TELITHROMYCIN

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Search structure


Trade Names	KETEK
Synonyms	HMR 3647 HMR-3647 Ketek Levviax NSC-758940 Telithromycin
Status
Molecule Category	UNKNOWN
ATC	J01FA15
UNII	KI8H7H19WL
EPA CompTox	DTXSID3046455


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

Structure


InChI Key	LJVAJPDWBABPEJ-PNUFFHFMSA-N
Smiles	CC[C@H]1OC(=O)[C@H](C)C(=O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(OC)C[C@@H](C)C(=O)[C@H](C)[C@H]2N(CCCCn3cnc(-c4cccnc4)c3)C(=O)O[C@]12C
InChI	InChI=1S/C43H65N5O10/c1-12-33-43(8)37(48(41(53)58-43)19-14-13-18-47-23-31(45-24-47)30-16-15-17-44-22-30)27(4)34(49)25(2)21-42(7,54-11)38(28(5)35(50)29(6)39(52)56-33)57-40-36(51)32(46(9)10)20-26(3)55-40/h15-17,22-29,32-33,36-38,40,51H,12-14,18-21H2,1-11H3/t25-,26-,27+,28+,29-,32+,33-,36-,37-,38-,40+,42-,43-/m1/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C43H65N5O10
Molecular Weight	812.02
AlogP	4.93
Hydrogen Bond Acceptor	14.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	11.0
Polar Surface Area	171.85
Molecular species	NEUTRAL
Aromatic Rings	2.0
Heavy Atoms	58.0

Bioactivity

Mechanism of Action	Action	Reference
Bacterial 70S ribosome inhibitor	INHIBITOR	DailyMed

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4	-	11800-11800	-	2	-
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A5	-	-	-	2	-
Enzyme Oxidoreductase	-	-	-	2	-
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel	-	40000	-	-	-
Other cytosolic protein	-	-	6	-	-
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides	-	3467	-	-	60
Transporter Primary active transporter ATP-binding cassette ABCB subfamily	-	4000-30000	-	-	-
Transporter Primary active transporter ATP-binding cassette ABCC subfamily	-	7100	-	-	-
Unclassified protein	-	-	6	-	-

Assay Description	Organism	Bioactivity	Reference
Antiplasmodial activity after 96 hrs against Plasmodium falciparum 3D7 as Malstat LDH activity	Plasmodium falciparum 3D7	280.0 nM
Antiplasmodial activity after 120 hrs against Plasmodium falciparum 3D7 as Malstat LDH activity	Plasmodium falciparum 3D7	440.0 nM
Antiplasmodial activity as ED50 against parasite growth after 48 hrs for Plasmodium falciparum 3D7	Plasmodium falciparum 3D7	6.56 ug.mL-1
Antiplasmodial activity as ED50 against parasite growth after 96 hrs for Plasmodium falciparum 3D7	Plasmodium falciparum 3D7	0.23 ug.mL-1
Inhibition of CYP3A in human liver microsomes assessed as hydroxymidazolam formation by time dependent inhibition assay	Homo sapiens	2.4 nM
Antibacterial activity against methicillin-sensitive Staphylococcus aureus ATCC 25923 assessed as decrease of CFU after 24 hrs	Staphylococcus aureus	1.78 ug.mL-1
Antibacterial activity against methicillin-sensitive Staphylococcus aureus ATCC 25923 infected in human THP1 cells assessed as decrease of CFU after 24 hrs	Staphylococcus aureus	0.11 ug.mL-1
Inhibition of protein synthesis using Escherichia coli S30 extracts preincubated for 10 mins measured after 50 mins by luciferase reporter gene assay	Escherichia coli	230.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	62.01 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	60.1 %
Binding affinity to Escherichia coli ribosomes after 2 hrs by fluorescence polarization assay in presence of BODIPY-labeled erythromycin A	Escherichia coli	6.4 nM
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	5.58 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	2.973 %
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	-0.19 %		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	-0.19 %

Cross References

Resources	Reference
ChEMBL	CHEMBL1136
DrugBank	DB00976
DrugCentral	2581
FDA SRS	KI8H7H19WL
Guide to Pharmacology	10878
PDB	TEL
PubChem	3002190
SureChEMBL	SCHEMBL5100
ZINC	ZINC000009574770

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).