Lamivudine, (+/-)-trans-

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

MedKoo CAT#: 598251

CAS#: 131086-22-1 (±-trans)

Description: Lamivudine, (+/-)-trans- is a reverse transcriptase inhibitor and zalcitabine analog in which a sulfur atom replaces the 3' carbon of the pentose ring. It is used to treat Human Immunodeficiency Virus Type 1 (HIV-1) and hepatitis B (HBV).

Chemical Structure

img
Lamivudine, (+/-)-trans-
CAS# 131086-22-1 (±-trans)
Instruction

Theoretical Analysis

MedKoo Cat#: 598251
Name: Lamivudine, (+/-)-trans-
CAS#: 131086-22-1 (±-trans)
Chemical Formula: C8H11N3O3S
Exact Mass: 229.05
Molecular Weight: 229.250
Elemental Analysis: C, 41.91; H, 4.84; N, 18.33; O, 20.94; S, 13.98

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

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

Synonym: Lamivudine, (+/-)-trans-; Lamivudine specified impurity B;

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

InChi Key: JTEGQNOMFQHVDC-BQBZGAKWSA-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

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 229.25 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.

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:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Heipertz RA Jr, Miller TG, Kelley CM, Delaney WE 4th, Locarnini SA, Isom HC. In vitro study of the effects of precore and lamivudine-resistant mutations on hepatitis B virus replication. J Virol. 2007 Apr;81(7):3068-76. Epub 2007 Jan 10. PubMed PMID: 17215289; PubMed Central PMCID: PMC1866076.

2: Xie Y, Liu Q, Wang CH, Tang CW. [Inhibition of transcription and expression of X gene by lamivudine]. Zhonghua Gan Zang Bing Za Zhi. 2005 Jan;13(1):27-30. Chinese. PubMed PMID: 15670487.

3: Bottecchia M, Ikuta N, Niel C, Araujo NM, O KM, Gomes SA. Lamivudine resistance and other mutations in the polymerase and surface antigen genes of hepatitis B virus associated with a fatal hepatic failure case. J Gastroenterol Hepatol. 2008 Jan;23(1):67-72. doi: 10.1111/j.1440-1746.2007.05238.x. PubMed PMID: 18171343.

4: Luo YY, Tao Y, Cai XF, Zhang WL, Long QX, Guo H, Huang AL, Hu JL. A novel method for nucleos(t)ide analogues susceptibility assay of hepatitis B virus by viral polymerase transcomplementation. Antiviral Res. 2016 Feb;126:99-107. doi: 10.1016/j.antiviral.2015.12.009. Epub 2015 Dec 29. PubMed PMID: 26738784.

5: Cheng AS, Chan HL, Leung WK, To KF, Go MY, Chan JY, Liew CT, Sung JJ. Expression of HBx and COX-2 in chronic hepatitis B, cirrhosis and hepatocellular carcinoma: implication of HBx in upregulation of COX-2. Mod Pathol. 2004 Oct;17(10):1169-79. PubMed PMID: 15218507.

6: Xie Y, Tang CW, Wang CH. [Effect of HBV X gene transfection on octreotide-inhibited growth of hepatocellular carcinoma cell line HepG2]. Ai Zheng. 2005 Aug;24(8):965-9. Chinese. PubMed PMID: 16086874.

7: Steinberg JL, Yeo W, Zhong S, Chan JY, Tam JS, Chan PK, Leung NW, Johnson PJ. Hepatitis B virus reactivation in patients undergoing cytotoxic chemotherapy for solid tumours: precore/core mutations may play an important role. J Med Virol. 2000 Mar;60(3):249-55. PubMed PMID: 10630955.

8: Lenci I, Tariciotti L, Baiocchi L, Manzia TM, Toti L, Craboledda P, Callea F, Angelico M, Tisone G. Primary yolk sac tumor of the liver: incidental finding in a patient transplanted for hepatocellular carcinoma. Transpl Int. 2008 Jun;21(6):598-601. doi: 10.1111/j.1432-2277.2008.00667.x. Epub 2008 Mar 18. PubMed PMID: 18363574.

9: Janssen HL, Higuchi H, Abdulkarim A, Gores GJ. Hepatitis B virus enhances tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) cytotoxicity by increasing TRAIL-R1/death receptor 4 expression. J Hepatol. 2003 Sep;39(3):414-20. PubMed PMID: 12927928.

10: Litwin S, Toll E, Jilbert AR, Mason WS. The competing roles of virus replication and hepatocyte death rates in the emergence of drug-resistant mutants: theoretical considerations. J Clin Virol. 2005 Dec;34 Suppl 1:S96-S107. PubMed PMID: 16461233.

11: Johnson MA, Moore KH, Yuen GJ, Bye A, Pakes GE. Clinical pharmacokinetics of lamivudine. Clin Pharmacokinet. 1999 Jan;36(1):41-66. Review. PubMed PMID: 9989342.

12: Coffin CS, Mulrooney-Cousins PM, Peters MG, van Marle G, Roberts JP, Michalak TI, Terrault NA. Molecular characterization of intrahepatic and extrahepatic hepatitis B virus (HBV) reservoirs in patients on suppressive antiviral therapy. J Viral Hepat. 2011 Jun;18(6):415-23. doi: 10.1111/j.1365-2893.2010.01321.x. PubMed PMID: 20626626; PubMed Central PMCID: PMC4142495.

13: Ugliarolo EA, Gagey D, Lantaño B, Moltrasio GY, Campos RH, Cavallaro LV, Moglioni AG. Synthesis and biological evaluation of novel homochiral carbocyclic nucleosides from 1-amino-2-indanols. Bioorg Med Chem. 2012 Oct 1;20(19):5986-91. doi: 10.1016/j.bmc.2012.07.028. Epub 2012 Jul 25. PubMed PMID: 22944333.

14: Pár A. [Hepatitis B virus (HBV) infection and hepatocarcinogenesis]. Orv Hetil. 2010 Jun 27;151(26):1045-53. doi: 10.1556/OH.2010.28881. Review. Hungarian. PubMed PMID: 20558351.

15: Rowland A, Mackenzie PI, Miners JO. Transporter-mediated uptake of UDP-glucuronic acid by human liver microsomes: assay conditions, kinetics, and inhibition. Drug Metab Dispos. 2015 Jan;43(1):147-53. doi: 10.1124/dmd.114.060509. Epub 2014 Nov 7. PubMed PMID: 25380805.

16: Rodriguez-Frías F, Tabernero D, Quer J, Esteban JI, Ortega I, Domingo E, Cubero M, Camós S, Ferrer-Costa C, Sánchez A, Jardí R, Schaper M, Homs M, Garcia-Cehic D, Guardia J, Esteban R, Buti M. Ultra-deep pyrosequencing detects conserved genomic sites and quantifies linkage of drug-resistant amino acid changes in the hepatitis B virus genome. PLoS One. 2012;7(5):e37874. doi: 10.1371/journal.pone.0037874. Epub 2012 May 30. PubMed PMID: 22666402; PubMed Central PMCID: PMC3364280.