LINEZOLID

Search structure
Trade Names:
Synonyms:
Status: Approved (2000)
Entry Type: Small molecule
Molecule Category: Parent
ATC: J01XX08
UNII: ISQ9I6J12J

Structure
InChI Key TYZROVQLWOKYKF-ZDUSSCGKSA-N
Smile CC(=O)NC[C@H]1CN(c2ccc(N3CCOCC3)c(F)c2)C(=O)O1
InChI
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C16H20FN3O4
Molecular Weight 337.35
AlogP 1.12
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 4.0
Polar Surface Area 71.11
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 24.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Bacterial 70S ribosome inhibitor DailyMed PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- - - - 6
Enzyme Oxidoreductase
- 2100-17000 - 7900-55000 7-76

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Osteomyelitis 4 D010019 ClinicalTrials
Bacterial Infections 4 D001424 ClinicalTrials
Tuberculosis, Multidrug-Resistant 3 D018088 ClinicalTrials
Pneumonia, Bacterial 3 D018410 ClinicalTrials
Skin Diseases 3 D012871 ClinicalTrials
Tuberculosis 3 D014376 ClinicalTrials
Tuberculosis, Pulmonary 3 D014397 ClinicalTrials
Staphylococcal Infections 3 D013203 ClinicalTrials
Gram-Positive Bacterial Infections 3 D016908 ClinicalTrials
Tuberculosis, Multidrug-Resistant 3 D018088 ClinicalTrials
Optic Nerve Diseases 3 D009901 ClinicalTrials
Abscess 3 D000038 ClinicalTrials
Cellulitis 3 D002481 ClinicalTrials
Pneumonia, Pneumococcal 3 D011018 ClinicalTrials
Cystic Fibrosis 2 D003550 ClinicalTrials
Meningitis 2 D008581 ClinicalTrials
Burns 1 D002056 ClinicalTrials

Related Entries

MCS

Side Effects from Label

Side effects Relative Frequency (%) Labels
Skin and subcutaneous tissue disorders Dermatitis 15.2
Skin and subcutaneous tissue disorders Rash 15.2
Investigations Body temperature increased 14.1
Gastrointestinal disorders Diarrhoea 12.1
Gastrointestinal disorders Diarrhoea 10.8
Immune system disorders Anaphylactic shock 10.1
Gastrointestinal disorders Vomiting 9.4
Gastrointestinal disorders Vomiting 9.1
Nervous system disorders Headache 8.8
Nervous system disorders Headache 8.4
Gastrointestinal disorders Diarrhoea 8.3
Gastrointestinal disorders Diarrhoea 8.2
Gastrointestinal disorders Diarrhoea 8.0
Infections and infestations Sepsis 8.0
Gastrointestinal disorders Diarrhoea 7.8
Blood and lymphatic system disorders Anaemia 7.1
Skin and subcutaneous tissue disorders Dermatitis 7.1
Skin and subcutaneous tissue disorders Rash 7.1
Infections and infestations Sepsis 7.1
Skin and subcutaneous tissue disorders Dermatitis 7.0
Skin and subcutaneous tissue disorders Rash 7.0
Gastrointestinal disorders Nausea 6.6
Nervous system disorders Headache 6.5
Gastrointestinal disorders Diarrhoea 6.4
Gastrointestinal disorders Vomiting 6.4
Gastrointestinal disorders Diarrhoea 6.3
Gastrointestinal disorders Nausea 6.2
Gastrointestinal disorders Diarrhoea 6.1
Gastrointestinal disorders Diarrhoea 5.7
Nervous system disorders Headache 5.7
Blood and lymphatic system disorders Anaemia 5.6
Nervous system disorders Headache 5.5
Gastrointestinal disorders Diarrhoea 5.3
Gastrointestinal disorders Diarrhoea 5.2
Infections and infestations Upper respiratory tract infection 5.2
Gastrointestinal disorders Nausea 5.1
Gastrointestinal disorders Diarrhoea 4.8
Injury, poisoning and procedural complications Injury 4.8
Blood and lymphatic system disorders Thrombocytopenia 4.7
Gastrointestinal disorders Nausea 4.6
Gastrointestinal disorders Nausea 4.5
Nervous system disorders Headache 4.4
Gastrointestinal disorders Vomiting 4.3
Infections and infestations Upper respiratory tract infection 4.2
Infections and infestations Candida infection 4.0
Respiratory, thoracic and mediastinal disorders Cough 4.0
Gastrointestinal disorders Diarrhoea 4.0
Nervous system disorders Headache 4.0
Gastrointestinal disorders Oral candidiasis 4.0
Gastrointestinal disorders Diarrhoea 3.8
Gastrointestinal disorders Nausea 3.7
Infections and infestations Upper respiratory tract infection 3.7
Gastrointestinal disorders Vomiting 3.7
Investigations Body temperature increased 3.6
Gastrointestinal disorders Nausea 3.5
Cardiac disorders Dyspnoea 3.3
Injury, poisoning and procedural complications Injury 3.3
Gastrointestinal disorders Nausea 3.3
Gastrointestinal disorders Nausea 3.2
Investigations Body temperature increased 3.0
Gastrointestinal disorders Diarrhoea 3.0
Cardiac disorders Dizziness 3.0
Metabolism and nutrition disorders Hypokalaemia 3.0
Investigations Body temperature increased 2.9
Gastrointestinal disorders Pharyngitis 2.9
Gastrointestinal disorders Vomiting 2.9
Gastrointestinal disorders Abdominal pain 2.8
Convulsion 2.8
Metabolism and nutrition disorders Hypokalaemia 2.8
Injury, poisoning and procedural complications Injury 2.8
Infections and infestations Pneumonia 2.8
Blood and lymphatic system disorders Thrombocytosis 2.8
Gastrointestinal disorders Diarrhoea 2.7
Nervous system disorders Headache 2.7
Skin and subcutaneous tissue disorders Dermatitis 2.6
Cardiac disorders Dizziness 2.6
Skin and subcutaneous tissue disorders Rash 2.6
Nervous system disorders Insomnia 2.5
Gastrointestinal disorders Abdominal pain 2.4
Respiratory, thoracic and mediastinal disorders Cough 2.4
Nervous system disorders Headache 2.4
Gastrointestinal disorders Vomiting 2.4
Respiratory, thoracic and mediastinal disorders Apnoea 2.3
Skin and subcutaneous tissue disorders Dermatitis 2.3
Gastrointestinal disorders Diarrhoea 2.3
Metabolism and nutrition disorders Fluid retention 2.3
Gastrointestinal disorders Gastrointestinal haemorrhage 2.3
General disorders and administration site conditions Generalised oedema 2.3
Skin and subcutaneous tissue disorders Rash 2.3
Gastrointestinal disorders Vomiting 2.3
Gastrointestinal disorders Constipation 2.2
Skin and subcutaneous tissue disorders Dermatitis 2.2
Nervous system disorders Headache 2.2
Skin and subcutaneous tissue disorders Rash 2.2
Blood and lymphatic system disorders Anaemia 2.1
Investigations Body temperature increased 2.1
Gastrointestinal disorders Constipation 2.1
Nervous system disorders Headache 2.1
Gastrointestinal disorders Abdominal pain 2.0
Respiratory, thoracic and mediastinal disorders Apnoea 2.0
Convulsion 2.0
Skin and subcutaneous tissue disorders Dermatitis 2.0
Cardiac disorders Dizziness 2.0
Gastrointestinal disorders Dysgeusia 2.0
Injury, poisoning and procedural complications Injury 2.0
Gastrointestinal disorders Nausea 2.0
General disorders and administration site conditions Pain 2.0
Infections and infestations Pneumonia 2.0
Skin and subcutaneous tissue disorders Pruritus 2.0
Skin and subcutaneous tissue disorders Rash 2.0
Skin and subcutaneous tissue disorders Skin disorder 2.0
Blood and lymphatic system disorders Thrombocytopenia 2.0
Blood and lymphatic system disorders Thrombocytosis 2.0
Gastrointestinal disorders Vomiting 2.0
Gastrointestinal disorders Diarrhoea 1.9
Cardiac disorders Dizziness 1.9
Blood and lymphatic system disorders Eosinophilia 1.9
Nervous system disorders Headache 1.9
Gastrointestinal disorders Nausea 1.9
Blood and lymphatic system disorders Thrombocytopenia 1.9
Gastrointestinal disorders Vomiting 1.9
Cardiac disorders Dizziness 1.8
Gastrointestinal disorders Dysgeusia 1.8
Gastrointestinal disorders Nausea 1.8
Infections and infestations Vulvovaginal candidiasis 1.8
Infections and infestations Vulvovaginal mycotic infection 1.8
Infections and infestations Candida infection 1.7
Nervous system disorders Insomnia 1.7
Gastrointestinal disorders Oral candidiasis 1.7
Gastrointestinal disorders Abdominal pain 1.6
Investigations Body temperature increased 1.6
Skin and subcutaneous tissue disorders Dermatitis 1.6
Gastrointestinal disorders Diarrhoea 1.6
Gastrointestinal disorders Gastrointestinal pain 1.6
Investigations Liver function test abnormal 1.6
General disorders and administration site conditions Pain 1.6
Gastrointestinal disorders Pharyngitis 1.6
Skin and subcutaneous tissue disorders Rash 1.6
Infections and infestations Vulvovaginal candidiasis 1.6
Infections and infestations Vulvovaginal mycotic infection 1.6
Cardiac disorders Dizziness 1.5
Infections and infestations Fungal infection 1.5
Gastrointestinal disorders Vomiting 1.5
Blood and lymphatic system disorders Anaemia 1.4
Skin and subcutaneous tissue disorders Dermatitis 1.4
Blood and lymphatic system disorders Eosinophilia 1.4
Gastrointestinal disorders Nausea 1.4
Skin and subcutaneous tissue disorders Pruritus 1.4
Skin and subcutaneous tissue disorders Rash 1.4
Gastrointestinal disorders Abdominal pain 1.3
Nervous system disorders Headache 1.3
Investigations Liver function test abnormal 1.3
Gastrointestinal disorders Tongue discolouration 1.3
Infections and infestations Vulvovaginal candidiasis 1.3
Infections and infestations Vulvovaginal mycotic infection 1.3
Gastrointestinal disorders Abdominal pain 1.2
Skin and subcutaneous tissue disorders Dermatitis 1.2
Gastrointestinal disorders Diarrhoea 1.2
Gastrointestinal disorders Gastrointestinal pain 1.2
Skin and subcutaneous tissue disorders Rash 1.2
Ear and labyrinth disorders Vertigo 1.2
Gastrointestinal disorders Vomiting 1.2
Infections and infestations Candida infection 1.1
Skin and subcutaneous tissue disorders Dermatitis 1.1
Cardiac disorders Dizziness 1.1
Gastrointestinal disorders Dysgeusia 1.1
Gastrointestinal disorders Oral candidiasis 1.1
Skin and subcutaneous tissue disorders Rash 1.1
Gastrointestinal disorders Tongue discolouration 1.1
Infections and infestations Vulvovaginal candidiasis 1.1
Infections and infestations Vulvovaginal mycotic infection 1.1
Gastrointestinal disorders Abdominal pain 1.0
Blood and lymphatic system disorders Anaemia 1.0
Infections and infestations Candida infection 1.0
Gastrointestinal disorders Dysgeusia 1.0
Cardiac disorders Dyspnoea 1.0
Blood and lymphatic system disorders Eosinophilia 1.0
Metabolism and nutrition disorders Fluid retention 1.0
Gastrointestinal disorders Gastrointestinal haemorrhage 1.0
General disorders and administration site conditions Generalised oedema 1.0
Nervous system disorders Headache 1.0
Gastrointestinal disorders Oral candidiasis 1.0
Gastrointestinal disorders Pharyngitis 1.0
Skin and subcutaneous tissue disorders Skin disorder 1.0
Infections and infestations Upper respiratory tract infection 1.0
Gastrointestinal disorders Vomiting 1.0
Infections and infestations Vulvovaginal candidiasis 1.0
Infections and infestations Vulvovaginal mycotic infection 1.0
Gastrointestinal disorders Abdominal pain 0.9
Infections and infestations Candida infection 0.9
Respiratory, thoracic and mediastinal disorders Cough 0.9
Gastrointestinal disorders Dysgeusia 0.9
Nervous system disorders Headache 0.9
Gastrointestinal disorders Oral candidiasis 0.9
General disorders and administration site conditions Pain 0.9
Skin and subcutaneous tissue disorders Skin disorder 0.9
Gastrointestinal disorders Vomiting 0.9
Gastrointestinal disorders Abdominal pain 0.8
Gastrointestinal disorders Diarrhoea 0.8
Blood and lymphatic system disorders Eosinophilia 0.8
Nervous system disorders Headache 0.8
Investigations Liver function test abnormal 0.8
Skin and subcutaneous tissue disorders Pruritus 0.8
Gastrointestinal disorders Dysgeusia 0.7
Gastrointestinal disorders Abdominal pain 0.6
Infections and infestations Vulvovaginal candidiasis 0.6
Infections and infestations Vulvovaginal mycotic infection 0.6
Gastrointestinal disorders Abdominal pain 0.5
Investigations Body temperature increased 0.5
Infections and infestations Candida infection 0.5
Investigations Liver function test abnormal 0.5
Gastrointestinal disorders Oral candidiasis 0.5
Gastrointestinal disorders Pharyngitis 0.5
Infections and infestations Vulvovaginal candidiasis 0.5
Infections and infestations Vulvovaginal mycotic infection 0.5
Gastrointestinal disorders Abdominal pain 0.4
Blood and lymphatic system disorders Anaemia 0.4
Infections and infestations Candida infection 0.4
Skin and subcutaneous tissue disorders Dermatitis 0.4
Cardiac disorders Dizziness 0.4
Blood and lymphatic system disorders Eosinophilia 0.4
Investigations Liver function test abnormal 0.4
Gastrointestinal disorders Oral candidiasis 0.4
Skin and subcutaneous tissue disorders Pruritus 0.4
Skin and subcutaneous tissue disorders Rash 0.4
Ear and labyrinth disorders Vertigo 0.4
Gastrointestinal disorders Vomiting 0.4
Infections and infestations Vulvovaginal candidiasis 0.4
Infections and infestations Vulvovaginal mycotic infection 0.4
Cardiac disorders Dizziness 0.3
Gastrointestinal disorders Dysgeusia 0.3
Infections and infestations Fungal infection 0.3
Gastrointestinal disorders Tongue discolouration 0.3
Gastrointestinal disorders Dysgeusia 0.2
Infections and infestations Fungal infection 0.2
Investigations Liver function test abnormal 0.2
Gastrointestinal disorders Tongue discolouration 0.2
Infections and infestations Fungal infection 0.1

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
10.84
Nervous system disorders
10.03
Gastrointestinal disorders
8.77
Blood and lymphatic system disorders
8.46
Investigations
7.56
Injury, poisoning and procedural complications
6.48
Infections and infestations
5.68
Metabolism and nutrition disorders
5.51
Skin and subcutaneous tissue disorders
5.34
Respiratory, thoracic and mediastinal disorders
4.43
Vascular disorders
4.31
Psychiatric disorders
3.8
Musculoskeletal and connective tissue disorders
3.38
Immune system disorders
3.23
Cardiac disorders
3.07
Renal and urinary disorders
2.8

Cross References

Resources Reference
CAS NUMBER 165800-03-3
ChEBI 63607
ChEMBL CHEMBL126
DrugBank DB00601
DrugCentral 1584
EPA CompTox DTXSID5046489
FDA SRS ISQ9I6J12J
Human Metabolome Database HMDB0014739
Guide to Pharmacology 10827
KEGG C08146
PDB ZLD
PharmGKB PA450233
PubChem 441401
SureChEMBL SCHEMBL5027
ZINC ZINC000002008866
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