1.0 2011-09-21 00:35:49 UTC 2015-07-21 06:57:54 UTC FDB023854 Demethylated antipyrine Demethylated antipyrine is a novel potent free radical scavenger that has been clinically used to reduce the neuronal damage following ischemic stroke. Demethylated antipyrine exerts neuroprotective effects by inhibiting endothelial injury and by ameliorating neuronal damage in brain ischemia. Demethylated antipyrine provides the desirable features of NOS: it increases eNOS (beneficial NOS for rescuing ischemic stroke) and decreases nNOS and iNOS (detrimental NOS). Post- reperfusion brain edema and hemorrhagic events induced by thrombolytic therapy may be reduced by demethylated antipyrine pretreatment. Increased productions of superoxide and NO in the brain after reperfusion and a concomitant surge in oxygen free radicals with increased NO during recirculation lead to formation of peroxynitrite, a super potent radical. Demethylated antipyrine, which inhibits oxidation and enhances NO production derived from increased eNOS expression, may improve and conserve cerebral blood flow without peroxynitrite generation during reperfusion. Clinical experience with demethylated antipyrine suggests that this drug has a wide therapeutic time window. Demethylated antipyrine can exert a wide range of inhibitory effects on water-soluble and lipid soluble peroxyl radical-induced peroxidation systems, and appears to display combined properties of both, vitamin C and E. Demethylated antipyrine can scavenge not only hydroxyl radicals but also other free radicals, although it has no major effect on superoxide anion radicals. Demethylated antipyrine apparently traps hydroxyl radicals and inhibits OH-dependent lipid peroxidation or tyrosine nitration induced by peroxynitrite (ONOO-). Lipid peroxidation starts with lipid radical (L) production after free radical-mediated extraction of proton from unsaturated fatty acid. Subsequently lipid peroxyl radical (LOO) is generated by addition of oxygen atom, and a further L is produced by LOO-mediated extraction of proton from another unsaturated fatty acid. Demethylated antipyrine can inhibit lipid peroxidation by scavenging not only hydroxyl radicals but also other free radicals including LOO. Under physiological conditions, 50% of demethylated antipyrine is present as an anion form, and electrons released from demethylated antipyrine anion exert radical scavenging. Subsequently, demethylated antipyrine radicals are generated. They react readily with oxygen atoms, and form peroxyl radical of demethylated antipyrine, and eventually 2-oxo-3-(phenylhydrazone)- butanoic acid (OPB). (PMID: 16834755, CNS Drug Rev. 2006 Spring;12(1):9-20.) [HMDB] 1-Phenyl-3-methyl-1H-4,5-dihydropyrazol-5-one 1-Phenyl-3-methyl-2-pyrazolin-5-one 1-Phenyl-3-methyl-5-oxopyrazole 1-Phenyl-3-methyl-5-pyrazolinone 1-Phenyl-3-methyl-5-pyrazolone 2,4-Dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one 3-Methyl-1-phenyl-1H-pyrazol-5-one 3-Methyl-1-phenyl-2-pyrazolin-5-one 3-Methyl-1-phenyl-2-pyrazoline-5-one 3-Methyl-1-phenyl-4,5-dihydropyrazol-5-one 3-Methyl-1-phenyl-4,5-dihydropyrazole-5-one 3-Methyl-1-phenyl-5-pyrazolone 3-Methyl-1-phenylpyrazol-5(4H)-one 3-Methyl-1-phenylpyrazolin-5-one 5-Methyl-2-phenyl-2H-pyrazol-3(4H)-one 5-Methyl-2-phenylpyrazol-3-one Edarabone Edaravone Methylphenylpyrazolone Norantipyrine Norphenazone C10H10N2O 174.1992 174.079312952 5-methyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one 5-methyl-2-phenyl-1H-pyrazol-3-one 89-25-8 CC1=CC(=O)N(N1)C1=CC=CC=C1 InChI=1S/C10H10N2O/c1-8-7-10(13)12(11-8)9-5-3-2-4-6-9/h2-7,11H,1H3 KZQYIMCESJLPQH-UHFFFAOYSA-N belongs to the class of organic compounds known as phenylpyrazoles. Phenylpyrazoles are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group. Phenylpyrazoles Organic compounds Organoheterocyclic compounds Azoles Pyrazoles Aromatic heteromonocyclic compounds Azacyclic compounds Benzene and substituted derivatives Heteroaromatic compounds Hydrocarbon derivatives Lactams Organic oxides Organonitrogen compounds Organooxygen compounds Organopnictogen compounds Pyrazolones Vinylogous amides Aromatic heteromonocyclic compound Azacycle Benzenoid Heteroaromatic compound Hydrocarbon derivative Lactam Monocyclic benzene moiety Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenylpyrazole Pyrazolinone Vinylogous amide Solid logp 0.59 ALOGPS logs -0.96 ALOGPS solubility 1.93e+01 g/l ALOGPS logp 1.28 ChemAxon pka_strongest_acidic 8.27 ChemAxon pka_strongest_basic 1.62 ChemAxon iupac 5-methyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one ChemAxon average_mass 174.1992 ChemAxon mono_mass 174.079312952 ChemAxon smiles CC1=CC(=O)N(N1)C1=CC=CC=C1 ChemAxon formula C10H10N2O ChemAxon inchi InChI=1S/C10H10N2O/c1-8-7-10(13)12(11-8)9-5-3-2-4-6-9/h2-7,11H,1H3 ChemAxon inchikey KZQYIMCESJLPQH-UHFFFAOYSA-N ChemAxon polar_surface_area 32.34 ChemAxon refractivity 62.14 ChemAxon polarizability 18.55 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 15851 Specdb::CMs 133435 Specdb::CMs 141169 Specdb::MsIr 2380 Specdb::MsIr 2381 Specdb::MsIr 2382 Specdb::MsMs 301123 Specdb::MsMs 301124 Specdb::MsMs 301125 Specdb::MsMs 343573 Specdb::MsMs 343574 Specdb::MsMs 343575 Specdb::MsMs 2262640 Specdb::MsMs 2262641 Specdb::MsMs 2262642 Specdb::MsMs 3080274 Specdb::MsMs 3080275 Specdb::MsMs 3080276 Specdb::NmrOneD 67952 Specdb::NmrOneD 67953 Specdb::NmrOneD 67954 Specdb::NmrOneD 67955 Specdb::NmrOneD 67956 Specdb::NmrOneD 67957 Specdb::NmrOneD 67958 Specdb::NmrOneD 67959 Specdb::NmrOneD 67960 Specdb::NmrOneD 67961 Specdb::NmrOneD 67962 Specdb::NmrOneD 67963 Specdb::NmrOneD 67964 Specdb::NmrOneD 67965 Specdb::NmrOneD 67966 Specdb::NmrOneD 67967 Specdb::NmrOneD 67968 Specdb::NmrOneD 67969 Specdb::NmrOneD 67970 Specdb::NmrOneD 67971 HMDB06240 31530 #<Reference:0x000055ce32652718> 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