Pyrazinamide

from Wikipedia, the free encyclopedia
Structural formula
Structure of pyrazinamide
General
Non-proprietary name Pyrazinamide
other names

Pyrazine carboxamide

Molecular formula C 5 H 5 N 3 O
Brief description

white solid

External identifiers / databases
CAS number 98-96-4
EC number 202-717-6
ECHA InfoCard 100.002.470
PubChem 1046
DrugBank DB00339
Wikidata Q417571
Drug information
ATC code

J04 AK01

Drug class

Anti-tuberculosis drugs

properties
Molar mass 123.11 g · mol -1
Physical state

firmly

Melting point

189-191 ° C

pK s value

0.5

solubility
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Pyrazinamide , abbreviated to PZA, is a tuberculostatic agent that has a bactericidal effect on Mycobacterium tuberculosis , the causative agent of tuberculosis , but not on the cattle form ( Mycobacterium bovis ) or atypical mycobacteria . If the active ingredient is used in the initial phase , it shortens the therapy and reduces the frequency of recurrences .

Mechanism of action

Structural formula of pyrazine carboxylic acid

The exact mechanism of action is not yet known. What is certain is that the active ingredient in the form of pyrazine carboxylic acid accumulates in the pathogens, is split by an amidase and can no longer leave the bacterium in this way. Like isoniazid , it is believed to interfere with NAD .

Pyrazinamide is given orally. It also crosses the blood-brain barrier , has a half-life of ten to twelve hours and is excreted renally . It works better at low pH values than at high ones ; it is particularly effective against intracellular germs and germs in casifying, tubercular, dead tissue .

Side effects

The liver toxicity must be taken into account , permanent monitoring of the liver parameters is necessary. In addition, allergic reactions such as increased sensitivity to light , platelet deficiency or sideroblastic anemia can occur. Pyrazinamide reduces the excretion of uric acid, which increases the uric acid concentration in the plasma ( hyperuricemia ). This can lead to an acute attack of gout .

Trade names

Monopreparations

Pyrafat (D, A), various generics (D, A, CH)

Combination preparations

Rifater (D, A, CH), Rimstar (CH), Tebesium Trio (D)

Individual evidence

  1. ↑ a b c data sheet pyrazinecarboxamide from Sigma-Aldrich , accessed on November 5, 2016 ( PDF ).
  2. ↑ a b Entry on pyrazinamide. In: Römpp Online . Georg Thieme Verlag, accessed on July 12, 2019.
  3. ↑ External identifiers or database links for pyrazine carboxylic acid : CAS number: 98-97-5, EC number: 202-718-1, ECHA InfoCard: 100.002.471 , PubChem : 1047 , ChemSpider : 1018 , Wikidata : Q7263414 .