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Chemistry

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Also known as: Pyrazinecarboxamide, 98-96-4, Pyrazine-2-carboxamide, Zinamide, Pyrazinoic acid amide, 2-pyrazinecarboxamide
Molecular Formula
C5H5N3O
Molecular Weight
123.11  g/mol
InChI Key
IPEHBUMCGVEMRF-UHFFFAOYSA-N
FDA UNII
2KNI5N06TI

Pyrazinamide
A pyrazine that is used therapeutically as an antitubercular agent.
Pyrazinamide is an Antimycobacterial.
1 2D Structure

Pyrazinamide

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
pyrazine-2-carboxamide
2.1.2 InChI
InChI=1S/C5H5N3O/c6-5(9)4-3-7-1-2-8-4/h1-3H,(H2,6,9)
2.1.3 InChI Key
IPEHBUMCGVEMRF-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CN=C(C=N1)C(=O)N
2.2 Other Identifiers
2.2.1 UNII
2KNI5N06TI
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Tisamid

2.3.2 Depositor-Supplied Synonyms

1. Pyrazinecarboxamide

2. 98-96-4

3. Pyrazine-2-carboxamide

4. Zinamide

5. Pyrazinoic Acid Amide

6. 2-pyrazinecarboxamide

7. Aldinamide

8. Pirazinamid

9. Aldinamid

10. Tebrazid

11. Unipyranamide

12. Farmizina

13. Pirazimida

14. Eprazin

15. Novamid

16. Pyrafat

17. Pyrazine Carboxylamide

18. Pyrazineamide

19. Isopas

20. 2-carbamylpyrazine

21. Pyrazinecarboxylic Acid Amide

22. Pyrazinamidum

23. Pyrazide

24. Rozide

25. Pirazinamide

26. Pyrazine Carboxamide

27. D-50

28. Pyramizade

29. Mk 56

30. Pza

31. Nci-c01785

32. Mfcd00006132

33. Nsc 14911

34. .alpha.-pyrazinamide

35. T 165

36. Pirazinamida

37. Nsc-14911

38. Tisamid

39. 2kni5n06ti

40. Mls000069730

41. Pezetamid

42. Piraldina

43. Chebi:45285

44. Nsc14911

45. Pyrazinamide (pyrazinoic Acid Amide)

46. Ncgc00015833-09

47. Pyrazinamdie

48. Smr000036662

49. Pirazinamide [dcit]

50. C5h5n3o

51. Dsstox_cid_1215

52. Dsstox_rid_76014

53. Dsstox_gsid_21215

54. Pyrazinamidum [inn-latin]

55. Pirazinamida [inn-spanish]

56. Rifafour

57. D-50 (van)

58. Drg 0124

59. Cas-98-96-4

60. Ccris 545

61. Pyrazinamide (tn)

62. Rifafour E-200

63. Hsdb 3576

64. Sr-01000076077

65. Einecs 202-717-6

66. Unii-2kni5n06ti

67. Brn 0112306

68. Pyrazinamida

69. Pyrizinamide

70. Pyrazine Amide

71. Azt + Pyrazinamide Combination

72. Pyrazine-2-carboxylic Acid Amide

73. Pyrazinamide,(s)

74. Pyrazinamide [usp:inn:ban:jan]

75. Prestwick_811

76. Pyranzinoic Acid Amide

77. 2-pyrazine Carboxamide

78. Spectrum_000902

79. Opera_id_735

80. Prestwick0_000514

81. Prestwick1_000514

82. Prestwick2_000514

83. Prestwick3_000514

84. Spectrum2_001305

85. Spectrum3_001046

86. Spectrum4_001186

87. Spectrum5_001026

88. Lopac-p-7136

89. Pyrazinamide [mi]

90. Pyrazinamide [inn]

91. Pyrazinamide [jan]

92. Chembl614

93. P 7136

94. Pyrazinamide [hsdb]

95. Wln: T6n Dnj Bvz

96. Pyrazinamide [vandf]

97. Pyrazine-2-carboximidic Acid

98. Lopac0_001011

99. Schembl24102

100. Bspbio_000467

101. Bspbio_002572

102. Kbiogr_001851

103. Kbioss_001382

104. Pyrazinamide [mart.]

105. 5-25-04-00178 (beilstein Handbook Reference)

106. Mls002222347

107. Bidd:gt0228

108. Divk1c_000241

109. Pyrazinamide [usp-rs]

110. Pyrazinamide [who-dd]

111. Pyrazinamide [who-ip]

112. Spectrum1500518

113. Spbio_001369

114. Spbio_002388

115. Bpbio1_000515

116. Gtpl7287

117. Zinc2005

118. Dtxsid9021215

119. Hms500m03

120. Kbio1_000241

121. Kbio2_001382

122. Kbio2_003950

123. Kbio2_006518

124. Kbio3_001792

125. Pyrazinamide (jp17/usp/inn)

126. Ninds_000241

127. Bdbm228814

128. Hms1569h09

129. Hms1920n08

130. Hms2092e09

131. Hms2096h09

132. Hms2235g17

133. Hms3259o04

134. Hms3263k03

135. Hms3371g09

136. Hms3655a10

137. Hms3713h09

138. Kuc109577n

139. Pharmakon1600-01500518

140. Pyrazinamide [orange Book]

141. Pyrazinamide [ep Monograph]

142. Pyrazinamide [usp Impurity]

143. Act01761

144. Amy14180

145. Bcp30257

146. Hy-b0271

147. Ksc-27-052e

148. Pyrazine-[d3]-carboxamide-[15n]

149. Pyrazinamide [usp Monograph]

150. Tox21_110237

151. Tox21_202059

152. Tox21_302771

153. Tox21_501011

154. Ccg-39243

155. Nsc757304

156. Pyrazinamidum [who-ip Latin]

157. Rifater Component Pyrazinamide

158. S1762

159. Stk801661

160. Akos000120280

161. Tox21_110237_1

162. Db00339

163. Lp01011

164. Nc00534

165. Nsc-757304

166. Pyrazinecarboxamide, Analytical Standard

167. Sdccgsbi-0050984.p005

168. Idi1_000241

169. Pyrazinamide Component Of Rifater

170. Ncgc00015833-01

171. Ncgc00015833-02

172. Ncgc00015833-03

173. Ncgc00015833-04

174. Ncgc00015833-05

175. Ncgc00015833-06

176. Ncgc00015833-07

177. Ncgc00015833-08

178. Ncgc00015833-10

179. Ncgc00015833-11

180. Ncgc00015833-12

181. Ncgc00015833-15

182. Ncgc00015833-16

183. Ncgc00015833-25

184. Ncgc00090695-01

185. Ncgc00090695-03

186. Ncgc00090695-04

187. Ncgc00090695-05

188. Ncgc00090695-06

189. Ncgc00090695-07

190. Ncgc00256336-01

191. Ncgc00259608-01

192. Ncgc00261696-01

193. Pyrazinoic Acid Amide; Pyrazinamide; Pza

194. Cas- 98-96-4

195. Sy013550

196. Ts-01626

197. Sbi-0050984.p004

198. Db-002866

199. Ab00052083

200. B2122

201. Bb 0253141

202. Eu-0101011

203. Ft-0659757

204. P0633

205. Sw196945-3

206. C01956

207. D00144

208. D70481

209. 1,2-dihydro-1,2,4-triazol-3-one;pyrazinamide

210. Ab00052083-16

211. Ab00052083_17

212. Ab00052083_18

213. A845937

214. Ac-907/25014068

215. Q417571

216. Sr-01000076077-1

217. Sr-01000076077-4

218. Sr-01000076077-6

219. W-100059

220. Z33546644

221. Pyrazinamide, British Pharmacopoeia (bp) Reference Standard

222. Pyrazinamide, European Pharmacopoeia (ep) Reference Standard

223. 2-carbamylpyrazine ;aldinamid ;aldinamide; Pyrazinoic Acid Amide

224. Pyrazinamide, United States Pharmacopeia (usp) Reference Standard

225. Pyrazinamide, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 123.11 g/mol
Molecular Formula C5H5N3O
XLogP3-0.6
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count1
Exact Mass123.043261792 g/mol
Monoisotopic Mass123.043261792 g/mol
Topological Polar Surface Area68.9 Ų
Heavy Atom Count9
Formal Charge0
Complexity115
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NamePyrazinamide
PubMed HealthPyrazinamide (By mouth)
Drug ClassesAntitubercular
Drug LabelPyrazinamide, the pyrazine analogue of nicotinamide, is an antituberculous agent. It is a white crystalline powder, stable at room temperature, and sparingly soluble in water. Pyrazinamide has the following structural formula:C5H5N3O M.W.123.11Each P...
Active IngredientPyrazinamide
Dosage FormTablet
RouteOral
Strength500mg
Market StatusPrescription
CompanyDava Pharms; Mikart

2 of 2  
Drug NamePyrazinamide
PubMed HealthPyrazinamide (By mouth)
Drug ClassesAntitubercular
Drug LabelPyrazinamide, the pyrazine analogue of nicotinamide, is an antituberculous agent. It is a white crystalline powder, stable at room temperature, and sparingly soluble in water. Pyrazinamide has the following structural formula:C5H5N3O M.W.123.11Each P...
Active IngredientPyrazinamide
Dosage FormTablet
RouteOral
Strength500mg
Market StatusPrescription
CompanyDava Pharms; Mikart

4.2 Therapeutic Uses

Antitubercular Agents

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


Pyrazinamide is indicated in combination with other antimycobacterial drugs, in the treatment of tuberculosis. Pyrazinamide is effective only against mycobacteria. /Included in US product labeling/

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional 21 st ed. Volume 1. MICROMEDEX Thomson Health Care, Englewood, CO. 2001. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 2521


Rifampin, isoniazid, and pyrazinamide combination is indicated in the initial phase of the short-course treatment of all forms of tuberculosis. During this phase, which should last 2 months, rifampin, isoniazid, and pyrazinamide combination should be administered on a daily, continuous basis. Additional medications are indicated if multidrug-resistant tuberculosis is suspected. /Included in US product labeling/

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional 21 st ed. Volume 1. MICROMEDEX Thomson Health Care, Englewood, CO. 2001. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 2607


Pyrazinamide has become an important component of short-term (6 month) multiple-drug therapy of tuberculosis.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1281


4.3 Drug Warning

Patients hypersensitive to ethionamide, isoniazid, niacin (nicotinic acid), or other chemically related medications may be hypersensitive to this medication also.

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional 21 st ed. Volume 1. MICROMEDEX Thomson Health Care, Englewood, CO. 2001. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 2521


Pyrazinamide should be used only when close observation of the patient is possible. Serum AST (SGOT), ALT (SGPT), and uric acid concentrations should be determined prior to and every 2-4 weeks during pyrazinamide therapy. If signs of hepatic damage occur, pyrazinamide should be discontinued.

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional 21 st ed. Volume 1. MICROMEDEX Thomson Health Care, Englewood, CO. 2001. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 504


Hepatotoxicity is the most commonly reported adverse effect, with elevated transaminase levels being the earliest indication of toxicity...Pyrazinamide decreases the tubular excretion of uric acid, which may induce an acute gouty arthritis. Other adverse reactions include nausea, vomiting, dysuria, malaise, fever and skin rashes.

Ford MD, Delaney KA, Ling LJ, Erickson T; Clinical Toxicology. W.B. Saunders Company., Philadelphia, PA. 2001, p. 443


The drug inhibits excretion of urate, resulting in hyperuricemia in nearly all patients; acute episodes of gout have occurred. Other untoward effects that have been observed with pyrazinamide are arthralgias, anorexia, nausea and vomiting, dysuria, malaise and fever.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1282


For more Drug Warnings (Complete) data for PYRAZINAMIDE (19 total), please visit the HSDB record page.


4.4 Drug Indication

For the initial treatment of active tuberculosis in adults and children when combined with other antituberculous agents.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Pyrazinamide kills or stops the growth of certain bacteria that cause tuberculosis (TB). It is used with other drugs to treat tuberculosis. It is a highly specific agent and is active only against Mycobacterium tuberculosis. In vitro and in vivo, the drug is active only at a slightly acid pH. Pyrazinamie gets activated to Pyrazinoic acid in the bacilli where it interferes with fatty acid synthase FAS I. This interferes with the bacteriums ability to synthesize new fatty acids, required for growth and replication.


5.2 MeSH Pharmacological Classification

Antitubercular Agents

Drugs used in the treatment of tuberculosis. They are divided into two main classes: "first-line" agents, those with the greatest efficacy and acceptable degrees of toxicity used successfully in the great majority of cases; and "second-line" drugs used in drug-resistant cases or those in which some other patient-related condition has compromised the effectiveness of primary therapy. (See all compounds classified as Antitubercular Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
PYRAZINAMIDE
5.3.2 FDA UNII
2KNI5N06TI
5.3.3 Pharmacological Classes
Antimycobacterial [EPC]
5.4 ATC Code

J04AK01

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


J - Antiinfectives for systemic use

J04 - Antimycobacterials

J04A - Drugs for treatment of tuberculosis

J04AK - Other drugs for treatment of tuberculosis

J04AK01 - Pyrazinamide


5.5 Absorption, Distribution and Excretion

Absorption

Rapidly and well absorbed from the gastrointestinal tract.


Route of Elimination

Approximately 70% of an oral dose is excreted in the urine, mainly by glomerular filtration within 24 hours


Pyrazinamide is well absorbed from the gastrointestinal tract, and it is widely distributed throughout the body. The oral administration of 500 mg produces plasma concentrations of about 9-12 ug/ml at two hours and 7 ug/ml at 8 hours.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1281


Pyrazinamide is well absorbed from the GI tract. Following a single 500 mg oral dose in healthy adults, peak plasma concentrations of pyrazinamide ranging from 9-12 ug/ml are attained within 2 hours; plasma concentrations of the drug average 7 ug/ml at 8 hours and 2 ug/ml at 24 hours. Plasma concentrations following doses of 20-25 mg/kg reportedly range from 3-50 ug/ml. Plasma concentrations of pyrazinoic acid, the major active metabolite of pyrazinamide, generally are greater than those of the parent drug and peak within 4-8 hours after an oral dose of the drug.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 508


In a single-dose study in healthy fasting males, the extent of absorption (as measured by area under the plasma concentration-time curve) of isoniazid, rifampin, or pyrazinamide in dosages of 250, 6O0, or 1500 mg, respectively, was similar whether the drugs were administered individually as capsules (rifampin) and tablets (isoniazid and pyrazinamide) or as a fixed combination containing isoniazid 50 mg, rifampin 120 mg, and pyrazinamide 300 mg per tablet.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 508


Pyrazinamide is widely distributed into body tissues and fluids including the liver, lungs, and CSF. In a limited number of adults with tuberculous meningitis, mean serum and CSF concentrations of pyrazinamide 2 hours after an oral dose of approximately 41 mg/kg were 52 and 39 ug/ml, respectively. Within 5 hours after an oral dose, CSF concentrations of pyrazinamide are reported to be approximately equal to concurrent plasma concentrations of the drug. Plasma protein binding of pyrazinamide (determined by ultrafiltration) in a limited number of healthy men averaged approximately 17% at a pyrazinamide concentration of 20 ug/ml. It is not known if pyrazinamide crosses the placenta. It is not known if pyrazinamide is distributed into milk.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 508


For more Absorption, Distribution and Excretion (Complete) data for PYRAZINAMIDE (12 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Hepatic.


Pyrazinamide is hydrolyzed to pyrazinoic acid and subsequently hydroxylated to 5-hydroxypyrazinoic acid, the major excretory product.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1281


The major metabolic pathway of pyrazinamide is conversion to pyrazinoic acid followed by subsequent conversion to hydroxypyrazinoic acid, a reaction catalyzed by xanthine oxidase.

American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 1645


Eight healthy volunteers were treated with a single dose of pyrazinamide 35 mg/kg. The aim of the study was to evaluate the pharmacokinetic profile of the product and of its metabolites. Urine and blood samples were collected till the 60th h. The kinetics of pyrazinamide could be characterized as follows: CPmax = 50.1 micrograms/ml, tmax less than 1 h, t1/2 alpha = 3.2 h, t1/2 beta = 23 h, U(0-60 h) = 1.6% of the dose administered. The kinetics of the main metabolite, the pyrazinoic acid, gave the following values: CPmax = 66.6 micrograms/ml, tmax = 4 h, t1/2 beta = 12.3 h, U(0-60 h) = 37.5%, of the administered dose.

Bareggi S et al; Arzeimittelforschung 37(7): p.849-854 (1987)


All available data support the idea that the PZA metabolite pyrazinoic acid (PA) is the active compound against M. tuberculosis. ... Caffeine, which is widely used as a drug and is a common constituent of most diets, shares with PZA the same metabolic enzyme, xanthine oxidase (XO).

Mehmedagic A et al; Biopharm Drug Dispos 23(5): p.191-195 (2002)


5.7 Biological Half-Life

9-10 hours (normal conditions)


The plasma half-life is 9-10 hours in patients with normal renal function.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1281


The half-life of pyrazinamide is 23 hours. ... The elimination half-life is 10 to 16 hours.

American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 1645


The plasma half-life of pyrazinamide is 9-10 hours in patients with normal renal and hepatic function. The plasma half-life of the drug may be prolonged in patients with impaired renal or hepatic function.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 508


5.8 Mechanism of Action

Pyrazinamide diffuses into active _M. tuberculosis_ that express pyrazinamidase enzyme that converts pyrazinamide to the active form pyrazinoic acid. Pyrazinoic acid can leak out under acidic conditions to be converted to the protonated conjugate acid, which is readily diffused back into the bacilli and accumulate intracellularly. The net effect is that more pyrazinoic acid accumulates inside the bacillus at acid pH than at neutral pH. Pyrazinoic acid was thought to inhibit the enzyme fatty acid synthase (FAS) I, which is required by the bacterium to synthesise fatty acids. However, this theory was thought to have been discounted. However, further studies reproduced the results of FAS I inhibition as the putative mechanism first in whole cell assay of replicating M. tuberculosis bacilli which have shown that pyrazinoic acid and its ester inhibit the synthesis of fatty acids. This study was followed by in vitro assay of tuberculous FAS I enzyme that tested the activity with pyrazinamide, pyrazinoic acid and several classes of pyrazinamide analogs. Pyrazinamide and its analogs inhibited the activity of purified FAS I. It has also been suggested that the accumulation of pyrazinoic acid disrupts membrane potential and interferes with energy production, necessary for survival of M. tuberculosis at an acidic site of infection. Pyrazinoic acid has also been shown to bind to the ribosomal protein S1 (RpsA) and inhibit trans-translation. This may explain the ability of the drug to kill dormant mycobacteria.


Pyrazinamide may be bacteriostatic or bactericidal in action, depending on the concentration of the drug attained at the site of the infection and the susceptibility of the infecting organism. In vitro and in vivo, the drug is active only at a slightly acidic pH. The exact mechanism of action of pyrazinamide has not been fully elucidated. The antimycobacterial activity of pyrazinamide appears to partly depend on conversion of the drug to pyrazinoic acid. Susceptible strains of Mycobacterium tuberculosis produce pyrazinamidase, an enzyme that deaminates pyrazinamide to pyrazinoic acid, and the in vitro susceptibility of a given strain of the organism appears to correspond to its pyrazinamidase activity. In vitro studies indicate that pyrazinoic acid has specific antimycobacterial activity against Mycobacterium tuberculosis. In addition, the fact that pyrazinoic acid lowers the pH of the environment below that which is necessary for growth of Mycobacterium tuberculosis appears to contribute to the drug's antimycobacterial activity in vitro.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 508


Unknown; pyrazinamide may be bacteriostatic or bactericidal, depending on its concentration and the susceptibility of the organism. It is active in vitro at an acidic pH of 5.6 or less, similar to that found in early, active tubercular inflammatory lesions.

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional 21 st ed. Volume 1. MICROMEDEX Thomson Health Care, Englewood, CO. 2001. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 2521


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07-Jan-2021
31-Aug-2024
KGS
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DOSAGE - TABLET;ORAL - 50MG;300MG;120MG

USFDA APPLICATION NUMBER - 50705

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DOSAGE - TABLET;ORAL - 500MG

USFDA APPLICATION NUMBER - 80157

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