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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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1 G
₩16,69,472

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1 G
₩16,69,472

About This Item

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

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Quality Level

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

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1 of 4

This Item
M9659M2133M0905
assay

≥99.0% (TLC)

assay

≥98% (HPLC)

assay

≥98% (TLC)

assay

≥98% (TLC)

suitability

suitable for fluorescence

suitability

-

suitability

-

suitability

-

solubility

DMF: 20 mg/mL, clear, colorless

solubility

pyridine: 50 mg/mL, clear, colorless to faintly yellow

solubility

DMF: 20 mg/mL, clear, colorless to faintly yellow

solubility

pyridine: 10 mg/mL, clear, colorless to faintly yellow

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

300

form

powder

form

powder

form

powder

form

powder

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

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.[1]

Biochem/physiol Actions

Prothionamide is the second line of drug used in leprosy and in tuberculosis. It is highly effective against Mycobacterium tuberculosis.[2] In patients with multidrug-resistant tuberculosis (MDR-TB), prothionamide causes the development of hepatitis.[3] 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.[4]

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

Signal Word

Warning

Hazard Statements

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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    R M Clegg et al.
    Biochemistry, 22(20), 4797-4804 (1983-09-27)
    Temperature-jump relaxation methods have been used to study the binding kinetics of fluorescent 4-methylumbelliferyl glycosides of N-acetyl-beta-D-glucosamine and its beta (1 leads to 4)-linked di- and trisaccharides with wheat germ agglutinin. The mono- and disaccharide derivatives yielded biexponential progress curves.
    C Emiliani et al.
    The International journal of biochemistry, 23(2), 215-219 (1991-01-01)
    1. Rat liver beta-N-acetylhexosaminidase was separated into several different molecular forms by DEAE-cellulose chromatography. 2. The subunit composition of the isoenzymes, as well as the similarities to human hexosaminidases, were determined by using the specific active alpha subunit substrate 4-methylumbelliferyl-beta-N-acetylglucosamine-6-sulphate.
    C T Yuen et al.
    Annals of clinical biochemistry, 21 ( Pt 4), 295-300 (1984-07-01)
    This paper describes a comparison of the recently developed substrate 2-methoxy-4-(2'-nitrovinyl)-phenyl-2-acetamido-2-deoxy-beta-D-gluc opyranoside (MNP-GlcNAc) and the corresponding 4-methylumbelliferyl substrate (4-MU-GlcNAc) for the determination of urinary NAG. A good correlation (r = 0.977) was found between NAG activities in 366 urine samples
    Nick Konkol et al.
    Journal of microbiological methods, 80(2), 178-182 (2009-12-23)
    A wide variety of cultural heritage materials are susceptible to fungal deterioration. The paper, canvas, and stone constituents of our cultural heritage are subjected to harmful physical and chemical processes as they are slowly consumed by fungi. Remediation of fungal
    W He et al.
    Prenatal diagnosis, 14(1), 17-22 (1994-01-01)
    A new fluorogenic substrate, 4-methylumbelliferyl beta-D-glucosaminide, was used for the assay of acetyl CoA:glucosaminide N-acetyltransferase in chorionic villi, cultured villus cells, and amniocytes. Optimal conditions for the assay and the ranges of enzyme activity were established for the various types

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