Compound: nalidixic acid
SMILES: O=c1c(C(=O)O)cn(CC)c2c1ccc(n2)C
InChIKey: MHWLWQUZZRMNGJ-UHFFFAOYSA-N
Synonyms: nalidixic acid, 389-08-2, Nalidixin, NegGram, Nevigramon, Nalidixan, Nalidic acid, Nalidixinic acid, Wintomylon, Dixiben, Nalurin, Naxuril, Nogram, Urisal, Nalix, 1-Ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid, Betaxina, Specifin, Urodixin, Negram, Uralgin, Uriben, Uriclar, Uroneg, Acide nalidixique, Acido nalidixico, Acide nalidixico, NSC-82174, WIN 18,320, Acidum nalidixicum, 1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid, 1-Ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid, NCI-C56199, 3-Carboxy-1-ethyl-7-methyl-1,8-naphthyridin-4-one, 1,4-Dihydro-1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid, 1,8-Naphthyridine-3-carboxylic acid, 1-ethyl-1,4-dihydro-7-methyl-4-oxo-, 3-Carboxy-1-ethyl-7-methyl-1,8-naphthidin-4-one, WIN-18320, Win 18320, 1-Ethyl-7-methyl-1,4-dihydro-1,8-naphthyridin-4-one-3-carboxylic acid, 1-Aethyl-7-methyl-1,8-naphthyridin-4-on-3-karbonsaeure, 3B91HWA56M, DTXSID3020912, CHEBI:100147, NSC82174, Acide 1-etil-7-metil-1,8-naftiridin-4-one-3-carbossilico, DTXCID70912, 1-Ethyl-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid, Acid, Nalidixic, 1-Ethyl-7-methyl-4-oxo-1,4-dihydro-(1,8)naphthyridine-3-carboxylic acid, Neg Gram, Sodium Nalidixic Acid, Anhydrous, RefChem:55688, Anhydrous, Nalidixate Sodium, J01MB02, 206-864-7, Nalidixate, Uronidix, Innoxalon, Nalitucsan, Unaserus, Sicmylon, Cybis, Dixinal, Jicsron, Uroman, Kusnarin, Nalidicron, Nicelate, Narigix, Poleon, Uropan, Specifen, Eucistin, Nalidixane, MFCD00006884, Nalidixic acid (NegGram), MLS000028504, 1,8-Naphthyridine-3-carboxylic acid,1-ethyl-1,4-dihydro-7-methyl-4-oxo-, 1,8-Naphthyridine-3-carboxylicacid, 1-ethyl-1,4-dihydro-7-methyl-4-oxo-, NCGC00018181-08, SMR000058264, Wintron, 1,4-Dihydro-1-ethyl-7-methyl-1,8-naphthyridin-4-one-3-carboxylic acid, Acido nalidissico, Nalidixic acid 100 microg/mL in Acetonitrile, Acido nalidissico [DCIT], Acide nalidixico [Italian], Acide nalidixique [French], Eucisten, Nalidixic, Acide nalidixique [INN-French], Acido nalidixico [INN-Spanish], Acidum nalidixicum [INN-Latin], CAS-389-08-2, NegGram (TN), CCRIS 2365, HSDB 3241, EINECS 206-864-7, BRN 0750515, UNII-3B91HWA56M, Innoxalomn, nalidixic-acid, Nalidixanum;, Wintomylon;, SR-01000003086, Negram;, Cybis;, 1-Aethyl-7-methyl-1,8-naphthyridin-4-on-3-karbonsaeure [German], Acide 1-etil-7-metil-1,8-naftiridin-4-one-3-carbossilico [Italian], NALIDIXICACID, WIN 183203, CHEMBL5, Spectrum_000918, Nalidixic acid [USAN:USP:INN:BAN:JAN], Maybridge1_007101, Opera_ID_1064, Prestwick0_000187, Prestwick1_000187, Prestwick2_000187, Prestwick3_000187, Spectrum2_001360, Spectrum3_000075, Spectrum4_000817, Spectrum5_001540, Nalidixic acid (Standard), Epitope ID:613449, Nalidixic acid, >=98%, UPCMLD-DP129, NALIDIXIC ACID [MI], NCIOpen2_004342, Lopac0_000837, Oprea1_010545, SCHEMBL21736, BSPBio_000113, BSPBio_001889, KBioGR_001333, KBioSS_001398, NALIDIXIC ACID [INN], NALIDIXIC ACID [JAN], 5-25-07-00384 (Beilstein Handbook Reference), MLS001148578, MLS002303041, MLS004820190, MLS006011875, 1-ethyl-7-methyl-4-oxo-1, BIDD:GT0529, DivK1c_000058, NALIDIXIC ACID [HSDB], NALIDIXIC ACID [USAN], SPECTRUM1500756, SPBio_001579, SPBio_002034, NALIDIXIC ACID [VANDF], BPBio1_000125, orb1710668, orb3025294, NALIDIXIC ACID [MART.], NALIDIXIC ACID [WHO-DD], SCHEMBL29367723, UPCMLD-DP129:001, BDBM21691, GTPL12773, HMS500C20, HMS561K17, HY-B0398R, KBio1_000058, KBio2_001398, KBio2_003966, KBio2_006534, KBio3_001109, MSK5735, NINDS_000058, HMS1921G10, HMS2092K04, HMS2232H24, HMS3259O13, HMS3374G11, HMS3656K05, HMS5080P10, Pharmakon1600-01500756, Nalidixic acid (JP18/USP/INN), Nalidixic acid, analytical standard, ALBB-021275, HY-B0398, MSK5735-1000DM, Tox21_110835, Tox21_201477, Tox21_302754, BBL012279, CCG-39298, EBC-04219, MSK5735-100M, NALIDIXIC ACID [EP IMPURITY], NALIDIXIC ACID [ORANGE BOOK], NSC757432, SBB002146, STK735579, NALIDIXIC ACID [USP IMPURITY], 1-Ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxilic acid, AKOS000120074, Tox21_110835_1, AN16320, DB00779, NC00494, NSC-757432, SDCCGSBI-0050814.P004, IDI1_000058, NCGC00018181-01, NCGC00018181-02, NCGC00018181-03, NCGC00018181-04, NCGC00018181-05, NCGC00018181-06, NCGC00018181-07, NCGC00018181-09, NCGC00018181-10, NCGC00018181-12, NCGC00018181-13, NCGC00021730-03, NCGC00021730-04, NCGC00021730-05, NCGC00021730-06, NCGC00021730-07, NCGC00256581-01, NCGC00259028-01, AS-13289, NCI60_041807, SMR004703506, SY049448, WLN: T66 BN EV JNJ B2 DVQ I1, Nalidixic acid 100 microg/mL in Methanol, SBI-0050814.P003, DB-049349, Nalidixic acid 1000 microg/mL in Methanol, 1, 1-ethyl-1,4-dihydro-7-methyl-4-oxo-, N0490, NS00009829, S2328, SW219624-1, T0909, 1-Ethyl-1,8-naphthyridine-3-carboxilic acid, 1-Ethyl-1,8-naphthyridine-3-carboxylic acid, EN300-20573, VU0239598-6, C05079, D00183, D91720, Nalidixic acid Solution in Methanol, 100ug/mL, Nalidixic acid, meets USP testing specifications, F358268, Q281082, SR-01000003086-4, SR-01000003086-6, BRD-K47886988-001-21-4, BRD-K47886988-001-22-2, BRD-K47886988-323-03-0, Nalidixic acid Solution in DMSO/Methanol, 1000ug/mL, SR-01000003086-10, F0850-6751, Z104478940, 1-Ethyl-7-methyl-1,8-naphthyridin-4-one-3-carboxylic acid, 1-ethyl-7-methyl-4-oxo-[1,8]naphthyridine-3-carboxylic acid, Nalidixic acid, European Pharmacopoeia (EP) Reference Standard, Nalidixic acid, United States Pharmacopeia (USP) Reference Standard, 1-ethyl-7-methyl-4-oxohydropyridino[2,3-b]pyridine-3-carboxylic acid, 1-ETHYL-7-METHYL-4-OXO-1,4-DIHYDRO[1,8]NAPHTHYRIDINE-3-CARBOXYLIC ACID, InChI=1/C12H12N2O3/c1-3-14-6-9(12(16)17)10(15)8-5-4-7(2)13-11(8)14/h4-6H,3H2,1-2H3,(H,16,17
Theoretical properties:
molecular_formula: C12H12N2O3
molecular_weight: 232.23 g/mol
exact_mass: 232.08479225 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 2
heavy_atom_count: 17
topological_polar_surface_area: 70.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: PALE BUFF, CRYSTALLINE POWDER
color: PALE BUFF, CRYSTALLINE POWDER
odor: ODORLESS
melting_point: 444 to 446 °F (NTP, 1992)
solubility: less than 1 mg/mL at 70 °F (NTP, 1992)
Descriptions:
{"pubchem": "Nalidixic Acid can cause cancer according to The National Toxicology Program.", "chebi": "A monocarboxylic acid comprising 1,8-naphthyridin-4-one substituted by carboxylic acid, ethyl and methyl groups at positions 3, 1, and 7, respectively. An orally administered antibacterial, it is used in the treatment of lower urinary-tract infections due to Gram-negative bacteria, including the majority of <em>E. coli</em>, <em>Enterobacter</em>, <em>Klebsiella</em>, and <em>Proteus</em> species.", "chembl": "NALIDIXIC ACID is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Nalidixic acid (tradenames Nevigramon, NegGram, Wintomylon and WIN 18,320) is the first of the synthetic quinolone antibiotics.\nIn a technical sense, it is a naphthyridone, not a quinolone: its ring structure is a 1,8-naphthyridine nucleus that contains two nitrogen atoms, unlike quinoline, which has a single nitrogen atom.\nSynthetic quinolone antibiotics were discovered by George Lesher and coworkers as a byproduct of chloroquine manufacture in the 1960s; nalidixic acid itself was used clinically, starting in 1967.\nNalidixic acid is effective primarily against Gram-negative bacteria, with minor anti-Gram-positive activity. In lower concentrations, it acts in a bacteriostatic manner; that is, it inhibits growth and reproduction. In higher concentrations, it is bactericidal, meaning that it kills bacteria instead of merely inhibiting their growth.\nIt has historically been used for treating urinary tract infections, caused, for example, by Escherichia coli, Proteus, Shigella, Enterobacter, and Klebsiella. It is no longer clinically used for this indication in the US as less toxic and more effective agents are available. The marketing authorization for nalidixic acid has been suspended throughout the EU.\nIt is also a tool in studies as a regulation of bacterial division. It selectively and reversibly blocks DNA replication in susceptible bacteria. Nalidixic acid and related antibiotics inhibit a subunit of DNA gyrase and topoisomerase IV and induce formation of cleavage complexes. It also inhibits the nicking-closing activity on the subunit of DNA gyrase that releases the positive binding stress on the supercoiled DNA."}