Drug Details

General Information of the Drug (ID: DR6878)
Name
lamivudine
Synonyms
lamivudine; 134678-17-4; Epivir; Zeffix; Heptovir; Epivir-HBV; Heptodin; 3TC; BCH-189; (-)-2'-Deoxy-3'-thiacytidine; 2',3'-Dideoxy-3'-thiacytidine; 4-amino-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one; 3'-Thia-2',3'-dideoxycytidine; GR-109714X; (-)-BCH-189; beta-L-2',3'-Dideoxy-3'-thiacytidine; beta-L-3'-Thia-2',3'-dideoxycytidine; (-)NGPB-21; 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one; GR 109714X; 136891-12-8; UNII-2T8Q726O95; BCH 189, (-)-; Hepitec; MFCD00869739; (-)-1-((2R,5S)-2-(Hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine; 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2(1H)-one; CHEBI:63577; (-)-1-[(2R,5S)-2-(Hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine; 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]-1,2-DIHYDROPYRIMIDIN-2-ONE; 2T8Q726O95; Heptivir; Lamivir; Zefix; 4-Amino-1-(cis-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one; GR109714X; 4-AMINO-1-[(2R,5S)-2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL]-2(1H)-PYRIMIDINONE; BCH 189; Lamivudine [USAN:BAN:INN]; (-)-(2'R,5'S)-1-[2'-Hydroxymethyl-5'-(1,3-oxathiolanyl)]cytosine; 2(1H)-Pyrimidinone, 4-amino-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-; Epivir(TM); HHA & Lamivudine; Lamivudine & GNA; SMR000466319; Epivir (TN); (-)-BCH 189; DTHC; CHEMBL141; HSDB 7155; DRG-0126; 3TC and NV-01; (-)-SddC; Lamivudeine; Lamivudine (JAN/USP/INN); 3TC & GNA; 3TC & SST; HHA & 3TC; (+/-)-SddC; CCRIS 9274; NSC620753; 2(1H)-Pyrimidinone, 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-; BCH-790; Lamivudine [USAN:USP:INN:BAN]; NCGC00159341-04; Lamivudine, 98%; GG-714; Lamivudine (EPIVIR); CPD000466319; (+/-)-3TC; (+/-)-BCH-189; 2(1H)-Pyrimidinone, 4-amino-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-, (2R-cis)-; MLS000759424; MLS001424097; MLS006011910; BIDD:GT0033; SCHEMBL109675; AMY384; PYR356; ZINC12346; HMS2051D21; HMS3259F08; HMS3713C16; HY-B0250; ANW-43098; BBL033871; BDBM50366817; s1706; SBB066293; STK801940; lamivudine & TNF-alpha & IFN-gamma; AKOS005622556; AKOS015854841; Lamivudine, >=98% (HPLC), powder; AB07588; AC-1416; CCG-100984; DB00709; KS-1073; MCULE-2096184994; NC00234; NC00705; NSC 760061; NCGC00159341-05; NCGC00159341-18; L0217; SW197614-3; C07065; D00353; J10244; M-9795; 24222-EP2269989A1; 24222-EP2272516A2; 24222-EP2272825A2; 24222-EP2292227A2; 24222-EP2298761A1; 24222-EP2298783A1; 24222-EP2305243A1; 24222-EP2305640A2; 24222-EP2305680A2; 24222-EP2314590A1; AB00639995-06; AB00639995-08; AB00639995_09; Lamivudeine 100 microg/mL in Acetonitrile:Water; 200973-EP2272825A2; 678L174; Q422631; SR-01000759420; J-700183; Q-201275; SR-01000759420-5; Lamivudine, British Pharmacopoeia (BP) Reference Standard; Lamivudine, European Pharmacopoeia (EP) Reference Standard; (2R,5S)-1-[2-(Hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine; .beta.-L-(-)-2',3'-dideoxy-3'-thiacytidine & Sho-Saiko-To; Lamivudine, United States Pharmacopeia (USP) Reference Standard; (+/-) (Cis)-1-[2-(Hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine; (-)-L-2',3'-DIDEOXY-3'-THIACYTIDINE; LAMIVUDINE; EPIVIR; Lamivudine, 1.0 mg/mL in methanol, certified reference material; Lamivudine, Pharmaceutical Secondary Standard; Certified Reference Material; (+/-)-(cis)-4-Amino-1-(2-hydroxymethyl-1,3-oxathiolan-5-yl)-(1H)-pyrimidin-2-one; 2(1H)-Pyrimidinone, 4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl], (+/-) (Cis); 3-[(5S,2R)-2-(hydroxymethyl)(1,3-oxathiolan-5-yl)]-6-amino-3-hydropyrimidin-2- 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]-(1H)-pyrimidin-2-one; cis(+/-)-4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone; Lamivudine for system suitability 1, European Pharmacopoeia (EP) Reference Standard; Lamivudine for system suitability 2, European Pharmacopoeia (EP) Reference Standard; 1117764-41-6; 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)
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Molecular Type
Small molecule
Disease Hepatitis C virus infection [ICD-11: 1E51] Approved [1]
Structure
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2D MOL

3D MOL

ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability
Bioavailability
86% of drug becomes completely available to its intended biological destination(s)
Clearance
The renal clearance of drug is 199.7 +/- 56.9 mL/min
Elimination
67% of drug is excreted from urine in the unchanged form
Half-life
The concentration or amount of drug in body reduced by one-half in 5 - 7 hours
Metabolism
The drug is metabolized via sulfotransferases
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 21.80938 micromolar/kg/day
Unbound Fraction
The unbound fraction of drug in plasma is 0.94%
Vd
The volume of distribution (Vd) of drug is 1.3 +/- 0.4 L/kg
Water Solubility
The ability of drug to dissolve in water is measured as 70 mg/mL
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C8H11N3O3S
PubChem CID
60825
Canonical SMILES
C1C(OC(S1)CO)N2C=CC(=NC2=O)N
InChI
1S/C8H11N3O3S/c9-5-1-2-11(8(13)10-5)6-4-15-7(3-12)14-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7+/m0/s1
InChIKey
JTEGQNOMFQHVDC-NKWVEPMBSA-N
CAS Number
CAS 134678-17-4
ChEBI ID
CHEBI:63577
TTD Drug ID
D07TQV
DrugBank ID
DB00709
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Penciclovir      Homo sapiens     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Huh-7 CVCL_0336 Adult hepatocellular carcinoma Homo sapiens
                    Experimental
                    Result(s)		 These results suggest that combinations of 3TC and PCV may act synergistically against HBV in vivo.
    β. A List of Natural Product(s) Able to Reverse the Resistance of This Drug
          Glycyrrhizin      Glycyrrhiza glabra     Click to Show/Hide the Molecular Data of This NP
                 Reversing Drug Resistance     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression ABCC2  Molecule Info 
Pathway MAP
Up-regulation Expression ABCC3  Molecule Info 
Pathway MAP
Up-regulation Expression ABCC4  Molecule Info 
Pathway MAP
Up-regulation Expression ABCC5  Molecule Info 
Pathway MAP
                    In-vitro Model Huh-7 CVCL_0336 Adult hepatocellular carcinoma Homo sapiens
                    Experimental
                    Result(s)		 The combination of glycyrrhizin and lamivudine inhibit the cisplatin efflux from the HCC cells, acting as modulators to reverse cisplatin resistance.
Target and Pathway
Target(s) HIV reverse transcriptase (HIV RT)  Molecule Info  [4]
References
Reference 1 Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
Reference 2 Synergistic inhibition of hepadnaviral replication by lamivudine in combination with penciclovir in vitro. Hepatology. 1997 Jul;26(1):216-25.
Reference 3 The combination of glycyrrhizin and lamivudine can reverse the cisplatin resistance in hepatocellular carcinoma cells through inhibition of multidrug resistance-associated proteins. Int J Oncol. 2007 Dec;31(6):1465-72.
Reference 4 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
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