Lamivudine

An antiviral drug used in combination with other antiretroviral agents for the treatment of HIV infection. It is also active against hepatitis B virus and is used for the treatment of chronic hepatitis B.

CAS Number: 134678-17-4

Molecular Mass: 229.26 g/mol

Formula: C₈H₁₁N₃O₃S

Smiles: O=C1N=C(N)C=CN1C2OC(SC2)CO

Synonymes:

Lamivudine, 2(1H)-Pyrimidinone, 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-, 2(1H)-Pyrimidinone, 4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-, (2R-cis)-, 1,3-Oxathiolane, 2(1H)-pyrimidinone deriv., 4-Amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone, (-)-BCH 189, GR 109714X, Lamivudine, BCH 189, (-)-, (-)-2′-Deoxy-3′-thiacytidine, β-L-3′-Thia-2′,3′-dideoxycytidine, Epivir, Zeffix, Heptovir, Epivir HBV, L-SddC, Zefix, Hepitec, β-L-2′,3′-Dideoxy-3′-thiacytidine, 3TC, Lamivir, Heptodin, Virolam, 2-Hydroxymethyl-5-(cytosin-1-yl)-1,3-oxathiolane, cis(-)-2-Hydroxymethyl-5-(cytosin-1-yl)-1,3-oxathiolane, Lamidine, 29: PN: WO2016077321 SEQID: 29 claimed sequence, Hiviral, MeSH ID: D019259

Bioactivity: Nucleoside reverse transcriptase inhibitor (NRTI)

Solubility in Different Solvents

Solvent	Temperature [K]	Crystal form	Solubility [mg/mL]	Reference
1-Butanol	278.0	Form II	2.9	[1]
1-Butanol	288.0	Form II	3.7	[1]
1-Butanol	298.0	Form II	5.4	[1]
1-Butanol	308.0	Form II	6.3	[1]
1-Butanol	318.0	Form II	8.8	[1]
1-Propanol	278.0	Form II	4.1	[1]
1-Propanol	288.0	Form II	5.1	[1]
1-Propanol	298.0	Form II	7.2	[1]
1-Propanol	308.0	Form II	9.4	[1]
1-Propanol	318.0	Form II	13.3	[1]
2-Butanol	278.0	Form II	2.1	[1]
2-Butanol	288.0	Form II	3.0	[1]
2-Butanol	298.0	Form II	4.0	[1]
2-Butanol	308.0	Form II	5.6	[1]
2-Butanol	318.0	Form II	7.8	[1]
Acetone	278.0	Form II	0.57	[1]
Acetone	288.0	Form II	0.74	[1]
Acetone	298.0	Form II	0.94	[1]
Acetone	308.0	Form II	1.52	[1]
Acetone	318.0	Form II	2.58	[1]
Acetonitrile	278.0	Form II	0.47	[1]
Acetonitrile	288.0	Form II	0.54	[1]
Acetonitrile	298.0	Form II	0.91	[1]
Acetonitrile	298.0	-	0.96^?	-
Acetonitrile	308.0	Form II	1.45	[1]
Acetonitrile	318.0	Form II	2.15	[1]
Ethanol	278.0	-	7.0	[1]
Ethanol	288.0	-	8.8	[1]
Ethanol	298.0	Form II	11.4	[1]
Ethanol	308.0	-	15.2	[1]
Ethanol	318.0	-	19.6	[1]
Ethyl acetate	278.0	Form II	0.019	[1]
Ethyl acetate	288.0	Form II	0.037	[1]
Ethyl acetate	298.0	Form II	0.057	[1]
Ethyl acetate	308.0	Form II	0.086	[1]
Ethyl acetate	318.0	Form II	0.128	[1]
Isopropanol	278.0	Form II	2.7	[1]
Isopropanol	288.0	Form II	3.8	[1]
Isopropanol	298.0	Form II	4.9	[1]
Isopropanol	308.0	Form II	6.4	[1]
Isopropanol	318.0	Form II	8.0	[1]
Methanol	278.0	Form I	18.7	[1]
Methanol	288.0	Form I	22.8	[1]
Methanol	298.0	Form I	28.3	[1]
Methanol	308.0	Form I	35.8	[1]
Methanol	318.0	Form I	48.8	[1]
Water	278.0	Form I	37.8	[1]
Water	288.0	Form I	52.8	[1]
Water	298.0	Form I	84.9	[1]
Water	308.0	Form I	149.6	[1]
Water	318.0	Form I	360.0	[1]

Thermodynamic parameters of solution

Solvent	Temperature [K]	Crystal form	ΔH_sol [kJ/mol]	ΔS_sol [J/mol/K]	ΔG_sol [kJ/mol]	Reference
1-Butanol	298.0	Form II	20.33	-	-	[1]
1-Propanol	298.0	Form II	20.92	19.66	15.1	[1]
2-Butanol	298.0	Form II	23.81	-	-	[1]
Acetone	278.0	Form II	8.49	-	-	[1]
Acetone	298.0	Form II	28.12	-	-	[1]
Acetone	318.0	Form II	47.74	-	-	[1]
Acetonitrile	278.0	Form II	19.08	-	-	[1]
Acetonitrile	298.0	Form II	28.84	-	-	[1]
Acetonitrile	298.0	-	-	-	13.5	-
Acetonitrile	318.0	Form II	38.66	-	-	[1]
Ethanol	298.0	Form II	19.83	17.99	14.48	[1]
Ethyl acetate	298.0	Form II	34.48	-	-	[1]
Isopropanol	298.0	Form II	25.56	32.64	15.9	[1]
Methanol	278.0	Form I	10.25	-	-	[1]
Methanol	298.0	Form I	17.61	-	-	[1]
Methanol	318.0	Form I	25.02	-	-	[1]
Water	298.0	Form I	23.93	38.49	12.51	[1]

Molecule 3D descriptors

Descriptor	Value
PMI1	440.8490
PMI2	1767.4966
PMI3	1912.1017
NPR1	0.2306
NPR2	0.9244
RadiusOfGyration	2.9977
InertialShapeFactor	0.0021
Eccentricity	0.9731
Asphericity	0.4648
SpherocityIndex	0.2530
PBF	0.8202