TOBRAMYCIN

Search structure
Trade Names:
Synonyms:
Status: Approved (1975)
Entry Type: Small molecule
Molecule Category: Parent
ATC: J01GB01
UNII: VZ8RRZ51VK

Structure
InChI Key NLVFBUXFDBBNBW-PBSUHMDJSA-N
Smile NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](N)[C@H]3O)[C@H]2O)[C@H](N)C[C@@H]1O
InChI
InChI=1S/C18H37N5O9/c19-3-9-8(25)2-7(22)17(29-9)31-15-5(20)1-6(21)16(14(15)28)32-18-13(27)11(23)12(26)10(4-24)30-18/h5-18,24-28H,1-4,19-23H2/t5-,6+,7+,8-,9+,10+,11-,12+,13+,14-,15+,16-,17+,18+/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C18H37N5O9
Molecular Weight 467.52
AlogP -6.3
Hydrogen Bond Acceptor 14.0
Hydrogen Bond Donor 10.0
Number of Rotational Bond 6.0
Polar Surface Area 268.17
Molecular species BASE
Aromatic Rings 0.0
Heavy Atoms 32.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR 70S ribosome inhibitor FDA PubMed Wikipedia
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Other cytosolic protein
- - 4110 - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 105

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Bacterial Infections 4 D001424 ClinicalTrials
Conjunctivitis, Bacterial 3 D003234 ClinicalTrials
Pseudomonas Infections 3 D011552 ClinicalTrials
Cataract 3 D002386 ClinicalTrials
Pneumonia 3 D011014 ClinicalTrials
Fractures, Bone 3 D050723 ClinicalTrials
Blepharitis 3 D001762 ClinicalTrials
Bronchiectasis 2 D001987 ClinicalTrials
Pneumonia, Bacterial 2 D018410 ClinicalTrials
Renal Insufficiency, Chronic 1 D051436 ClinicalTrials
Dry Eye Syndromes 1 D015352 ClinicalTrials
Bronchopulmonary Dysplasia 1 D001997 ClinicalTrials
Osteomyelitis 0 D010019 ClinicalTrials

Related Entries

MCS

Scaffolds

Salt
Mixture
Mixture
Mixture

Side Effects from Label

Side effects Relative Frequency (%) Labels
Respiratory, thoracic and mediastinal disorders Cough 48.4
Respiratory, thoracic and mediastinal disorders Cough
Respiratory, thoracic and mediastinal disorders Cough 46.1
Investigations Body temperature increased
Respiratory, thoracic and mediastinal disorders Increased bronchial secretion
Respiratory, thoracic and mediastinal disorders Sputum increased
General disorders and administration site conditions Asthenia
Gastrointestinal disorders Pharyngitis
Cardiac disorders Dyspnoea
Gastrointestinal disorders Pharyngitis 38.0
Respiratory, thoracic and mediastinal disorders Increased bronchial secretion 37.6
Respiratory, thoracic and mediastinal disorders Sputum increased 37.6
General disorders and administration site conditions Asthenia 35.7
Infections and infestations Rhinitis 34.5
Respiratory, thoracic and mediastinal disorders Lung disorder 33.8
Cardiac disorders Dyspnoea 33.7
Infections and infestations Rhinitis
Investigations Body temperature increased 32.9
Nervous system disorders Headache
Respiratory, thoracic and mediastinal disorders Lung disorder 31.4
Respiratory, thoracic and mediastinal disorders Lung disorder
Respiratory, thoracic and mediastinal disorders Cough 31.1
Investigations Forced expiratory volume decreased 31.1
Respiratory, thoracic and mediastinal disorders Lung disorder 30.1
Cardiac disorders Chest pain
Investigations Forced expiratory volume decreased
General disorders and administration site conditions Decreased appetite
Nervous system disorders Headache 26.7
Cardiac disorders Chest pain 26.0
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Gastrointestinal pain
Cardiac disorders Haemoptysis
Gastrointestinal disorders Vomiting
Immune system disorders Asthma
Respiratory, thoracic and mediastinal disorders Productive cough 19.6
Cardiac disorders Haemoptysis 19.4
Respiratory, thoracic and mediastinal disorders Rales 18.9
General disorders and administration site conditions Decreased appetite 18.6
Respiratory, thoracic and mediastinal disorders Productive cough 18.2
Investigations Pulmonary function test decreased 16.3
Nervous system disorders Respiratory depression 16.3
Gastrointestinal disorders Nausea
Immune system disorders Asthma 15.9
Respiratory, thoracic and mediastinal disorders Rales
Investigations Body temperature increased 15.6
Cardiac disorders Dyspnoea 15.6
Investigations Pulmonary function test decreased
Nervous system disorders Respiratory depression
Investigations Weight decreased
Gastrointestinal disorders Oropharyngeal pain 14.0
Gastrointestinal disorders Vomiting 14.0
Nervous system disorders Dysphonia 13.6
Cardiac disorders Haemoptysis 13.0
Gastrointestinal disorders Abdominal pain 12.8
Gastrointestinal disorders Gastrointestinal pain 12.8
General disorders and administration site conditions Pain
Investigations Body temperature increased 12.4
Cardiac disorders Dyspnoea 12.4
Cardiac disorders Haemoptysis 12.4
Nervous system disorders Headache 12.0
Nervous system disorders Headache 11.4
Gastrointestinal disorders Nausea 11.2
Gastrointestinal disorders Oropharyngeal pain 10.5
Gastrointestinal disorders Diarrhoea
Investigations Weight decreased 10.1
Psychiatric disorders Hyperventilation
Gastrointestinal disorders Nausea 9.6
Infections and infestations Sinusitis
Ear and labyrinth disorders Ear pain
Infections and infestations Upper respiratory tract infection 8.6
Investigations Red blood cell sedimentation rate increased 8.42
Respiratory, thoracic and mediastinal disorders Nasal congestion 8.1
General disorders and administration site conditions Pain 8.1
Investigations Pulmonary function test decreased 8.1
Infections and infestations Sinusitis 8.1
Musculoskeletal and connective tissue disorders Back pain
Infections and infestations Lower respiratory tract infection
Cardiac disorders Dizziness
Gastrointestinal disorders Nausea 7.5
Ear and labyrinth disorders Ear pain 7.4
Respiratory, thoracic and mediastinal disorders Nasal congestion 7.2
Respiratory, thoracic and mediastinal disorders Rales 7.1
Musculoskeletal and connective tissue disorders Back pain 7.0
Respiratory, thoracic and mediastinal disorders Epistaxis 7.0
Gastrointestinal disorders Dysgeusia
Investigations Pulmonary function test decreased 6.8
Infections and infestations Upper respiratory tract infection 6.8
Respiratory, thoracic and mediastinal disorders Wheezing 6.8
Gastrointestinal disorders Dysgeusia 6.6
Cardiac disorders Chest discomfort 6.5
Cardiac disorders Chest pain 6.5
Respiratory, thoracic and mediastinal disorders Epistaxis
Gastrointestinal disorders Diarrhoea 6.2
General disorders and administration site conditions Discomfort 6.2
General disorders and administration site conditions Feeling abnormal 6.2
General disorders and administration site conditions Ill-defined disorder 6.2
General disorders and administration site conditions Malaise 6.2
Respiratory, thoracic and mediastinal disorders Rales 6.2
Gastrointestinal disorders Vomiting 6.2
Respiratory, thoracic and mediastinal disorders Wheezing 6.2
Skin and subcutaneous tissue disorders Dermatitis
Skin and subcutaneous tissue disorders Rash
Cardiac disorders Dizziness 5.8
Infections and infestations Lower respiratory tract infection 5.8
Nervous system disorders Dysphonia 5.79
Gastrointestinal disorders Vomiting 5.7
Skin and subcutaneous tissue disorders Dermatitis 5.4
Psychiatric disorders Hyperventilation 5.4
Skin and subcutaneous tissue disorders Rash 5.4
General disorders and administration site conditions Discomfort
General disorders and administration site conditions Feeling abnormal
General disorders and administration site conditions Ill-defined disorder
General disorders and administration site conditions Malaise
Respiratory, thoracic and mediastinal disorders Wheezing 5.26
Investigations Red blood cell sedimentation rate increased
Musculoskeletal and connective tissue disorders Musculoskeletal chest pain 4.8
Musculoskeletal and connective tissue disorders Musculoskeletal chest pain 4.5
Gastrointestinal disorders Throat irritation 4.5
Gastrointestinal disorders Diarrhoea 4.2
Gastrointestinal disorders Dysgeusia 3.9
Investigations Forced expiratory volume decreased 3.9
Nervous system disorders Dysphonia 3.8
Respiratory, thoracic and mediastinal disorders Wheezing
Respiratory, thoracic and mediastinal disorders Epistaxis 3.16
Investigations Blood glucose increased 2.9
Cardiac disorders Chest discomfort 2.9
Cardiac disorders Chest pain 2.9
Infections and infestations Bronchitis 2.63
Respiratory, thoracic and mediastinal disorders Laryngeal pain 2.63
Respiratory, thoracic and mediastinal disorders Epistaxis 2.6
Skin and subcutaneous tissue disorders Dermatitis 2.4
Skin and subcutaneous tissue disorders Rash 2.4
Skin and subcutaneous tissue disorders Dermatitis 2.3
Skin and subcutaneous tissue disorders Rash 2.3
Infections and infestations Tonsillitis 2.11
Gastrointestinal disorders Diarrhoea 1.9
Respiratory, thoracic and mediastinal disorders Epistaxis 1.9
Gastrointestinal disorders Throat irritation 1.9
Nervous system disorders Dysphonia
Respiratory, thoracic and mediastinal disorders Laryngeal pain
Gastrointestinal disorders Diarrhoea 1.58
Blood and lymphatic system disorders Eosinophilia 1.58
Investigations Immunoglobulins increased 1.58
Investigations Forced expiratory volume decreased 1.0
Infections and infestations Bronchitis
Gastrointestinal disorders Diarrhoea
Investigations Blood glucose increased 0.5
Gastrointestinal disorders Dysgeusia 0.5

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Respiratory, thoracic and mediastinal disorders
27.63
General disorders and administration site conditions
12.5
Infections and infestations
9.99
Investigations
8.92
Cardiac disorders
6.34
Gastrointestinal disorders
5.88
Injury, poisoning and procedural complications
4.0
Nervous system disorders
3.8
Vascular disorders
2.94
Psychiatric disorders
2.38
Immune system disorders
2.19
Congenital, familial and genetic disorders
2.15
Metabolism and nutrition disorders
2.07

Cross References

Resources Reference
CAS NUMBER 32986-56-4
ChEBI 28864
ChEMBL CHEMBL1747
DrugBank DB00684
DrugCentral 2684
EPA CompTox DTXSID8023680
FDA SRS VZ8RRZ51VK
Human Metabolome Database HMDB0014822
Guide to Pharmacology 10930
KEGG C00397
PDB TOY
PharmGKB PA451704
PubChem 36294
SureChEMBL SCHEMBL2838
ZINC ZINC000008214692
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