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| Targets |
Prothionamide targets Mycobacterium tuberculosis and other mycobacterial species. It is active against Mycobacterium tuberculosis, Mycobacterium leprae murium, and Mycobacterium avium. The precise mechanism of action remains unknown, but it is believed to involve the flavin monooxygenase EtaA of Mycobacterium tuberculosis. It is an inhibitor of InhA.
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| ln Vitro |
In vitro, prothionamide exhibits antibacterial activity against Mycobacterium tuberculosis and other mycobacterial species. It is a thioamide anti-tuberculosis agent with activity against both drug-sensitive and drug-resistant strains. The compound is used in susceptibility testing and drug combination studies.
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| ln Vivo |
In vivo, prothionamide is used as a second-line drug for the treatment of tuberculosis and leprosy. It has been used in trials studying the treatment of MDR-TB and HIV infections. The compound is administered orally in combination with other anti-tuberculosis agents for patients who do not respond to first-line drugs.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for prothionamide typically involve studying its effects on mycobacterial targets. The compound is incubated with purified InhA enzyme or mycobacterial cell lysates, and enzyme activity is measured using appropriate substrates. Inhibition of InhA activity is quantified to determine IC₅₀ values.
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| Cell Assay |
In vitro cell-based assays for prothionamide typically employ cultures of Mycobacterium tuberculosis or other mycobacterial species. Bacteria are cultured in appropriate medium and treated with various concentrations of the compound. Minimum inhibitory concentration (MIC) values are determined by broth microdilution or agar dilution methods. Bacterial growth is assessed by measuring optical density or colony counting.
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| Animal Protocol |
In vivo animal studies with prothionamide have been conducted in animal models of tuberculosis infection. The compound is administered orally or by other routes to infected animals. Efficacy is assessed by measuring bacterial burden in tissues, survival, and histopathological examination. However, specific study protocols are not detailed in the available literature.
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| ADME/Pharmacokinetics |
Pharmacokinetic (PK) properties of prothionamide indicate it is orally active. The compound is a second-line anti-tuberculosis drug. Specific PK parameters such as half-life, Cₘₐₓ, and bioavailability have not been detailed in the available literature. The compound is soluble in ethanol and methanol.
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| Toxicity/Toxicokinetics |
The toxicity profile of prothionamide has been characterized in clinical use. Common adverse effects include gastrointestinal disturbances, hepatotoxicity, and neurological effects. The compound is used as a second-line agent when first-line drugs are ineffective or not tolerated.
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| References | |
| Additional Infomation |
Prothionamide belongs to the pyridine class of compounds. Prothionamide has been used in clinical trials for the treatment of multidrug-resistant tuberculosis and HIV infection. Prothionamide is a thioamide derivative with anti-tuberculosis activity. Prothionamide forms a covalent adduct, PTH-NAD, with bacterial nicotinamide adenine dinucleotide (NAD). This adduct competitively inhibits 2-trans-enoyl-ACP reductase (inhA), an enzyme essential for mycolic acid synthesis. This leads to increased cell wall permeability, decreased cellular resistance to damage, and ultimately cell lysis. Mycolic acid is a long-chain fatty acid and an important component of the mycobacterial cell wall, playing a crucial role in resisting cell damage and mycobacterial virulence. The effects and side effects of prothionamide are similar to those of ethionamide. It is often used in combination with other drugs.
Prothionamide is an approved second-line anti-tuberculosis drug used in combination therapy for MDR-TB and leprosy. It is not approved as a first-line agent. The compound is also known as Protionamide and 1321-TH. Molecular formula: C₉H₁₂N₂S; molecular weight: 180.27. |
| Molecular Formula |
C9H12N2S
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| Molecular Weight |
180.27
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| Exact Mass |
180.072
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| Elemental Analysis |
C, 59.97; H, 6.71; N, 15.54; S, 17.78
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| CAS # |
14222-60-7
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| Related CAS # |
Prothionamide-d5;1330261-26-1
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| PubChem CID |
666418
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| Appearance |
Light yellow to yellow solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
310.4±44.0 °C at 760 mmHg
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| Melting Point |
140ºC
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| Flash Point |
141.5±28.4 °C
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| Vapour Pressure |
0.0±0.7 mmHg at 25°C
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| Index of Refraction |
1.607
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| LogP |
1.75
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
12
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| Complexity |
159
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| Defined Atom Stereocenter Count |
0
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| SMILES |
S=C(C1=CC(CCC)=NC=C1)N
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| InChi Key |
VRDIULHPQTYCLN-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H12N2S/c1-2-3-8-6-7(9(10)12)4-5-11-8/h4-6H,2-3H2,1H3,(H2,10,12)
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| Chemical Name |
2-propylpyridine-4-carbothioamide
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| Synonyms |
2-Propyl-4-pyridinecarbothioamide; 2-Propyl-4-thiocarbamoylpyridine
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~554.72 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (13.87 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (13.87 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.5472 mL | 27.7362 mL | 55.4723 mL | |
| 5 mM | 1.1094 mL | 5.5472 mL | 11.0945 mL | |
| 10 mM | 0.5547 mL | 2.7736 mL | 5.5472 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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