An analogue of a nucleoside, being an N-glycosyl compound in which the nitrogen-containing moiety is a modified nucleotide base. They are commonly used as antiviral products to prevent viral replication in infected cells.
| Member | Definition | Role |
|---|
| 2-methylthio-n-6-isopentenyladenosine | A nucleoside analogue in which adenosine has been modified by substitution at C-2 by a methylthio (methylsulfanyl) group and at the 6-amino nitrogen by a Delta(2)-isopentenyl group. | 2-methylthio-N(6)-(Delta(2)-isopentenyl)adenosine |
| 2-thiouridine | A thiouridine in which the oxygen replaced by sulfur is that at C-2. | 2-thiouridine |
| 2'-deoxyadenylyl-(3'-5')-2'-deoxyadenosine | | dApdA |
| 2'-deoxyguanylyl-(3'-5')-2'-deoxycytidine | | dGpdC |
| 4-demethylwyosine | A nucleoside analogue having 6-methyl-3,5-dihydro-9H-imidazo[1,2-a]purin-9-one as the modified nucleobase. | 4-demethylwyosine |
| acadesine | A 1-ribosylimidazolecarboxamide in which the carboxamide group is situated at position 4 of the imidazole ring, which is further substituted at position 5 by an amino group. A purine nucleoside analogue and activator of AMP-activated protein kinase, it is is used for the treatment of acute lymphoblastic leukemia and is reported to have cardioprotective effects. | acadesine |
| adenylyl-(2'-5')-uridine | | ApU |
| allopurinol riboside | A nucleoside analogue that is allopurinol with a beta-D-ribofuranosyl moiety at the 1-position. | allopurinol riboside |
| azacitidine | An N-glycosyl-1,3,5-triazine that is 4-amino-1,3,5-triazin-2(1H)-one substituted by a beta-D-ribofuranosyl residue via an N-glycosidic linkage. An antineoplastic agent, it is used in the treatment of myeloid leukaemia. | 5-azacytidine |
| cyc 682 | A nucleoside analogue resulting from the formal condensation of the carboxy group of hexadecanoic acid with the amino group of CNDAC. It is the prodrug of CNDAC and is currently in clinical development for the treatment of acute myeloid leukemia (AML). | sapacitabine |
| cytidylyl-3',5'-adenosine | | CpA |
| emtricitabine | An organofluorine compound that is 5-fluorocytosine substituted at the 1 position by a 2-(hydroxymethyl)-1,3-oxathiolan-5-yl group (2R,5S configuration). It is used in combination therapy for the treatment of HIV-1 infection. | emtricitabine |
| fazarabine | An N-glycosyl-1,3,5-triazine that is 4-amino-1,3,5-triazin-2(1H)-one substituted by a beta-D-arabinofuranosyl residue via an N-glycosidic linkage. A synthetic analogue of cytosine arabinoside and 5-azacytidine that incorporates structural features of both compounds, it shows good activity against a variety of transplanted tumors. | fazarabine |
| floxuridine | A pyrimidine 2'-deoxyribonucleoside compound having 5-fluorouracil as the nucleobase; used to treat hepatic metastases of gastrointestinal adenocarcinomas and for palliation in malignant neoplasms of the liver and gastrointestinal tract. | floxuridine |
| flucytosine | An organofluorine compound that is cytosine that is substituted at position 5 by a fluorine. A prodrug for the antifungal 5-fluorouracil, it is used for the treatment of systemic fungal infections. | flucytosine |
| fludarabine phosphate | A purine arabinonucleoside monophosphate having 2-fluoroadenine as the nucleobase. A prodrug, it is rapidly dephosphorylated to 2-fluoro-ara-A and then phosphorylated intracellularly by deoxycytidine kinase to the active triphosphate, 2-fluoro-ara-ATP. Once incorporated into DNA, 2-fluoro-ara-ATP functions as a DNA chain terminator. It is used for the treatment of adult patients with B-cell chronic lymphocytic leukemia (CLL) who have not responded to, or whose disease has progressed during, treatment with at least one standard alkylating-agent containing regimenas. | fludarabine phosphate |
| fr 900848 | A polyketide that is 5'-amino-5'-deoxy-3,4,5,6-tetrahydrouridine in which one of the hydrogens of the amino group is substituted by a (1E,3E)-1-[(1R,1'R,1''R,1'''R,2S,2'R,2''R,2'''S)-2'''-{(E)-2-[(1R,2R)-2-methylcyclopropyl]ethenyl}[1,1':2',1'':2'',1'''-quater(cyclopropan)]-2-yl]-5-oxopenta-1,3-dien-5-yl group. It is a metabolite isolated from the bacterium, Streptoverticillium fervens and targets the catalytic subunit of the fungal UDP-glycosyltransferase, the first step in the biosynthesis of glycosylphosphatidylinositol (GPI) anchors. It exhibits broad spectrum antifungal activity against several pathogenic fungi including Mucorales. | jawsamycin |
| guanine ribonucleotidyl-(3'-5')-adenosine | | GpA |
| guanylyl-(3'-5')-guanosine | | GpG |
| isopentenyladenosine | A nucleoside analogue in which adenosine has been modified by substitution at the 6-amino nitrogen by a Delta(2)-isopentenyl group. | N(6)-(Delta(2)-isopentenyl)adenosine |
| lamivudine | A monothioacetal that consists of cytosine having a (2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl moiety attached at position 1. An inhibitor of HIV-1 reverse transcriptase, it is used as an antiviral in the treatment of AIDS and hepatitis B. | lamivudine |
| molnupiravir | A nucleoside analogue that is N(4)-hydroxycytidine in which the 5'-hydroxy group is replaced by a (2-methylpropanoyl)oxy group. It is the prodrug of the active antiviral ribonucleoside analog N(4)-hydroxycytidine (EIDD-1931), has activity against a number of RNA viruses including SARS-CoV-2, MERS-CoV, and seasonal and pandemic influenza viruses. It is currently in phase III trials for the treatment of patients with COVID-19. | molnupiravir |
| n(4)-hydroxycytidine | A nucleoside analogue that is cytidine which carries a hydroxy group at the N(4)-positon. It has broad-spectrum antiviral activity against influenza, SARS-CoV , SARS-CoV-2 and MERS-CoV. | N(4)-hydroxycytidine |
| nsc 65346 | A nucleoside analogue that is adenosine in which the nitrogen at position 7 is replaced by a carbamoyl-substituted carbon. It is a potent inhibitor of protein kinase C. | sangivamycin |
| oxetanocin a | A nucleoside analogue found in Bacillus megaterium in which an adenine moiety is attached to position 2 of a of an oxetane ring which is substituted at positions 3 and 4 by hydroxymethyl groups. | oxetanocin A |
| sq 22536 | A nucleoside analogue that is adenine in which the nitrogen at position 9 has been substituted by a tetrahydrofuran-2-yl group. It is an adenylate cyclase inhibitor. | 9-(tetrahydrofuryl)adenine |
| stavudine | A nucleoside analogue obtained by formal dehydration across positions 2 and 3 of thymidine. An inhibitor of HIV-1 reverse transcriptase | stavudine |
| tenofovir | A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens is replaced by a [(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(isopropyloxycarbonyloxymethyl) ester (disoproxil ester) prodrug is used as the fumaric acid salt in combination therapy for the treatment of HIV infection. | tenofovir (anhydrous) |
| thiouridine | A thiouridine in which the oxygen replaced by sulfur is that at C-4. | 4-thiouridine |
| triciribine | A nucleoside analogue in which the nucleobase portion is a 1,4,5,6,8-pentaazaacenaphthylene ring system substituted with an amino group at position 3, and a methyl group at position 5 and is bound to the beta-D-ribofuranosyl moiety by an N(1)-glycosidic linkage. | triciribine |
| trifluridine | A pyrimidine 2'-deoxyribonucleoside compound having 5-trifluoromethyluracil as the nucleobase. An antiviral drug used mainly in the treatment of primary keratoconjunctivitis and recurrent epithelial keratitis. | trifluridine |
| uridylyl-(3'-5')-adenosine | | UpA |
| wyosine | A nucleoside analogue having methyl (2S)-4-(4,6-dimethyl-9-oxo-4,9-dihydro-3H-imidazo[1,2-a]purin-7-yl)-2-[(methoxycarbonyl)amino]butanoate as the modified nucleobase. | wybutosine |
| zeatin riboside | A 9-ribosylzeatin having trans-zeatin as the nucleobase. | 9-ribosyl-trans-zeatin |