ethionamide 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
1083 536-33-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • ethioniamide
  • amidazine
  • ethionamide
A second-line antitubercular agent that inhibits mycolic acid synthesis.
  • Molecular weight: 166.24
  • Formula: C8H10N2S
  • CLOGP: 1.73
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 1
  • TPSA: 38.91
  • ALOGS: -2.30
  • ROTB: 2
  • Status: OFM
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.75 g O

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 100.45 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 80 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
S (Water solubility) 0.84 mg/mL Bocci G, Oprea TI, Benet LZ
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Bocci G, Oprea TI, Benet LZ

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 1.378 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 0.397 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 90.782 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 10.666 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 61.640 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 72.500 % High 1
herg hERG pIC50 3.865 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 4.677 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 10.740 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 56.240 % High 1
kinase-safety-class ACVR2A,ACVR2B,ALK,AURKA,AXL,BRAF,CAMK2B,CAMK2D,CDK5,CDK9,DDR1,DYRK1B,EIF2AK3,ERBB2,FLT3,GRK2,ITK,JAK2,MAP3K1,MAP3K21,MAP3K7,MAPK10,MAPK7,MARK4,NTRK2,PDK1,PDK2,PDK4,PIK3CD,PIM2,PRKCD,PRKDC,SIK2,SIK3,STK33,TEK,TTK,ULK1 38
kinase-selectivity-class AXL,BRAF,EIF2AK3,EPHB4,GRK2 5
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 1.734 High 1
mh-clint Mouse hepatocyte intrinsic clearance 42.954 High 1
mppb Mouse plasma protein binding (% unbound) 66.720 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 1.585 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 64.960 % High 1
rh-clint Rat hepatocyte intrinsic clearance 9.795 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 95.250 % High 1
rppb Rat plasma protein binding (% unbound) 48.730 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 935.406 uM High 1

Approvals:

DateAgencyCompanyOrphan
April 30, 1965 FDA WYETH PHARMS INC

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug resistance 207.74 56.24 49 753 30400 90597245
Drug reaction with eosinophilia and systemic symptoms 76.33 56.24 24 778 42734 90584911
Electrocardiogram QT prolonged 56.71 56.24 22 780 72434 90555211

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug resistance 177.97 42.49 57 1140 34191 42585947
Electrocardiogram QT prolonged 97.63 42.49 40 1157 47905 42572233
Urinary tract inflammation 62.74 42.49 10 1187 238 42619900
Neuropathy peripheral 53.43 42.49 34 1163 101819 42518319
Pathogen resistance 50.89 42.49 17 1180 11433 42608705
Hepatitis cholestatic 49.34 42.49 16 1181 9808 42610330
Conductive deafness 48.91 42.49 9 1188 508 42619630

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug resistance 352.76 43.15 99 1997 56275 110530928
Electrocardiogram QT prolonged 148.43 43.15 61 2035 108899 110478304
Neuropathy peripheral 104.99 43.15 56 2040 179221 110407982
Tuberculoma of central nervous system 71.25 43.15 12 2084 605 110586598
Anaemia 71.06 43.15 68 2028 547018 110040185
Pathogen resistance 70.51 43.15 22 2074 17650 110569553
Drug reaction with eosinophilia and systemic symptoms 69.59 43.15 33 2063 82062 110505141
Urinary tract inflammation 61.93 43.15 10 2086 388 110586815
Conductive deafness 57.09 43.15 9 2087 299 110586904
Optic neuropathy 47.07 43.15 12 2084 4646 110582557
Hepatitis cholestatic 46.35 43.15 16 2080 17550 110569653
Toxic optic neuropathy 43.96 43.15 9 2087 1319 110585884

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC J04AD03 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIMYCOBACTERIALS
DRUGS FOR TREATMENT OF TUBERCULOSIS
Thiocarbamide derivatives
FDA EPC N0000175483 Antimycobacterial
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000960 Hypolipidemic Agents
MeSH PA D000963 Antimetabolites
MeSH PA D000995 Antitubercular Agents
MeSH PA D054872 Fatty Acid Synthesis Inhibitors
CHEBI has role CHEBI:33231 antitubercular agent
CHEBI has role CHEBI:35679 antilipemic drug
CHEBI has role CHEBI:35816 leprostatic drug
CHEBI has role CHEBI:50185 fatty acid synthesis inhibitor
CHEBI has role CHEBI:50266 prodrug

Related Drugs by ATC class:

J04AD Thiocarbamide derivatives 2 drugs
protionamidetiocarlide

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Acute tuberculosis indication 25629007
Pulmonary tuberculosis indication 154283005 DOID:2957
Pulmonary Mycobacterium avium complex infection indication 186342000
Tuberculosis of meninges off-label use 58437007
Leprosy off-label use 81004002 DOID:1024
Atypical mycobacterial infection off-label use 111812000
Alcoholism contraindication 7200002
Hypothyroidism contraindication 40930008 DOID:1459
Hepatic failure contraindication 59927004
Diabetes mellitus contraindication 73211009 DOID:9351
Disease of liver contraindication 235856003 DOID:409




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 11.43 acidic
pKa2 5.85 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
Enoyl-[acyl-carrier-protein] reductase [NADH] Enzyme INHIBITOR DRUGBANK CHEMBL
Catalase-peroxidase Enzyme WOMBAT-PK
Polyphenol oxidase 2 Enzyme IC50 5.40 CHEMBL

External reference:

IDSource
4018059 VUID
N0000146400 NUI
D00591 KEGG_DRUG
4018059 VANDF
C0015021 UMLSCUI
CHEBI:4885 CHEBI
1JA PDB_CHEM_ID
CHEMBL1441 ChEMBL_ID
DB00609 DRUGBANK_ID
D005000 MESH_DESCRIPTOR_UI
2761171 PUBCHEM_CID
867 INN_ID
12954 IUPHAR_LIGAND_ID
OAY8ORS3CQ UNII
4127 RXNORM
4700 MMSL
d01100 MMSL
002851 NDDF
32800009 SNOMEDCT_US
414148003 SNOMEDCT_US

Pharmaceutical products:

None