TOBRAMYCIN

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Search structure


Trade Names	AKTOB BETHKIS KITABIS PAK TOBI TOBI PODHALER TOBRAMYCIN TOBREX
Synonyms	47663 Aktob Bethkis Bramitob Kitabis pak NSC-180514 Nebcin Nebicin Nebramycin Nebramycin factor 6 Nebramycin vi Nebris Obramycin Tobi Tobi podhaler Tobradex Tobradex St Tobralex Tobramycin Tobravisc Tobrex Tymbrineb Vantobra
Status
Molecule Category	Free-form
ATC	J01GB01 S01AA12
UNII	VZ8RRZ51VK
EPA CompTox	DTXSID8023680


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	NLVFBUXFDBBNBW-PBSUHMDJSA-N
Smiles	NC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](N)[C@H]3O)[C@H](N)C[C@@H]2N)[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

Bioactivity

Mechanism of Action	Action	Reference
70S ribosome inhibitor	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

Assay Description	Organism	Bioactivity	Reference
Dissociation constant for binding to mitochondrial 12S rRNA construct M3 was determined	Homo sapiens	430.0 nM
Tested for binding affinity against RNA construct E	None	680.0 nM
Dissociation constant of the compound	None	0.9 nM
Binding affinity to A-site RNA	None	80.0 nM
Antibacterial activity against Salmonella enterica serovars virchow isolate 101591 at pH 5.7 by bioluminescence assay	Salmonella enterica subsp. enterica serovar Virchow	75.0 ug.mL-1
Antibacterial activity against Salmonella enterica serovars virchow isolate 101591 at pH 7.0 by bioluminescence assay	Salmonella enterica subsp. enterica serovar Virchow	2.5 ug.mL-1
Antibacterial activity against Salmonella enterica serovars Typhimurium ATCC 14028 at pH 7.0 by bioluminescence assay	Salmonella enterica subsp. enterica serovar Typhimurium	1.0 ug.mL-1
Antibacterial activity against Salmonella enterica serovars Typhimurium ATCC 14028 at pH 5.7 by bioluminescence assay	Salmonella enterica subsp. enterica serovar Typhimurium	19.0 ug.mL-1
Inhibition of protein synthesis in Escherichia coli S30 extracts after 90 mins by coupled transcription/translation assay	Escherichia coli	15.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	197.1 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	105.18 %
Inhibition of circular DNA translation in Escherichia coli S30 extract after 60 mins by luciferase reporter gene assay	Escherichia coli	6.2 nM
Cytotoxicity against African green monkey Vero cells after 72 hrs by MTT assay	Chlorocebus sabaeus	200.0 ug.mL-1
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	2.66 %
Binding affinity to 16S rRNA A-site in Escherichia coli S30 extract assessed as inhibition of translation measured after 30 mins by coupled transcription/translation-based luciferase reporter gene assay	Escherichia coli	70.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	13.99 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.18 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.18 %
Anti-bioflim activity against Pseudomonas aeruginosa PAO1 assessed as inhibition of bioflim formation measured at MBIC50 concentration incubated for 24 hrs by crystal violet staining based assay	Pseudomonas aeruginosa	92.0 %

Related Entries

Cross References

Resources	Reference
ChEBI	28864
ChEMBL	CHEMBL1747
DrugBank	DB00684
DrugCentral	2684
FDA SRS	VZ8RRZ51VK
Human Metabolome Database	HMDB0014822
Guide to Pharmacology	10930
KEGG	C00397
PDB	TOY
PharmGKB	PA451704
PubChem	36294
SureChEMBL	SCHEMBL2838
ZINC	ZINC000008214692

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).