Linezolid

A synthetic oxazolidinone antibiotic used to treat serious infections caused by susceptible Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus faecium (VRE). Linezolid binds to the 23S ribosomal RNA of the bacterial 50S ribosomal subunit, preventing formation of the functional 70S translation initiation complex and thereby inhibiting protein synthesis. It is used for pneumonia, complicated skin and soft tissue infections, and certain resistant enterococcal infections

CAS Number: 165800-03-3

Molecular Mass: 337.35 g/mol

Formula: C₁₆H₂₀FN₃O₄

Smiles: CC(=O)NC[C@H]1CN(c2ccc(N3CCOCC3)c(F)c2)C(=O)O1

Synonymes:

Linezolid, linezolid, 165800-03-3, Zyvox, PNU-100766, U-100766, LINEZOLIDE, ISQ9I6J12J, N-(((S)-3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl)methyl)acetamide, N-[[(5S)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide, DTXSID5046489, U-100,766, PNU100766, DTXCID3026489, CHEBI:63607, Acetamide, N-((3-(3-fluoro-4-(4-morpholinyl)phenyl)-2-oxo-5-oxazolidinyl)methyl)-, (S)-, N-{[(5s)-3-(3-Fluoro-4-Morpholin-4-Ylphenyl)-2-Oxo-1,3-Oxazolidin-5-Yl]methyl}acetamide, N-({(5S)-3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide, N-{[(5S)-3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide, Linezolidum, Acetamide, N-[[3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-, (S)-, N-(((5S)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl)methyl)acetamide, N-[[(S)-3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl]methyl]acetamide, N-(((5S)-3-(3-fluoro-4-(morpholin-4-yl)phenyl)-2-oxo-1,3-oxazolidin-5-yl)methyl)acetamide, N-((3-(3-fluoro-4-morpholinylphenyl)-2-oxo-5-oxazolidinyl)methyl)acetamide, RefChem:5949, U100766, 100766, U, J01XX08, LINEZOLID IN SODIUM CHLORIDE 0.9% IN PLASTIC CONTAINER, (S)-N-((3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl)acetamide, Zyvoxid, Zyvoxam, PNU 100766, C16H20FN3O4, U 100766, MFCD00937825, N-[[(5S)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide, Acetamide, N-[[(5S)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-, CHEMBL126, (S)-N-[[3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl]methyl]acetamide, N-[[(5S)-3-(3-fluoro-4-morpholino-phenyl)-2-oxo-oxazolidin-5-yl]methyl]acetamide, ZLD, Zivoxid, Zyvoxa, Acetamide, N-(((5S)-3-(3-fluoro-4-(4-morpholinyl)phenyl)-2-oxo-5-oxazolidinyl)methyl)-, SMR000466335, Zyvox (TN), HSDB 7478, SR-01000759376, Linezolid & VRC3375, UNII-ISQ9I6J12J, Linezoid, Linezolid (JAN/USAN/INN), Linezolid [USAN:INN:BAN], NCGC00164628-01, Linezolid (Zyvox), Linezolid (Standard), 111GE017, CPD000466335, NDA 21-130 Zyvox (linezolid tablets), LINEZOLID [INN], LINEZOLID [JAN], LINEZOLID [MI], LINEZOLID [HSDB], LINEZOLID [USAN], LINEZOLID [VANDF], LinezolidPNU-100766, LINEZOLID [MART.], (S)-N-[[3-(3-fluoro-4-morpholinylphenyl)-2-oxo-5-oxazolidinyl]methyl]acetamide, LINEZOLID [USP-RS], LINEZOLID [WHO-DD], SCHEMBL5027, MLS000759444, MLS001424075, BIDD:GT0404, Benzotriazol-2-yl-acetonitrile, cid_441401, Linezolid (PNU-100766), orb1310657, orb3141296, SCHEMBL7992562, LINEZOLID [ORANGE BOOK], Linezolid, >=98% (HPLC), NDA 21-131 Zyvox for injection (linezolid injection), GTPL10827, LINEZOLID [USP MONOGRAPH], GLXC-04742, HMS2051F08, HMS2089K06, HMS3260C14, HMS3713K10, NDA 21-132 Zyvox oral suspension (linzolid oral suspension), MSK14235, Tox21_112246, Tox21_500096, BDBM50116067, EBC-08517, HB4443, HY-10394R, s1408, AKOS016340522, AF58050, CCG-101009, CS-0756, DB00601, KS-1178, NC00259, Linezolid 100 microg/mL in Acetonitrile, NCGC00260781-01, NCGC00263531-03, NCGC00263531-05, NCGC00263531-10, HY-10394, SY056734, CAS-165800-03-3, L0362, NS00008464, SW197639-3, C08146, D00947, AB00639994-06, AB00639994-08, AB00639994-09, AB00639994_10, AB00639994_11, F227724, Q411377, SR-01000759376-4, SR-01000759376-5, BRD-K66876909-001-11-8, BRD-K66876909-001-12-6, SR-01000759376-11, Z1515385084, Linezolid, United States Pharmacopeia (USP) Reference Standard, (S)-N-((3-fluoro-4-morpholinophenyl)-2-oxaoxazolidin-5-yl)methyl)acetamide, Linezolid, Pharmaceutical Secondary Standard, Certified Reference Material, (Linezolid)N-[3-(3-Fluoro-4-morpholin-4-yl-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide, (S)-N-((3-(3-fluoro-4-(4-morpholinyl)phenyl)-2-oxo-5-oxazolidinyl)methyl)acetamide, (S)-N-[ [3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-oxazolidin-5-yl]methyl]-acetamide, (S)-N-[[3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-acetamide, N-[(R)-3-(3-Fluoro-4-morpholin-4-yl-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide, N-[(S)-3-(3-Fluoro-4-morpholin-4-yl-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide, N-[[(5S)-3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl] methyl] acetamide, N-[3-(3-Fluoro-4-morpholin-4-yl-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide, N-[3-(3-Fluoro-4-morpholin-4-yl-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide(linezolid), (S)-3-(3-Fluoro-4-morpholin-4-yl-phenyl)-5-[(1-hydroxy-ethylamino)-methyl]-oxazolidin-2-one, N-((S)-2-oxo-3-(S)-2,3,3a,4-tetrahydro-1H-benzo[b]pyrrolo[1,2-d][1,4]oxazin-7-yl-oxazolidin-5-ylmethyl)-acetamide

Bioactivity: Oxazolidinone antibiotic; bacterial protein synthesis inhibitor (50S ribosomal subunit)

Solubility in Different Solvents

Solvent	Temperature [K]	Crystal form	Solubility [mg/mL]	Reference
1-Propanol	283.15	-	3.033	[67]
1-Propanol	288.13	-	3.897	[67]
1-Propanol	293.15	-	4.999	[67]
1-Propanol	298.15	-	6.414	[67]
1-Propanol	303.15	-	8.225	[67]
1-Propanol	308.15	-	10.53	[67]
1-Propanol	313.15	-	13.47	[67]
1-Propanol	318.15	-	17.21	[67]
Ethanol	283.15	-	4.423	[67]
Ethanol	288.13	-	5.733	[67]
Ethanol	293.15	-	7.404	[67]
Ethanol	298.15	-	9.546	[67]
Ethanol	303.15	-	12.27	[67]
Ethanol	308.15	-	15.73	[67]
Ethanol	313.15	-	20.12	[67]
Ethanol	318.15	-	25.67	[67]
Isopropanol	283.15	-	2.215	[67]
Isopropanol	288.13	-	2.911	[67]
Isopropanol	293.15	-	3.82	[67]
Isopropanol	298.15	-	5.004	[67]
Isopropanol	303.15	-	6.543	[67]
Isopropanol	308.15	-	8.541	[67]
Isopropanol	313.15	-	11.12	[67]
Isopropanol	318.15	-	14.46	[67]
Methanol	283.15	-	10.93	[67]
Methanol	288.13	-	14.6	[67]
Methanol	293.15	-	19.39	[67]
Methanol	298.15	-	25.88	[67]
Methanol	303.15	-	34.38	[67]
Methanol	308.15	-	45.58	[67]
Methanol	313.15	-	60.35	[67]
Methanol	318.15	-	79.78	[67]
Water	283.15	-	1.513	[67]
Water	288.15	-	1.714	[67]
Water	293.15	-	1.939	[67]
Water	298.15	-	2.192	[67]
Water	303.15	-	2.473	[67]
Water	308.15	-	2.787	[67]
Water	313.15	-	3.137	[67]
Water	318.15	-	3.52	[67]

Molecule 3D descriptors

Descriptor	Value
PMI1	938.0916
PMI2	5567.1403
PMI3	6111.0910
NPR1	0.1535
NPR2	0.9110
RadiusOfGyration	4.3242
InertialShapeFactor	0.0010
Eccentricity	0.9881
Asphericity	0.6092
SpherocityIndex	0.1511
PBF	0.8668