[CAS NO. 134678-17-4]  Lamivudine

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PRODUCTS SPECIFICATIONS [134678-17-4]

Catalog
HY-B0250
Brand
MCE
CAS
134678-17-4

DESCRIPTION [134678-17-4]

Overview

MDLMFCD00869739
Molecular Weight229.26
Molecular FormulaC8H11N3O3S
SMILESOC[C@H]1SC[C@@H](N2C(N=C(N)C=C2)=O)O1

For research use only. We do not sell to patients.


Summary

Lamivudine (BCH-189) is an orally active nucleoside reverse transcriptase inhibitor (NRTI). Lamivudine can inhibit HIV reverse transcriptase 1/2 and also the reverse transcriptase of hepatitis B virus . Lamivudine salicylate can penetrate the CNS [1] [2] .


In Vitro

Lamivudine (1 μM) is potent inhibitor of hepatitis B virus (HBV) replication, shows antiviral activity in primary duck hepatocyte (PDH) cultures derived from ducklings congenitally infected with the duck hepatitis B virus (DHBV) [1] .
Lamivudine (0-20 μM; 2, 4, 9 d) inhibits DHBV replication with 50% inhibitory concentration of 0.55 μM [1] .
Lamivudine, combinded with penciclovir (9-[2-hydroxy-1-(hydroxymethyl)ethoxymethyl]guanine [PCV]), (1 μM; 2, 4, 9 d) shows synergistic effect, acts potent function in reducing the normally recalcitrant viral covalently closed circular (CCC) DNA form of DHBV [1] .

MCE has not independently confirmed the accuracy of these methods. They are for reference only.


In Vivo

Lamivudine (20-500 mg/kg/d; p.o.; 15 or 45 d) causes oxidative stress and is toxic to rat liver [2] .
Lamivudine (50 mg/kg; i.p.; single dose) penetrates well in CNS and localizes in brain regions susceptible to HIV neurodegeneration in rat [3] .
Pharmacokinetic Parameters of Lamivudine in HIV-infected Rats [3]

Parameter C max (μg/mL) T max (h) T 1/2 (h) AUC (h·ng/mL)
Plasma 25,846 0.25 0.68 22,172
Brain 272 0.5 1.2 967
Pharmacokinetic data measured over a 24-h period, sampling was done at 0.25, 0.5, 1.0, 2.0, 4.0, 6.0, 8.0, and 24.0 h postdose.

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model: Wistar female rats [2]
Dosage: 20-500 mg/kg/day
Administration: Oral gavage; single or repeated dose; 15 or 45 days
Result: Increased activities of the aminotransferases (ALT and AST), γ-glutamyltransferase (GGT) and total protein concentration in serum at 500 mg/kg dose.
Increased activities of glutathione S-transferase (GST), GGT and superoxide dismutase (SOD) as well as concentrations of malondialdehyde (MDA) and protein at 20 mg/kg dose.
Caused multifocal lymphocyte population and hepatocyte edema degeneration in hepatic sinusoids of chickens.

Clinical Trial

NCT Number Sponsor Condition Start Date Phase
NCT00102206 National Institute of Allergy and Infectious Diseases (NIAID)|Eunice Kennedy Shriver National Institute of Child Health and Human Development (NICHD)
HIV Infections
Phase 2
NCT00002430 Merck Sharp & Dohme LLC|NIH AIDS Clinical Trials Information Service
HIV Infections
Not Applicable
NCT04054089 Cristina Mussini|University of Modena and Reggio Emilia
HIV Infections
September 2019 Phase 4

Appearance

Solid


Shipping

Room temperature in continental US; may vary elsewhere.


Storage

Powder -20°C 3 years
4°C 2 years
In solvent -80°C 6 months
-20°C 1 month

Solvent & Solubility

In Vitro:

DMSO : 50 mg/mL ( 218.09 mM ; Need ultrasonic)

H 2 O : ≥ 50 mg/mL ( 218.09 mM )

* "≥" means soluble, but saturation unknown.

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 4.3619 mL 21.8093 mL 43.6186 mL
5 mM 0.8724 mL 4.3619 mL 8.7237 mL
10 mM 0.4362 mL 2.1809 mL 4.3619 mL
* Please refer to the solubility information to select the appropriate solvent.
In Vivo:
  • 1.

    Add each solvent one by one: PBS

    Solubility: 100 mg/mL (436.19 mM); Clear solution; Need ultrasonic

  • 2.

    Add each solvent one by one: 10% DMSO >> 40% PEG300 >> 5% Tween-80 >> 45% saline

    Solubility: ≥ 2.5 mg/mL (10.90 mM); Clear solution

  • 3.

    Add each solvent one by one: 10% DMSO >> 90% (20% SBE-β-CD in saline)

    Solubility: ≥ 2.5 mg/mL (10.90 mM); Clear solution

  • 4.

    Add each solvent one by one: 10% DMSO >> 90% corn oil

    Solubility: ≥ 2.5 mg/mL (10.90 mM); Clear solution

* All of the co-solvents are available by MCE.


Synonyms

2(1H)-Pyrimidinone, 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-
2(1H)-Pyrimidinone, 4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-, (2R-cis)-
1,3-Oxathiolane, 2(1H)-pyrimidinone deriv.
4-Amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone
(-)-BCH 189
GR 109714X
Lamivudine
BCH 189, (-)-
(-)-2′-Deoxy-3′-thiacytidine
β-L-3′-Thia-2′,3′-dideoxycytidine
Epivir
Zeffix
Heptovir
Epivir HBV
L-SddC
Zefix
Hepitec
β-L-2′,3′-Dideoxy-3′-thiacytidine
3TC
Lamivir
Heptodin
Virolam
2-Hydroxymethyl-5-(cytosin-1-yl)-1,3-oxathiolane
cis(-)-2-Hydroxymethyl-5-(cytosin-1-yl)-1,3-oxathiolane
Lamidine
29: PN: WO2016077321 SEQID: 29 claimed sequence
Hiviral