Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR2296)
Drug Name
Nalidixic acid
Synonyms
Naladixic acid; Naldixic acid; Nalidic acid; Nalidicron; Nalidixan; Nalidixane; Nalidixate; Nalidixic; Nalidixic acid (JP15/USP/INN); Nalidixic acid USP27; Nalidixic acid [USAN:INN:BAN:JAN]; Nalidixin; Nalidixinic acid; Nalitucsan; Nalurin; Narigix; Naxuril; NegGram; NegGram (TN); Neggram (TN); Negram; Nevigramon; Nicelate; Nogram; Poleon; Sicmylon; Sodium Nalidixic Acid, Anhydrous; Sodium,Nalidixate; Specifen; Specifin; Unaserus; Uralgin; Uriben; Uriclar; Urisal; Urodixin; Uroman; Uroneg; Uronidix; Uropan; WIN 18,320; WIN 183203; WIN-18320; WIN-18320 (TN); Acid, Nalidixic; Acide nalidixico; Acide nalidixico [Italian]; Acide nalidixique; Acide nalidixique [French]; Acide nalidixique [INN-French]; Acido nalidissico; Acido nalidissico [DCIT]; Acido nalidixico; Acido nalidixico [INN-Spanish]; Acidum nalidixicum; Acidum nalidixicum [INN-Latin]; Betaxina; Dixiben; Dixinal; Eucistin; Innoxalon; Jicsron; Kusnarin; N-1200; NALIDIXATE SODIUM; Wil 18,320; Wintomylon; Wintomylon (TN); Wintron; ZERO/002632; 1,4-Dihydro-1-ethyl-7-methyl-1,8-naphthyridin-4-one-3-carboxylic acid; 1,4-Dihydro-1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid; 1-Aethyl-7-methyl-1,8-naphthyridin-4-on-3-karbonsaeure; 1-Aethyl-7-methyl-1,8-naphthyridin-4-on-3-karbonsaeure [German]; 1-Ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxilic acid; 1-Ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid; 1-Ethyl-7-methyl-1,4-dihydro-1,8-naphthyridin-4-one-3-carboxylic acid; 1-Ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid; 1-Ethyl-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid; 1-ethyl-7-methyl-1,4-dihydro-1,8-naphthyridin-4-one-3-ca rboxylic acid; 1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid; 3-Carboxy-1-ethyl-7-methyl-1,8-naphthidin-4-one; 3-Carboxy-1-ethyl-7-methyl-1,8-naphthyridin-4-one; Acide 1-etil-7-metil-1,8-naftiridin-4-one-3-carbossilico; Acide 1-etil-7-metil-1,8-naftiridin-4-one-3-carbossilico [Italian]; Cybis; Nalix; Sodium Nalidixic Acid, Monohydrate
Indication Infectious cystitis [ICD11: GC00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 232.23 Topological Polar Surface Area 70.5
Heavy Atom Count 17 Rotatable Bond Count 2
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
4421
PubChem SID
7525 ; 120913 ; 597740 ; 855620 ; 3136845 ; 5096866 ; 7735476 ; 7847251 ; 7980065 ; 8149659 ; 8152734 ; 11335233 ; 11360472 ; 11363812 ; 11366374 ; 11368936 ; 11371209 ; 11374472 ; 11377098 ; 11385372 ; 11446159 ; 11451821 ; 11461444 ; 11466215 ; 11467335 ; 11485315 ; 11485770 ; 11489176 ; 11489891 ; 11492632 ; 11494732 ; 14773844 ; 15047394 ; 17389812 ; 22391542 ; 24897719 ; 24897864 ; 26534558 ; 26612057 ; 26679680 ; 26746931 ; 26746932 ; 26751459 ; 26751460 ; 29223518 ; 46487920 ; 46507401 ; 47440076 ; 47440077 ; 47588827
ChEBI ID
CHEBI:100147
CAS Number
389-08-2
TTD Drug ID
D07JGT
Formula
C12H12N2O3
Canonical SMILES
CCN1C=C(C(=O)C2=C1N=C(C=C2)C)C(=O)O
InChI
1S/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)
InChIKey
MHWLWQUZZRMNGJ-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
7-hydroxymethyl nalidixic acid DM004520
160716
Oxidation - Hydrolyzationn 1 [4]
7-carboxy nalidixic acid DM004521 N. A. Oxidation - Oxidationn 2 [4]
7-hydroxymethyl nalidixic acid DM004520
160716
Unclear 2 [5]
7-hydroxymethyl nalidixic acid acylglucuronide DM004523 N. A. Unclear 2 [6]
Nalidixic acid glucuronide DM004526 N. A. Unclear 2 [6]
7-carboxy nalidixic acid glucuronide DM004522 N. A. Unclear 3 [7]
7-hydroxymethyl nalidixic acid etherglucuronide DM004524 N. A. Unclear 3 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004850 Nalidixic acid 7-hydroxymethyl nalidixic acid Oxidation - Hydrolyzationn Unclear [4]
MR004855 Nalidixic acid Nalidixic acid glucuronide Unclear Unclear [6]
MR004851 7-hydroxymethyl nalidixic acid 7-carboxy nalidixic acid Oxidation - Oxidationn Unclear [4]
MR004853 7-hydroxymethyl nalidixic acid 7-hydroxymethyl nalidixic acid acylglucuronide Unclear Unclear [6]
MR004852 7-carboxy nalidixic acid 7-carboxy nalidixic acid glucuronide Unclear Unclear [7]
MR004854 7-hydroxymethyl nalidixic acid acylglucuronide 7-hydroxymethyl nalidixic acid etherglucuronide Unclear Unclear [6]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Unclear metabolic mechanism (DME-unclear) DME1462 Salmonella enterica Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1533 Helicobacter rodentium Not Available Not Available [3]
References
1 Nalidixic acid was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Molecular level understanding of resistance to nalidixic acid in Salmonella enteric serovar typhimurium associates with the S83F sequence type. Eur Biophys J. 2016 Jan;45(1):35-44.
3 Helicobacter rodentium sp. nov., a urease-negative Helicobacter species isolated from laboratory mice. Int J Syst Bacteriol. 1997 Jul;47(3):627-34.
4 Pharmacokinetics of nalidixic acid in man: hydroxylation and glucuronidation
5 DrugBank(Pharmacology-Metabolism):Nalidixic acid
6 Probenecid inhibits the renal clearance and renal glucuronidation of nalidixic acid. A pilot experiment
7 #N/A

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