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Details

Stereochemistry ACHIRAL
Molecular Formula C9H12N2S
Molecular Weight 180.27
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROTIONAMIDE

SMILES

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

InChI

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

HIDE SMILES / InChI

Molecular Formula C9H12N2S
Molecular Weight 180.27
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
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
Record UNII
76YOO33643
Record Status Validated (UNII)
Record Version