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PHR1365

Lamivudine

Name: Lamivudine
Brand: SIAL

Pharmaceutical Secondary Standard; Certified Reference Material

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Synonym(s):

Lamivudine, 2′,3′-Dideoxy-3′-thiacytidine, 3TC, Epivir, Epivir-HBV, Heptovir, Zeffix

Empirical Formula (Hill Notation):

C₈H₁₁N₃O₃S

CAS Number:

134678-17-4

Molecular Weight:

229.26

MDL number:

MFCD00869739

PubChem Substance ID:

329823344

NACRES:

NA.24

grade

certified reference material
pharmaceutical secondary standard

Quality Level

300

Agency

traceable to BP 802
traceable to Ph. Eur. Y0000425
traceable to USP 1356836

API family

lamivudine

CofA

current certificate can be downloaded

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

SMILES string

NC1=NC(=O)N(C=C1)[C@@H]2CS[C@H](CO)O2

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

InChI key

JTEGQNOMFQHVDC-NKWVEPMBSA-N

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Related Categories

Analytical Reference Standards

Certified Reference Materials

Pharmacopeia & Metrological Institute Standards

General description

Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Lamivudine is a synthetic nucleoside analog that shows potential action against human immunodeficiency virus (HIV). It is one of the front line therapies used to treat HIV infection.

Application

Lamivudine may be used as a pharmaceutical reference standard for the determination of the analyte in pharmaceutical formulations and serum samples by chromatography and spectrophotometry techniques.

These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.

Biochem/physiol Actions

Lamivudine is a potent nucleoside analog reverse transcriptase inhibitor (nRTI). It is an analogue of cytidine, and can inhibit both types (1 and 2) of HIV reverse transcriptase as well as the reverse transcriptase of hepatitis B. It needs to be phosphorylated to its triphosphate form before it is active. 3TC-triphosphate also inhibits cellular DNA polymerase.

Analysis Note

These secondary standards offer multi-traceability to the USP, EP (PhEur) and BP primary standards, where they are available.

Other Notes

This Certified Reference Material (CRM) is produced and certified in accordance with ISO 17034 and ISO/IEC 17025. All information regarding the use of this CRM can be found on the certificate of analysis.

Footnote

To see an example of a Certificate of Analysis for this material enter LRAA1469 in the slot below. This is an example certificate only and may not be the lot that you receive.

Recommended products

Find a digital Reference Material for this product available on our online platform ChemisTwin® for NMR. You can use this digital equivalent on ChemisTwin® for your sample identity confirmation and compound quantification (with digital external standard). An NMR spectrum of this substance can be viewed and an online comparison against your sample can be performed with a few mouseclicks. Learn more here and start your free trial.

related product

Product No.

Description

Pricing

Signal Word

Warning

Hazard Statements

H361

Precautionary Statements

P201 - P308 + P313

Hazard Classifications

Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Simultaneous separation and determination of lamivudine and zidovudine in pharmaceutical formulations using the HPTLC method

Habte G, et al.

Analytical Letters, 42(11), 1552-1570 (2009)

Determination of lamivudine and zidovudine in binary mixtures using first derivative spectrophotometric, first derivative of the ratio-spectra and high-performance liquid chromatography-UV methods

Uslu B and Ozkan SA

Analytica Chimica Acta, 466(1), 175-185 (2002)

Simultaneous determination of zidovudine and lamivudine in human serum using HPLC with tandem mass spectrometry

Kenney KB, et al.

Journal of Pharmaceutical and Biomedical Analysis, 22(6), 967-983 (2000)

Simultaneous determination of lamivudine and stavudine in antiretroviral fixed dose combinations by first derivative spectrophotometry and high performance liquid chromatography

Kapoor N, et al.

Journal of Pharmaceutical and Biomedical Analysis, 41(3), 761-765 (2006)

The naturally occurring YMDD mutation among patients chronically infected HBV and untreated with lamivudine: a systematic review and meta-analysis.

Youwen Tan et al.

PloS one, 7(3), e32789-e32789 (2012-04-06)

Several recent reports have demonstrated that tyrosine (Y)-methionine (M)-aspartic acid (D)-aspartic acid (D) (YMDD) motif mutations can naturally occur in chronic HBV patients without antiviral treatment such as lamivudine therapy. This paper aims to assess the overall spontaneous incidence and

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