Details of the Drug

General Information of Drug (ID: DMI347A)

Drug Name

Lamivudine

Synonyms

lamivudine; 134678-17-4; Epivir; Zeffix; Heptovir; Epivir-HBV; Hepitec; Heptodin; BCH-189; 3TC; Heptivir; CIS-LAMIVUDINE; (-)-2'-Deoxy-3'-thiacytidine; 4-amino-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one; GR-109714X; 3'-Thia-2',3'-dideoxycytidine; (-)-BCH-189; Lamivudine [USAN:BAN:INN]; GR109714X; beta-L-3'-Thia-2',3'-dideoxycytidine; beta-L-2',3'-Dideoxy-3'-thiacytidine; (-)NGPB-21; 136891-12-8; 2',3'-Dideoxy-3'-thiacytidine; (-)-BCH 189; UNII-2T8Q726O95; HSDB 7155; GR 109714X; DTHC; LMV; Lamivir; Zefix; BCH 189; BCH189; BCH-790; DRG-0126; Epivir (TN); Epivir(TM); GG-714; HHA & 3TC; HHA & Lamivudine; Heptovir (TN); Lamivudine & GNA; Zeffix (TN); Epivir-HBV (TN); Lamivudine [USAN:INN:BAN]; Lamivudine (JAN/USP/INN); Lamivudine, (2S-cis)-Isomer; Beta-L-2',3'-Dideoxy-3'-thiacytidine; Beta-L-3'-Thia-2',3'-dideoxycytidine; Beta-L-(-)-2',3'-dideoxy-3'-thiacytidine & Sho-Saiko-To; (+/-)-(Cis)-1-[2-(Hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine; (+/-)-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; (-)-NGPB-21; (-)-SddC; (-)-beta-L-2',3'-Dideoxy-3'-thiacytidine; (2R,cis)-4-amino-1-(2-hydroxymethyl-1,3-oxathiolan-5-yl)-(1H)-pyrimidin-2-one; 2',3' Dideoxy 3' thiacytidine; 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); 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); 3TC & GNA; 3TC & SST; 3TC (AIDS INITIATIVE) (AIDS INITIATIVE); 3TC and NV-01; 3TC, Zeffix, Heptovir, Epivir, Epivir-HBV, Lamivudine; 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]pyrimidin-2-one; Efavirenz/lamivudine/tenofovir fumarate

Indication

Disease Entry	ICD 11	Status	REF
Chronic HBV infection	1E51.0Z	Approved	[1]
Human immunodeficiency virus infection	1C62	Approved	[1]
Human immunodeficiency virus-1 infection	1C62	Approved	[2]

Therapeutic Class

Anti-HIV Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

229.26

Topological Polar Surface Area (xlogp)

-0.9

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [3]
Bioavailability: 86% of drug becomes completely available to its intended biological destination(s) [4]
Clearance: The renal clearance of drug is 199.7 +/- 56.9 mL/min [5]
Elimination: 67% of drug is excreted from urine in the unchanged form [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 5 - 7 hours [6]
Metabolism: The drug is metabolized via sulfotransferases [7]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 21.80938 micromolar/kg/day [8]
Unbound Fraction: The unbound fraction of drug in plasma is 0.94% [6]
Vd: The volume of distribution (Vd) of drug is 1.3 +/- 0.4 L/kg [5]
Water Solubility: The ability of drug to dissolve in water is measured as 70 mg/mL [3]

Chemical Identifiers

Formula: C8H11N3O3S
IUPAC Name: 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one
Canonical SMILES: C1[C@H](O[C@H](S1)CO)N2C=CC(=NC2=O)N
InChI: 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

Cross-matching ID

PubChem CID: 60825
ChEBI ID: CHEBI:63577
CAS Number: 134678-17-4
DrugBank ID: DB00709
TTD ID: D07TQV
VARIDT ID: DR00116
INTEDE ID: DR0912
ACDINA ID: D00347

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Human immunodeficiency virus Reverse transcriptase (HIV RT)	TT84ETX	POL_HV1B1	Modulator	[9]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Organic cation transporter 1 (SLC22A1)	DTT79CX	S22A1_HUMAN	Substrate	[10]
Breast cancer resistance protein (ABCG2)	DTI7UX6	ABCG2_HUMAN	Substrate	[11]
Organic cation transporter 2 (SLC22A2)	DT9IDPW	S22A2_HUMAN	Substrate	[12]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Phosphorylcholine transferase A (PCYT1A)	DEQYXD4	PCY1A_HUMAN	Substrate	[13]
Phosphorylethanolamine transferase (PCYT2)	DEIX1PO	PCY2_HUMAN	Substrate	[13]
Deoxy-5'-nucleotidase 1 (NT5C)	DE4E31Z	NT5C_HUMAN	Substrate	[14]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Lamivudine (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Remdesivir	DMBFZ6L	Moderate	Increased risk of hepatotoxicity by the combination of Lamivudine and Remdesivir.	1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019]	[48]
Bedaquiline	DM3906J	Moderate	Increased risk of hepatotoxicity by the combination of Lamivudine and Bedaquiline.	Antimicrobial drug resistance [MG50-MG52]	[49]
Pexidartinib	DMS2J0Z	Major	Increased risk of hepatotoxicity by the combination of Lamivudine and Pexidartinib.	Bone/articular cartilage neoplasm [2F7B]	[50]
Cannabidiol	DM0659E	Moderate	Increased risk of hepatotoxicity by the combination of Lamivudine and Cannabidiol.	Epileptic encephalopathy [8A62]	[51]
Brentuximab vedotin	DMWLC57	Moderate	Increased risk of hepatotoxicity by the combination of Lamivudine and Brentuximab vedotin.	Hodgkin lymphoma [2B30]	[52]
Cobicistat	DM6L4H2	Moderate	Decreased metabolism of Lamivudine caused by Cobicistat mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[48]
Mipomersen	DMGSRN1	Major	Increased risk of hepatotoxicity by the combination of Lamivudine and Mipomersen.	Hyper-lipoproteinaemia [5C80]	[53]
Teriflunomide	DMQ2FKJ	Major	Increased risk of hepatotoxicity by the combination of Lamivudine and Teriflunomide.	Hyper-lipoproteinaemia [5C80]	[54]
BMS-201038	DMQTAGO	Major	Increased risk of hepatotoxicity by the combination of Lamivudine and BMS-201038.	Hyper-lipoproteinaemia [5C80]	[55]
Calaspargase pegol	DMQZBXI	Moderate	Increased risk of hepatotoxicity by the combination of Lamivudine and Calaspargase pegol.	Malignant haematopoietic neoplasm [2B33]	[56]
Idelalisib	DM602WT	Moderate	Increased risk of hepatotoxicity by the combination of Lamivudine and Idelalisib.	Mature B-cell leukaemia [2A82]	[57]
Orlistat	DMRJSP8	Moderate	Altered absorption of Lamivudine caused by Orlistat.	Obesity [5B80-5B81]	[58]
Leflunomide	DMR8ONJ	Major	Increased risk of hepatotoxicity by the combination of Lamivudine and Leflunomide.	Rheumatoid arthritis [FA20]	[54]
Trabectedin	DMG3Y89	Moderate	Increased risk of hepatotoxicity by the combination of Lamivudine and Trabectedin.	Solid tumour/cancer [2A00-2F9Z]	[51]
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⏷ Show the Full List of 14 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Isomalt	E00383	88735	Binding agent; Coating agent; Diluent; Flavoring agent; Suspending agent
Isopropyl alcohol	E00070	3776	Antimicrobial preservative; Solvent
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Crospovidone	E00626	Not Available	Disintegrant
Eisenoxyd	E00585	56841934	Colorant
Ferric hydroxide oxide yellow	E00539	23320441	Colorant
Ferrosoferric oxide	E00231	14789	Colorant
Hypromellose	E00634	Not Available	Coating agent
Magnesium stearate	E00208	11177	lubricant
Polyethylene glycol 400	E00653	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polysorbate 80	E00665	Not Available	Dispersing agent; Emollient; Emulsifying agent; Plasticizing agent; Solubilizing agent; Surfactant; Suspending agent
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Water	E00035	962	Solvent
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⏷ Show the Full List of 15 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Lamivudine 150 mg tablet	150 mg	Oral Tablet	Oral
Lamivudine 100 mg tablet	100 mg	Oral Tablet	Oral
Lamivudine 300 mg tablet	300 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

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