Lamivudine
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MedKoo CAT#: 318085

CAS#: 134678-17-4

Description: Lamivudine is an antiretroviral medication used to prevent and treat HIV/AIDS and used to treat chronic hepatitis B. It is of the nucleoside analog reverse transcriptase inhibitor (NRTI) class. Lamivudine is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.

Chemical Structure

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Lamivudine
CAS# 134678-17-4
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318085
Name: Lamivudine
CAS#: 134678-17-4
Chemical Formula: C8H11N3O3S
Exact Mass: 229.05
Molecular Weight: 229.256
Elemental Analysis: C, 41.91; H, 4.84; N, 18.33; O, 20.94; S, 13.99

Price and Availability

Size Price Availability Quantity
1g USD 90 Ready to ship
2g USD 150 Ready to ship
5g USD 300 Ready to ship
10g USD 450 2 Weeks
25g USD 850 2 Weeks
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Related CAS #: 134678-17-4   160552-55-6 (sulfoxide)   160552-54-5 (R-sulfoxide)   131086-22-1 (±-trans)  

Synonym: Lamivudine, 3TC, Epivir, Zeffix, Heptovir, BCH-189

IUPAC/Chemical Name: 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one

InChi Key: JTEGQNOMFQHVDC-NKWVEPMBSA-N

InChi Code: 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

SMILES Code: O=C1N=C(N)C=CN1[C@@H]2CS[C@H](CO)O2

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Certificate of Analysis:
View CoA: current batch, Lot#C20B02B03
Safety Data Sheet (SDS):
View Safety Data Sheet (SDS)
Instruction:
View handling instruction
Biological target: Lamivudine (BCH-189) is a nucleoside reverse transcriptase inhibitors (NRTIs) that inhibits HIV reverse transcriptase 1/2 and also the reverse transcriptase of hepatitis B virus.
In vitro activity: The aim of this study was to investigate if the nucleoside analogue lamivudine (LAM), a potent inhibitor of HBV replication, could restore the function of dendritic cells derived from patients with chronic hepatitis B (CHB) in an Asian population. Dendritic cells (DCs) derived from mononuclearcytes of patients with chronic HBV infection were cultured in the presence of IL-4, granulocytemacrophage colony-stimulating factors (GM-CSF) and gradient concentrations of LAM (0-2 mmol/L). The expression of CD1α on DC treated with 0.5 mmol/L LAM (LAM-DC 0.5 mmol/L) was significantly higher than that of DC untreated with LAM (54.1 ± 4.21 vs 33.57 ± 3.14, P < 0.05), and so was the expression of CD83 (20.24 ± 2.51 vs 12.83 ± 2.12, P < 0.05) as well as the expression of HLA-DR (74.5 ± 5.16 vs 52.8 ± 2.51, P < 0.05). Compared with control group, LAM-DC group (0.5 mmol/L) secreted significantly more IL-12 (910 ± 91.5 vs 268 ± 34.3 pg/mL, P < 0.05), had lower levels of IL-6 in the culture supernatant (28 ± 2.6 vs 55 ± 7.36 pg/mL, P < 0.05), markedly enhanced the stimulatory capacity in the allogeneic mixed leukocyte reaction (MLR) (1.87 ± 0.6 vs 1.24 ± 0.51, P < 0.05). . This indicates that, in addition to its potent anti-HBV replication role, LAM is able to modify the biological activities of DCs derived from patients with CHB infection. Therefore, LAM can be a potential candidate as an immunoregulatory therapeutic remedy used in the treatment of patients with CHB infection. World J Gastroenterol. 2007 Sep 14;13(34):4641-5. https://pubmed.ncbi.nlm.nih.gov/17729422/
In vivo activity: The modulatory effects of 3TC (lamivudine) on Alu RNA-induced IL-18 and IL-1β expression were examined in mouse RPE (retinal pigment epithelium) by a subretinal injection of Alu RNA and concomitant intravitreal injection of equimolar 3TC or 3,4-(M)CA. Similar to effects in cultured human RPE cells, 3TC suppressed Alu RNA-induced IL-18 expression by 42.1 ± 8.7% (P = 0.006) and IL-1β expression by 57.8 ± 12.4% (P = 0.030) compared with that observed by 3,4-(M)CA treatment (Figs. 2A and B). Fundus imaging of mouse eye at 7 days after subretinal transfection and intravitreal injection of 3,4-(M)CA revealed substantial retinal/RPE degeneration, whereas intravitreal injection of 3TC substantially reduced Alu RNA-induced retinal/RPE degeneration (Figs. 2C and D). This data suggests that Alu RNA accumulation contributes to RPE cell senescence in age-related macular degeneration and that this pathogenic process can be suppressed by 3TC. Transl Vis Sci Technol. 2020 Jul; 9(8): 1. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7422901/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 38.0 165.75
H2O 47.0 205.01

Preparing Stock Solutions

The following data is based on the product molecular weight 229.26 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Zheng PY, Zhang DY, Lu GF, Yang PC, Qi YM, Wang BS. Effects of lamivudine on the function of dendritic cells derived from patients with chronic hepatitis B virus infection. World J Gastroenterol. 2007 Sep 14;13(34):4641-5. doi: 10.3748/wjg.v13.i34.4641. PMID: 17729422; PMCID: PMC4611843. 2. Yamada K, Kaneko H, Shimizu H, Suzumura A, Namba R, Takayama K, Ito S, Sugimoto M, Terasaki H. Lamivudine Inhibits Alu RNA-induced Retinal Pigment Epithelium Degeneration via Anti-inflammatory and Anti-senescence Activities. Transl Vis Sci Technol. 2020 Jul 1;9(8):1. doi: 10.1167/tvst.9.8.1. PMID: 32855848; PMCID: PMC7422901 3. Yamada K, Kaneko H, Shimizu H, Suzumura A, Namba R, Takayama K, Ito S, Sugimoto M, Terasaki H. Lamivudine Inhibits Alu RNA-induced Retinal Pigment Epithelium Degeneration via Anti-inflammatory and Anti-senescence Activities. Transl Vis Sci Technol. 2020 Jul 1;9(8):1. doi: 10.1167/tvst.9.8.1. PMID: 32855848; PMCID: PMC7422901. 4. Wang Y, Xu S, Li S, Su H, Chang S, Li Y, Sun X, Zhao P, Cui Z. Lamivudine Inhibits the Replication of ALV-J Associated Acutely Transforming Virus and its Helper Virus and Tumor Growth In vitro and In vivo. Front Microbiol. 2015 Dec 1;6:1306. doi: 10.3389/fmicb.2015.01306. PMID: 26648914; PMCID: PMC4664723.
In vitro protocol: 1. Zheng PY, Zhang DY, Lu GF, Yang PC, Qi YM, Wang BS. Effects of lamivudine on the function of dendritic cells derived from patients with chronic hepatitis B virus infection. World J Gastroenterol. 2007 Sep 14;13(34):4641-5. doi: 10.3748/wjg.v13.i34.4641. PMID: 17729422; PMCID: PMC4611843. 2. Yamada K, Kaneko H, Shimizu H, Suzumura A, Namba R, Takayama K, Ito S, Sugimoto M, Terasaki H. Lamivudine Inhibits Alu RNA-induced Retinal Pigment Epithelium Degeneration via Anti-inflammatory and Anti-senescence Activities. Transl Vis Sci Technol. 2020 Jul 1;9(8):1. doi: 10.1167/tvst.9.8.1. PMID: 32855848; PMCID: PMC7422901
In vivo protocol: 1. Yamada K, Kaneko H, Shimizu H, Suzumura A, Namba R, Takayama K, Ito S, Sugimoto M, Terasaki H. Lamivudine Inhibits Alu RNA-induced Retinal Pigment Epithelium Degeneration via Anti-inflammatory and Anti-senescence Activities. Transl Vis Sci Technol. 2020 Jul 1;9(8):1. doi: 10.1167/tvst.9.8.1. PMID: 32855848; PMCID: PMC7422901. 2. Wang Y, Xu S, Li S, Su H, Chang S, Li Y, Sun X, Zhao P, Cui Z. Lamivudine Inhibits the Replication of ALV-J Associated Acutely Transforming Virus and its Helper Virus and Tumor Growth In vitro and In vivo. Front Microbiol. 2015 Dec 1;6:1306. doi: 10.3389/fmicb.2015.01306. PMID: 26648914; PMCID: PMC4664723.

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1: Greig SL, Deeks ED. Abacavir/dolutegravir/lamivudine single-tablet regimen: a review of its use in HIV-1 infection. Drugs. 2015 Apr;75(5):503-14. doi: 10.1007/s40265-015-0361-6. Review. Erratum in: Drugs. 2015 Apr;75(5):561. PubMed PMID: 25698454.

2: Kasırga E. Lamivudine resistance in children with chronic hepatitis B. World J Hepatol. 2015 Apr 28;7(6):896-902. doi: 10.4254/wjh.v7.i6.896. Review. PubMed PMID: 25937866; PubMed Central PMCID: PMC4411531.

3: Li H, Zhang HM, Chen LF, Chen YQ, Chen L, Ren H, Hu HD. Prophylactic lamivudine to improve the outcome of HBsAg-positive lymphoma patients during chemotherapy: a systematic review and meta-analysis. Clin Res Hepatol Gastroenterol. 2015 Feb;39(1):80-92. doi: 10.1016/j.clinre.2014.07.010. Epub 2014 Sep 4. Review. PubMed PMID: 25199680.

4: Zhang YL, Zhang J, Cui LY. Interferon-α combined with lamivudine versus lamivudine monotherapy for the emergence of YMDD mutations in chronic hepatitis B infection: a meta-analysis of randomized controlled trials. Hepatogastroenterology. 2015 Jan-Feb;62(137):133-9. Review. PubMed PMID: 25911883.

5: He M, Wu Y, Wang M, Chen W, Yuan W, Jiang J. The Clinical Value of Oxymatrine in Preventing Lamivudine Induced YMDD Mutation: A Meta-Analysis. Evid Based Complement Alternat Med. 2015;2015:971616. doi: 10.1155/2015/971616. Epub 2015 Oct 5. Review. PubMed PMID: 26508988; PubMed Central PMCID: PMC4609836.

6: Cruciani M, Malena M. Combination dolutegravir-abacavir-lamivudine in the management of HIV/AIDS: clinical utility and patient considerations. Patient Prefer Adherence. 2015 Feb 17;9:299-310. doi: 10.2147/PPA.S65199. eCollection 2015. Review. PubMed PMID: 25733823; PubMed Central PMCID: PMC4337619.

7: Ehrhardt S, Xie C, Guo N, Nelson K, Thio CL. Breastfeeding while taking lamivudine or tenofovir disoproxil fumarate: a review of the evidence. Clin Infect Dis. 2015 Jan 15;60(2):275-8. doi: 10.1093/cid/ciu798. Epub 2014 Oct 13. Review. PubMed PMID: 25313254.

8: Fernandez-Montero JV, Barreiro P, Labarga P, De Mendoza C, Soriano V. Dolutegravir, abacavir and lamivudine as HIV therapy. Expert Opin Pharmacother. 2014 May;15(7):1051-7. doi: 10.1517/14656566.2014.913023. Review. PubMed PMID: 24754315.

9: Liu F, Wang X, Wei F, Hu H, Zhang D, Hu P, Ren H. Efficacy and resistance in de novo combination lamivudine and adefovir dipivoxil therapy versus entecavir monotherapy for the treatment-naive patients with chronic hepatitis B: a meta-analysis. Virol J. 2014 Mar 28;11:59. doi: 10.1186/1743-422X-11-59. Review. PubMed PMID: 24673792; PubMed Central PMCID: PMC3986697.

10: Fabrizi F, Mangano S, Stellato T, Martin P, Messa P. Lamivudine treatment for hepatitis B in dialysis population : case reports and literature review. Acta Gastroenterol Belg. 2013 Dec;76(4):423-8. Review. PubMed PMID: 24592546.

11: Huang ZB, Zhao SS, Huang Y, Dai XH, Zhou RR, Yi PP, Chen RC, Li WT, Zhang BX, Li N, Fan XG. Comparison of the efficacy of Lamivudine plus adefovir versus entecavir in the treatment of Lamivudine-resistant chronic hepatitis B: a systematic review and meta-analysis. Clin Ther. 2013 Dec;35(12):1997-2006. doi: 10.1016/j.clinthera.2013.10.002. Epub 2013 Nov 13. Review. PubMed PMID: 24238791.

12: Ye XG, Su QM. Effects of entecavir and lamivudine for hepatitis B decompensated cirrhosis: meta-analysis. World J Gastroenterol. 2013 Oct 21;19(39):6665-78. doi: 10.3748/wjg.v19.i39.6665. Review. PubMed PMID: 24151397; PubMed Central PMCID: PMC3801384.

13: Shey MS, Kongnyuy EJ, Alobwede SM, Wiysonge CS. Co-formulated abacavir-lamivudine-zidovudine for initial treatment of HIV infection and AIDS. Cochrane Database Syst Rev. 2013 Mar 28;3:CD005481. doi: 10.1002/14651858.CD005481.pub3. Review. PubMed PMID: 23543540.

14: Chao DC, Hu KQ. Update on rescue therapies in patients with lamivudine-resistant chronic hepatitis B. Drug Des Devel Ther. 2013 Aug 20;7:777-88. doi: 10.2147/DDDT.S33947. eCollection 2013. Review. PubMed PMID: 23990707; PubMed Central PMCID: PMC3753145.

15: Jiang H, Wang J, Zhao W. Lamivudine versus telbivudine in the treatment of chronic hepatitis B: a systematic review and meta-analysis. Eur J Clin Microbiol Infect Dis. 2013 Jan;32(1):11-8. doi: 10.1007/s10096-012-1723-6. Epub 2012 Aug 17. Review. PubMed PMID: 22898727.

16: Ford N, Shubber Z, Hill A, Vitoria M, Doherty M, Mills EJ, Gray A. Comparative efficacy of Lamivudine and emtricitabine: a systematic review and meta-analysis of randomized trials. PLoS One. 2013 Nov 11;8(11):e79981. doi: 10.1371/journal.pone.0079981. eCollection 2013. Review. PubMed PMID: 24244586; PubMed Central PMCID: PMC3823593.

17: Liang J, Tang YF, Wu FS, Deng X. Entecavir versus lamivudine for the treatment of chronic hepatitis B: a systematic review. Pharmazie. 2012 Nov;67(11):883-90. Review. PubMed PMID: 23210236.

18: Chen Y, Ju T. Comparative meta-analysis of adefovir dipivoxil monotherapy and combination therapy of adefovir dipivoxil and lamivudine for lamivudine-resistant chronic hepatitis B. Int J Infect Dis. 2012 Mar;16(3):e152-8. doi: 10.1016/j.ijid.2011.11.006. Epub 2012 Jan 4. Review. PubMed PMID: 22226087.

19: Tan Y, Ding K, Su J, Trinh X, Peng Z, Gong Y, Chen L, Cui Q, Lei N, Chen X, Yu R. The naturally occurring YMDD mutation among patients chronically infected HBV and untreated with lamivudine: a systematic review and meta-analysis. PLoS One. 2012;7(3):e32789. doi: 10.1371/journal.pone.0032789. Epub 2012 Mar 27. Review. PubMed PMID: 22479339; PubMed Central PMCID: PMC3314000.

20: Zhong JH, Li le Q, Wu LC. Lamivudine with or without adefovir dipivoxil for postoperative hepatocellular carcinoma. Cochrane Database Syst Rev. 2011 Dec 7;(12):CD008713. doi: 10.1002/14651858.CD008713.pub2. Review. PubMed PMID: 22161435.