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Drug

D0075 | Lamivudine

Molecular Formula C8H11N3O3S
Molecular Weight 229.26
Structure
State solid
Clearance * Renal clearance = 199.7 ± 56.9 mL/min [300 mg oral dose, healthy subjects] * Renal clearance = 280.4 ± 75.2 mL/min [single IV dose, HIV-1-infected patients] * Total clearance = 398.5 ± 69.1 mL/min [HIV-1-infected patients]
Volume of distribution Apparent volume of distribution, IV administration = 1.3 ± 0.4 L/kg. Volume of distribution was independent of dose and did not correlate with body weight.
Route of elimination The majority of lamivudine is eliminated unchanged in urine by active organic cationic secretion. 5.2% ± 1.4% (mean ± SD) of the dose was excreted as the trans-sulfoxide metabolite in the urine. Lamivudine is excreted in human breast milk and into the milk of lactating rats.
Protein binding <36% bound to plasma protein.
Half life 5 to 7 hours (healthy or HBV-infected patients)
Absorption Lamivudine was rapidly absorbed after oral administration in HIV-infected patients. Absolute bioavailability in 12 adult patients was 86% ± 16% (mean ± SD) for the 150-mg tablet and 87% ± 13% for the oral solution. The peak serum lamivudine concentration (Cmax) was 1.5 ± 0.5 mcg/mL when an oral dose of 2 mg/kg twice a day was given to HIV-1 patients. When given with food, absorption is slower, compared to the fasted state.
Trade names Epivir
Description Antiviral; analogue of cytidine

J

J05AR24 Lamivudine, tenofovir disoproxil and doravirine


[J05AR] Antivirals for treatment of HIV infections, combinations


[J05A] DIRECT ACTING ANTIVIRALS


[J05] ANTIVIRALS FOR SYSTEMIC USE


[J] Antiinfectives for systemic use

J05AR16 Lamivudine and raltegravir


[J05AR] Antivirals for treatment of HIV infections, combinations


[J05A] DIRECT ACTING ANTIVIRALS


[J05] ANTIVIRALS FOR SYSTEMIC USE


[J] Antiinfectives for systemic use

J05AR13 Lamivudine, abacavir and dolutegravir


[J05AR] Antivirals for treatment of HIV infections, combinations


[J05A] DIRECT ACTING ANTIVIRALS


[J05] ANTIVIRALS FOR SYSTEMIC USE


[J] Antiinfectives for systemic use

J05AR12 Lamivudine and tenofovir disoproxil


[J05AR] Antivirals for treatment of HIV infections, combinations


[J05A] DIRECT ACTING ANTIVIRALS


[J05] ANTIVIRALS FOR SYSTEMIC USE


[J] Antiinfectives for systemic use

J05AR11 Lamivudine, tenofovir disoproxil and efavirenz


[J05AR] Antivirals for treatment of HIV infections, combinations


[J05A] DIRECT ACTING ANTIVIRALS


[J05] ANTIVIRALS FOR SYSTEMIC USE


[J] Antiinfectives for systemic use

J05AR07 Stavudine, lamivudine and nevirapine


[J05AR] Antivirals for treatment of HIV infections, combinations


[J05A] DIRECT ACTING ANTIVIRALS


[J05] ANTIVIRALS FOR SYSTEMIC USE


[J] Antiinfectives for systemic use

J05AR05 Zidovudine, lamivudine and nevirapine


[J05AR] Antivirals for treatment of HIV infections, combinations


[J05A] DIRECT ACTING ANTIVIRALS


[J05] ANTIVIRALS FOR SYSTEMIC USE


[J] Antiinfectives for systemic use

J05AR04 Zidovudine, lamivudine and abacavir


[J05AR] Antivirals for treatment of HIV infections, combinations


[J05A] DIRECT ACTING ANTIVIRALS


[J05] ANTIVIRALS FOR SYSTEMIC USE


[J] Antiinfectives for systemic use

J05AR02 Lamivudine and abacavir


[J05AR] Antivirals for treatment of HIV infections, combinations


[J05A] DIRECT ACTING ANTIVIRALS


[J05] ANTIVIRALS FOR SYSTEMIC USE


[J] Antiinfectives for systemic use

J05AR01 Zidovudine and lamivudine


[J05AR] Antivirals for treatment of HIV infections, combinations


[J05A] DIRECT ACTING ANTIVIRALS


[J05] ANTIVIRALS FOR SYSTEMIC USE


[J] Antiinfectives for systemic use

J05AF05 Lamivudine


[J05AF] Nucleoside and nucleotide reverse transcriptase inhibitors


[J05A] DIRECT ACTING ANTIVIRALS


[J05] ANTIVIRALS FOR SYSTEMIC USE


[J] Antiinfectives for systemic use

Toxicity Dose Time Species Model Method Action Positive criterion Reference
MEMBRANE POTENTIAL 347.2 µM 30 mins mouse liver mitochondria Rh123 fluorescence (excitation 485 nm, emission 535 nm) are recorded using a fluorescence multi-well plate reader (mCICCP (20 µM) treatments was considered as the 100% baseline for ΔΨm loss) decrease EC20 36
RESPIRATION 160.7 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Rotenone (2µM) was used as 100% baseline for complex I inhibition. decrease EC20 36
RESPIRATION 317.4 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Oligomycin A (1µM) was used as 100% baseline for complex II inhibition. decrease EC20 36
SWELLING > 400 µM 30 mins mouse liver mitochondria swelling assay: Absorbance at 545 nm using a fluorescence multi-well plate reader (CaCl2 (50 µM) was considered as the 100% baseline for the swelling ) increase EC20 36
MITOCHONDRIAL DNA METABOLIC PROCESS 194

Target Dose Time Species Model Method Action Positive criterion Reference
NADH:ubiquinone reductase 160.7 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Rotenone (2µM) was used as 100% baseline for complex I inhibition. inhibit EC20 36
Succinate dehydrogenase 317.4 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Oligomycin A (1µM) was used as 100% baseline for complex II inhibition. inhibit EC20 36
DNA polymerase gamma 194
Cytochrome c 30 mins mouse liver mitochondria Cytochrome c release was evaluated using ELISA kit ( 20 µg/ml Alamethicin was used as 100% baseline) Negative EC20 36

Pictogram Signal Statements Precautionary Statement Codes
Warning

Aggregated GHS information provided by 128 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


Reported as not meeting GHS hazard criteria by 1 of 128 companies. For more detailed information, please visit ECHA C&L website


Of the 9 notification(s) provided by 127 of 128 companies with hazard statement code(s):


H315 (30.71%): Causes skin irritation [Warning Skin corrosion/irritation]


H319 (30.71%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]


H335 (30.71%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure


Respiratory tract irritation]


H361 (68.5%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]


H373 (28.35%): Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]


Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.


 P201, P202, P260, P261, P264, P271, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P314, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

  • Alanine aminotransferase increased

  • Chronic hepatitis B

  • Fibrosis

  • Foetor hepaticus

  • Hepatic failure

  • Hepatitis B

  • Hepatitis B DNA decreased

  • Hepatitis B e antigen positive

  • Hepatitis B surface antigen positive

  • Hepatitis C

  • Hepatitis chronic active

  • Hepatitis D

  • Hepatitis viral

  • Hepatocellular injury

  • Immunodeficiency

  • Infection

  • Inflammation

  • Liver disorder

  • Pancreatitis

  • Pathogen resistance

  • Viral infection

  • Abdominal distension (0.03)

  • Pruritus (0.01)

  • Abdominal discomfort

  • Abdominal pain

  • Acne

  • Anaemia

  • Asthenia

  • Blood creatine phosphokinase increased

  • Body temperature increased

  • Breath sounds abnormal

  • Bronchitis

  • Cough

  • Decreased appetite

  • Dermatitis

  • Diarrhoea

  • Discomfort

  • Dizziness

  • Dyspepsia

  • Fatigue

  • Feeling abnormal

  • Folliculitis

  • Fungal skin infection

  • Gastrointestinal infection

  • Gastrointestinal pain

  • Headache

  • Hepatomegaly

  • Hyperhidrosis

  • Ill-defined disorder

  • Infection

  • Inflammation

  • Liver function test abnormal

  • Lymphadenopathy

  • Malaise

  • Musculoskeletal discomfort

  • Musculoskeletal pain

  • Myalgia

  • Nasopharyngitis

  • Nausea

  • Neuropathy peripheral

  • Neutropenia

  • Oropharyngeal discomfort

  • Oropharyngeal pain

  • Pain

  • Pharyngitis

  • Rash

  • Respiration abnormal

  • Respiratory disorder

  • Respiratory tract infection

  • Rhinorrhoea

  • Sinusitis

  • Sleep disorder

  • Splenomegaly

  • Stomatitis

  • Thrombocytopenia

  • Viral infection

  • Viral skin infection

  • Vomiting

  • Wheezing

    • (+/-) (Cis)-1-[2-(Hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine (+/-)-(cis)-4-Amino-1-(2-hydroxymethyl-1,3-oxathiolan-5-yl)-(1H)-pyrimidin-2-one (+/-)-3TC
    (+/-)-BCH-189 (+/-)-SddC (-)-(2'R,5'S)-1-[2'-Hydroxymethyl-5'-(1,3-oxathiolanyl)]cytosine
    (-)-1-((2R,5S)-2-(Hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine (-)-1-[(2R,5S)-2-(Hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine (-)-2'-Deoxy-3'-thiacytidine
    (-)-BCH 189 (-)-BCH-189 (-)-L-2',3'-DIDEOXY-3'-THIACYTIDINE
    (-)-SddC (-)NGPB-21 (2R,5S)-1-[2-(Hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine
    (2R,cis)-4-amino-1-(2-hydroxymethyl-1,3-oxathiolan-5-yl)-(1H)-pyrimidin-2-one .beta.-L-(-)-2',3'-dideoxy-3'-thiacytidine & Sho-Saiko-To 134678-17-4
    136891-12-8 2',3'-Dideoxy-3'-thiacytidine 2(1H)-Pyrimidinone, 4-amino-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-
    2(1H)-Pyrimidinone, 4-amino-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-, (2R-cis)- 2(1H)-Pyrimidinone, 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]- 2(1H)-Pyrimidinone, 4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl], (+/-) (Cis)
    2(1H)-Pyrimidinone, 4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl], (-)(2R,5S) & Galanthus Nivalis Agglutinin (GNA) 2(1H)-Pyrimidinone, 4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl], (-)(2R,5S) & Hippeastrum hybrid agglutinin( HHA) 200973-EP2272825A2
    24222-EP2269989A1 24222-EP2272516A2 24222-EP2272825A2
    24222-EP2292227A2 24222-EP2298761A1 24222-EP2298783A1
    24222-EP2305243A1 24222-EP2305640A2 24222-EP2305680A2
    24222-EP2314590A1 2T8Q726O95 3'-Thia-2',3'-dideoxycytidine
    3-[(5S,2R)-2-(hydroxymethyl)(1,3-oxathiolan-5-yl)]-6-amino-3-hydropyrimidin-2- one 3TC 3TC & GNA
    3TC & SST 3TC (AIDS INITIATIVE) (AIDS INITIATIVE) 3TC and NV-01
    4-AMINO-1-[(2R,5S)-2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL]-1,2-DIHYDROPYRIMIDIN-2-ONE 4-AMINO-1-[(2R,5S)-2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL]-2(1H)-PYRIMIDINONE 4-Amino-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-2(1H)-pyrimidinone
    4-amino-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-Oxathiolan-5-yl]-(1H)-pyrimidin-2-one 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2(1H)-one
    4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-[1,3]-oxathiolan-5-yl]-(1H)-pyrimidin-2-one 480434-79-5
    678L174 AB00639995-06 AB00639995-08
    AB00639995_09 AB07588 AC-1416
    AKOS005622556 AKOS015854841 ANW-43098
    BBL033871 BCH 189 BCH 189, (-)-
    BCH-189 BCH-790 BDBM50366817
    BIDD:GT0033 C07065 C8H11N3O3S
    CCG-100984 CCRIS 9274 CHEBI:63577
    CHEMBL141 CIS-LAMIVUDINE CPD000466319
    CS-2230 CTK3J2124 Certified Reference Material
    D00353 DB00709 DRG-0126
    DTHC EPIVIR Epivir
    Epivir (TN) Epivir(TM) Epivir-HBV
    FT-0082667 FT-0601626 FT-0650554
    GG-714 GR 109714X GR-109714X
    GR109714X HHA & 3TC HHA & Lamivudine
    HMS2051D21 HMS3259F08 HMS3713C16
    HSDB 7155 HY-B0250 Hepitec
    Heptivir Heptodin Heptovir
    J-700183 J10244 JTEGQNOMFQHVDC-NKWVEPMBSA-N
    KS-0000023D KS-1073 L0217
    LAMIVUDINE LMV LS-2107
    Lamivir Lamivudin Lamivudina
    Lamivudine & GNA Lamivudine (EPIVIR) Lamivudine (JAN/USP/INN)
    Lamivudine [USAN:BAN:INN] Lamivudine [USAN:INN:BAN] Lamivudine [USAN:USP:INN:BAN]
    Lamivudine for system suitability 1, European Pharmacopoeia (EP) Reference Standard Lamivudine for system suitability 2, European Pharmacopoeia (EP) Reference Standard Lamivudine(Epivir)
    Lamivudine, 1.0 mg/mL in methanol, certified reference material Lamivudine, 98% Lamivudine, >=98% (HPLC), powder
    Lamivudine, British Pharmacopoeia (BP) Reference Standard Lamivudine, European Pharmacopoeia (EP) Reference Standard Lamivudine, Pharmaceutical Secondary Standard
    Lamivudine, United States Pharmacopeia (USP) Reference Standard Lamivudinum M-9795
    MCULE-2096184994 MFCD00869739 MLS000759424
    MLS001424097 MLS006011910 NC00234
    NC00705 NCGC00159341-04 NCGC00159341-05
    NSC620753 PYR356 Q-201275
    Q422631 RTC-020973 SAM001246582
    SAM002589994 SBB066293 SC-15184
    SCHEMBL109675 SMR000466319 SR-01000759420
    SR-01000759420-5 ST24030826 STK801940
    SW197614-3 UNII-2T8Q726O95 ZINC12346
    Zeffix Zefix beta-L-2',3'-Dideoxy-3'-thiacytidine
    beta-L-3'-Thia-2',3'-dideoxycytidine cis(+/-)-4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone lamivudine
    lamivudine & TNF-alpha & IFN-gamma s1706

    DrugBank Name Lamivudine
    DrugBank DB00709
    CAS Number 1117764-41-6, 134678-17-4, 134680-32-3, 136891-12-8, 480434-79-5
    PubChem Compound 60825
    KEGG Compound ID C07065
    KEGG Drug D00353
    PubChem.Substance 46507855
    ChEBI 63577
    PharmGKB PA450163
    ChemSpider 54812
    BindingDB 50366817.0
    TTD DAP000167
    Wikipedia Lamivudine
    HET 3TC
    DPD 122

    1. Chan et al. (2005)
    2. Dykens et al. (2007)