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Namespace Prefixes

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Statements

Subject Item
n2:DB00709
rdf:type
n5:Drug
n5:description
A reverse transcriptase inhibitor and zalcitabine analog in which a sulfur atom replaces the 3' carbon of the pentose ring. It is used to treat Human Immunodeficiency Virus Type 1 (HIV-1) and hepatitis B (HBV).
n5:dosage
n21:271B4AC2-363D-11E5-9242-09173F13E4C5 n21:271B4AC3-363D-11E5-9242-09173F13E4C5 n21:271B4ABB-363D-11E5-9242-09173F13E4C5 n21:271B4ABC-363D-11E5-9242-09173F13E4C5 n21:271B4ABD-363D-11E5-9242-09173F13E4C5 n21:271B4ABE-363D-11E5-9242-09173F13E4C5 n21:271B4ABF-363D-11E5-9242-09173F13E4C5 n21:271B4AC0-363D-11E5-9242-09173F13E4C5 n21:271B4AC1-363D-11E5-9242-09173F13E4C5
n5:generalReferences
# Fox Z, Dragsted UB, Gerstoft J, Phillips AN, Kjaer J, Mathiesen L, Youle M, Katlama C, Hill A, Bruun JN, Clumeck N, Dellamonica P, Lundgren JD: A randomized trial to evaluate continuation versus discontinuation of lamivudine in individuals failing a lamivudine-containing regimen: the COLATE trial. Antivir Ther. 2006;11(6):761-70. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17310820
n5:group
investigational approved
n5:halfLife
5 to 7 hours (healthy or HBV-infected patients)
n5:indication
For the treatment of HIV infection and chronic hepatitis B (HBV).
n5:manufacturer
n17:271B4AB3-363D-11E5-9242-09173F13E4C5 n17:271B4AB4-363D-11E5-9242-09173F13E4C5
owl:sameAs
n33:DB00709 n34:DB00709
dcterms:title
Lamivudine
adms:identifier
n10:63577 n12:Lamivudine n20:50046287 n22:54812 n23:60825 n24:46507855 n25:0173-0742-00 n26:PA450163 n27:C07065 n28:D00353 n29:DB00709
n5:mechanismOfAction
Lamivudine is a synthetic nucleoside analogue and is phosphorylated intracellularly to its active 5'-triphosphate metabolite, lamivudine triphosphate (L-TP). This nucleoside analogue is incorporated into viral DNA by HIV reverse transcriptase and HBV polymerase, resulting in DNA chain termination.
n5:packager
n17:271B4AA6-363D-11E5-9242-09173F13E4C5 n17:271B4AAD-363D-11E5-9242-09173F13E4C5 n17:271B4AAE-363D-11E5-9242-09173F13E4C5 n17:271B4AAB-363D-11E5-9242-09173F13E4C5 n17:271B4AAC-363D-11E5-9242-09173F13E4C5 n17:271B4AB1-363D-11E5-9242-09173F13E4C5 n17:271B4AB2-363D-11E5-9242-09173F13E4C5 n17:271B4AAF-363D-11E5-9242-09173F13E4C5 n17:271B4AB0-363D-11E5-9242-09173F13E4C5 n17:271B4AA4-363D-11E5-9242-09173F13E4C5 n17:271B4AA5-363D-11E5-9242-09173F13E4C5 n17:271B4AA2-363D-11E5-9242-09173F13E4C5 n17:271B4AA3-363D-11E5-9242-09173F13E4C5 n17:271B4AA9-363D-11E5-9242-09173F13E4C5 n17:271B4AAA-363D-11E5-9242-09173F13E4C5 n17:271B4AA7-363D-11E5-9242-09173F13E4C5 n17:271B4AA8-363D-11E5-9242-09173F13E4C5
n5:patent
n7:6004968 n7:2070230 n7:2100269 n7:7119202
n5:routeOfElimination
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.
n5:synonym
(-)-1-((2R,5S)-2-(Hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine Lamivudine Lamivudinum 3'-Thia-2',3'-dideoxycytidine Epivir Lamivudin beta-L-3'-Thia-2',3'-dideoxycytidine 3TC beta-L-2',3'-Dideoxy-3'-thiacytidine (-)-2'-Deoxy-3'-thiacytidine Lamivudina 2',3'-Dideoxy-3'-thiacytidine
n5:toxicity
The most common reported adverse reactions (incidence ≥15%) in adults were headache, nausea, malaise and fatigue, nasal signs and symptoms, diarrhea, and cough.
n5:volumeOfDistribution
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.
n13:hasAHFSCode
n14:08-18-08-20
n5:foodInteraction
Take without regard to meals. Food does not decrease the extent of absorption, but it decreases the Cmax by slowing the rate of absorption.
n5:mixture
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n5:proteinBinding
<36% bound to plasma protein.
n5:salt
n5:synthesisReference
Jinliang LI, Feng LV, "PROCESS FOR STEREOSELECTIVE SYNTHESIS OF LAMIVUDINE." U.S. Patent US20100249409, issued September 30, 2010.
n15:hasConcept
n16:M0028682
foaf:page
n4:lamivudine.html n11:lamivudine.htm n31:com1513.shtml
n5:IUPAC-Name
n8:271B4AC8-363D-11E5-9242-09173F13E4C5
n5:InChI
n8:271B4ACE-363D-11E5-9242-09173F13E4C5
n5:Molecular-Formula
n8:271B4ACD-363D-11E5-9242-09173F13E4C5
n5:Molecular-Weight
n8:271B4ACA-363D-11E5-9242-09173F13E4C5
n5:Monoisotopic-Weight
n8:271B4ACB-363D-11E5-9242-09173F13E4C5
n5:SMILES
n8:271B4ACC-363D-11E5-9242-09173F13E4C5
n5:Water-Solubility
n8:271B4ADE-363D-11E5-9242-09173F13E4C5 n8:271B4AC6-363D-11E5-9242-09173F13E4C5
n5:logP
n8:271B4AE0-363D-11E5-9242-09173F13E4C5 n8:271B4AC4-363D-11E5-9242-09173F13E4C5 n8:271B4AC7-363D-11E5-9242-09173F13E4C5
n5:logS
n8:271B4AC5-363D-11E5-9242-09173F13E4C5
n13:hasATCCode
n30:J05AF05
n5:H-Bond-Acceptor-Count
n8:271B4AD4-363D-11E5-9242-09173F13E4C5
n5:H-Bond-Donor-Count
n8:271B4AD5-363D-11E5-9242-09173F13E4C5
n5:InChIKey
n8:271B4ACF-363D-11E5-9242-09173F13E4C5
n5:Polar-Surface-Area--PSA-
n8:271B4AD0-363D-11E5-9242-09173F13E4C5
n5:Polarizability
n8:271B4AD2-363D-11E5-9242-09173F13E4C5
n5:Refractivity
n8:271B4AD1-363D-11E5-9242-09173F13E4C5
n5:Rotatable-Bond-Count
n8:271B4AD3-363D-11E5-9242-09173F13E4C5
n5: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.
n5:affectedOrganism
Hepatitis B virus Human Immunodeficiency Virus
n5:casRegistryNumber
134678-17-4
n5:category
n5: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]
n5:containedIn
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n5:Bioavailability
n8:271B4ADA-363D-11E5-9242-09173F13E4C5
n5:Ghose-Filter
n8:271B4ADC-363D-11E5-9242-09173F13E4C5
n5:MDDR-Like-Rule
n8:271B4ADD-363D-11E5-9242-09173F13E4C5
n5:Melting-Point
n8:271B4ADF-363D-11E5-9242-09173F13E4C5
n5:Number-of-Rings
n8:271B4AD9-363D-11E5-9242-09173F13E4C5
n5:Physiological-Charge
n8:271B4AD8-363D-11E5-9242-09173F13E4C5
n5:Rule-of-Five
n8:271B4ADB-363D-11E5-9242-09173F13E4C5
n5:Traditional-IUPAC-Name
n8:271B4AC9-363D-11E5-9242-09173F13E4C5
n5:pKa--strongest-acidic-
n8:271B4AD6-363D-11E5-9242-09173F13E4C5
n5:pKa--strongest-basic-
n8:271B4AD7-363D-11E5-9242-09173F13E4C5