Nucleosides and Nucleotides

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),

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)

Applications Ganciclovir derivative.

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),

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

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).