| Identification | More | [Name]
Protionamide | [CAS]
14222-60-7 | [Synonyms]
2-PROPYL-THIOISONICOTINAMIDE
PROTHIONAMIDE
PROTIONAMIDE
1321th
2-propyl-4-pyridinecarbothioamid
2-propyl-4-pyridinecarbothioamide
2-propyl-4-thiocarbamoylpyridine
2-propylisonicotinylthioamide
2-Propylpyridine-4-carbothionamide
2-propylthio-isonicotinamid
9778r.p.
ektebin
peteha
protion
protionamid
protionizina
tebeform
trevintix
tuberex
Prothionamide (BP88)Prothionamide | [EINECS(EC#)]
238-093-7 | [Molecular Formula]
C3H7NO | [MDL Number]
MFCD00464119 | [Molecular Weight]
73.09 | [MOL File]
14222-60-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
140-143°C | [Boiling point ]
310.4±44.0 °C(Predicted) | [density ]
1.1015 (rough estimate) | [refractive index ]
1.5300 (estimate) | [storage temp. ]
Inert atmosphere,Store in freezer, under -20°C | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
12.14±0.29(Predicted) | [color ]
Yellow | [Merck ]
14,7891 | [InChI]
InChI=1S/C9H12N2S/c1-2-3-8-6-7(9(10)12)4-5-11-8/h4-6H,2-3H2,1H3,(H2,10,12) | [InChIKey]
VRDIULHPQTYCLN-UHFFFAOYSA-N | [SMILES]
C1(CCC)=NC=CC(C(N)=S)=C1 | [CAS DataBase Reference]
14222-60-7(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
Protionamide is Yellow Solid
| [Uses]
An anti-tuberculosis agent. It has also been used to treat Leprosy. Antibacterial (tuberculostatic). | [Uses]
Protionamide is an antibacterial used against Mycobacterium tuberculosis bacteria.
| [Definition]
ChEBI: Prothionamide is a member of pyridines. | [Biological Activity]
Prothionamide is the second line of drug used in leprosy and in tuberculosis. It is highly effective against Mycobacterium tuberculosis. In patients with multidrug-resistant tuberculosis (MDR-TB)prothionamide causes the development of hepatitis. In rare casesit causes drug reaction with eosinophilia and systemic symptoms (DRESS) in patients with MDR-TB. DRESS is characterized by feverhematologic abnormalitiesskin eruptionand internal organ disruption. | [Synthesis]
GENERAL METHODS: To a reaction flask containing pyridine-4-carboxamide derivatives (1 eq.) was added tetrahydrofuran (THF, 5 mL/millimole) at room temperature and protected by argon and mixed with stirring. Subsequently, Lawesson's reagent (1.5 eq.) was added to the reaction system and the reaction was continuously stirred at room temperature for 48 to 72 hours. Upon completion of the reaction, the THF solvent was removed by distillation under reduced pressure. The residue was extracted by partitioning with saturated aqueous sodium bicarbonate (25 mL) and ethyl acetate (25 mL), and the extraction was repeated with ethyl acetate (2 x 25 mL). The organic phases were combined and dried with anhydrous magnesium sulfate (MgSO4) and subsequently concentrated under vacuum. Finally, the product was further purified by fast column chromatography (elution gradient: 0-3% methanol/dichloromethane, using a puriFlash 15-SI-HC 25G column, elution time 45 min). | [storage]
Store at -20°C | [References]
[1] European Journal of Medicinal Chemistry, 2018, vol. 159, p. 35 - 46
[2] Bulletin de la Societe Chimique de France, 1958, p. 687,691 |
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| Company Name: |
J & K SCIENTIFIC LTD.
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| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
China Langchem Inc.
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| Telephone: |
0086-21-58956006 |
| Website: |
www.chemicalbook.com/ShowSupplierProductsList19141/0_EN.htm |
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