Lamivudine

Athanor · official

C₈H₁₁N₃O₃S · 229.26 g/mol

IUPAC name: 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one

Also called 3TC, Epivir, HIV, hepatitis B

Drugs Rings

Open in Athanor

Drawn from its SMILES with RDKit

WarningCauses skin irritation · Causes serious eye irritation · May cause respiratory irritation · Suspected of damaging fertility or the unborn child · May causes damage to organs through prolonged or repeated exposure

Names and identifiers

IUPAC name: 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one
Synonyms: 3TC, Epivir, HIV
+ 38 more
hepatitis B, Zeffix, Epivir-HBV, 4-amino-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one, (-)-2'-Deoxy-3'-thiacytidine, GR-109714X, VIROLAM, (-)-BCH-189, GR109714X, 3'-Thia-2',3'-dideoxycytidine, Lamivudine teva, beta-L-2',3'-Dideoxy-3'-thiacytidine, beta-L-3'-Thia-2',3'-dideoxycytidine, 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]-2(1H)-PYRIMIDINONE, BCH 189, (-)-, Lamivudina, Lamivudinum, GR 109714X, (-)-1-((2R,5S)-2-(Hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine, BCH189, 4-AMINO-1-[(2R,5S)-2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL]-1,2-DIHYDROPYRIMIDIN-2-ONE, CHEBI:63577, 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2(1H)-one, 2T8Q726O95, NSC-760061, (-)-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, TRIUMEQ COMPONENT LAMIVUDINE, LAMIVUDINE TEVA PHARMA B.V., TRIZIVIR COMPONENT LAMIVUDINE, DELSTRIGO COMPONENT LAMIVUDINE, 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)-, LAMIVUDINE/ZIDOVUDINE TEVA COMPONENT LAMIVUDINE, DTXSID7023194, Epivir HBV, 2(1H)-Pyrimidinone, 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-
Molecular formula: C₈H₁₁N₃O₃S
Empirical formula: C₈H₁₁N₃O₃S
Molecular weight: 229.26 g/mol
Exact mass: 229.05211
CAS number: 134678-17-4
PubChem CID: 60825
Canonical SMILES: C1C(OC(S1)CO)N2C=CC(=NC2=O)N
Isomeric 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
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Physical properties

TemperaturePressureDensity

log P: log Kow = -9.54 @ 25 °C (estimated)[1]
Vapor pressure: 8.3 × 10⁻¹⁶ mmHg @ 25 °C (estimated)[1]

Each value as its source reports it, with the source's number after it (listed under References). Where several sources report a property, the row shows the value most of them agree on, the rule the app uses; open the values to see every one.

Calculated

Heavy atoms: 15
Rings: 2
Aromatic rings: 1
Fraction sp³ carbons (Fsp3): 0.5
H-bond donors: 2
H-bond acceptors: 6 computed here · PubChem 4
Rotatable bonds: 2
TPSA (Å²): 90.4 computed here · PubChem 113
Formal charge: 0
XLogP3: -0.9 PubChem
Complexity: 331 PubChem
Stereocenters: 2 definedCIP: C6: S · C9: R
Double-bond geometry: None specified
Point group: C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

C41.91%
H4.84%
N18.33%
O20.94%
S13.99%

Isotope pattern

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P: -0.59 Crippen (Wildman and Crippen 1999)
log S (water solubility): -1.05 ESOL (Delaney 2004), log mol/L
Synthetic accessibility: 3.81 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

Molecular weight ≤ 500: 229.26
log P ≤ 5 (Crippen): -0.59
H-bond donors ≤ 5: 2
H-bond acceptors ≤ 10: 6

Passes all four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

Warning

Most widely reported: 133 company reports to ECHA. Source [2].

Harmful or irritant
Health hazard

H315Causes skin irritation (30.1% of reports)
H319Causes serious eye irritation (30.1% of reports)
H335May cause respiratory irritation (30.1% of reports)
H361Suspected of damaging fertility or the unborn child (69.2% of reports)
H373May causes damage to organs through prolonged or repeated exposure (30.1% of reports)

Precautionary statements: P203, P260, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501

View all classifications (2)

[2] European Chemicals Agency (ECHA)This chemical does not meet GHS hazard criteria for 0.8% (1 of 133) of reports.
[2] European Chemicals Agency (ECHA) · 133 reports · WarningH315, H319, H335, H361, H373

Always read the supplier’s safety data sheet before working with it.

Spectra

Experimental spectra held by these sources; each link opens the source's own record.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

[1]Hazardous Substances Data Bank (HSDB) · Public domain (US NLM) · via PubChem · retrieved 2026-10-14
[2]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
[3]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
[4]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
[5]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
[6]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
·Literature on PubChem

Data last updated 2026-10-14.