1.0 2011-09-21 00:19:28 UTC 2015-07-21 06:57:21 UTC FDB022776 5-Hydroxypyrazinamide Pyrazinamide Pyrazinamide is a drug used to treat tuberculosis in afflicted patients. The drug is largely bacteriostatic, but can be bacteriocidal on actively replicating tuberculosis bacteria. -- Wikipedia; Pyrazinamide is a generic drug and is available in a wide variety of presentations. Pyrazinamide tablets are usually 500mg and form the bulkiest part of the standard tuberculosis treatment regimen. Pyrazinamide tablets are so large that some patients find them impossible to swallow: pyrazinamide syrup is an option for these patients. -- Wikipedia; Pyrazinamide is also available as part of fixed dose combinations with other TB drugs such as isoniazid and rifampicin (Rifater is an example). -- Wikipedia; Pyrazinamide is well absorbed orally. It crosses inflamed meninges and is an essential part of the treatment of tuberculous meningitis. It is metabolised by the liver and the metabolic products are excreted by the kidneys. -- Wikipedia; Pyrazinamide is a pro-drug that stops the growth of Mycobacterium tuberculosis. M. tuberculosis has the enzyme pyrazinamidase which is only active at acidic pH. Pyrazinamidase converts pyrazinamide to the active form, pyrazinoic acid. Pyrazinoic acid inhibits the enzyme fatty acid synthetase I, which is required by the bacterium to synthesise fatty acids. Mutations of the pyrazinamidase gene (pncA) are responsible for pyrazinamide resistance in M. tuberculosis. -- Wikipedia [HMDB] 2-Carboxamido-5-hydroxypyrazine 5-hydroxy-(8CI)-pyrazinecarboxamide 5-Hydroxypyrazinecarboxamide C5H5N3O2 139.1121 139.038176419 5-oxo-4,5-dihydropyrazine-2-carboxamide 5-oxo-4H-pyrazine-2-carboxamide 13924-96-4 NC(=O)C1=CNC(=O)C=N1 InChI=1S/C5H5N3O2/c6-5(10)3-1-8-4(9)2-7-3/h1-2H,(H2,6,10)(H,8,9) XENWQEOTDAQROM-UHFFFAOYSA-N belongs to the class of organic compounds known as pyrazinecarboxamides. Pyrazinecarboxamides are compounds containing a pyrazine ring which bears a carboxamide. Pyrazinecarboxamides Organic compounds Organoheterocyclic compounds Diazines Pyrazines Aromatic heteromonocyclic compounds 2-heteroaryl carboxamides Azacyclic compounds Heteroaromatic compounds Hydrocarbon derivatives Lactams Organic oxides Organonitrogen compounds Organooxygen compounds Organopnictogen compounds Primary carboxylic acid amides Vinylogous amides 2-heteroaryl carboxamide Aromatic heteromonocyclic compound Azacycle Carboxamide group Carboxylic acid derivative Heteroaromatic compound Hydrocarbon derivative Lactam Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary carboxylic acid amide Pyrazinecarboxamide Vinylogous amide Solid logp -1.60 ALOGPS logs -1.30 ALOGPS solubility 6.95e+00 g/l ALOGPS logp -1.5 ChemAxon pka_strongest_acidic 9.91 ChemAxon pka_strongest_basic -1.4 ChemAxon iupac 5-oxo-4,5-dihydropyrazine-2-carboxamide ChemAxon average_mass 139.1121 ChemAxon mono_mass 139.038176419 ChemAxon smiles NC(=O)C1=CNC(=O)C=N1 ChemAxon formula C5H5N3O2 ChemAxon inchi InChI=1S/C5H5N3O2/c6-5(10)3-1-8-4(9)2-7-3/h1-2H,(H2,6,10)(H,8,9) ChemAxon inchikey XENWQEOTDAQROM-UHFFFAOYSA-N ChemAxon polar_surface_area 84.55 ChemAxon refractivity 33.71 ChemAxon polarizability 12.05 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 24671 Specdb::CMs 27712 Specdb::CMs 99735 Specdb::CMs 168215 Specdb::MsIr 1505 Specdb::MsIr 1506 Specdb::MsIr 1507 Specdb::MsMs 320635 Specdb::MsMs 320636 Specdb::MsMs 320637 Specdb::MsMs 368053 Specdb::MsMs 368054 Specdb::MsMs 368055 Specdb::MsMs 2441740 Specdb::MsMs 2441741 Specdb::MsMs 2441742 Specdb::MsMs 2520122 Specdb::MsMs 2520123 Specdb::MsMs 2520124 Specdb::NmrOneD 9982 Specdb::NmrOneD 9983 Specdb::NmrOneD 9984 Specdb::NmrOneD 9985 Specdb::NmrOneD 9986 Specdb::NmrOneD 9987 Specdb::NmrOneD 9988 Specdb::NmrOneD 9989 Specdb::NmrOneD 9990 Specdb::NmrOneD 9991 Specdb::NmrOneD 9992 Specdb::NmrOneD 9993 Specdb::NmrOneD 9994 Specdb::NmrOneD 9995 Specdb::NmrOneD 9996 Specdb::NmrOneD 9997 Specdb::NmrOneD 9998 Specdb::NmrOneD 9999 Specdb::NmrOneD 10000 Specdb::NmrOneD 10001 HMDB01978 #<Reference:0x000055ce31677f28> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823