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
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)
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/17227913Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17227913
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
Primary Target | Pharmacology | Condition | Potency |
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Target ID: enoyl-acyl ACP reductase, M. leprae Sources: https://www.ncbi.nlm.nih.gov/pubmed/17227913 |
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Target ID: enoyl-acyl ACP reductase, M. tuberculosis Sources: https://www.ncbi.nlm.nih.gov/pubmed/17227913 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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[Use of the antioxidant ionol to prevent damage to the heart from prolonged administration of antitubercular preparations]. | 1983 Oct |
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New agents active against Mycobacterium avium complex selected by molecular topology: a virtual screening method. | 2004 Jan |
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Extensively drug resistant tuberculosis in a high income country: a report of four unrelated cases. | 2008 May 2 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16525107
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/4965553
Unknown
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WHO-ATC |
J04AD01
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WHO-VATC |
QJ04AD01
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NCI_THESAURUS |
C280
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8871
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DB12667
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76YOO33643
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238-093-7
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Prothionamide
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100000088340
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758962
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PROTIONAMIDE
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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. | ||
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m9270
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D011515
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2314
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CHEMBL1378024
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ACTIVE MOIETY