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
- Molecular Weight:
- 229.26
- MOL File:
- 134678-17-4.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/6/7 16:07:22
| 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 |
| form | powder |
| pka | 13.83±0.10(Predicted) |
| 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) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS08 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H361 | |||||||||
| Precautionary statements | P280 | |||||||||
| 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 | |||||||||
| NFPA 704 |
|
Lamivudine price More Price(5)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | PHR1365 | Lamivudine Pharmaceutical Secondary Standard; Certified Reference Material | 134678-17-4 | 1G | ₹8346.08 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | L1295 | Lamivudine ≥98% (HPLC), powder | 134678-17-4 | 10MG | ₹10857.48 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | L1295 | Lamivudine ≥98% (HPLC), powder | 134678-17-4 | 50MG | ₹39771.05 | 2022-06-14 | Buy |
| TCI Chemicals (India) | L0217 | Lamivudine | 134678-17-4 | 100MG | ₹2400 | 2022-05-26 | Buy |
| TCI Chemicals (India) | L0217 | Lamivudine | 134678-17-4 | 1G | ₹6800 | 2022-05-26 | Buy |
Lamivudine Chemical Properties,Uses,Production
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).
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%).
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.
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.
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
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| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| Jigs Chemical ltd | +919099003427 | Gujarat, India | 239 | 58 | Inquiry |
| ANWITA APIS | +919000311012 | Hyderabad, India | 198 | 58 | Inquiry |
| J S LABS | +91-7330612784 +91-7330612784 | Tamil Nadu, India | 160 | 58 | Inquiry |
| Styrax Pharma Pvt Ltd | +91-4048583333 +91-9848912103 | Telangana, India | 24 | 58 | Inquiry |
| Aurobindo Pharma Limited | +914066725000 | Telangana, India | 112 | 58 | Inquiry |
| Cipla Ltd | +912224826000 | Maharashtra, India | 133 | 58 | Inquiry |
| Hetero Drugs Limited | +91-4023704923 +91-4023704923 | Telangana, India | 296 | 58 | Inquiry |
| KRS Pharmaceuticals Pvt. Ltd. | +91-4023176686 +91-9848996298 | Hyderabad, India | 36 | 58 | Inquiry |
| HRV Global Life Sciences | +91-9820219686 +91-9820219686 | Telangana, India | 379 | 58 | Inquiry |
| VIVIN DRUGS AND PHARMACEUTICALS LTD | +91-22670456625 +91-224067045635 | Telangana, India | 22 | 58 | Inquiry |
| Supplier | Advantage |
|---|---|
| Jigs Chemical ltd | 58 |
| ANWITA APIS | 58 |
| J S LABS | 58 |
| Styrax Pharma Pvt Ltd | 58 |
| Aurobindo Pharma Limited | 58 |
| Cipla Ltd | 58 |
| Hetero Drugs Limited | 58 |
| KRS Pharmaceuticals Pvt. Ltd. | 58 |
| HRV Global Life Sciences | 58 |
| VIVIN DRUGS AND PHARMACEUTICALS LTD | 58 |
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