ChemicalBook > CAS DataBase List > Lamivudine

Lamivudine

Product Name
Lamivudine
CAS No.
134678-17-4
Chemical Name
Lamivudine
Synonyms
3TC;4-AMino-1-[(2R,5S)-2-(hydroxyMethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyriMidinone;Epivir;Zefix;3¢L-SddC;Zeffix;,3¢Hepitec;Heptivir
CBNumber
CB1290608
Molecular Formula
C8H11N3O3S
Formula Weight
229.26
MOL File
134678-17-4.mol
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Lamivudine Property

Melting point:
177 °C
alpha 
D21 -135° (c = 0.38 in methanol)
Boiling point:
475.4±55.0 °C(Predicted)
Density 
1.73±0.1 g/cm3(Predicted)
refractive index 
-142 ° (C=1, MeOH)
Flash point:
9℃
storage temp. 
2-8°C
solubility 
water: soluble10mg/mL, clear
pka
13.83±0.10(Predicted)
form 
powder
color 
white to beige
Water Solubility 
70g/L(temperature not stated)
Merck 
14,5352
BCS Class
1,3
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
InChIKey
JTEGQNOMFQHVDC-NKWVEPMBSA-N
CAS DataBase Reference
134678-17-4(CAS DataBase Reference)
EPA Substance Registry System
2(1H)-Pyrimidinone, 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]- (134678-17-4)
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Safety

Risk Statements 
63-36/37/38
Safety Statements 
26-36
RIDADR 
UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany 
3
RTECS 
UW7361333
HS Code 
29349990
Hazardous Substances Data
134678-17-4(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H361Suspected of damaging fertility or the unborn child

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
1356847
Product name
Lamivudine Resolution Mixture A
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
10MG
Price
$1370
Updated
2024/03/01
Sigma-Aldrich
Product number
1356836
Product name
Lamivudine
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$436
Updated
2024/03/01
Sigma-Aldrich
Product number
BP802
Product name
Lamivudine
Purity
British Pharmacopoeia (BP) Reference Standard
Packaging
200MG
Price
$221
Updated
2023/06/20
TCI Chemical
Product number
L0217
Product name
Lamivudine
Purity
>98.0%(HPLC)(T)
Packaging
100mg
Price
$17
Updated
2024/03/01
TCI Chemical
Product number
L0217
Product name
Lamivudine
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$85
Updated
2024/03/01
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Lamivudine Chemical Properties,Usage,Production

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.

Chemical Properties

White solid from methanol-ethyl acetate. [α]D21-132° (C=1.08, methanol). Or crystallised from boiling ethanol, melting point 160-162°C. [α]D21-135° (C=0.38, methanol).

Originator

BioChem Pharma (Canada)

History

Lamivudine[134678-17-4] is produced by GlaxoSmithKline LLC. In the early 1990s, it was used by some countries in Europe and North America to treat AIDS. In the mid-1990s, medical experts found that it had an inhibitory effect on the DNA of hepatitis B virus. In 1998, the US Food and Drug Administration (FDA) first approved it as a treatment drug for hepatitis B. In 1999, the China Food and Drug Administration approved this drug as a hepatitis B treatment drug, with the Chinese trade name "Heputin".

Uses

Lamivudine (Epivir-HBV) 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. It is used to treat hepatitis B infection. It is also used along with other medications to treat human immunodeficiency virus (HIV) infection in adults and children 3 months of age and older.

Definition

ChEBI: Lamivudine is a monothioacetal that consists of cytosine having a (2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl moiety attached at position 1. An inhibitor of HIV-1 reverse transcriptase.

Synthesis

Aqueous hydrochloric acid (6N, 30 ml) was slowly added to a solution of 20 gm of the solid (2R-cis)-4-Amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidi- none.S-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate in water (200 ml) at 45-50 deg C. Stirred the reaction for 1 hour at room temperature. The solid S-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate was filtered and the aqueous layer was neutralized with aqueous sodium hydroxide solution (30%, 20 ml). The solvent was recovered under vacuum at 40-45 deg C., the product obtained was dissolved in methanol (200 ml), filtered to remove the inorganic salts, the filtrate was concentrated under vacuum at 40-45 deg C. and the residual solid obtained was dissolved in ethanol (50 ml), heated to 50 deg C., slowly allowed to room temperature, cooled to 10 deg C., filtered and dried at 40-45 deg C. to obtain 5 gm of Lamivudine(Chiral purity: 97.5%).

brand name

Epivir (GlaxoSmithKline).

Acquired resistance

Long-term lamivudine administration frequently elicits viral resistance characterized by a reincrease of viral replication in an adherent patient. The incidence of lamivudine resistance is 14% to 32% after 1 year of treatment, 38% after 2 years, and 53% to 76% after 3 years.

Pharmacokinetics

The pharmacokinetics of lamivudine are similar in patients with HIV-1 or HBV infection, and healthy volunteers. The drug is rapidly absorbed after oral administration, with maximum serum concentrations usually attained 0.5 to 1.5 hours after the dose.

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.

Side effects

Lamivudine oral tablet can cause mild or serious side effects. The more common side effects that can occur with lamivudine include:
cough,diarrhea,fatigue,headache,malaise (general discomfort),nasal symptoms, such as a runny nose,nausea.

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 ganciclovir
Cytotoxic drugs: avoid concomitant use with clarithromycin.
Orlistat: absorption may be reduced by orlistat.

Metabolism

Lamivudine is metabolised intracellularly to the active antiviral triphosphate. Hepatic metabolism is low (5-10%) and the majority of lamivudine is excreted unchanged in the urine via glomerular filtration and active secretion (organic cationic transport system).

References

[1] ROUSSOSA. Lamivudine treatment for acute severe hepatitis B: report of a case and review of the literature.[J]. Acta gastro-enterologica Belgica, 2008, 71 1: 30-32.
[2] ARTSE J WainbergM A. Mechanisms of nucleoside analog antiviral activity and resistance during human immunodeficiency virus reverse transcription.[J]. Antimicrobial Agents and Chemotherapy, 1996, 40 3: 527-540. DOI:10.1128/AAC.40.3.527.
[3] COATESJ A. (-)-2’-deoxy-3’-thiacytidine is a potent, highly selective inhibitor of human immunodeficiency virus type 1 and type 2 replication in vitro.[J]. Antimicrobial Agents and Chemotherapy, 1992, 36 4: 733-739. DOI:10.1128/AAC.36.4.733.
[4] KONGHUI. Targeted P2X7/NLRP3 signaling pathway against inflammation, apoptosis, and pyroptosis of retinal endothelial cells in diabetic retinopathy.[J]. Cell Death & Disease, 2022, 13 4: 336. DOI:10.1038/s41419-022-04786-w.
[5] KUMAR P N, PATEL P. Lamivudine for the treatment of HIV[J]. Expert Opinion on Drug Metabolism & Toxicology, 2010, 6: 105-114. DOI:10.1517/17425250903490418.
[6] PERRYC M FauldsD. Lamivudine. A review of its antiviral activity, pharmacokinetic properties and therapeutic efficacy in the management of HIV infection.[J]. Drugs, 1997, 53 4: 657-680. DOI:10.2165/00003495-199753040-00008.
[7] RAJURKARMIHIR. Reverse Transcriptase Inhibition Disrupts Repeat Element Life Cycle in Colorectal Cancer.[J]. Cancer discovery, 2022, 12 6: 1462-1481. DOI:10.1158/2159-8290.CD-21-1117.

Lamivudine Preparation Products And Raw materials

Raw materials

Silica gel Lead tetraacetate Silicon tetrahydride CHLOROETHANE Sodium borohydride Sodium periodate Bromide Tetrabutylammonium fluoride Praseodymium(III) nitrate hexahydrate

Preparation Products

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Lamivudine Suppliers

Americas 1 Belgium 1 Brazil 12 Canada 7 CHINA 489 Colombia 1 Europe 3 France 3 Germany 6 India 127 Indonesia 1 Japan 1 Malaysia 1 Mexico 1 Nepal 1 Nigeria 1 Philippines 1 Poland 1 Russia 1 Singapore 1 South Africa 1 South Korea 7 Spain 1 Ukraine 1 United Arab Emirates 1 United Kingdom 19 United States 67 Uruguay 1 Global 758
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View Lastest Price from Lamivudine manufacturers

Sinoway Industrial co., ltd.
Product
Lamivudine 134678-17-4
Price
US $185.00-65.00/Kg/Bag
Min. Order
1Kg/Bag
Purity
99% up, USP
Supply Ability
20 tons
Release date
2023-12-15
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Lamivudine 134678-17-4
Price
US $0.00-0.00/Kg/Drum
Min. Order
1KG
Purity
98%min
Supply Ability
500kg
Release date
2021-10-19
Baoji Guokang Bio-Technology Co., Ltd.
Product
Lamivudine 134678-17-4
Price
US $412.00/Kg/Bag
Min. Order
1KG
Purity
99%
Supply Ability
1T
Release date
2021-06-04

134678-17-4, LamivudineRelated Search:

ALTRENOGEST Tris(hydroxymethyl)aminomethane 1,4-Dioxane Glycine 6-Aminocaproic acid Tris(hydroxymethyl)nitromethane Zidovudine Lamivudine salicylate Emtricitabine [1R-[1(2S*,5R*),2beta,5alpha]]-5-(4-Amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylic acid 5-methyl-2-(1-methylethyl)cyclohexyl ester LAMIVUDINE FOR SYSTEM SUITABILITY 1 Entecavir Cytosine (1R,2S,5R)-Menthyl-(2R,5S)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-[1,3]oxathiolane-2-carboxylic acid Lamivudine Resolution Mixture B Adefovir dipivoxil LAMIVUDINE-15N2,13C Lamivudine

  • LaMivudine(Epivir)
  • 4-AMino-1-[(2R,5S)-2-(hydroxyMethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyriMidinone
  • 3TC (-)-1-[(2R,5S)-2-(Hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine
  • LaMivudine-13C-d2
  • 3TC/Epivir-HBV
  • 4-AMino-1-((2R,5S)-2-(hydroxyMethyl)-1,3-oxathiolan-5-yl)pyriMidin-2(1H)-one
  • cis-Lamivudine
  • (-)-BCH-189
  • (-)-BETA-L-2',3'-DIDEOXY-3'-THIACYTIDINE
  • 2''-DEOXY-3''-THIACYTIDINE (LAMIVUDINE)
  • (-)-1-[(2R,5S)-2-(Hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine
  • (-)-ILTI-189
  • (2R-cis)-4-Amino-1-[2-(hydroxymethyl)-1，3-oxathiolan-5-y1]-2(1H)-pyrimidinone
  • 2(1H)-Pyrimidinone, 4-amino-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)
  • Heptivir
  • (+)-1-[(2S,5R)-2-(Hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine
  • (+)-β-D-BCH-189
  • 1-[(2S,5R)-2-(Hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine
  • 1-[(2S,5R)-2-Hydroxymethyl-1,3-oxathiolan-5-yl]cytosine
  • Lamivudine
  • Lamivudine (200 mg)
  • Lamivudine Resolution Mixture A (10 mg)
  • LaMivudine Resolution Mixture A
  • 4-aMino-1-[(2R,5S)-2-(hydroxyMethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyriMidin-2-one
  • Lamivudine CAS 134678-17-4
  • Lamivudine, 98%, a potent nucleoside analog reverse transcriptase inhibitor
  • Lamivudine HCl
  • 4-amino-1-[(2R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2-pyrimidinone
  • LAMIVUDINE (BCH-189)
  • (-)-B-L-2',3'-DIDEOXY-3'-THIACYTIDINE
  • (2r-cis)-4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1h)-pyrimidinone
  • 2'-deoxy-3'-thiacytidine
  • Lamivudine(3Tc)
  • 1,3-Oxathiolan-5-Yl-2-(Lh)-Pyrimidinone,Lamivudine
  • 4-AMINO-1-((2R,5S)-2-HYDROXYMETHYL-[1,3]OXATHIOLAN-5-YL)-1H-PYRIMIDIN-2-ONE
  • 3TC
  • 3'-THIA-2',3'-DIDEOXYCYTIDINE
  • (-)-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cystosine
  • (-)-2&cent
  • (-)NGPB-21
  • (2R-cis)-4-amino-1-
  • ,3&cent
  • 2(1H)-Pyrimidinone,4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-,(2R-cis)-
  • 3&cent
  • 3'-thia-2',3'-dideoxcytidine
  • -deoxy-3&cent
  • Epivir
  • GR109714X
  • -thia-2&cent
  • -thiacytidine
  • LAMIVUDINE [2''-DEOXY-3''-THIACYTIDINE]
  • 3TC, (-)-BCH-189, 3Thia-23dideoxycytidine
  • LAMIVUDINE (3TC) ALUMINIUM
  • 1,3-Oxathiolane, 2(1H)-pyrimidinone deriv.
  • 2(1H)-Pyrimidinone, 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]- (9CI)
  • b-L-3'-Thia-2',3'-dideoxycytidine
  • Epivir HBV
  • Hepitec