Drug Details

General Information of the Drug (ID: DR6829)
Name
Linezolid
Synonyms
linezolid; 165800-03-3; Zyvox; (S)-N-((3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl)acetamide; Zyvoxid; PNU-100766; U-100766; Zyvoxam; PNU 100766; U 100766; C16H20FN3O4; UNII-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; CHEMBL126; ISQ9I6J12J; N-[[(5S)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide; CHEBI:63607; Linezolid, 98%; MFCD00937825; U-100,766; Acetamide, N-[[(5S)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-; (S)-N-[[3-(3-fluoro-4-morpholinylphenyl)-2-oxo-5-oxazolidinyl]methyl]acetamide; N-{[(5s)-3-(3-Fluoro-4-Morpholin-4-Ylphenyl)-2-Oxo-1,3-Oxazolidin-5-Yl]methyl}acetamide; ZLD; Zivoxid; Zyvoxa; Acetamide, N-(((5S)-3-(3-fluoro-4-(4-morpholinyl)phenyl)-2-oxo-5-oxazolidinyl)methyl)-; 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-morpholino-phenyl)-2-oxo-oxazolidin-5-yl]methyl]acetamide; SMR000466335; Zyvox (TN); HSDB 7478; SR-01000759376; Linezolid & VRC3375; Linezoid; Linezolid (JAN/USAN/INN); Linezolid [USAN:INN:BAN]; (S)-N-[[3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl]methyl]acetamide; NCGC00164628-01; Linezolid (Zyvox); N-{[(5S)-3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide; PNU100766; 111GE017; CPD000466335; NDA 21-130 Zyvox (linezolid tablets); SCHEMBL5027; DSSTox_CID_26489; DSSTox_RID_81660; DSSTox_GSID_46489; cc-154; MLS000759444; MLS001424075; BIDD:GT0404; Benzotriazol-2-yl-acetonitrile; cid_441401; Linezolid (PNU-100766); QCR-88; DTXSID5046489; Linezolid, >=98% (HPLC); NDA 21-131 Zyvox for injection (linezolid injection); GTPL10827; SYN3021; (R)-N-((3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl)acetamide; HMS2051F08; HMS2089K06; HMS3260C14; HMS3713K10; NDA 21-132 Zyvox oral suspension (linzolid oral suspension); BCP05586; ZINC2008866; Tox21_112246; Tox21_500096; BDBM50116067; s1408; AKOS016340522; AM84567; BCP9000855; CCG-101009; CS-0756; DB00601; KS-1178; NC00259; Acetamide, N-((3-(3-fluoro-4-(4-morpholinyl)phenyl)-2-oxo-5-oxazolidinyl)methyl)-, (S)-; Linezolid 100 microg/mL in Acetonitrile; NCGC00260781-01; NCGC00263531-03; NCGC00263531-05; NCGC00263531-10; HY-10394; AB0012049; CAS-165800-03-3; SW197639-3; C08146; D00947; J90009; M-8338; AB00639994-06; AB00639994-08; AB00639994-09; AB00639994_10; AB00639994_11; 800L033; A810662; Q411377; Q-201308; SR-01000759376-4; SR-01000759376-5; 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-[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; N-[[(5S)-3-(3-fluoranyl-4-morpholin-4-yl-phenyl)-2-oxidanylidene-1,3-oxazolidin-5-yl]methyl]ethanamide
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Molecular Type
Small molecule
Disease Bacterial infection [ICD-11: 1A00-1C4Z] Approved [1]
Structure
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2D MOL

3D MOL

ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability
Bioavailability
99% of drug becomes completely available to its intended biological destination(s)
Clearance
The drug present in the plasma can be removed from the body at the rate of 1.8 mL/min/kg
Elimination
30% of drug is excreted from urine in the unchanged form
Half-life
The concentration or amount of drug in body reduced by one-half in 4.5 hours
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 50.8162 micromolar/kg/day
Unbound Fraction
The unbound fraction of drug in plasma is 0.69%
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.58 L/kg
Water Solubility
The ability of drug to dissolve in water is measured as 8 mg/mL
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Formula
C16H20FN3O4
PubChem CID
441401
Canonical SMILES
CC(=O)NCC1CN(C(=O)O1)C2=CC(=C(C=C2)N3CCOCC3)F
InChI
1S/C16H20FN3O4/c1-11(21)18-9-13-10-20(16(22)24-13)12-2-3-15(14(17)8-12)19-4-6-23-7-5-19/h2-3,8,13H,4-7,9-10H2,1H3,(H,18,21)/t13-/m0/s1
InChIKey
TYZROVQLWOKYKF-ZDUSSCGKSA-N
CAS Number
CAS 165800-03-3
ChEBI ID
CHEBI:63607
TTD Drug ID
D07UYO
DrugBank ID
DB00601
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Fosfomycin      Streptomyces fradiae     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Staphylococcus aureus strains Microorganism model Staphylococcus aureus
                    Experimental
                    Result(s)		 Linezolid combined with fosfomycin at 4x MIC showed the best synergistic antibacterial effect, and this effect was retained after 24 hours.
Target and Pathway
Target(s) Bacterial 23S ribosomal RNA (Bact 23S rRNA)  Molecule Info  [3]
References
Reference 1 How many modes of action should an antibiotic have Curr Opin Pharmacol. 2008 Oct;8(5):564-73.
Reference 2 In vitro activity and post-antibiotic effects of linezolid in combination with fosfomycin against clinical isolates of Staphylococcus aureus. Infect Drug Resist. 2018 Nov 1;11:2107-2115.
Reference 3 Genome sequencing of linezolid-resistant Streptococcus pneumoniae mutants reveals novel mechanisms of resistance. Genome Res. 2009 Jul;19(7):1214-23.
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