Lamivudine
Structural formula | ||||||||||||||||||||||
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Non-proprietary name | Lamivudine | |||||||||||||||||||||
other names |
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Molecular formula | C 8 H 11 N 3 O 3 S | |||||||||||||||||||||
Brief description |
white to almost white, polymorphic powder |
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Drug information | ||||||||||||||||||||||
ATC code | ||||||||||||||||||||||
Drug class |
Antiviral agent , nucleoside reverse transcriptase inhibitors |
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Mechanism of action | ||||||||||||||||||||||
properties | ||||||||||||||||||||||
Molar mass | 229.257 g · mol -1 | |||||||||||||||||||||
Physical state |
firmly |
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Melting point |
160-162 ° C |
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solubility |
soluble in water (70 mg ml −1 ), slightly soluble in methanol , sparingly soluble in ethanol |
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safety instructions | ||||||||||||||||||||||
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Toxicological data | ||||||||||||||||||||||
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
Lamivudine , 3TC for short (trade names: Epivir ® , Zeffix ® ; manufacturer: GlaxoSmithKline ) is a drug for the treatment of HIV-1 infected patients as part of an antiretroviral therapy ( HAART ) and chronic HBV infection.
It is a chemical analog of the nucleoside cytidine and belongs to the group of nucleoside reverse transcriptase inhibitors (NRTIs).
history
Lamivudine has been approved in Germany since 1995. In the fixed combination Kivexa with abacavir (ABC), it is currently the second most common NRTI backbone of HIV therapy after Truvada ( tenofovir plus emtricitabine ).
pharmacology
Lamivudine is converted to a 5'-triphosphate intracellularly. Like other nucleoside analogues, it can be incorporated into the viral DNA and leads to the breakdown of DNA synthesis.
Pharmacokinetics
The bioavailability of lamivudine after oral administration is approximately 80%. After the usual dosage (2 mg / kg body weight twice a day), the maximum serum concentrations are 1.5 to 1.9 mg / l. Simultaneous food intake does not significantly affect bioavailability . The volume of distribution is given as 1.3 l / kg body weight. With a half-life of 5 to 7 hours, the drug is eliminated mainly unchanged by the kidneys. The binding to plasma proteins is low. In renal insufficiency (clearance <50 ml / min), a dose of 150 mg is administered only every 24 hours; If the kidney function is restricted to a greater extent, the individual dose should first be halved and then further adjusted according to the individual situation.
Side effects
Side effects that may occur with treatment are:
Common: headache , insomnia , cough , nasal symptoms, nausea, vomiting, abdominal pain, diarrhea, rash, alopecia , arthralgia, muscle discomfort, fatigue, malaise, fever
Uncommon: neutropenia , anemia , thrombocytopenia , transient increase in liver enzymes
Rare: pancreatitis , increased serum amylase , hepatitis , angioedema , rhabdomyolysis
Very rare: erythroblastopenia , lactic acidosis , peripheral neuropathy
Resistances
In monotherapy, HI viruses develop resistance to lamivudine relatively easily: a single mutation in the genetic material (M184V or M184I) is sufficient to make HIV highly resistant to lamivudine. Therefore, lamivudine for HIV therapy must always be given in combination with at least one other antiretroviral drug.
Dosage forms
Lamivudine is administered orally: for example in the form of tablets of 100 mg, 150 mg or 300 mg and an oral solution. There are also fixed combinations with zidovudine or abacavir.
Individual evidence
- ↑ a b c LAMIVUDINE CRS data sheet (PDF) at EDQM , accessed on February 26, 2009.
- ↑ a b Entry on lamivudine in the DrugBank of the University of Alberta .
- ↑ a b Lamivudine data sheet from Sigma-Aldrich , accessed on April 7, 2011 ( PDF ).
- ↑ a b lamivudine , information from the magazine for chemotherapy, from issue 6, 1996.
- ↑ GSK: ViiV Healthcare Fachinformation Epivir , February 2019, accessed on April 10, 2019.
Trade names
3TC (CH), Epivir (D, A), Zeffix (D, CH),
Combivir (D, A, CH), Kivexa (D, A, CH), Trizivir (D, CH), Dovato (D)
Web links
- European Public Assessment Report (EPAR) and product information for Zeffix on the European Medicines Agency website
- Chapter 7: Antiretrovirals and Essential Drugs in HIV Book 2011. The book on HIV and AIDS.
- Chapter 6.2: Substance classes, drug overview in HIV-Buch 2011. The book on HIV and AIDS.