Lamivudine sulfoxide, (R)- | CAS#160552-54-5 | reverse transcriptase inhibitor

MedKoo Cat#: 598256 | Name: Lamivudine sulfoxide, (R)-

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Lamivudine sulfoxide, (R)- is a metabolite of Lamivudine; a potent nucleoside reverse transcriptase inhibitor and antiviral agent. Lamivudine has been used for treatment of chronic hepatitis B.

Chemical Structure

Lamivudine sulfoxide, (R)-

CAS#160552-54-5 (R-sulfoxide)

Theoretical Analysis

MedKoo Cat#: 598256

Name: Lamivudine sulfoxide, (R)-

CAS#: 160552-54-5 (R-sulfoxide)

Chemical Formula: C8H11N3O4S

Exact Mass: 245.0470

Molecular Weight: 245.25

Elemental Analysis: C, 39.18; H, 4.52; N, 17.13; O, 26.09; S, 13.07

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Related CAS #

134678-17-4 160552-55-6 (sulfoxide) 160552-54-5 (R-sulfoxide) 131086-22-1 (±-trans)

Synonym

Lamivudine sulfoxide, (R)-; Lamivudine impurity H; GI-138870X; GI 138870X; GI138870X;

IUPAC/Chemical Name

4-amino-1-((2R,3R,5S)-2-(hydroxymethyl)-3-oxido-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one

InChi Key

LJMQAXFNQNADRZ-AJHSIVBLSA-N

InChi Code

InChI=1S/C8H11N3O4S/c9-5-1-2-11(8(13)10-5)6-4-16(14)7(3-12)15-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7+,16+/m0/s1

SMILES Code

O=C1N=C(N)C=CN1[C@@H](O[C@H]2CO)C[S@]2=O

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

Shelf Life

>3 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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Lamivudine sulfoxide, (R)- is a metabolite of Lamivudine; a potent nucleoside reverse transcriptase inhibitor and antiviral agent.

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, granulocyte-macrophage 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. Reference: 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. Reference: Transl Vis Sci Technol. 2020 Jul; 9(8): 1. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7422901/

Preparing Stock Solutions

The following data is based on the product molecular weight 245.25 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.

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:

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.

1: Plumb RS, Gray RD, Harker AJ, Taylor S. High-performance chromatographic assay for the sulphoxide metabolite of 2'-deoxy-3'-thiacytidine in human urine. J Chromatogr B Biomed Appl. 1996 Dec 13;687(2):457-61. PubMed PMID: 9017472.