Lamivudine

Base Information

• Chemical Name: Lamivudine
• CAS No.: 134678-17-4
• Deprecated CAS: 480434-79-5,1117764-41-6
• Molecular Formula: C8H11N3O3S
• Molecular Weight: 229.26
• Hs Code.: 29349990
• UNII: 2T8Q726O95
• DSSTox Substance ID: DTXSID7023194
• Nikkaji Number: J457.051K
• Wikipedia: Lamivudine
• Wikidata: Q422631
• NCI Thesaurus Code: C1471
• RXCUI: 68244
• Metabolomics Workbench ID: 43017
• ChEMBL ID: CHEMBL141
• Mol file: 134678-17-4.mol

Synonyms:2',3' Dideoxy 3' thiacytidine;2',3'-Dideoxy-3'-thiacytidine;2(1H)-Pyrimidinone, 4-amino-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-, (2R-cis)-;3TC Lamivudine;BCH 189;BCH-189;BCH189;Epivir;GR 109714X;GR-109714X;GR109714X;Lamivudine;Lamivudine, (+)-cis-;Lamivudine, (+-)-trans-;Lamivudine, (2S-cis)-Isomer;Lamivudine, 3TC

Chemical Property of Lamivudine

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 4.91E-11mmHg at 25°C
• Melting Point: 177 °C
• Refractive Index: -142 ° (C=1, MeOH)
• Boiling Point: 475.4 °C at 760mmHg
• PKA: 13.83±0.10(Predicted)
• Flash Point: 241.3 °C
• PSA: 115.67000
• Density: 1.73 g/cm³
• LogP: -0.01290
• Storage Temp.: Freezer
• Solubility.: water: soluble10mg/mL, clear
• Water Solubility.: 70g/L(temperature not stated)
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 229.05211239
• Heavy Atom Count: 15
• Complexity: 331

Purity/Quality:

99%min ^*data from raw suppliers

Lamivudine ^*data from reagent suppliers

Safty Information:

• Statements: 63-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiviral Agents
• Canonical SMILES: C1C(OC(S1)CO)N2C=CC(=NC2=O)N
• Isomeric SMILES: C1[C@H](O[C@H](S1)CO)N2C=CC(=NC2=O)N
• Recent ClinicalTrials: Pilot Study to Investigate the Safety and Feasibility of AntiRetroviral Therapy for Alzheimer's Disease
• Recent EU Clinical Trials: A randomised non-inferiority trial with nested PK to assess DTG/3TC fixed dose formulations for the maintenance of virological suppression in children
• Recent NIPH Clinical Trials: Randomized control study for the effectiveness of tenofovir in nucleoside/nucleotide analogue-treated patients with chronic HBV infection
• Description: Lamivudine is a new generation orally active nucleoside analog launched in the U.S.A. for use in combination with zidovudine (AZT) as a first-line therapy for patients with HIV infection. Lamivudine is rapidly converted to phosphorylated metabolites in the body which act as inhibitors and chain terminators of HIV reverse transcriptase (RT), the enzyme required for the replication of the HIV genome. Lamivudine has similar inhibitory potency to RT as AZT but is 10 times less toxic and is active against AZT-resistant strains of HIV.
• Uses: Lamivudine is used along with other medications to treat human immunodeficiency virus (HIV) infection in adults and children 3 months of age and older. Lamivudine (Epivir-HBV) is used to treat hepatitis B infection. Lamivudine is in a class of medications called nucleoside reverse transcriptase inhibitors (NRTIs). It works by decreasing the amount of HIV and hepatitis B in the blood.
• Clinical Use: Lamivudine is indicated for the treatment of HIV when used in combination with other antiretroviral agents.A lower dose than that used to treat HIV is approved for the treatment of HBV.
• Drug interactions: There are potentially dangerous interactions with other drugs when used in combination.Antimicrobials: trimethoprim inhibits the excretion of lamivudine.Antivirals: avoid concomitant use with foscarnet, emtricitabine, and IV ganciclovirCytotoxic drugs: avoid concomitant use with clarithromycin.Orlistat: absorption may be reduced by orlistat.

Technology Process of Lamivudine

There total 73 articles about Lamivudine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.63%

lamivudine salicyclic acid salt (173522-96-8) → lamivudine (134678-17-4)

Guidance literature:

With triethylamine; In ethanol; at 50 ℃; for 1h;

Reference yield: 90.0%

C7H5NO4*C8H11N3O3S → lamivudine (134678-17-4)

Guidance literature:

With triethylamine; In ethanol; at 70 - 75 ℃; Inert atmosphere; Industry scale;

Reference yield: 87.17%

(2R,5S)-5-(4-amino-2-oxo-pyrimidin-1-yl)-1,3-oxathiolane-2-methyl-(2'S-isopropyl-5'R-methyl-1'R-cyclohexyl)-carbonic acid diester (1012053-56-3) → lamivudine (134678-17-4)

Guidance literature:

With potassium carbonate; In methanol; at 0 - 25 ℃; for 3h;

upstream raw materials:

cis-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-(cytosin-1'-yl)-1,3-oxathiolane

cis-2-benzoyloxymethyl-5-(N'4-acetylcytosin-1'-yl)-1,3-oxathiolane

cis/trans-2-benzoyloxymethyl-5-(cytosin-1'-yl)-1,3-oxathiolane

L-menthyl 5-cytosin-1-yl-1,3-oxathiolane-2-carboxylate

Downstream raw materials:

lamivudine

lamivudine salicyclic acid salt

Lamivudine sulfoxide

Refernces

• 1、 Mandala, Devender,Chada, Sravanthi,Watts, Paul. "Semi-continuous multi-step synthesis of lamivudine". . p. 3444 - 3454. Retrieved 2017.
• 2、 Aher, Umesh P.,Jadhav, Harishchandra S.,Jayashree, B. S.,Shenoy, Gautham G.,Singh, Girij P.,Srivastava, Dhananjai. "Large-Scale Stereoselective Synthesis of 1,3-Oxathiolane Nucleoside, Lamivudine, via ZrCl4-Mediated N-Glycosylation". . p. 387 - 397. Retrieved 2020.
• 3、 Mear, Sarah Jane,Nguyen, Long V.,Rochford, Ashley J.,Jamison, Timothy F.. "Synthesis of (±)-Emtricitabine and (±)-Lamivudine by Chlorotrimethylsilane-Sodium Iodide-Promoted Vorbrüggen Glycosylation". . p. 2887 - 2897. Retrieved 2022/02/07.