Lamivudine

Details

• Internal ID: 916ea919-1341-4e5f-be2f-810a41ee5888
• Taxonomy: Nucleosides, nucleotides, and analogues > Nucleoside and nucleotide analogues > 3-thia pyrimidine nucleosides
• IUPAC Name: 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one
• 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
• InChI Key: JTEGQNOMFQHVDC-NKWVEPMBSA-N
• Popularity: 16,843 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₁₁N₃O₃S
• Molecular Weight: 229.26 g/mol
• Exact Mass: 229.05211239 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -0.59
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 134678-17-4
• Epivir
• Zeffix
• Epivir-HBV
• 4-amino-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one
• (-)-2'-Deoxy-3'-thiacytidine
• VIROLAM
• 3'-Thia-2',3'-dideoxycytidine
• GR-109714X
• GR109714X
• Lamivudine teva
• (-)-BCH-189
• 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
• BCH 189, (-)-
• 4-AMINO-1-[(2R,5S)-2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL]-2(1H)-PYRIMIDINONE
• Lamivudina
• Lamivudinum
• GR 109714X
• (-)-1-((2R,5S)-2-(Hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine
• BCH189
• CHEBI:63577
• 4-AMINO-1-[(2R,5S)-2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL]-1,2-DIHYDROPYRIMIDIN-2-ONE
• 2T8Q726O95
• NSC-760061
• 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
• DTXSID7023194
• (-)-1-[(2R,5S)-2-(Hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine
• 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
• Epivir HBV
• 2(1H)-Pyrimidinone, 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-
• lamivudine oral
• 3TC Lamivudine
• 2',3' Dideoxy 3' thiacytidine
• 4-amino-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-1,2-dihydropyrimidin-2-one
• 4-amino-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2-one
• Lamivudine, 3TC
• RefChem:798426
• J05AF05
• DTXCID001508532
• 603-844-3
• Heptovir
• 136891-12-8
• BCH-189
• Heptodin
• Lamivir
• 3TC
• CIS-LAMIVUDINE
• MFCD00869739
• 4-Amino-1-(cis-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one
• (-)NGPB-21
• Hepitec
• Heptivir
• Zefix
• 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]-, rel-
• Epivir(TM)
• HHA & Lamivudine
• Lamivudine & GNA
• SMR000466319
• Epivir (TN)
• (-)-BCH 189
• DTHC
• rac-cis-Lamivudine ((2RS,5SR)-Lamivudine)
• CHEMBL141
• HSDB 7155
• DRG-0126
• 3TC and NV-01
• 3TC;2',3'-Dideoxy-3'-thiacytidine;(-)-BCH-189
• (-)-SddC
• Lamivudine (JAN/USP/INN)
• 3TC & GNA
• 3TC & SST
• HHA & 3TC
• (+/-)-SddC
• CCRIS 9274
• NSC620753
• UNII-2T8Q726O95
• BCH-790
• Lamivudine [USAN:USP:INN:BAN]
• NCGC00159341-04
• GG-714
• Lamivudine (Standard)
• Lamivudine (EPIVIR)
• CPD000466319
• LAMIVUDINE [MI]
• (+/-)-3TC
• (+/-)-BCH-189
• LAMIVUDINE [INN]
• LAMIVUDINE [JAN]
• LAMIVUDINE [HSDB]
• LAMIVUDINE [USAN]
• LAMIVUDINE [VANDF]
• LAMIVUDINE [MART.]
• 2(1H)-Pyrimidinone, 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-, rel-
• LAMIVUDINE [USP-RS]
• LAMIVUDINE [WHO-DD]
• LAMIVUDINE [WHO-IP]
• Lamivudine, cis-(+/-)-
• US4RZW252L
• MLS000759424
• MLS001424097
• MLS006011910
• BIDD:GT0033
• LAMIVUDINE [EMA EPAR]
• SCHEMBL109675
• Lamivudine - Bio-X trade mark
• orb1310390
• LAMIVUDINE [EP IMPURITY]
• LAMIVUDINE [ORANGE BOOK]
• GTPL12673
• HY-B0250R
• LAMIVUDINE [EP MONOGRAPH]
• KIVEXA COMPONENT LAMIVUDINE
• GLXC-05058
• HMS2051D21
• HMS3259F08
• HMS3713C16
• LAMIVUDINE [USP MONOGRAPH]
• EPZICOM COMPONENT LAMIVUDINE
• LAMIVUDINUM [WHO-IP LATIN]
• TEMIXYS COMPONENT LAMIVUDINE
• ALBB-038661
• COMBIVIR COMPONENT LAMIVUDINE
• HY-B0250
• MSK10170
• BBL033871
• BDBM50366817
• s1706
• SBB066293
• STK801940
• lamivudine & TNF-alpha & IFN-gamma
• AKOS005622556
• AKOS015854841
• Lamivudine, >=98% (HPLC), powder
• (-)-BCH189
• AC-1416
• CCG-100984
• DB00709
• KS-1073
• NC00234
• NC00705
• NL06295
• NSC 760061
• NCGC00159341-05
• NCGC00159341-18
• NCGC00159341-20
• BL164607
• EMTRICITABINE IMPURITY C [WHO-IP]
• L0217
• NS00007004
• SW197614-3
• C07065
• D00353
• EN300-123034
• Lamivudine 100 microg/mL in Acetonitrile:Water
• P17147
• AB00639995-06
• AB00639995-08
• AB00639995_09
• 678L174
• F227713
• Q422631
• SR-01000759420
• SR-01000759420-5
• BRD-K02992638-001-11-8
• Z1509637175
• 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
• cis(+/-)-2-Hydroxymethyl-5-(cytosin-1-yl)-1,3-oxathiolane
• 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)
• 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]-, 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
• rel-4-Amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone
• 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)
• 4-AMINO-1-((2R,5S)-2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL)PYRIMIDIN-2(1H)-ONE [WHO-IP]

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9690	96.90%
Caco-2	-	0.8053	80.53%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	+	0.8857	88.57%
Subcellular localzation	Mitochondria	0.5543	55.43%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9596	95.96%
OATP1B3 inhibitior	+	0.9435	94.35%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9723	97.23%
P-glycoprotein inhibitior	-	0.9753	97.53%
P-glycoprotein substrate	-	0.9090	90.90%
CYP3A4 substrate	-	0.6201	62.01%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8944	89.44%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.7933	79.33%
CYP2C19 inhibition	-	0.8282	82.82%
CYP2D6 inhibition	-	0.9206	92.06%
CYP1A2 inhibition	-	0.8687	86.87%
CYP2C8 inhibition	-	0.9882	98.82%
CYP inhibitory promiscuity	-	0.8870	88.70%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.4774	47.74%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9541	95.41%
Skin irritation	-	0.7813	78.13%
Skin corrosion	-	0.9357	93.57%
Ames mutagenesis	-	0.7204	72.04%
Human Ether-a-go-go-Related Gene inhibition	-	0.6026	60.26%
Micronuclear	+	0.9800	98.00%
Hepatotoxicity	+	0.9501	95.01%
skin sensitisation	-	0.8609	86.09%
Respiratory toxicity	+	0.9556	95.56%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.7066	70.66%
Acute Oral Toxicity (c)	III	0.6225	62.25%
Estrogen receptor binding	-	0.6319	63.19%
Androgen receptor binding	+	0.6979	69.79%
Thyroid receptor binding	+	0.8320	83.20%
Glucocorticoid receptor binding	-	0.6052	60.52%
Aromatase binding	+	0.5489	54.89%
PPAR gamma	+	0.7722	77.22%
Honey bee toxicity	-	0.9499	94.99%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	-	0.4465	44.65%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293224	P10636	Microtubule-associated protein tau	3548.1 nM	Potency	PMID: 21855181
CHEMBL1293235	P02545	Prelamin-A/C	35481.3 nM	Potency	PMID: 26003344

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.04%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.88%	97.09%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	89.45%	98.46%
CHEMBL3384	Q16512	Protein kinase N1	87.29%	80.71%
CHEMBL226	P30542	Adenosine A1 receptor	87.27%	95.93%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.62%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.07%	86.33%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	85.03%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.66%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.43%	94.45%
CHEMBL4208	P20618	Proteasome component C5	84.41%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.09%	95.56%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	82.78%	93.10%
CHEMBL2581	P07339	Cathepsin D	81.57%	98.95%

Plants that contains it

• Strychnos vanprukii

Cross-Links

• PubChem: 60825
• NPASS: NPC469972
• ChEMBL: CHEMBL141
• LOTUS: LTS0272395
• wikiData: Q422631