J) is an impurity of Lamivudine (L172500). (2R-cis)-1-[2-(Hydroxymethyl)-1,3-oxathiolan-5-yl]-2,4(1H,3H)-pyrimidinedione is also being further studied to determine its potential as an anti-HIV agent.
References Jeong, L., et al.: J. Med. Chem., 36, 181 (1993)

Impurity Capecitabine EP Impurity D
Applications 5'-Deoxy-5-fluoro-N-[(2-methylbutoxy)carbonyl]cytidine (Capecitabine EP Impurity D) is a Capecitabine analog which shows antitumor activity.

Applications A labelled 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),

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),