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Drug

D0077 | Linezolid

Molecular Formula C16H20FN3O4
Molecular Weight 337.35
Structure
State solid
Volume of distribution * 40 to 50 L [healthy adult volunteers]
Protein binding 0.31
Half life 4.5-5.5 hours
Absorption Linezolid is rapidly and extensively absorbed after oral dosing. Maximum plasma concentrations are reached approximately 1 to 2 hours after dosing, and the absolute bioavailability is approximately 100%.
Trade names Zyvox, Zyvoxid
Description Antibacterial; oxazolidinone class

J

J01XX08 Linezolid


[J01XX] Other antibacterials


[J01X] OTHER ANTIBACTERIALS


[J01] ANTIBACTERIALS FOR SYSTEMIC USE


[J] Antiinfectives for systemic use

Toxicity Dose Time Species Model Method Action Positive criterion Reference
ELECTRON TRANSPORT CHAIN 50 μM bovine heart mitochondria Measurement of complex I activity Negative p < 0.05 3
ELECTRON TRANSPORT CHAIN 50 μM bovine heart mitochondria Measurement of complex II + III activity Negative p < 0.05 3
ELECTRON TRANSPORT CHAIN 50 μM bovine heart mitochondria Measurement of complex II + III activity Negative p < 0.05 3
ELECTRON TRANSPORT CHAIN 50 μM bovine heart mitochondria Measurement of complex IV activity Negative p < 0.05 3
ELECTRON TRANSPORT CHAIN 50 μM bovine heart mitochondria Measurement of complex V activity Negative p < 0.05 3
MITOCHONDRIAL PROTEIN TRANSLATION 197
MITOCHONDRIAL PROTEIN TRANSLATION 16 ± 2 μM Isolated rat heart mitochondria Mitochondrial protein synthesis (MPS) assay with [35S]methionine IC50 282
MITOCHONDRIAL PROTEIN TRANSLATION 12.8 ± 2.8 μM rat liver mitochondria Mitochondrial protein synthesis assay (The incorporation of [35S]methionine into mitochondrial protein was determined by a filter paper disk assay ) IC50 281
MITOCHONDRIAL PROTEIN TRANSLATION haplo-insufficiency profiling (HIP), a well-validated chemical genomics platform developed in the yeast S. Cerevisiae. inhibitor 288

Target Dose Time Species Model Method Action Positive criterion Reference
NADH:ubiquinone reductase 50 μM bovine heart mitochondria Measurement of complex I activity Negative p < 0.05 3
Succinate dehydrogenase 50 μM bovine heart mitochondria Measurement of complex II + III activity Negative p < 0.05 3
Quinol--cytochrome-c reductase 50 μM bovine heart mitochondria Measurement of complex II + III activity Negative p < 0.05 3
Cytochrome c oxidase 50 μM bovine heart mitochondria Measurement of complex IV activity Negative p < 0.05 3
ATP synthase 50 μM bovine heart mitochondria Measurement of complex V activity Negative p < 0.05 3

Pictogram Signal Statements Precautionary Statement Codes
Danger

Aggregated GHS information provided by 50 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


H372 (80%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]


H373 (12%): Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]


Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.


 P260, P264, P270, P314, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

  • Bacteraemia

  • Cellulitis gangrenous

  • Decubitus ulcer

  • Diabetes mellitus

  • Diabetic foot infection

  • Infection

  • Necrotising fasciitis

  • Osteomyelitis

  • Urinary tract infection

  • Abdominal pain

  • Anaemia

  • Anaphylactic shock

  • Apnoea

  • Body temperature increased

  • Candida infection

  • Constipation

  • Convulsion

  • Cough

  • Dermatitis

  • Diarrhoea

  • Dizziness

  • Dysgeusia

  • Dyspnoea

  • Eosinophilia

  • Fluid retention

  • Fungal infection

  • Gastrointestinal haemorrhage

  • Gastrointestinal pain

  • Generalised oedema

  • Headache

  • Hypokalaemia

  • Injury

  • Insomnia

  • Liver function test abnormal

  • Nausea

  • Oral candidiasis

  • Pain

  • Pharyngitis

  • Pneumonia

  • Pruritus

  • Rash

  • Sepsis

  • Skin disorder

  • Thrombocytopenia

  • Thrombocytosis

  • Tongue discolouration

  • Upper respiratory tract infection

  • Vertigo

  • Vomiting

  • Vulvovaginal candidiasis

  • Vulvovaginal mycotic infection

    • (Linezolid)N-[3-(3-Fluoro-4-morpholin-4-yl-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide (R)-N-((3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl)acetamide (S)-3-(3-Fluoro-4-morpholin-4-yl-phenyl)-5-[(1-hydroxy-ethylamino)-methyl]-oxazolidin-2-one
    (S)-N-((3-(3-fluoro-4-(4-morpholinyl)phenyl)-2-oxo-5-oxazolidinyl)methyl)acetamide (S)-N-((3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl)acetamide (S)-N-((3-fluoro-4-morpholinophenyl)-2-oxaoxazolidin-5-yl)methyl)acetamide
    (S)-N-[ [3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-oxazolidin-5-yl]methyl]-acetamide (S)-N-[[3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl]methyl]acetamide (S)-N-[[3-(3-fluoro-4-morpholinylphenyl)-2-oxo-5-oxazolidinyl]methyl]acetamide
    (S)-N-[[3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-acetamide 111GE017 165800-03-3
    800L033 A810662 AB0012049
    AB00639994-06 AB00639994-08 AB00639994-09
    AB00639994_10 AB00639994_11 AK105905
    AKOS016340522 AM84567 AX8042607
    Acetamide, N-(((5S)-3-(3-fluoro-4-(4-morpholinyl)phenyl)-2-oxo-5-oxazolidinyl)methyl)- Acetamide, N-((3-(3-fluoro-4-(4-morpholinyl)phenyl)-2-oxo-5-oxazolidinyl)methyl)-, (S)- Acetamide, N-[[(5S)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-
    BCP05586 BCP9000855 BDBM50116067
    BIDD:GT0404 Benzotriazol-2-yl-acetonitrile C-20237
    C08146 C16H20FN3O4 CAS-165800-03-3
    CC-29960 CCG-101009 CHEBI:63607
    CHEMBL126 CPD000466335 CS-0756
    Certified Reference Material D00947 DB00601
    DSSTox_CID_26489 DSSTox_GSID_46489 DSSTox_RID_81660
    DTXSID5046489 FT-0080803 FT-0602524
    GA2609 HMS2051F08 HMS2089K06
    HMS3260C14 HMS3713K10 HSDB 7478
    HY-10394 ISQ9I6J12J J90009
    KS-00000BB5 KS-1178 LINEZOLIDE
    LS-173594 Linezoid Linezolid & VRC3375
    Linezolid (JAN/USAN/INN) Linezolid (PNU-100766) Linezolid (Zyvox)
    Linezolid [USAN:INN:BAN] Linezolid [USAN:INN] Linezolid(Zyvox)
    Linezolid, 98% Linezolid, >=98% (HPLC) Linezolid, Pharmaceutical Secondary Standard
    Linezolid, United States Pharmacopeia (USP) Reference Standard Linezolidum M-8338
    MFCD00937825 MLS000759444 MLS001424075
    N-(((S)-3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl)methyl)acetamide N-((3-(3-fluoro-4-morpholinylphenyl)-2-oxo-5-oxazolidinyl)methyl)acetamide 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-fluoro-4-(morpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide N-({5S)-3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide, N-[[(S)-3-(3-Fluoro-4-morpholinophenyl)-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)
    N-[[(5S)-3-(3-fluoranyl-4-morpholin-4-yl-phenyl)-2-oxidanylidene-1,3-oxazolidin-5-yl]methyl]ethanamide N-[[(5S)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide N-[[(5S)-3-(3-fluoro-4-morpholino-phenyl)-2-oxo-oxazolidin-5-yl]methyl]acetamide
    N-[[(5S)-3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-acetamide N-[[(5S)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-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-{[(5s)-3-(3-Fluoro-4-Morpholin-4-Ylphenyl)-2-Oxo-1,3-Oxazolidin-5-Yl]methyl}acetamide NC00259 NCGC00164628-01
    NCGC00260781-01 NCGC00263531-03 NCGC00263531-10
    NDA 21-130 Zyvox (linezolid tablets) NDA 21-131 Zyvox for injection (linezolid injection) NDA 21-132 Zyvox oral suspension (linzolid oral suspension)
    PNU 100766 PNU-100766 Q-201308
    Q411377 QCR-88 SAM001246624
    SC-11638 SCHEMBL5027 SMR000466335
    SR-01000759376 SR-01000759376-4 SR-01000759376-5
    ST2408359 SW197639-3 SYN3021
    TYZROVQLWOKYKF-ZDUSSCGKSA-N Tox21_112246 Tox21_500096
    U 100766 U-100,766 U-100766
    UNII-ISQ9I6J12J ZINC2008866 ZLD
    Zivoxid Zyvox Zyvox (TN)
    Zyvoxa Zyvoxam Zyvoxid
    cid_441401 linezolid s1408

    DrugBank Name Linezolid
    DrugBank DB00601
    CAS Number 165800-03-3
    PubChem Compound 441401
    KEGG Compound ID C08146
    KEGG Drug D00947
    PubChem.Substance 46504452
    ChEBI 63607
    PharmGKB PA450233
    ChemSpider 390139
    BindingDB 50116067.0
    TTD DAP000398
    Wikipedia Linezolid
    HET ZLD
    DPD 12110

    1. Vuda et al. (2016)