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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

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C9H12N2S
Molecular Weight 180.27
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
New agents active against Mycobacterium avium complex selected by molecular topology: a virtual screening method.
2004 Jan
A decade surveillance study of Mycobacterium xenopi disease and antimicrobial susceptibility levels in a reference teaching hospital of northern Italy: HIV-associated versus non-HIV-associated infection.
2004 Jul-Aug
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
Substance Class Chemical
Created
by admin
on Sat Dec 16 12:51:47 GMT 2023
Edited
by admin
on Sat Dec 16 12:51:47 GMT 2023
Record UNII
UU8HBM89ZQ
Record Status Validated (UNII)
Record Version
  • Download
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