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Details

Stereochemistry ACHIRAL
Molecular Formula C9H12N2S.ClH
Molecular Weight 216.731
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2-Propylthioisonicotinamide monohydrochloride

SMILES

Cl.CCCC1=NC=CC(=C1)C(N)=S

InChI

InChIKey=KRWYKWASDKBOGK-UHFFFAOYSA-N
InChI=1S/C9H12N2S.ClH/c1-2-3-8-6-7(9(10)12)4-5-11-8;/h4-6H,2-3H2,1H3,(H2,10,12);1H

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including http://www.tbonline.info/posts/2011/8/24/prothionamide/ https://www.ncbi.nlm.nih.gov/pubmed/16525107

Protionamide is a thioamide derivative with antitubercular activity, usually involving to treat MDR TB and leprosy. It has the same active substances and cross-resistance with ethionamide. Prothionamide is part of a group of drugs thioamides. The side effects of prothionamide are similar to ethionamide. Prothionamide is most commonly associated with nausea and vomiting. It may cause depression and hallucinations. Rarely, prothionamide will cause jaundice, menstrual disturbances and peripheral neuropathy. Prothionamide has received approval in Germany for the treatment of TB and drug resistant TB. While prothionamide is widely used to treat MDR TB, there is little published evidence demonstrating safety and efficacy. Protionamide forms a covalent adduct with bacterial nicotinamide adenine dinucleotide (NAD), PTH-NAD, which competitively inhibits 2-trans-enoyl-ACP reductase (inhA), an enzyme essential for mycolic acid synthesis. This results in increased cell wall permeability and decreased resistance against cell injury eventually leading to cell lysis. Mycolic acids, long-chain fatty acids, are essential mycobacterial cell wall components and play a key role in resistance to cell injury and mycobacterial virulence.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: enoyl-acyl ACP reductase, M. leprae
Target ID: enoyl-acyl ACP reductase, M. tuberculosis
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[Use of the antioxidant ionol to prevent damage to the heart from prolonged administration of antitubercular preparations].
1983 Oct
[Effects of two treatment regimens for drug-resistant tuberculosis in tuberculosis control project areas: a comparative study].
2008 Dec 30
[Tuberculosis or sarcoidosis].
2008 Oct-Dec
Disseminated multiorgan MDR-TB resistant to virtually all first-line drugs.
2009 Dec
[A study on the activity of clofazimine with antituberculous drugs against Mycobacterium tuberculosis].
2010 Sep
Activity of linezolid-containing regimens against multidrug-resistant tuberculosis in mice.
2014 Feb
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/26586647
lepromatous leprosy: six times a week at doses of either 250 mg or 500 mg childhood tuberculosis: 15-20 mg/kg with a maximum daily dose of 1000 mg
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
2-Propylthioisonicotinamide monohydrochloride
Systematic Name English
4-Pyridinecarbothioamide, 2-propyl-, hydrochloride (1:1)
Systematic Name English
4-Pyridinecarbothioamide, 2-propyl-, monohydrochloride
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID50239626
Created by admin on Sat Dec 16 12:51:47 GMT 2023 , Edited by admin on Sat Dec 16 12:51:47 GMT 2023
PRIMARY
PUBCHEM
3022324
Created by admin on Sat Dec 16 12:51:47 GMT 2023 , Edited by admin on Sat Dec 16 12:51:47 GMT 2023
PRIMARY
ECHA (EC/EINECS)
298-147-0
Created by admin on Sat Dec 16 12:51:47 GMT 2023 , Edited by admin on Sat Dec 16 12:51:47 GMT 2023
PRIMARY
FDA UNII
UU8HBM89ZQ
Created by admin on Sat Dec 16 12:51:47 GMT 2023 , Edited by admin on Sat Dec 16 12:51:47 GMT 2023
PRIMARY
CAS
93778-13-3
Created by admin on Sat Dec 16 12:51:47 GMT 2023 , Edited by admin on Sat Dec 16 12:51:47 GMT 2023
PRIMARY