ETHIONAMIDE

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Search structure


Trade Names	TRECATOR
Synonyms	1314 TH 1314-TH BAYER 5312 Ethionamide Ethionamidum NSC-255115 Nizotin Trecator Trecator-sc
Status
Molecule Category	Free-form
ATC	J04AD03
UNII	OAY8ORS3CQ
EPA CompTox	DTXSID0020577


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

Structure


InChI Key	AEOCXXJPGCBFJA-UHFFFAOYSA-N
Smiles	CCc1cc(C(N)=S)ccn1
InChI	InChI=1S/C8H10N2S/c1-2-7-5-6(8(9)11)3-4-10-7/h3-5H,2H2,1H3,(H2,9,11)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C8H10N2S
Molecular Weight	166.25
AlogP	1.28
Hydrogen Bond Acceptor	2.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	2.0
Polar Surface Area	38.91
Molecular species	NEUTRAL
Aromatic Rings	1.0
Heavy Atoms	11.0

Bioactivity

Mechanism of Action	Action	Reference
Enoyl-[acyl-carrier-protein] reductase inhibitor	INHIBITOR	PubMed PubMed PubMed

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Oxidoreductase	-	4000	-	-	88-107
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides	-	-	-	-	66

Assay Description	Organism	Bioactivity	Reference
Antimycobacterial activity of compound against Mycobacterium tuberculosis H37Rv at 2.50 ug/mL	Mycobacterium tuberculosis	90.0 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	66.2 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	90.88 %
Inhibition of tyrosinase in mouse B16F10 cells assessed as reduction of melanin production at 10 uM relative to control	Mus musculus	107.0 %
Inhibition of tyrosinase in mouse B16F10 cells assessed as reduction of melanin production at 20 uM relative to control	Mus musculus	104.0 %
Inhibition of tyrosinase in mouse B16F10 cells assessed as reduction of melanin production at 50 uM relative to control	Mus musculus	104.0 %
Inhibition of tyrosinase in mouse B16F10 cell lysates using DOPA as substrate relative to control	Mus musculus	88.0 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600)	Staphylococcus aureus subsp. aureus	13.26 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600)	Escherichia coli	2.06 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600)	Klebsiella pneumoniae	13.14 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600)	Pseudomonas aeruginosa	20.55 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600	Acinetobacter baumannii	16.23 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630	Candida albicans	1.99 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570)	Cryptococcus neoformans	-7.71 %
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	-1.84 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	18.18 %
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	-0.13 %		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	-0.13 %
Inhibition of PGL1 synthesis in Mycobacterium leprae infected Swiss Webster mouse macrophages assessed as decrease in [U-14C]PA incorporation at 2 uM preincubated for 4 days post infection followed by [U-14C]PA addition and measured after 7 days by liquid scintillation counter analysis relative to control	Mycobacterium leprae	77.0 %
Inhibition of PGL1 synthesis in Mycobacterium leprae infected Swiss Webster mouse macrophages assessed as decrease in [U-14C]PA incorporation at 20 uM preincubated for 4 days post infection followed by [U-14C]PA addition and measured after 7 days by liquid scintillation counter analysis relative to control	Mycobacterium leprae	97.0 %

Related Entries

Cross References

Resources	Reference
ChEBI	4885
ChEMBL	CHEMBL1441
DrugBank	DB00609
DrugCentral	1083
FDA SRS	OAY8ORS3CQ
Human Metabolome Database	HMDB0014747
KEGG	C07665
PharmGKB	PA164768738
PubChem	2761171
SureChEMBL	SCHEMBL27007
ZINC	ZINC000003872520

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).