PYRAZINAMIDE

Drugs in Pregnancy and Lactation.

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Name: PYRAZINAMIDE
Class: Antituberculosis Agent
Risk Factor:    CM

Fetal Risk Summary

Pyrazinamide is a synthetic antituberculosis agent derived from niacinamide. Animal reproduction studies have not been conducted with this drug (1).

A single report has been located that describes the use of pyrazinamide in a pregnant woman. She had been treated for cavitary pulmonary tuberculosis with three other agents for 5 months before the addition of pyrazinamide at 26 weeks' gestation for persistent positive sputum cultures (2). No drug-related fetal toxicity was mentioned. However, this and other References caution that pyrazinamide should not be routinely used because of the lack of information pertaining to its fetal effects (2,3 and 4).

Breast Feeding Summary

Pyrazinamide is excreted into human milk. In one non-breast-feeding patient given an oral 1-g dose of pyrazinamide, the peak concentration of the drug, 1.5 µg/mL, was measured in the milk at 3 hours (5). The peak concentration in the maternal plasma, 42.0 µg/mL, occurred at 2 hours.

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References

  1. Product information. Pyrazinamide. Lederle Laboratories, 2000.
  2. Margono F, Mroueh J, Garely A, White D, Duerr A, Minkoff HL. Resurgence of active tuberculosis among pregnant women. Obstet Gynecol 1994;83:911–4.
  3. American Thoracic Society. Treatment of tuberculosis and tuberculosis infection in adults and children. Am Rev Respir Dis 1986;134:355–63.
  4. Hamadeh MA, Glassroth J. Tuberculosis and pregnancy. Chest 1992;101:1114–20.
  5. Holdiness MR. Antituberculosis drugs and breast-feeding. Arch Intern Med 1984;144:1888.

Index

Q&A about Pyrazinamide

tan K
Pyrazinamide?
Any one can give me sites or tell me how pyrazinamide is made? Can it be detailed pls. The conditions and requirements of wad compound. If best, the yield of the product obtained. Thanks! :) Wish for an good answer asap!
Dr Dave P
The best way to make it would be from pyrazine-2-carboxylic acid.

React the acid with SOCl2 to make the acid chloride, and then quench the acid chloride in an excess of ammonium hydroxide. After neutralization to pH 7 you should have the product in fairly high yield:

R-COOH + SOCl2 --> R-COCl + HCl + SO2

R-COCl + NH3 (from NH4OH) --> R-CONH2 + HCl