525:
502:
40:
31:
3245:
933:. Under acidic conditions of pH 5 to 6, the pyrazinoic acid that slowly leaks out converts to the protonated conjugate acid, which is thought to diffuse easily back into the bacilli and accumulate. The net effect is that more pyrazinoic acid accumulates inside the bacillus at acid pH than at neutral pH.
948:
at an acidic site of infection. However, since an acidic environment is not essential for pyrazinamide susceptibility and pyrazinamide treatment does not lead to intrabacterial acidification nor rapid disruption of membrane potential, this model has also been discounted. Pyrazinoic acid was proposed
812:, which is dose-related. The old dose for pyrazinamide was 40–70 mg/kg daily and the incidence of drug-induced hepatitis has fallen significantly since the recommended dose has been reduced to 12–30 mg/kg daily. In the standard four-drug regimen (isoniazid, rifampicin, pyrazinamide,
1012:
mutations are not likely to be associated with pyrazinamide resistance. Currently, three main methods of testing are used for pyrazinamide resistance: 1) phenotypic tests where a tuberculosis strain is grown in the presence of increasing concentrations of pyrazinamide, 2) measuring levels of
1008:, is fully susceptible to pyrazinoic acid and pyrazinamide resistance of this strain was previously associated with decreased pyrazinamidase activity. Further, this strain was found to be susceptible to pyrazinamide in a mouse model of tuberculosis. Thus, current data indicate that
1050:, and is available in a wide variety of presentations. Pyrazinamide tablets form the bulkiest part of the standard tuberculosis treatment regimen. Pyrazinamide tablets are so large, some people find them impossible to swallow: pyrazinamide syrup is an option.
816:), pyrazinamide is the most common cause of drug-induced hepatitis. It is not possible to clinically distinguish pyrazinamide-induced hepatitis from hepatitis caused by isoniazid or rifampicin; test dosing is required (this is discussed in detail in
1582:
Blumberg HM, Burman WJ, Chaisson RE, Daley CL, Etkind SC, Friedman LN, et al. (February 2003). "American
Thoracic Society/Centers for Disease Control and Prevention/Infectious Diseases Society of America: treatment of tuberculosis".
1476:
British
Thoracic Society (October 1984). "A controlled trial of 6 months' chemotherapy in pulmonary tuberculosis. Final report: results during the 36 months after the end of chemotherapy and beyond. British Thoracic Society".
898:(WHO) recommends its use in pregnancy; and extensive clinical experience shows that it is safe. In the US, pyrazinamide is not used in pregnancy, citing insufficient evidence of safety. Pyrazinamide is removed by
1067:
Pyrazinamide was first discovered and patented in 1936, but not used against tuberculosis until 1952. Its discovery as an antitubercular agent was remarkable since it has no activity against tuberculosis
2272:
Piersimoni C, Mustazzolu A, Iacobino A, Giannoni F, Santoro G, Gherardi G, et al. (December 2016). "Pyrazinamide susceptibility testing: proposed new standard with the BACTECTM MGITTM 960 system".
1546:
Yee D, Valiquette C, Pelletier M, Parisien I, Rocher I, Menzies D (June 2003). "Incidence of serious side effects from first-line antituberculosis drugs among patients treated for active tuberculosis".
944:
although this has been discounted. The accumulation of pyrazinoic acid was also suggested to disrupt membrane potential and interfere with energy production, necessary for survival of
970:), triggering its degradation. This is an unusual mechanism of action in that pyrazinamide does not directly block the action of its target, but indirectly triggers its destruction.
2127:"Activity of n-propyl pyrazinoate against pyrazinamide-resistant Mycobacterium tuberculosis: investigations into mechanism of action of and mechanism of resistance to pyrazinamide"
2082:
Scorpio A, Zhang Y (June 1996). "Mutations in pncA, a gene encoding pyrazinamidase/nicotinamidase, cause resistance to the antituberculous drug pyrazinamide in tubercle bacillus".
1715:
Zimhony O, Cox JS, Welch JT, Vilchèze C, Jacobs WR (September 2000). "Pyrazinamide inhibits the eukaryotic-like fatty acid synthetase I (FASI) of
Mycobacterium tuberculosis".
766:
Pyrazinamide is used in the first 2 months of treatment to reduce the duration of treatment required. Regimens not containing pyrazinamide must be taken for 9 months or more.
740:
2225:"Potential for erroneous results indicating resistance when using the Bactec MGIT 960 system for testing susceptibility of Mycobacterium tuberculosis to pyrazinamide"
961:
1685:
3290:
988:, which encodes a pyrazinamidase and converts pyrazinamide to its active form pyrazinoic acid, are responsible for the majority of pyrazinamide resistance in
138:
1019:
gene of tuberculosis. Concerns exist that the most widely used method for phenotypic resistance testing may overestimate the number of resistant strains.
2870:
2945:
62:
2860:
2375:
605:
2176:"Activity of pyrazinamide in a murine model against Mycobacterium tuberculosis isolates with various levels of in vitro susceptibility"
1271:
2353:
1441:"Controlled clinical trial of 4 short-course regimens of chemotherapy (three 6-month and one 8-month) for pulmonary tuberculosis".
1402:"Clinical and molecular analysis of patients with renal hypouricemia in Japan-influence of URAT1 gene on urinary urate excretion"
1350:"Effect of pyrazinamide and probenecid on peritoneal urate transport kinetics during continuous ambulatory peritoneal dialysis"
1153:
966:
1083:
was known to have activity against tuberculosis and pyrazinamide was thought to have a similar effect. Experiments in mice at
3199:
2889:
1861:"Uncoupling Environmental pH and Intrabacterial Acidification from Pyrazinamide Susceptibility in Mycobacterium tuberculosis"
1230:
718:
2457:
690:
Common side effects include nausea, loss of appetite, muscle and joint pains, and rash. More serious side effects include
3159:
2938:
1313:"Controlled trial of four thrice-weekly regimens and a daily regimen all given for 6 months for pulmonary tuberculosis".
1053:
Pyrazinamide is also available as part of fixed-dose combinations with other TB drugs such as isoniazid and rifampicin (
650:
113:
1265:
1202:
1022:
Global resistance of tuberculosis to pyrazinamide has been estimated to be in 16% of all cases, and 60% of people with
2875:
1120:
1023:
625:
3265:
3216:
2906:
2368:
801:(arthralgia), but this is not usually so severe that patients need to stop taking it. Pyrazinamide can precipitate
2865:
1760:"Effects of pyrazinamide on fatty acid synthesis by whole mycobacterial cells and purified fatty acid synthase I"
950:
883:
Pyrazinamide is well absorbed orally. It crosses inflamed meninges and is an essential part of the treatment of
259:
168:
94:
2931:
330:
520:
381:
2560:
2361:
481:
3235:
3053:
735:
591:
450:
2383:
1285:
1180:
895:
2642:
1625:
Whitfield MG, Soeters HM, Warren RM, York T, Sampson SL, Streicher EM, et al. (28 July 2015).
497:
1511:
729:
Pyrazinamide is only used in combination with other drugs such as isoniazid and rifampicin in the
470:
3204:
2894:
2528:
2512:
124:
52:
1034:
The abbreviations PZA and Z are standard, and used commonly in the medical literature, although
698:, and sensitivity to sunlight. It is not recommended in those with significant liver disease or
2620:
2517:
2405:
2388:
884:
860:
817:
730:
2311:
Zhang Y, Mitchison D (January 2003). "The curious characteristics of pyrazinamide: a review".
1013:
pyrazinamidase enzyme produced by the tuberculosis strain, or 3) looking for mutations in the
430:
3295:
3270:
2687:
2507:
824:
744:
717:
Pyrazinamide was first made in 1936, but did not come into wide use until 1972. It is on the
321:
2342:
1255:
2855:
2533:
2038:
1981:
1924:
1638:
1400:
Ichida K, Hosoyamada M, Hisatome I, Enomoto A, Hikita M, Endou H, Hosoya T (January 2004).
1084:
1000:
mutations and pyrazinamide resistance has not been established. The pyrazinamide-resistant
840:
759:
390:
226:
370:
8:
1827:
937:
753:
684:
276:
131:
2042:
1985:
1928:
1642:
683:. It is not generally recommended for the treatment of latent tuberculosis. It is taken
524:
501:
285:
3285:
2249:
2224:
2107:
2059:
2026:
2025:
Gopal P, Sarathy JP, Yee M, Ragunathan P, Shin J, Bhushan S, et al. (April 2020).
2002:
1970:"Anti-tubercular Activity of Pyrazinamide is Independent of trans-Translation and RpsA"
1969:
1945:
1912:
1885:
1860:
1836:
1811:
1740:
1661:
1626:
1418:
1401:
1379:
1073:, due to not being active at a neutral pH, so would ordinarily not be expected to work
836:
2200:
2175:
2151:
2126:
1784:
1759:
1627:"A Global Perspective on Pyrazinamide Resistance: Systematic Review and Meta-Analysis"
1326:
894:
Pyrazinamide is routinely used in pregnancy in the UK and the rest of the world; the
3280:
3130:
2392:
2384:
2320:
2290:
2254:
2205:
2156:
2099:
2064:
2007:
1950:
1890:
1841:
1789:
1732:
1697:
1666:
1600:
1564:
1528:
1494:
1490:
1458:
1454:
1423:
1371:
1330:
1261:
1236:
1226:
1198:
1116:
711:
183:
86:
1775:
1512:
American
Thoracic Society; CDC; Infectious Diseases Society of America (June 2003).
1383:
1149:
72:
2282:
2244:
2236:
2195:
2187:
2146:
2138:
2111:
2091:
2054:
2046:
1997:
1989:
1940:
1932:
1880:
1872:
1831:
1823:
1779:
1771:
1744:
1724:
1656:
1646:
1592:
1556:
1486:
1450:
1413:
1361:
1322:
1293:
1188:
537:
196:
151:
1004:
strain DHMH444, which harbors a mutation in the carboxy terminal coding region of
3275:
3249:
3062:
2683:
2674:
1911:
Shi W, Zhang X, Jiang X, Yuan H, Lee JS, Barry CE, et al. (September 2011).
1651:
930:
782:
310:
214:
204:
953:, but more detailed experiments have shown that it does not have this activity.
3210:
2998:
2988:
2900:
2825:
2569:
2419:
2050:
1993:
1366:
1349:
1088:
926:
809:
770:
695:
1560:
1223:
Medical-surgical nursing : assessment and management of clinical problems
1091:
confirmed its ability to kill tuberculosis and it was rapidly used in humans.
39:
3259:
3175:
2993:
2759:
2746:
2737:
2651:
2597:
1513:
1240:
1035:
899:
774:
707:
513:
22:
2923:
1936:
1221:
Lewis SM, Dirksen SR, Heitkemper MM, Bucher L, Harding M (5 December 2013).
996:
gene have also been identified. However, a direct association between these
3116:
3019:
2959:
2730:
2721:
2708:
2587:
2546:
2541:
2396:
2324:
2294:
2258:
2068:
2011:
1954:
1894:
1845:
1793:
1736:
1701:
1670:
1604:
1596:
1568:
1532:
1427:
1375:
1080:
1047:
778:
748:
676:
664:
461:
146:
2286:
2209:
2160:
2142:
2103:
1498:
1462:
1334:
3184:
3179:
3105:
3070:
3029:
3024:
2819:
2785:
2751:
2741:
2664:
2628:
2485:
2438:
2240:
2027:"Pyrazinamide triggers degradation of its target aspartate decarboxylase"
1876:
80:
2191:
1298:
350:
3154:
3138:
3096:
3080:
3075:
3014:
2983:
2968:
2837:
2813:
2801:
2691:
2470:
2453:
2428:
2095:
1913:"Pyrazinamide inhibits trans-translation in Mycobacterium tuberculosis"
1193:
957:
941:
813:
798:
680:
668:
567:
361:
1290:
World Health
Organization model list of essential medicines: 21st list
3170:
3034:
2831:
2808:
2780:
2725:
2717:
2610:
2605:
2582:
2490:
2443:
2433:
2414:
2223:
Chedore P, Bertucci L, Wolfe J, Sharma M, Jamieson F (January 2010).
868:
848:
844:
703:
699:
672:
296:
239:
66:
2271:
1968:
Dillon NA, Peterson ND, Feaga HA, Keiler KC, Baughn AD (July 2017).
992:
strains. A few pyrazinamide-resistant strains with mutations in the
902:, so doses should always be given at the end of a dialysis session.
3110:
3101:
3039:
2792:
2577:
2475:
1069:
956:
The current hypothesis is that pyrazinoic acid blocks synthesis of
832:
410:
341:
108:
1728:
590:
3165:
2660:
2465:
1075:
1055:
911:
864:
856:
1038:
discourages the abbreviating of drug names to prevent mistakes.
2480:
1399:
828:
441:
244:
30:
1545:
2698:
1859:
Peterson ND, Rosen BC, Dillon NA, Baughn AD (December 2015).
888:
872:
786:
581:
421:
219:
1220:
797:
The most common (roughly 1%) side effect of pyrazinamide is
486:
2955:
1581:
1015:
980:
852:
802:
691:
401:
2313:
2275:
2222:
1690:
1624:
1585:
American
Journal of Respiratory and Critical Care Medicine
1549:
American
Journal of Respiratory and Critical Care Medicine
1187:. World Health Organization. pp. 136, 140, 594, 608.
1113:
Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition
940:(FAS) I, which is required by the bacterium to synthesize
714:
class of medications. How it works is not entirely clear.
2024:
1967:
1858:
1347:
1284:
1179:
1475:
1302:. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
891:
and the metabolic products are excreted by the kidneys.
1714:
1686:"The curious characteristics of pyrazinamide: a review"
1260:. Karger Medical and Scientific Publishers. p. 8.
949:
to bind to the ribosomal protein S1 (RpsA) and inhibit
719:
World Health Organization's List of Essential Medicines
1809:
3233:
1152:. The American Society of Health-System Pharmacists.
743:(DOT). It is never used on its own. It has no other
721:. Pyrazinamide is available as a generic medication.
2173:
633:
InChI=1S/C5H5N3O/c6-5(9)4-3-7-1-2-8-4/h1-3H,(H2,6,9)
1757:
805:flares by decreasing renal excretion of uric acid.
329:
2871:Isoniazid/pyridoxine/sulfamethoxazole/trimethoprim
2174:Klemens SP, Sharpe CA, Cynamon MH (January 1996).
2124:
1812:"Mechanisms of Pyrazinamide Action and Resistance"
936:Pyrazinoic acid was thought to inhibit the enzyme
808:The most dangerous side effect of pyrazinamide is
1910:
667:. For active tuberculosis, it is often used with
3257:
1348:Spaia S, Magoula I, Tsapas G, Vayonas G (2000).
1253:
309:
1906:
1904:
1183:(2009). Stuart MC, Kouimtzi M, Hill SR (eds.).
747:. In particular, it is not used to treat other
284:
2310:
1758:Boshoff HI, Mizrahi V, Barry CE (April 2002).
1683:
1395:
1393:
1115:. Jones & Bartlett Learning. p. 415.
3291:World Health Organization essential medicines
2953:
2939:
2369:
2125:Speirs RJ, Welch JT, Cynamon MH (June 1995).
1810:Zhang Y, Shi W, Zhang W, Mitchison D (2014).
1406:Journal of the American Society of Nephrology
2861:Ethambutol/isoniazid/pyrazinamide/rifampicin
2081:
1901:
1751:
1677:
921:Pyrazinamide diffuses into the granuloma of
469:
112:
2075:
1708:
1390:
1341:
188:In general: ℞ (Prescription only)
2946:
2932:
2376:
2362:
1144:
1142:
1140:
1138:
1136:
1134:
1132:
523:
500:
369:
2248:
2199:
2150:
2058:
2018:
2001:
1944:
1884:
1835:
1783:
1660:
1650:
1417:
1365:
1297:
1192:
1175:
1173:
1171:
1106:
1104:
929:converts pyrazinamide to the active form
389:
1805:
1803:
1479:British Journal of Diseases of the Chest
1110:
763:are innately resistant to pyrazinamide.
1539:
1434:
1274:from the original on 10 September 2017.
1129:
496:
349:
85:
3258:
1278:
1225:(9th ed.). St. Louis, MO: Mosby.
1168:
1101:
905:
514:
2927:
2357:
2306:
2304:
2180:Antimicrobial Agents and Chemotherapy
2131:Antimicrobial Agents and Chemotherapy
1865:Antimicrobial Agents and Chemotherapy
1800:
1684:Zhang Y, Mitchison D (January 2003).
1620:
1618:
1616:
1614:
1292:. Geneva: World Health Organization.
1156:from the original on 20 December 2016
706:is safe but it is likely okay during
449:
429:
177:
103:
71:
2349:. U.S. National Library of Medicine.
1828:10.1128/microbiolspec.mgm2-0023-2013
1216:
1214:
150:
1469:
878:
409:
300:
13:
2301:
1611:
1419:10.1097/01.ASN.0000105320.04395.D0
1306:
960:. Pyrazinoic acid binds weakly to
792:
14:
3307:
2876:Rifampicin/isoniazid/pyrazinamide
2335:
1521:MMWR. Recommendations and Reports
1354:Peritoneal Dialysis International
1254:Donald PR, van Helden PD (2011).
1211:
3243:
2229:Journal of Clinical Microbiology
1029:
1024:multidrug-resistant tuberculosis
925:, where the tuberculosis enzyme
554:
548:
38:
29:
2866:Ethambutol/isoniazid/rifampicin
2265:
2216:
2167:
2118:
1961:
1852:
1776:10.1128/JB.184.8.2167-2172.2002
1575:
1505:
1321:(8213): 171–174. January 1981.
1041:
724:
638:Key:IPEHBUMCGVEMRF-UHFFFAOYSA-N
1449:(3): 153–166. September 1983.
1247:
777:in the diagnosis of causes of
702:. It is unclear if use during
663:is a medication used to treat
560:
542:
1:
1327:10.1016/S0140-6736(02)95623-0
1257:Antituberculosis Chemotherapy
1094:
973:
773:drug and consequently has an
1652:10.1371/journal.pone.0133869
1491:10.1016/0007-0971(84)90165-7
1455:10.1016/0041-3879(83)90011-9
887:. It is metabolised by the
7:
3054:Xanthine oxidase inhibitors
2760:Thioacetazone (amithiozone)
2561:Protein synthesis inhibitor
1514:"Treatment of tuberculosis"
10:
3312:
2051:10.1038/s41467-020-15516-1
1994:10.1038/s41598-017-06415-5
1367:10.1177/089686080002000109
1062:
736:Mycobacterium tuberculosis
532:Chemical and physical data
3194:
3147:
3129:
3089:
3061:
3052:
3007:
2976:
2967:
2884:
2848:
2772:
2707:
2673:
2650:
2641:
2619:
2596:
2568:
2559:
2527:
2499:
2452:
2413:
2404:
1561:10.1164/rccm.200206-626OC
1286:World Health Organization
1181:World Health Organization
914:that stops the growth of
896:World Health Organization
769:Pyrazinamide is a potent
741:directly observed therapy
710:. Pyrazinamide is in the
646:
621:
601:
579:
566:
536:
531:
512:
480:
460:
440:
420:
400:
380:
360:
340:
320:
295:
275:
255:
250:
238:
225:
213:
203:
195:
167:
162:
137:
123:
93:
79:
61:
57:Rifater, Tebrazid, others
51:
46:
37:
28:
2643:Cell envelope antibiotic
2529:Topoisomerase inhibitors
3266:Anti-tuberculosis drugs
2621:Polypeptide antibiotics
2513:Calcium aminosalicylate
2347:Drug Information Portal
1937:10.1126/science.1208813
1764:Journal of Bacteriology
962:aspartate decarboxylase
2518:Sodium aminosalicylate
2406:Nucleic acid inhibitor
2389:tuberculosis treatment
1597:10.1164/rccm.167.4.603
885:tuberculous meningitis
861:interstitial nephritis
818:tuberculosis treatment
745:indicated medical uses
267:pyrazine-2-carboxamide
2688:arabinosyltransferase
2508:4-Aminosalicylic acid
2287:10.5588/ijtld.16.0360
2143:10.1128/aac.39.6.1269
2031:Nature Communications
1816:Microbiology Spectrum
2856:Ethambutol/isoniazid
2241:10.1128/JCM.01775-09
1877:10.1128/aac.00967-15
841:sideroblastic anemia
760:Mycobacterium leprae
2724:synth. inhibition:
2192:10.1128/AAC.40.1.14
2043:2020NatCo..11.1661G
1986:2017NatSR...7.6135D
1929:2011Sci...333.1630S
1923:(6049): 1630–1632.
1643:2015PLoSO..1033869W
1185:WHO Model Formulary
1111:Hamilton R (2015).
938:fatty acid synthase
906:Mechanism of action
754:Mycobacterium bovis
25:
3221:Never to phase III
3131:Mitotic inhibitors
2911:Never to phase III
2393:leprostatic agents
2385:Antimycobacterials
2096:10.1038/nm0696-662
1974:Scientific Reports
1046:Pyrazinamide is a
910:Pyrazinamide is a
21:
3231:
3230:
3125:
3124:
3048:
3047:
2921:
2920:
2768:
2767:
2758:Others/unsorted:
2637:
2636:
2555:
2554:
2281:(12): 1677–1680.
1871:(12): 7320–7326.
1555:(11): 1472–1477.
1232:978-0-323-10089-2
978:Mutations in the
951:trans-translation
712:antimycobacterial
658:
657:
592:Interactive image
482:CompTox Dashboard
181:
106:
3303:
3248:
3247:
3246:
3239:
3063:purine analogues
3059:
3058:
2974:
2973:
2948:
2941:
2934:
2925:
2924:
2648:
2647:
2566:
2565:
2411:
2410:
2378:
2371:
2364:
2355:
2354:
2350:
2329:
2328:
2308:
2299:
2298:
2269:
2263:
2262:
2252:
2220:
2214:
2213:
2203:
2171:
2165:
2164:
2154:
2137:(6): 1269–1271.
2122:
2116:
2115:
2079:
2073:
2072:
2062:
2022:
2016:
2015:
2005:
1965:
1959:
1958:
1948:
1908:
1899:
1898:
1888:
1856:
1850:
1849:
1839:
1807:
1798:
1797:
1787:
1770:(8): 2167–2172.
1755:
1749:
1748:
1723:(9): 1043–1047.
1712:
1706:
1705:
1681:
1675:
1674:
1664:
1654:
1622:
1609:
1608:
1579:
1573:
1572:
1543:
1537:
1536:
1518:
1509:
1503:
1502:
1473:
1467:
1466:
1438:
1432:
1431:
1421:
1397:
1388:
1387:
1369:
1345:
1339:
1338:
1310:
1304:
1303:
1301:
1282:
1276:
1275:
1251:
1245:
1244:
1218:
1209:
1208:
1196:
1177:
1166:
1165:
1163:
1161:
1146:
1127:
1126:
1108:
1059:is an example).
879:Pharmacokinetics
654:
653:
594:
574:
562:
556:
550:
544:
527:
516:
505:
504:
490:
488:
473:
453:
433:
413:
393:
373:
353:
333:
313:
303:
302:
288:
230:
179:
176:
154:
116:
105:
102:
89:
75:
42:
33:
26:
24:
20:
3311:
3310:
3306:
3305:
3304:
3302:
3301:
3300:
3256:
3255:
3254:
3244:
3242:
3234:
3232:
3227:
3226:
3211:Clinical trials
3190:
3143:
3121:
3085:
3044:
3003:
2963:
2954:Drugs used for
2952:
2922:
2917:
2916:
2901:Clinical trials
2880:
2844:
2764:
2703:
2684:Ethylenediamine
2675:Arabinogalactan
2669:
2633:
2615:
2592:
2570:Aminoglycosides
2551:
2532:
2523:
2495:
2448:
2418:
2400:
2382:
2341:
2338:
2333:
2332:
2309:
2302:
2270:
2266:
2221:
2217:
2172:
2168:
2123:
2119:
2084:Nature Medicine
2080:
2076:
2023:
2019:
1966:
1962:
1909:
1902:
1857:
1853:
1808:
1801:
1756:
1752:
1717:Nature Medicine
1713:
1709:
1682:
1678:
1637:(7): e0133869.
1623:
1612:
1580:
1576:
1544:
1540:
1527:(RR-11): 1–77.
1516:
1510:
1506:
1474:
1470:
1440:
1439:
1435:
1398:
1391:
1346:
1342:
1312:
1311:
1307:
1283:
1279:
1268:
1252:
1248:
1233:
1219:
1212:
1205:
1178:
1169:
1159:
1157:
1148:
1147:
1130:
1123:
1109:
1102:
1097:
1065:
1044:
1032:
1002:M. tuberculosis
990:M. tuberculosis
986:M. tuberculosis
976:
946:M. tuberculosis
931:pyrazinoic acid
923:M. tuberculosis
916:M. tuberculosis
908:
881:
795:
793:Adverse effects
783:hyperuricosuria
727:
649:
647:
642:
639:
634:
629:
628:
617:
614:
609:
608:
597:
572:
559:
553:
547:
508:
484:
476:
456:
436:
416:
396:
376:
356:
336:
316:
299:
291:
271:
268:
263:
262:
228:
205:Bioavailability
197:Pharmacokinetic
191:
158:
126:
119:
17:
12:
11:
5:
3309:
3299:
3298:
3293:
3288:
3283:
3278:
3273:
3268:
3253:
3252:
3229:
3228:
3225:
3224:
3223:
3222:
3219:
3208:
3202:
3196:
3195:
3192:
3191:
3189:
3188:
3182:
3173:
3168:
3157:
3151:
3149:
3145:
3144:
3142:
3141:
3135:
3133:
3127:
3126:
3123:
3122:
3120:
3119:
3114:
3108:
3099:
3093:
3091:
3087:
3086:
3084:
3083:
3078:
3073:
3067:
3065:
3056:
3050:
3049:
3046:
3045:
3043:
3042:
3037:
3032:
3027:
3022:
3017:
3011:
3009:
3005:
3004:
3002:
3001:
2999:Isobromindione
2996:
2991:
2989:Sulfinpyrazone
2986:
2980:
2978:
2971:
2965:
2964:
2951:
2950:
2943:
2936:
2928:
2919:
2918:
2915:
2914:
2913:
2912:
2909:
2898:
2892:
2886:
2885:
2882:
2881:
2879:
2878:
2873:
2868:
2863:
2858:
2852:
2850:
2846:
2845:
2843:
2842:
2826:Nitroimidazole
2822:
2817:
2805:
2789:
2776:
2774:
2770:
2769:
2766:
2765:
2763:
2762:
2755:
2754:
2749:
2744:
2738:Thiocarbamides
2734:
2733:
2728:
2714:
2712:
2705:
2704:
2702:
2701:
2695:
2694:
2680:
2678:
2671:
2670:
2668:
2667:
2657:
2655:
2645:
2639:
2638:
2635:
2634:
2632:
2631:
2625:
2623:
2617:
2616:
2614:
2613:
2608:
2602:
2600:
2594:
2593:
2591:
2590:
2585:
2580:
2574:
2572:
2563:
2557:
2556:
2553:
2552:
2550:
2549:
2544:
2538:
2536:
2525:
2524:
2522:
2521:
2515:
2503:
2501:
2497:
2496:
2494:
2493:
2488:
2483:
2478:
2473:
2468:
2462:
2460:
2450:
2449:
2447:
2446:
2441:
2436:
2431:
2425:
2423:
2420:RNA polymerase
2408:
2402:
2401:
2381:
2380:
2373:
2366:
2358:
2352:
2351:
2343:"Pyrazinamide"
2337:
2336:External links
2334:
2331:
2330:
2300:
2264:
2235:(1): 300–301.
2215:
2166:
2117:
2090:(6): 662–667.
2074:
2017:
1960:
1900:
1851:
1799:
1750:
1707:
1676:
1610:
1591:(4): 603–662.
1574:
1538:
1504:
1485:(4): 330–336.
1468:
1433:
1412:(1): 164–173.
1389:
1340:
1305:
1277:
1267:978-3805596282
1266:
1246:
1231:
1210:
1204:978-9241547659
1203:
1167:
1150:"Pyrazinamide"
1128:
1121:
1099:
1098:
1096:
1093:
1064:
1061:
1043:
1040:
1031:
1028:
975:
972:
927:pyrazinamidase
907:
904:
880:
877:
810:hepatotoxicity
794:
791:
785:. It acts on
771:antiuricosuric
726:
723:
696:liver toxicity
656:
655:
644:
643:
641:
640:
637:
635:
632:
624:
623:
622:
619:
618:
616:
615:
613:O=C(N)c1nccnc1
612:
604:
603:
602:
599:
598:
596:
595:
587:
585:
577:
576:
570:
564:
563:
557:
551:
545:
540:
534:
533:
529:
528:
518:
510:
509:
507:
506:
493:
491:
478:
477:
475:
474:
466:
464:
458:
457:
455:
454:
446:
444:
438:
437:
435:
434:
426:
424:
418:
417:
415:
414:
406:
404:
398:
397:
395:
394:
386:
384:
378:
377:
375:
374:
366:
364:
358:
357:
355:
354:
346:
344:
338:
337:
335:
334:
326:
324:
318:
317:
315:
314:
306:
304:
293:
292:
290:
289:
281:
279:
273:
272:
270:
269:
266:
258:
257:
256:
253:
252:
248:
247:
242:
236:
235:
232:
223:
222:
217:
211:
210:
207:
201:
200:
193:
192:
190:
189:
186:
173:
171:
165:
164:
160:
159:
157:
156:
143:
141:
135:
134:
129:
127:administration
121:
120:
118:
117:
99:
97:
91:
90:
83:
77:
76:
69:
59:
58:
55:
49:
48:
44:
43:
35:
34:
15:
9:
6:
4:
3:
2:
3308:
3297:
3294:
3292:
3289:
3287:
3284:
3282:
3279:
3277:
3274:
3272:
3269:
3267:
3264:
3263:
3261:
3251:
3241:
3240:
3237:
3220:
3218:
3215:
3214:
3212:
3209:
3206:
3203:
3201:
3198:
3197:
3193:
3186:
3183:
3181:
3177:
3176:Urate oxidase
3174:
3172:
3169:
3167:
3164:
3161:
3158:
3156:
3153:
3152:
3150:
3146:
3140:
3137:
3136:
3134:
3132:
3128:
3118:
3115:
3112:
3109:
3107:
3103:
3100:
3098:
3095:
3094:
3092:
3088:
3082:
3079:
3077:
3074:
3072:
3069:
3068:
3066:
3064:
3060:
3057:
3055:
3051:
3041:
3038:
3036:
3033:
3031:
3028:
3026:
3023:
3021:
3018:
3016:
3013:
3012:
3010:
3006:
3000:
2997:
2995:
2994:Benzbromarone
2992:
2990:
2987:
2985:
2982:
2981:
2979:
2975:
2972:
2970:
2966:
2961:
2957:
2949:
2944:
2942:
2937:
2935:
2930:
2929:
2926:
2910:
2908:
2905:
2904:
2902:
2899:
2896:
2893:
2891:
2888:
2887:
2883:
2877:
2874:
2872:
2869:
2867:
2864:
2862:
2859:
2857:
2854:
2853:
2851:
2847:
2840:
2839:
2834:
2833:
2828:
2827:
2823:
2821:
2818:
2815:
2811:
2810:
2806:
2803:
2799:
2795:
2794:
2790:
2787:
2783:
2782:
2778:
2777:
2775:
2773:Other/unknown
2771:
2761:
2757:
2756:
2753:
2750:
2748:
2747:Prothionamide
2745:
2743:
2739:
2736:
2735:
2732:
2729:
2727:
2723:
2719:
2716:
2715:
2713:
2710:
2706:
2700:
2697:
2696:
2693:
2689:
2685:
2682:
2681:
2679:
2676:
2672:
2666:
2662:
2659:
2658:
2656:
2653:
2652:Peptidoglycan
2649:
2646:
2644:
2640:
2630:
2627:
2626:
2624:
2622:
2618:
2612:
2609:
2607:
2604:
2603:
2601:
2599:
2595:
2589:
2586:
2584:
2581:
2579:
2576:
2575:
2573:
2571:
2567:
2564:
2562:
2558:
2548:
2545:
2543:
2540:
2539:
2537:
2535:
2530:
2526:
2519:
2516:
2514:
2510:
2509:
2505:
2504:
2502:
2498:
2492:
2489:
2487:
2484:
2482:
2479:
2477:
2474:
2472:
2469:
2467:
2464:
2463:
2461:
2459:
2455:
2451:
2445:
2442:
2440:
2437:
2435:
2432:
2430:
2427:
2426:
2424:
2421:
2416:
2412:
2409:
2407:
2403:
2398:
2394:
2390:
2386:
2379:
2374:
2372:
2367:
2365:
2360:
2359:
2356:
2348:
2344:
2340:
2339:
2326:
2322:
2318:
2314:
2307:
2305:
2296:
2292:
2288:
2284:
2280:
2276:
2268:
2260:
2256:
2251:
2246:
2242:
2238:
2234:
2230:
2226:
2219:
2211:
2207:
2202:
2197:
2193:
2189:
2185:
2181:
2177:
2170:
2162:
2158:
2153:
2148:
2144:
2140:
2136:
2132:
2128:
2121:
2113:
2109:
2105:
2101:
2097:
2093:
2089:
2085:
2078:
2070:
2066:
2061:
2056:
2052:
2048:
2044:
2040:
2036:
2032:
2028:
2021:
2013:
2009:
2004:
1999:
1995:
1991:
1987:
1983:
1979:
1975:
1971:
1964:
1956:
1952:
1947:
1942:
1938:
1934:
1930:
1926:
1922:
1918:
1914:
1907:
1905:
1896:
1892:
1887:
1882:
1878:
1874:
1870:
1866:
1862:
1855:
1847:
1843:
1838:
1833:
1829:
1825:
1821:
1817:
1813:
1806:
1804:
1795:
1791:
1786:
1781:
1777:
1773:
1769:
1765:
1761:
1754:
1746:
1742:
1738:
1734:
1730:
1729:10.1038/79558
1726:
1722:
1718:
1711:
1703:
1699:
1695:
1691:
1687:
1680:
1672:
1668:
1663:
1658:
1653:
1648:
1644:
1640:
1636:
1632:
1628:
1621:
1619:
1617:
1615:
1606:
1602:
1598:
1594:
1590:
1586:
1578:
1570:
1566:
1562:
1558:
1554:
1550:
1542:
1534:
1530:
1526:
1522:
1515:
1508:
1500:
1496:
1492:
1488:
1484:
1480:
1472:
1464:
1460:
1456:
1452:
1448:
1444:
1437:
1429:
1425:
1420:
1415:
1411:
1407:
1403:
1396:
1394:
1385:
1381:
1377:
1373:
1368:
1363:
1359:
1355:
1351:
1344:
1336:
1332:
1328:
1324:
1320:
1316:
1309:
1300:
1295:
1291:
1287:
1281:
1273:
1269:
1263:
1259:
1258:
1250:
1242:
1238:
1234:
1228:
1224:
1217:
1215:
1206:
1200:
1195:
1190:
1186:
1182:
1176:
1174:
1172:
1155:
1151:
1145:
1143:
1141:
1139:
1137:
1135:
1133:
1124:
1122:9781284057560
1118:
1114:
1107:
1105:
1100:
1092:
1090:
1086:
1082:
1078:
1077:
1072:
1071:
1060:
1058:
1057:
1051:
1049:
1039:
1037:
1036:best practice
1030:Abbreviations
1027:
1025:
1020:
1018:
1017:
1011:
1007:
1003:
999:
995:
991:
987:
983:
982:
971:
969:
968:
963:
959:
954:
952:
947:
943:
939:
934:
932:
928:
924:
919:
917:
913:
903:
901:
900:haemodialysis
897:
892:
890:
886:
876:
874:
870:
866:
862:
858:
854:
850:
846:
842:
838:
834:
830:
826:
821:
819:
815:
811:
806:
804:
800:
790:
788:
784:
780:
776:
775:off-label use
772:
767:
764:
762:
761:
756:
755:
750:
746:
742:
738:
737:
732:
722:
720:
715:
713:
709:
708:breastfeeding
705:
701:
697:
693:
688:
686:
682:
678:
675:, and either
674:
670:
666:
662:
652:
645:
636:
631:
630:
627:
620:
611:
610:
607:
600:
593:
589:
588:
586:
583:
578:
571:
569:
565:
541:
539:
535:
530:
526:
522:
519:
517:
515:ECHA InfoCard
511:
503:
499:
498:DTXSID9021215
495:
494:
492:
483:
479:
472:
468:
467:
465:
463:
459:
452:
448:
447:
445:
443:
439:
432:
428:
427:
425:
423:
419:
412:
408:
407:
405:
403:
399:
392:
388:
387:
385:
383:
379:
372:
368:
367:
365:
363:
359:
352:
348:
347:
345:
343:
339:
332:
328:
327:
325:
323:
319:
312:
308:
307:
305:
298:
294:
287:
283:
282:
280:
278:
274:
265:
264:
261:
254:
249:
246:
243:
241:
237:
234:9 to 10 hours
233:
231:
224:
221:
218:
216:
212:
208:
206:
202:
198:
194:
187:
185:
175:
174:
172:
170:
166:
161:
153:
148:
145:
144:
142:
140:
136:
133:
130:
128:
122:
115:
110:
101:
100:
98:
96:
92:
88:
84:
82:
78:
74:
70:
68:
64:
60:
56:
54:
50:
47:Clinical data
45:
41:
36:
32:
27:
19:
3296:Orphan drugs
3271:Carboxamides
3162:
3117:Topiroxostat
3111:Myo-inositol
3020:Atorvastatin
2849:Combinations
2836:
2830:
2824:
2807:
2798:Pyrazinamide
2797:
2791:
2779:
2731:Methaniazide
2722:mycolic acid
2709:Mycolic acid
2588:Streptomycin
2547:Moxifloxacin
2542:Gatifloxacin
2506:
2387:, including
2346:
2316:
2312:
2278:
2274:
2267:
2232:
2228:
2218:
2186:(1): 14–16.
2183:
2179:
2169:
2134:
2130:
2120:
2087:
2083:
2077:
2034:
2030:
2020:
1977:
1973:
1963:
1920:
1916:
1868:
1864:
1854:
1819:
1815:
1767:
1763:
1753:
1720:
1716:
1710:
1693:
1689:
1679:
1634:
1630:
1588:
1584:
1577:
1552:
1548:
1541:
1524:
1520:
1507:
1482:
1478:
1471:
1446:
1442:
1436:
1409:
1405:
1360:(1): 47–52.
1357:
1353:
1343:
1318:
1314:
1308:
1299:10665/325771
1289:
1280:
1256:
1249:
1222:
1184:
1158:. Retrieved
1112:
1081:nicotinamide
1074:
1068:
1066:
1054:
1052:
1048:generic drug
1045:
1042:Presentation
1033:
1021:
1014:
1009:
1005:
1001:
997:
993:
989:
985:
979:
977:
965:
955:
945:
935:
922:
920:
915:
909:
893:
882:
825:side effects
822:
807:
796:
779:hypouricemia
768:
765:
758:
752:
749:mycobacteria
734:
728:
725:Medical uses
716:
689:
677:streptomycin
665:tuberculosis
661:Pyrazinamide
660:
659:
648:
462:NIAID ChemDB
227:Elimination
169:Legal status
163:Legal status
114:Pyrazinamide
95:License data
23:Pyrazinamide
18:
3207:from market
3185:Pegloticase
3180:Rasburicase
3106:Phytic acid
3071:Allopurinol
3030:Guaifenesin
3025:Fenofibrate
2969:Uricosurics
2897:from market
2820:Bedaquiline
2786:Clofazimine
2752:Thiocarlide
2742:Ethionamide
2690:inhibitor:
2665:Cycloserine
2629:Capreomycin
2598:Oxazolidone
2486:Solasulfone
2454:Antifolates
2439:Rifapentine
2319:(1): 6–21.
2037:(1): 1661.
1980:(1): 6135.
1822:(4): 1–12.
1696:(1): 6–21.
1194:10665/44053
1079:. However,
942:fatty acids
799:joint pains
575: g·mol
521:100.002.470
431:CHEBI:45285
251:Identifiers
81:MedlinePlus
53:Trade names
3260:Categories
3155:Cinchophen
3139:Colchicine
3097:Febuxostat
3081:Tisopurine
3076:Oxypurinol
3015:Amlodipine
2984:Probenecid
2838:Pretomanid
2814:Terizidone
2802:Morinamide
2718:Hydrazides
2692:Ethambutol
2663:analogue:
2534:quinolones
2471:Acedapsone
2429:Rifampicin
2415:Rifamycins
1160:8 December
1095:References
974:Resistance
958:coenzyme A
814:ethambutol
681:ethambutol
669:rifampicin
580:3D model (
568:Molar mass
391:2KNI5N06TI
362:ChemSpider
322:IUPHAR/BPS
277:CAS Number
260:IUPAC name
215:Metabolism
16:Medication
3286:Pyrazines
3217:Phase III
3205:Withdrawn
3171:Sevelamer
3102:Inositols
3035:Lesinurad
3008:secondary
2907:Phase III
2895:Withdrawn
2832:Delamanid
2809:Isoxazole
2781:Phenazine
2726:Isoniazid
2611:Sutezolid
2606:Linezolid
2583:Kanamycin
2491:Sulfoxone
2444:Rifalazil
2434:Rifabutin
2422:inhibitor
1241:228373703
869:porphyria
867:, rarely
849:urticaria
845:skin rash
731:treatment
704:pregnancy
700:porphyria
673:isoniazid
451:ChEMBL614
240:Excretion
229:half-life
125:Routes of
73:Monograph
67:Drugs.com
3281:Prodrugs
3250:Medicine
3040:Losartan
2793:Pyrazine
2578:Amikacin
2476:Diucifon
2325:12701830
2295:27931346
2259:19923479
2069:32245967
2012:28733601
1955:21835980
1895:26369957
1846:25530919
1794:11914348
1737:10973326
1702:12701830
1671:26218737
1631:PLOS ONE
1605:12588714
1569:12569078
1533:12836625
1443:Tubercle
1428:14694169
1384:19352495
1376:10716583
1288:(2019).
1272:Archived
1154:Archived
1070:in vitro
984:gene of
853:pruritus
837:anorexia
833:vomiting
827:include
685:by mouth
651:(verify)
342:DrugBank
139:ATC code
132:By mouth
109:DailyMed
3166:aspirin
2977:primary
2661:Alanine
2466:Dapsone
2250:2812260
2210:8787871
2161:7574514
2112:8579133
2104:8640557
2060:7125159
2039:Bibcode
2003:5522395
1982:Bibcode
1946:3502614
1925:Bibcode
1917:Science
1886:4649215
1837:4268777
1745:7409751
1662:4517823
1639:Bibcode
1499:6386028
1463:6356538
1335:6109855
1085:Lederle
1076:in vivo
1063:History
1056:Rifater
912:prodrug
865:malaise
857:dysuria
739:and as
573:123.115
538:Formula
351:DB00339
297:PubChem
286:98-96-4
209:>90%
155:)
149: (
147:J04AK01
111::
87:a682402
3276:Enones
3236:Portal
3200:WHO-EM
3163:except
3160:NSAIDs
2890:WHO-EM
2481:Promin
2323:
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2208:
2201:163048
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1315:Lancet
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871:, and
829:nausea
823:Other
606:SMILES
471:007697
442:ChEMBL
411:D00144
245:kidney
184:℞-only
182:
107:
3148:Other
3090:other
2711:layer
2699:SQ109
2677:layer
2654:layer
2108:S2CID
1741:S2CID
1517:(PDF)
1380:S2CID
1089:Merck
889:liver
873:fever
787:URAT1
626:InChI
582:JSmol
422:ChEBI
220:liver
2956:gout
2391:and
2321:PMID
2291:PMID
2255:PMID
2206:PMID
2157:PMID
2100:PMID
2065:PMID
2008:PMID
1951:PMID
1891:PMID
1842:PMID
1790:PMID
1733:PMID
1698:PMID
1667:PMID
1601:PMID
1565:PMID
1529:PMID
1495:PMID
1459:PMID
1424:PMID
1372:PMID
1331:PMID
1262:ISBN
1237:OCLC
1227:ISBN
1199:ISBN
1162:2016
1117:ISBN
1087:and
1016:pncA
1010:rpsA
1006:rpsA
998:rpsA
994:rpsA
981:pncA
967:PanD
831:and
803:gout
781:and
757:and
692:gout
402:KEGG
382:UNII
371:1017
331:7287
311:1046
199:data
63:AHFS
2960:M04
2500:ASA
2458:DSI
2397:J04
2283:doi
2245:PMC
2237:doi
2196:PMC
2188:doi
2147:PMC
2139:doi
2092:doi
2055:PMC
2047:doi
1998:PMC
1990:doi
1941:PMC
1933:doi
1921:333
1881:PMC
1873:doi
1832:PMC
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1780:PMC
1772:doi
1768:184
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1657:PMC
1647:doi
1593:doi
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1557:doi
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1487:doi
1451:doi
1414:doi
1362:doi
1323:doi
1294:hdl
1189:hdl
733:of
679:or
487:EPA
301:CID
152:WHO
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