Description
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.
Chemical properties
| Chemical formula | Net charge | Average mass |
|---|---|---|
| C8H11N3O3S | 0 | 229.25600 |
Nomenclature
| IUPAC | SMILES | InChI | InChIKey | Synonyms |
|---|---|---|---|---|
| 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2(1H)-one | Nc1ccn([C@@H]2CS[C@H](CO)O2)c(=O)n1 | InChI=1S/C8H11N3O3S/c9-5-1-2-11(8(13)10-5)6-4-15-7(3-12)14-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7+/m0/s1 | JTEGQNOMFQHVDC-NKWVEPMBSA-N |
|
Citations
- Chen, Y, et al. 2012. Comparative meta-analysis of adefovir dipivoxil monotherapy and combination therapy of adefovir dipivoxil and lamivudine for lamivudine-resistant chronic hepatitis B. International Journal of Infectious Diseases : IJID : Official Publication of the International Society For Infectious Diseases. 16(3).
- Kanda, T, et al. 2012. Efficacy of lamivudine or entecavir on acute exacerbation of chronic hepatitis B. International Journal of Medical Sciences. 9(1).
- Karatayli, E, et al. 2011. Molecular characterization of a novel entecavir mutation pattern isolated from a multi-drug refractory patient with chronic hepatitis B infection. Journal of Clinical Virology : the Official Publication of the Pan American Society For Clinical Virology. 53(2).
- Keller, AN, et al. 2017. Drugs and drug-like molecules can modulate the function of mucosal-associated invariant T cells. Nature Immunology. 18(4).
- Kim, HJ, et al. 2011. The influence of YMDD mutation patterns on clinical outcomes in patients with adefovir add-on lamivudine combination treatment. Liver International : Official Journal of the International Association For the Study of the Liver. 32(2).
- Kim, SS, et al. 2011. Adefovir-based combination therapy with entecavir or lamivudine for patients with entecavir-refractory chronic hepatitis B. Journal of Medical Virology. 84(1).
- Kuklenyik, Z, et al. 2009. On-line coupling of anion exchange and ion-pair chromatography for measurement of intracellular triphosphate metabolites of reverse transcriptase inhibitors. Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences. 877(29).
- Kurokawa, M, et al. 2012. Long-term effect of lamivudine treatment on the incidence of hepatocellular carcinoma in patients with hepatitis B virus infection. Journal of Gastroenterology. 47(5).
- Lada, O, et al. 2011. Long-term outcome of primary non-responders to tenofovir therapy in HIV/HBV-co-infected patients: impact of HBV genotype G. Liver International : Official Journal of the International Association For the Study of the Liver. 32(1).
- Lee, SH, et al. 2011. Pre-existing YMDD mutants in treatment-naïve patients with chronic hepatitis B are not selected during lamivudine therapy. Journal of Medical Virology. 84(2).
- Lin, CL, et al. 2011. Identification of hepatitis B virus rtS117F substitution as a compensatory mutation for rtM204I during lamivudine therapy. The Journal of Antimicrobial Chemotherapy. 67(1).
- Matta, MK, et al. 2012. A novel LC-MS/MS method for simultaneous quantification of tenofovir and lamivudine in human plasma and its application to a pharmacokinetic study. Biomedical Chromatography : BMC. 26(10).
- Milpied-Homsi, B, et al. 2014. Antiviral drug allergy. Immunology and Allergy Clinics of North America. 34(3).
- Nishijima, T, et al. 2012. Efficacy and safety of once-daily ritonavir-boosted darunavir and abacavir/lamivudine for treatment-naïve patients: a pilot study. AIDS (London, England). 26(5).
- Ostrov, DA, et al. 2018. Methyldopa blocks MHC class II binding to disease-specific antigens in autoimmune diabetes. The Journal of Clinical Investigation. 128(5).
- Papatheodoridis, GV, et al. 2002. Nucleoside analogues for chronic hepatitis B: antiviral efficacy and viral resistance. The American Journal of Gastroenterology. 97(7).
- Rower, JE, et al. 2011. Validation of a sensitive LC/MS/MS method for the determination of zidovudine and lamivudine in human plasma. Biomedical Chromatography : BMC. 26(1).
- Shahabadi, N, et al. 2011. Interaction of calf thymus DNA with the antiviral drug Lamivudine. DNA and Cell Biology. 31(1).
- Zhao, J, et al. 2011. The natural YMDD mutations of hepatitis B virus in Western China. Scandinavian Journal of Infectious Diseases. 44(1).
- Zhong, Y, et al. 2011. Synthesis, stability and pharmacological evaluation of a novel codrug consisting of lamivudine and ursolic acid. European Journal of Pharmaceutical Sciences : Official Journal of the European Federation For Pharmaceutical Sciences. 45(1-2).