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HCID 60825Erstellt: 27. Oktober 2026

Lamivudine

rac-cis-Lamivudine ((2RS,5SR)-Lamivudine) · 4-Amino-1-(cis-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one · 2(1H)-Pyrimidinone, 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-, rel-

https://huagongshe.com/de/chemical/60825

Molekülstruktur von Lamivudine

Identifikatoren & physikalische Daten

CAS No.134678-17-4
SummenformelC8H11N3O3S
Durchschnittliche Molmasse229,26 g/mol
Monoisotopische Masse229,05211221 g/mol
SMILESNc1ccn([C@@H]2CS[C@H](CO)O2)c(=O)n1
InChIKeyJTEGQNOMFQHVDC-NKWVEPMBSA-N
PubChem CID60825
ChEMBLCHEMBL141
ChEBICHEBI:63577
EC No.603-844-3
DTXSIDDTXSID7023194

Chemische & physikalische Eigenschaften

XLogP-0,9
Polarare Oberfläche (TPSA)113
H-Brücken-Donoren2
H-Brücken-Akzeptoren4
Frei drehbare Bindungen2
Schwere Atome15
Formalladung0
Komplexität331
StoffklassenPharmaceutical
ArzneimittelPharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Used in Switzerland
LogP (Verteilungskoeffizient)log Kow = -9.54 @ 25 °C /Estimated/-1.4-0.91
Color/FormCrystals from boiling ethanol
LöslichkeitIn water, 70,000 mg/L @ 20 °C2.76e+00 g/L
Human DrugsBreast FeedingLactationMilk, HumanAnti-Infective AgentsAntiviral AgentsAnti-HIV AgentsAnti-Retroviral AgentsReverse Transcriptase InhibitorsFDA approved drugs -> Active ingredientEMA approved medicines: Human medicine
Schmelzpunkt160-162 °C160 - 162 °C187-188℃
Dampfdruck8.3X10-16 mm Hg @ 25 °C /Estimated/
Henry-KonstanteHenry's Law constant = 1.9X10-22 atm-cu m/mol @ 25 °C /Estimated/
Physical DescriptionSolid
Collision Cross Section153.1 Ų [M+Na]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID7023194]
Other Experimental PropertiesHydroxyl radical reaction rate constant = 2.3X10-10 cu cm/molec-sec @ 25 °C /Estimated/
Siedepunkt475.4±55.0 °C(Predicted)
Dichte1.73
Lagerbedingungen2-8°C(protect from light)
pKa (Säurekonstante)13.83±0.10(Predicted)

Sicherheit & Vorschriften

GHS-EinstufungThis chemical does not meet GHS hazard criteria for 0.8% (1 of 133) of reports.WarningH315 (30.1%): Causes skin irritation [Warning Skin corrosion/irritation]P203, P260, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 133 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
FDA-AnforderungenThe Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl lamivudine, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
Hazard Classes and CategoriesSkin Irrit. 2 (30.1%)
EntsorgungsverfahrenSRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations.
WechselwirkungenConcurrent administration of lamivudine 150 mg twice a day, indinavir 800 mg every eight hours, and zidovudine 200 mg every eight hours resulted in a 6% decrease in the AUC of lamivudine, no change in AUC of indinavir, and a 36% increase in the AUC of zidovudineno adjustment in dose in necessary.Lamivudine and zidovudine fixed dose combination tablet should not be administered concomitantly with lamivudine tablets or lamivudine oral solution.In one small study, concurrent administration of sulfamethoxazole and trimethoprim combination resulted in a 44% increase in lamivudine AUC, and a decrease of 29% in lamivudine oral clearance and a 30% decrease in lamivudine renal clearancethe phamacokinetic properties of sulfamethoxazole and trimethoprim were not altered by concurrent administration of lamivudine
no adjustment in dose is necessary unless the patient has renal function impairment.
Lamivudine and zalcitabine may inhibit the phosphorylation of one another and concurrent administration is not recommended.
HepatotoxicityElevations in serum ALT levels occur in a proportion of patients with chronic hepatitis B treated with lamivudine. These elevations appear to be due to a transient flare in the underlying chronic hepatitis B and occur in three situations during and after therapy: upon initiation of therapy (treatment flares), upon development of antiviral resistance (breakthrough flares), and shortly after stopping therapy (withdrawal flares). Treatment flares typically occur during the first few months of therapy and are marked by asymptomatic elevations in serum aminotransferase levels and rarely with jaundice or symptoms (Case 1). These flares occur during the rapid decrease in HBV DNA levels with initiation of therapy. An exacerbation of hepatitis also typically occurs after development of lamivudine resistance, a few weeks or months after the initial appearance of the mutant HBV strain and rise in HBV DNA levels (Case 2). Finally, withdrawal flares occur between 4 and 12 weeks after stopping lamivudine and can be severe, symptomatic and even lead to clinical decompensation, acute liver failure and either death or need for emergency liver transplantation. Resistance and withdrawal flares typically occur as HBV DNA levels are high or rising.
Unerwünschte WirkungenSevere adverse effects include:
Milk Concentrations...Lamivudine and zidovudine freely crossed the placenta and were secreted in breast milk.
ToxizitätsübersichtLamivudine is usually well tolerated with milder toxicities compared to other NRTIs. If an overdose of lamivudine occurs, supportive care should be provided with monitoring. Dialysis is not a reliable treatment for an overdose of lamivudine. No human trials to date have shown evidence of carcinogenesis, mutagenesis, or fertility impairment.
Human Toxicity Excerpts/HUMAN EXPOSURE STUDIES/ There are no adequate and controlled studies to date using lamivudine in pregnant women, and the drug should be used during pregnancy only if the potential benefits justify the potential risks to the fetus./HUMAN EXPOSURE STUDIES/ In clinical studies in HIV-infected pediatric patients who received lamivudine in conjunction with zidovudine, paresthesia and peripheral neuropathies have been reported in up to 15% of patients. Pancreatitis, including some fatalities, has occurred in 14-18% of HIV-infected pediatric patients receiving lamivudine alone or in conjunction with other nucleoside antiretroviral agents. Other adverse effects reported in pediatric patients receiving lamivudine in conjunction with zidovudine were similar to those reported in adults and include GI effects, hepatic effects, sensitivity reactions, and hematologic effects./HUMAN EXPOSURE STUDIES/ Lactic acidosis and severe hepatomegaly with steatosis, including some fatalities, have been reported rarely in patients receiving lamivudine and also have been reported in patients receiving other nucleoside reverse transcriptase inhibitors. Most reported cases have involved womenobesity and long-term therapy with nucleoside reverse transcriptase inhibitors also may be risk factors. Lamivudine should be used with caution in patients with known risk factors for liver diseasehowever, lactic acidosis and severe hepatomegaly with steatosis have been reported in patients with no known risk factors./CASE REPORTS/ The aim of this report is to describe five patients with lamivudine-induced pure red cell aplasia, an association not previously described. We describe patients with unresponsive anemia in whom a complete study including blood cell counts, reticulocyte counts, hemolysis tests, and bone marrow aspiration was performed. Pure red cell aplasia was considered when anemia was associated with normal leukocyte and platelet counts with a corrected reticulocyte count below 1% and less than 5% bone marrow erythroid progenitors in the absence of positive hemolysis tests. Complete remission was considered when bone marrow erythroid progenitors were at least 16%. Five male patients had pure red cell aplasia with a median age of 32 years (range 29 to 37 years). Before lamivudine, they had hemoglobin >11.8 g/dL without transfusion requirements. After receiving the drug, hemoglobin dropped to 5.2 g/dl (4.3 to 6.1 g/dL) with high transfusion requirements and mean bone marrow erythroid progenitors of 1.84% (0 to 4%). Withdrawal of lamivudine was attempted to confirm the diagnosis. Seven weeks after stopping lamivudine, hemoglobin rose up to 12.8 g/dL (11 .3 to 13.8 g/dL) and bone marrow erythroid progenitors increased up to 25.6% (21 to 40%) without transfusion requirements. Lamivudine-induced pure red cell aplasia may be a cause of anemia unresponsive to conventional treatment in AIDS.
Carcinogen ClassificationLamivudine (3TC)TR-569: Toxicology and Carcinogenesis Studies of Mixtures of 3&#039-Azido-3&#039-Deoxythymidine (AZT), Lamivudine (3TC), Nevirapine (NVP), and Nelfinavir Mesylate (NFV) (CASRNs 30516-87-1, 134678-17-4, 129618-40-2, 159989-65-8) in B6C3F1 Mice (Transplacental Exposure Studies) (2013 )04/05/11No EvidenceEquivocal Evidence- AZT - Under the conditions of this transplacental exposure study, there was no evidence of carcinogenic activity of AZT in male B6C3F1 mice whose dams were exposed to 80, 160, or 240 mg/kg by gavage. There was equivocal evidence of carcinogenic activity of AZT in female B6C3F1 mice based on increased incidences of thyroid gland neoplasms (primarily adenoma) and subcutaneous skin fibrosarcoma or sarcoma.
Drug Induced Liver InjuryDrug Induced Liver Injury Rank (DILIrank 2.0)LamivudinevLess-DILI-concern3Warnings & precautionsDOI:10.1016/j.drudis.2016.02.015
Non-Human Toxicity Excerpts/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Reproduction studies in rats or rabbits using oral lamivudine in dosages up to 4 or 1 g/kg daily, respectively, have not revealed evidence of teratogenicity./LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ there was evidence of early embryolethality in rabbits receiving lamivudine at dosages similar to the recommended dosages in humans, this effect was not seen in rats receiving lamivudine at dosages 60 times the recommended human dosage for /hepatitis B virus/ infection and 35 times the recommended human dosage for HIV infection./GENOTOXICITY/ Lamivudine was not mutagenic in a microbial mutagenicity screen or an in vitro cell transformation assay, but showed weak in vitro mutagenic activity ... in the mouse lymphoma assay./GENOTOXICITY/ There was no evidence of genotoxic activity in rats given oral dosages up to 2 g/kg./GENOTOXICITY/ The carcinogenic potential of lamivudine has been studied in mice and rats. No evidence of carcinogenicity was seen in long-term studies in mice or rats.
Antidote and Emergency TreatmentBasic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
USGS Health-Based Screening Levels for Evaluating Water-QualityLamivudinePharmaceuticalSmith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP
AlarmwortWarnung
GefahrenhinweiseCode Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H302