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Compound Detail

CHEMBL1441

ETHIONAMIDE
💊 Approved Drug
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💊 Approved Drug
CCc1cc(C(N)=S)ccn1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1441
Name ETHIONAMIDE
Phase Approved
Structure Type MOL
InChI Key AEOCXXJPGCBFJA-UHFFFAOYSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL5315130

Known Names

1314 TH 1314-TH BAYER 5312 Ethionamide Ethionamidum Etionamida Nizotin NSC-255115 Trecator Trecator-sc
2
Targets
3
Activities
1
Assay Types
0
PK Parameters
20
Publications
10
Known Names
4
Indications
1
Mechanisms

Molecular Properties

166.2
MW (Da)
1.28
ALogP
2
HBA
1
HBD
38.9
PSA (Ų)
0.67
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1965
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product Prodrug
USAN Year 1961

Extended Properties

Molecular Formula C8H10N2S
MW 166.25
Aromatic Rings 1
Heavy Atoms 11
NP-Likeness -1.28

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Enoyl-[acyl-carrier-protein] reductase inhibitor INHIBITOR Enoyl-[acyl-carrier-protein] reductase [NADH] ✓ ✓

Indications

Tuberculosis Tuberculosis, Multidrug-Resistant Tuberculosis, Pulmonary Osteomyelitis

ATC Classification

J04AD03
ethionamide
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIMYCOBACTERIALS

Activity Summary

IC50 3 meas. best 5.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tyrosinase
CHEMBL3318
 IC50 5.4 5.4 4000.0 1
Mycolicibacterium smegmatis
CHEMBL613088
 IC50 5.17 5.145 6750.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Tyrosinase IC50 = 4000.0 nM 5.4 Inhibition of mushroom tyrosinase using L-tyrosine as substrate 26544630
Mycolicibacterium smegmatis IC50 = 6750.0 nM 5.17 Antimycobacterial activity against Mycobacterium smegmatis by GFP-based fluoresc... 19786608
Mycolicibacterium smegmatis IC50 = 7660.0 nM 5.12 Antimycobacterial activity against Mycobacterium smegmatis assessed as growth in... 19786608

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1561
20566771 10.1128/aac.00453-10 Mycolicibacterium smegmatis 19
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
26544630 10.1016/j.ejmech.2015.10.033 Tyrosinase 7
20713679 10.1128/aac.00661-10 Mycobacterium tuberculosis 6
33826327 10.1021/acs.jmedchem.0c01833 Mycobacterium tuberculosis 6
30268015 10.1016/j.ejmech.2018.09.038 Mycobacterium tuberculosis 5
19786608 10.1128/aac.00803-09 Mycolicibacterium smegmatis 4
19581465 10.1128/aac.00590-09 Mycobacteroides chelonae 4
17785510 10.1128/aac.00433-07 Mycobacterium tuberculosis 4
27914363 10.1016/j.ejmech.2016.11.048 Mycobacterium tuberculosis 3
21232949 10.1016/j.bmcl.2010.12.084 Mycobacterium tuberculosis 3
20014752 10.1021/tx900326k Hepatotoxicity 3
34414766 10.1021/acs.jmedchem.1c00837 Mycobacterium tuberculosis 3
35612311 10.1021/acs.jmedchem.2c00227 Mycobacterium tuberculosis 3
17220416 10.1128/aac.01063-06 Mycobacterium tuberculosis 3
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2

Data from ChEMBL 36 via Core Engine