Lamivudine (CED0001859)

Record Information

Version

1.0

Creation Date

2016-05-22 03:42:20 UTC

Update Date

2026-08-24 12:18:53 UTC

Accession Number

CHEM016749

Identification

Common Name

Lamivudine

Class

Small Molecule

Description

Lamivudine is an organic compound with the formula C8H11N3O3S and an average molecular weight of 229.25 g/mol. Lamivudine belongs to the 3'-thia pyrimidine nucleosides, a subclass of nucleoside and nucleotide analogues within the organic compounds. It functions as an antiviral drug (PMC10054433). The compound acts as an inhibitor or modulator of Protein P and targets the Gag-Pol polyprotein (gag-pol) as well as Reverse transcriptase/RNaseH (pol). Regarding its distribution and exposure, lamivudine is found in or released from 10 recorded sources. These include healthcare, pharmaceuticals, and veterinary products such as antivirals, as well as household cleaning and consumer products including cigar cigarettes, non electric simulated smoking devices, and other smoking requisites. Additionally, it is associated with electrical and electronic equipment, specifically antennas, coils, electrically stimulated smoking devices, radio transmission systems, television systems, and one other source. The recorded route of exposure for this compound is oral.

Contaminant Type

Human Neurotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2',3' Dideoxy 3' thiacytidine	MeSH
BCH-189	MeSH
BCH 189	MeSH
2',3'-Dideoxy-3'-thiacytidine	MeSH
3TC	MeSH
Lamivudine	MeSH
Lamivudine, (2S-cis)-isomer	MeSH
Epivir	MeSH

Chemical Formula

C₈H₁₁N₃O₃S

Average Molecular Mass

229.250 g/mol

Monoisotopic Mass

229.052 g/mol

CAS Registry Number

134678-17-4

IUPAC Name

1-[(2S,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-4-imino-1,4-dihydropyrimidin-2-ol

Traditional Name

lamivudine

SMILES

[H][C@]1(CO)O[C@]([H])(CS1)N1C=CC(=N)N=C1O

InChI Identifier

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+/m1/s1

InChI Key

JTEGQNOMFQHVDC-RQJHMYQMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-thia pyrimidine nucleosides. These are nucleoside analogues with a structure that consists of a pyrimidine base, which is N-substituted at the 1-position with a 3'-thia derivative (1,3-oxazolidine) of the ribose moiety that is characteristic of nucleosides.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Nucleoside and nucleotide analogues

Sub Class

3'-thia pyrimidine nucleosides

Direct Parent

3'-thia pyrimidine nucleosides

Alternative Parents

Substituents

3'-thia pyrimidine nucleoside
Aminopyrimidine
Pyrimidone
Hydropyrimidine
Pyrimidine
Imidolactam
Monothioacetal
Oxathiolane
Heteroaromatic compound
Organoheterocyclic compound
Azacycle
Oxacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary amine
Primary alcohol
Amine
Organooxygen compound
Organonitrogen compound
Alcohol
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

antiviral drug

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.45 g/L	ALOGPS
logP	-0.81	ALOGPS
logP	-0.12	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	5.91	ChemAxon
pKa (Strongest Basic)	2.51	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	89.14 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	66.58 m³·mol⁻¹	ChemAxon
Polarizability	21.97 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0910000000-93346cf49eef73914c7c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-4900000000-07c6901608fdcd9b93b8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03dj-9600000000-5e58e487d2a852e72115	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-4970000000-db3826710ed881faa506	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00n0-1900000000-f8fcf86f0a9e8e88d032	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-9100000000-7bf9d4c9292e16f5a8cf	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
2504.0	Log mg/kg	[1400:4500]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
351	Antivirals	Healthcare, pharmaceuticals & veterinary products	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
508	Coils	Electrical & Electronic Equipment	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
530	Radio Transmission Systems	Electrical & Electronic Equipment	Not Available
537	Television Systems	Electrical & Electronic Equipment	Not Available
539	Video Games	Electrical & Electronic Equipment	Not Available
556	Cigar Cigarettes	Household cleaning & consumer products	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
560	Other Smoking Requisites	Household cleaning & consumer products	Not Available
609	Aftershave	Personal care & cosmetics	Not Available
613	Depilatories	Personal care & cosmetics	Not Available
617	Lip Care Products	Personal care & cosmetics	Not Available
643	Headwear	Textiles, leather & furnishings	Not Available
653	Sewing	Textiles, leather & furnishings	Not Available

Pathways

4 pathways

Lamivudine Metabolism Pathway

Lamivudine Action Pathway

Lamivudine Anti-viral Action Pathway

Lamivudine Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Reverse transcriptase/RNaseH	Q72547	Human immunodeficiency virus 1	Predicted (SEA)	30.984
Click to view 3D structure	Heat shock factor protein 1	P38532	Mus musculus	Predicted (SEA)	321.673
Click to view 3D structure	Adenosine kinase	P9WID4	Mycobacterium tuberculosis (strain CDC 1551 / Oshkosh)	Predicted (SEA)	40.4816
Click to view 3D structure	Core antigen	Q03732	Hepatitis B virus	Predicted (SEA)	1.40129
Click to view 3D structure	Ribonuclease pancreatic	P61823	Bos taurus	Predicted (SEA)	32.4631
Click to view 3D structure	Tyrosine--tRNA ligase	P0AGJ9	Escherichia coli (strain K12)	Predicted (SEA)	58.6983
Click to view 3D structure	Adenosine kinase	P55263	Humans	Predicted (SEA)	342.303
Click to view 3D structure	Adenosine receptor A1	P25099	Rattus norvegicus	Predicted (SEA)	2547.23
Click to view 3D structure	Alpha-1,2-mannosidase (BT_3965)	Q8A0Q6	Bacteroides thetaiotaomicron	Predicted (SEA)	6.30579
Click to view 3D structure	Alpha-1,2-mannosidase, putative (BT_3130)	Q8A325	Bacteroides thetaiotaomicron	Predicted (SEA)	6.30579
Click to view 3D structure	Adenosine deaminase	P56658	Bos taurus	Predicted (SEA)	100.036
Click to view 3D structure	Thymidine kinase, cytosolic	P04183	Humans	Predicted (SEA)	23.5105
Click to view 3D structure	Beta-mannosidase B	Q8AAK6	Bacteroides thetaiotaomicron (strain ATCC 29148 / DSM 2079 / NCTC 10582 / E50 / VPI-5482)	Predicted (SEA)	12.0666
Click to view 3D structure	Cytidine deaminase	P32320	Humans	Predicted (SEA)	46.3981
Click to view 3D structure	Adenosine receptor A3	P0DMS8	Humans	Predicted (SEA)	5401.57
Click to view 3D structure	Thymidine kinase 2	D3ZGQ2	Rattus norvegicus	Predicted (SEA)	191.743
Click to view 3D structure	Adenosine receptor A1	P30542	Humans	Predicted (SEA)	5138.36
Click to view 3D structure	Adenosine receptor A2a	P29274	Humans	Predicted (SEA)	5428.35
Click to view 3D structure	Thymidine kinase	P06479	Human herpesvirus 1 (strain SC16) (HHV-1) (Human herpes simplex virus1)	Predicted (SEA)	42.1164
Click to view 3D structure	Adenosine receptor A2a	P30543	Rattus norvegicus	Predicted (SEA)	3434.24
Click to view 3D structure	Solute carrier family 28 member 3	Q9HAS3	Humans	Predicted (SEA)	60.4888
Click to view 3D structure	Adenosine deaminase	P00813	Humans	Predicted (SEA)	160.681
Click to view 3D structure	Adenosine receptor A1	Q60612	Mus musculus	Predicted (SEA)	940.808
Click to view 3D structure	Adenosine receptor A3	P28647	Rattus norvegicus	Predicted (SEA)	1948.8
Click to view 3D structure	Adenosine deaminase	Q86GS5	Plasmodium falciparum	Predicted (SEA)	45.6196