ethionamide 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
	1083	536-33-4

Description:

Molecule	Description
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: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

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: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
0.75	g	O

ADMET properties:

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

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Approvals:

Date	Agency	Company	Orphan
April 30, 1965	FDA	WYETH PHARMS INC

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Drug resistance	205.42	45.40	50	817	22883	63465272
Drug reaction with eosinophilia and systemic symptoms	75.59	45.40	25	842	33811	63454344
Electrocardiogram QT prolonged	51.63	45.40	22	845	59508	63428647

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Drug resistance	165.15	41.43	53	1158	25874	34929846
Electrocardiogram QT prolonged	72.68	41.43	33	1178	40919	34914801
Neuropathy peripheral	50.69	41.43	33	1178	83230	34872490
Urinary tract inflammation	42.35	41.43	7	1204	169	34955551
Neuropsychiatric symptoms	42.03	41.43	9	1202	893	34954827

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Drug resistance	328.24	35.79	95	2062	42118	79700113
Electrocardiogram QT prolonged	113.09	35.79	53	2104	90333	79651898
Neuropathy peripheral	85.48	35.79	51	2106	141254	79600977
Drug reaction with eosinophilia and systemic symptoms	81.28	35.79	38	2119	64206	79678025
Tuberculoma of central nervous system	67.58	35.79	12	2145	575	79741656
Anaemia	62.52	35.79	68	2089	444947	79297284
Pathogen resistance	51.53	35.79	18	2139	14324	79727907
Vomiting	45.07	35.79	71	2086	665757	79076474
Hypothyroidism	42.62	35.79	23	2134	52369	79689862
Toxic optic neuropathy	42.04	35.79	9	2148	1144	79741087

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	J04AD03	ANTIINFECTIVES FOR SYSTEMIC USE ANTIMYCOBACTERIALS DRUGS FOR TREATMENT OF TUBERCULOSIS Thiocarbamide derivatives
CHEBI has role	CHEBI:33231	antitubercular agents
CHEBI has role	CHEBI:35679	antilipemic drugs
CHEBI has role	CHEBI:35816	leprostatic drugs
CHEBI has role	CHEBI:50185	fatty acid synthesis inhibitors
CHEBI has role	CHEBI:50266	Prodrugs
FDA EPC	N0000175483	Antimycobacterial
MeSH PA	D000900	Anti-Bacterial Agents
MeSH PA	D000890	Anti-Infective Agents
MeSH PA	D000963	Antimetabolites

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

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Disease	Relation	SNOMED_ID	DOID
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

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (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:

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Target	Class	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Enoyl-[acyl-carrier-protein] reductase [NADH]	Enzyme	INHA_MYCTU	INHIBITOR			DRUGBANK	CHEMBL
Catalase-peroxidase	Enzyme	KATG_MYCTO				WOMBAT-PK
Polyphenol oxidase 2	Enzyme	PPO2_AGABI		IC50	5.40	CHEMBL

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External reference:

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ID	Source
002851	NDDF
1JA	PDB_CHEM_ID
2761171	PUBCHEM_CID
32800009	SNOMEDCT_US
4018059	VUID
4018059	VANDF
4127	RXNORM
414148003	SNOMEDCT_US
4700	MMSL
867	INN_ID

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Trecator	HUMAN PRESCRIPTION DRUG LABEL	1	0008-4117	TABLET, FILM COATED	250 mg	ORAL	NDA	25 sections

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