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SMB00387

Sigma-Aldrich

Prothionamide

≥99% (HPLC)

Synonym(s):

Prothionamide, 2-propyl-4-pyridinecarbothioamide, 2-propylisonicotinylthioamide, 2-propylthioisonicotinamide, 2-Propyl-4-pyridinecarbothioamide, 2-Propylisonicotinylthioamide

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About This Item

Empirical Formula (Hill Notation):
C9H12N2S
CAS Number:
14222-60-7
Molecular Weight:
180.27
MDL number:
MFCD00464119
UNSPSC Code:
51102829
PubChem Substance ID:
329824982
NACRES:
NA.85

Quality Level

200

Assay

≥99% (HPLC)

form

powder

color

yellow

antibiotic activity spectrum

mycobacteria

Mode of action

enzyme | interferes

storage temp.

−20°C

SMILES string

NC(C1=CC(CCC)=NC=C1)=S

InChI

1S/C9H12N2S/c1-2-3-8-6-7(9(10)12)4-5-11-8/h4-6H,2-3H2,1H3,(H2,10,12)

InChI key

VRDIULHPQTYCLN-UHFFFAOYSA-N

General description

Chemical structure: pyridine
Prothionamide is an analogue of ethionamide, and is better tolerated and less toxic than ethionamide. It contains a propyl group instead of an ethyl group at the α position.

Biochem/physiol Actions

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.

Storage and Stability

Keep container tightly closed in a dry and well-ventilated place. Storage class (TRGS 510) Non Combustible liquids.

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Storage class (TRGS 510): Non Combustible Solids

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000409258
0000409258
0000404632
0000375489
0000368693

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A Yilmaz et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 152, 262-271 (2015-07-29)
Prothionamide (PTH) is the secondary drug used against Mycobacterium tuberculosis bacteria and leprosy. The aim of this work was to investigate the potential energy surface map, anharmonic and harmonic vibrational spectra, NBO analysis and ELF (Electron Localization Function) of the
Han-Lin Hsu et al.
Journal of the Formosan Medical Association = Taiwan yi zhi, 109(12), 923-927 (2011-01-05)
Timely and intensive monitoring for, and management of, adverse effects caused by anti-tuberculosis drugs are essential components of control programs for multidrug-resistant tuberculosis (MDR-TB). This retrospective case series was conducted in northern Taiwan from January 2007 to December 2008 at
Acceptability of thioamides. II. Prothionamide.
D K Gupta
Journal of postgraduate medicine, 23(4), 181-185 (1977-10-01)
A case of DRESS syndrome induced by the antituberculosis drugs, prothionamide, and para-aminosalycilic acid.
Joo-Hee Kim et al.
Annals of allergy, asthma & immunology : official publication of the American College of Allergy, Asthma, & Immunology, 110(2), 118-119 (2013-01-29)

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