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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
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
[Use of the antioxidant ionol to prevent damage to the heart from prolonged administration of antitubercular preparations].
1983 Oct
Rapamycin and less immunosuppressive analogs are toxic to Candida albicans and Cryptococcus neoformans via FKBP12-dependent inhibition of TOR.
2001 Nov
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
[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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:56:59 GMT 2023
Edited
by admin
on Fri Dec 15 15:56:59 GMT 2023
Record UNII
76YOO33643
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PROTIONAMIDE
INN   MART.   MI   WHO-DD   WHO-IP  
INN  
Official Name English
PROTHIONAMIDE [JAN]
Common Name English
NSC-758962
Code English
PROTIONAMIDE [MART.]
Common Name English
PROTIONAMIDE [WHO-IP]
Common Name English
Protionamide [WHO-DD]
Common Name English
PROTHIONAMIDE
Common Name English
RP-9778
Code English
PROTIONAMIDE [MI]
Common Name English
2-PROPYLTHIOISONICOTINAMIDE
Systematic Name English
RP 9778
Code English
protionamide [INN]
Common Name English
PROTIONAMIDUM [WHO-IP LATIN]
Common Name English
TREVINTIX
Brand Name English
TH-1321
Code English
Classification Tree Code System Code
WHO-ATC J04AD01
Created by admin on Fri Dec 15 15:56:59 GMT 2023 , Edited by admin on Fri Dec 15 15:56:59 GMT 2023
WHO-VATC QJ04AD01
Created by admin on Fri Dec 15 15:56:59 GMT 2023 , Edited by admin on Fri Dec 15 15:56:59 GMT 2023
NCI_THESAURUS C280
Created by admin on Fri Dec 15 15:56:59 GMT 2023 , Edited by admin on Fri Dec 15 15:56:59 GMT 2023
Code System Code Type Description
RXCUI
8871
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PRIMARY RxNorm
DRUG BANK
DB12667
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PRIMARY
FDA UNII
76YOO33643
Created by admin on Fri Dec 15 15:56:59 GMT 2023 , Edited by admin on Fri Dec 15 15:56:59 GMT 2023
PRIMARY
CAS
14222-60-7
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PRIMARY
INN
2031
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PRIMARY
EPA CompTox
DTXSID7045940
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PRIMARY
NCI_THESAURUS
C72605
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PRIMARY
EVMPD
SUB10141MIG
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PRIMARY
PUBCHEM
666418
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PRIMARY
ECHA (EC/EINECS)
238-093-7
Created by admin on Fri Dec 15 15:56:59 GMT 2023 , Edited by admin on Fri Dec 15 15:56:59 GMT 2023
PRIMARY
WIKIPEDIA
Prothionamide
Created by admin on Fri Dec 15 15:56:59 GMT 2023 , Edited by admin on Fri Dec 15 15:56:59 GMT 2023
PRIMARY
SMS_ID
100000088340
Created by admin on Fri Dec 15 15:56:59 GMT 2023 , Edited by admin on Fri Dec 15 15:56:59 GMT 2023
PRIMARY
NSC
758962
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PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
PROTIONAMIDE
Created by admin on Fri Dec 15 15:56:59 GMT 2023 , Edited by admin on Fri Dec 15 15:56:59 GMT 2023
PRIMARY Description: Yellow crystals or a crystalline powder; odourless or almost odourless. Solubility: Practically insoluble in water; soluble in ethanol (~750 g/l) TS and methanol R; slightly soluble in ether R. Category: Antileprosy drug. Storage: Protionamide should be kept in a well-closed container, protected from light. Definition: Protionamide contains not less than 98.0% and not more than 101.0% of C9H12N2S, calculated with reference to the dried substance.
MERCK INDEX
m9270
Created by admin on Fri Dec 15 15:56:59 GMT 2023 , Edited by admin on Fri Dec 15 15:56:59 GMT 2023
PRIMARY Merck Index
MESH
D011515
Created by admin on Fri Dec 15 15:56:59 GMT 2023 , Edited by admin on Fri Dec 15 15:56:59 GMT 2023
PRIMARY
DRUG CENTRAL
2314
Created by admin on Fri Dec 15 15:56:59 GMT 2023 , Edited by admin on Fri Dec 15 15:56:59 GMT 2023
PRIMARY
ChEMBL
CHEMBL1378024
Created by admin on Fri Dec 15 15:56:59 GMT 2023 , Edited by admin on Fri Dec 15 15:56:59 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY