Nucléosides et Nucléotides

Applications Gemcitabine (G305000) derivative.

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);

Applications Emtricitabine N,N’-Methylene Dimer is a derivative compound of Emtricitabine (E525000), a reverse transcriptase inhibitor. It is effective antiviral agent against HIV, and other viruses replicating in a similiar manner. A nucleoside analog structurally related to Lamivudine (L172500).
References FASEB J., 13, 1511 (1999), Molina, J.-M., et al.: J. InfecSchinazi, R.F., et al.: Antimicrob. Ag. Chemother., 36, 2423 (1992), Shockeor, J.P., et al.: Xenobioica, 26, 189 (1996), Feng, J.Y., et al.: . Dis., 182, 599 (2000)

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);

Applications A 2-substituted 2’-Deoxyadenosine (D231620). Used in the synthesis of oligonucleotides.
References Ishikawa, F., et al.: J. Mol. Biol., 70, 475 (1972), Hattori, M., et al.: Biochemistry, 13, 2754 (1974), Kazimierczuk, Z., et al.: J. Med. Chem., 33, 1683 (1990),

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).

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),

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).

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 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),

Applications An irreversible inhibitor of the mammalian DNA repair protein, O6-alkylguanine-DNA alkyltransferase. Assists in the protection against carcinogenic and therapeutic alkylating agents.
References Dolan, M.E., et al.: Proc. Natl. Acad. Sci. USA, 87, 5356 (1990), Goodtzova, K., et al.: Biochemistry, 33, 385 (1994), Elder, R.H., et al.: Biochem. J., 298, 231 (1994)

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);

Applications Gemcitabine intermediate.
References Balzarini, J., et al.: Biochem. Pharmacol., 1988, 37, 2847 (1988), Hertel, L., et al.: Cancer Res., 50, 4417 (1990), Marquez, V., et al.: J. Med. Chem., 33, 978 (1990),

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),

Impurity Lamivudine EP Impurity B
Applications 2’-Epi-Lamivudine (Lamivudine EP Impurity B) is an epimer of Lamivudine (L172500); an antiviral that inhibits HIV-reverse transcriptase.
References Lin, T. et al.: J. Med. Chem., 39, 1757 (1996); Schinazi, R.F. et al.: Antimicrob. Agents Chemother.,36, 672 (1992);

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),

Applications 6,7-Dimethylpterin, a derivative of Folic Acid (F680300) is used as a biomarker for a non-invasive cancer diagnosis. Also can function as chromophores in light sensitive proteins allowing for analysis of target cells.
References Kritskii, M.S. et al.: Dokl. Akad. Nauk., 380, 408 (2001); Gamagedara, S. et al.: Clin. Chim. Acta., 412, 128 (2011);

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),

Applications Folic acid dihydrate

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);

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 3-(3-Azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione is an impurity of Zidovudine (A825000). Zidovudine is an antiviral agent used in the clinical treatment of HIV infections.
References Radatus, B.K., Org. Process. Res. Dev., 15, 1281 (2011)

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),

Applications An intermediate used in the preparation of Zanamivir derivatives.
References Andrews, D., et al.: Eur. J. Med. Chem., 34, 563 (1999), Altamore, T., et al.: Bioorg. Med. Chem., 14, 1126 (2006),

Entecavir (1R,3R,4S) diastereomer is a synthetic compound and is an analytical standard for HPLC. This product is an impurity of the drug Entecavir. The impurity is characterized by a retention time of 17.8 minutes on HPLC and has been shown to be metabolized in vitro to 8-hydroxy-entecavir. The purity of this product is 98% with a CAS number of 1367369-78-5.

Gemcitabine hydrochloride is an analog of the natural nucleoside cytidine. It is a chemotherapeutic drug that is used in the treatment of pancreatic, lung and breast cancer. Gemcitabine hydrochloride is metabolized to its active form by deamination of cytosine residues in DNA. This conversion is catalyzed by the enzyme cytidine deaminase. Gemcitabine hydrochloride has been shown to be effective against metastatic pancreatic cancer and advanced-stage non-small cell lung cancer, as well as early-stage breast cancer. Gemcitabine hydrochloride has also been shown to be effective against certain types of lymphoma and leukemia.

Acyclovir Impurity K is a drug product that is used as an analytical reference standard for metabolism studies. Acyclovir Impurity K is a natural product and an impurity of acyclovir, which has CAS No. 1797131-64-6. The chemical name of this drug is 3-hydroxy-2,5,6,7-tetrahydro-1H-[1]benzopyran-2,4(3H)-dione. It can be synthesized in the laboratory by custom synthesis or it can be obtained from a commercial supplier as an impurity standard. This product is used to help with drug development and research and development in the pharmaceutical industry. It can also be used as a high purity HPLC standard for pharmacopoeia testing purposes.

Remdesivir related compound 12 is a synthetic drug product. It is an impurity standard used for the production of the active pharmaceutical ingredient, remdesivir. The substance is a custom synthesis and can be synthesized to meet customer specifications. Remdesivir related compound 12 has been studied in animal models for metabolism studies and human pharmacokinetic studies. This substance is also used for research and development, as well as niche drug development.

Triphenylmethanol (TPM) is an inhibitor of the enzyme alcohol dehydrogenase. It is synthesized by reacting p-hydroxybenzoic acid with a hydroxyl group in the presence of trifluoroacetic acid and potassium carbonate. The reaction solution was then analyzed by x-ray crystallography, revealing the molecular structure of TPM. TPM binds to the metal ion in a hydroxyl group, preventing alcohol dehydrogenase from oxidizing ethanol to acetaldehyde. This mechanism also explains why TPM inhibits other enzymes that use this same metal ion cofactor such as carboxypeptidase A and aminopeptidase P, which are involved in protein synthesis and degradation.

Intermediate in the synthesis of ribavirin

Enantiomer of Lamivudine