Protionamide Chemical Properties

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)

Safety Information

RTECS 

NS0650000

HazardClass 

IRRITANT

HS Code 

2933399990

Toxicity

LD50 in mice, rats (g/kg): 1.0, 1.32 orally (Il'in)

Protionamide Usage And Synthesis

Chemical Properties

Protionamide is Yellow Solid

Uses

Protionamide is an antibacterial used against Mycobacterium tuberculosis bacteria.

Uses

An anti-tuberculosis agent. It has also been used to treat Leprosy. Antibacterial (tuberculostatic).

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 cases, it causes drug reaction with eosinophilia and systemic symptoms (DRESS) in patients with MDR-TB. DRESS is characterized by fever, hematologic abnormalities, skin eruption, and 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).

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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