Details of the Drug

General Information of Drug (ID: DMRM0JV)

Drug Name
Nalidixic Acid
Synonyms
Betaxina; Cybis; Dixiben; Dixinal; Eucistin; Innoxalon; Jicsron; Kusnarin; Nalidicron; Nalidixan; Nalidixane; Nalidixate; Nalidixic; Nalidixin; Nalitucsan; Nalix; Nalurin; Narigix; Naxuril; NegGram; Negram; Nevigramon; Nicelate; Nogram; Poleon; Sicmylon; Specifen; Specifin; Unaserus; Uralgin; Uriben; Uriclar; Urisal; Urodixin; Uroman; Uroneg; Uronidix; Uropan; Wintomylon; Wintron; Acide nalidixico; Acide nalidixico [Italian]; Acide nalidixique; Acide nalidixique [French]; Acido nalidissico; Acido nalidissico [DCIT]; Acido nalidixico; Acidum nalidixicum; NALIDIXATE SODIUM; Naladixic acid; Naldixic acid; Nalidic acid; Nalidixinic acid; Nalidixic acid USP27; WIN 183203; Acid, Nalidixic; Acide nalidixique [INN-French]; Acido nalidixico [INN-Spanish]; Acidum nalidixicum [INN-Latin]; N-1200; NegGram (TN); Neggram (TN); Sodium Nalidixic Acid, Anhydrous; Sodium Nalidixic Acid, Monohydrate; Sodium,Nalidixate; WIN 18,320; WIN-18320; Wil 18,320; Wintomylon (TN); ZERO/002632; WIN-18320 (TN); Nalidixic acid (JP15/USP/INN); Nalidixic acid [USAN:INN:BAN:JAN]; 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]; 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
Indication
Disease Entry ICD 11 Status REF
Urinary tract infection GC08 Approved [1]
Therapeutic Class
Antibiotics
Affected Organisms
Enteric bacteria and other eubacteria
ATC Code
J01MB02: Nalidixic Acid
J01MB: Other quinolones
J01M: QUINOLONE ANTIBACTERIALS
J01: ANTIBACTERIALS FOR SYSTEMIC USE
J: ANTIINFECTIVES FOR SYSTEMIC USE
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 232.23
Logarithm of the Partition Coefficient (xlogp) 1.4
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 5
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [2]
Bioavailability
96% of drug becomes completely available to its intended biological destination(s) [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 1.1 - 2.5 hours [4]
Metabolism
The drug is metabolized via the hepatic []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 287.2016 micromolar/kg/day [5]
Water Solubility
The ability of drug to dissolve in water is measured as 0.054 mg/mL [2]
Chemical Identifiers
Formula
C12H12N2O3
IUPAC Name
1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid
Canonical SMILES
CCN1C=C(C(=O)C2=C1N=C(C=C2)C)C(=O)O
InChI
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
Cross-matching ID
PubChem CID
4421
ChEBI ID
CHEMBL100147
CAS Number
389-08-2
UNII
3B91HWA56M
DrugBank ID
DB00779
TTD ID
D07JGT
INTEDE ID
DR2296
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
DNA topoisomerase II (TOP2) TT0IHXV TOP2A_HUMAN ; TOP2B_HUMAN Inhibitor [6]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Collagenase 3 (MMP13) OTY8BZIE MMP13_HUMAN Gene/Protein Processing [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Nalidixic Acid
DDI Drug Name DDI Drug ID Severity Mechanism Disease REF
Plazomicin DMKMBES Moderate Increased risk of nephrotoxicity by the combination of Nalidixic acid and Plazomicin. Urinary tract infection [GC08] [8]
Coadministration of a Drug Treating the Disease Different from Nalidixic Acid (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Idarubicin DMM0XGL Minor Decreased absorption of Nalidixic acid due to intestinal mucosa variation caused by Idarubicin. Acute myeloid leukaemia [2A60] [9]
Aminophylline DML2NIB Moderate Decreased metabolism of Nalidixic acid caused by Aminophylline mediated inhibition of CYP450 enzyme. Asthma [CA23] [10]
Temozolomide DMKECZD Minor Decreased absorption of Nalidixic acid due to intestinal mucosa variation caused by Temozolomide. Brain cancer [2A00] [9]
Ketoprofen DMRKXPT Moderate Additive CNS depression effects by the combination of Nalidixic acid and Ketoprofen. Chronic pain [MG30] [11]
Capecitabine DMTS85L Minor Decreased absorption of Nalidixic acid due to intestinal mucosa variation caused by Capecitabine. Colorectal cancer [2B91] [9]
Mestranol DMG3F94 Moderate Decreased absorption of Nalidixic acid due to formation of complexes caused by Mestranol. Contraceptive management [QA21] [12]
Mycophenolic acid DMRBMAU Moderate Altered absorption of Nalidixic acid due to GI flora changes caused by Mycophenolic acid. Crohn disease [DD70] [13]
Stiripentol DMMSDOY Moderate Decreased metabolism of Nalidixic acid caused by Stiripentol mediated inhibition of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [14]
Mefenamic acid DMK7HFI Moderate Additive CNS stimulant effects by the combination of Nalidixic acid and Mefenamic acid. Female pelvic pain [GA34] [11]
Procarbazine DMIK367 Minor Decreased absorption of Nalidixic acid due to intestinal mucosa variation caused by Procarbazine. Hodgkin lymphoma [2B30] [9]
Didanosine DMI2QPE Moderate Decreased absorption of Nalidixic acid due to formation of complexes caused by Didanosine. Human immunodeficiency virus disease [1C60-1C62] [15]
Bempedoic acid DM1CI9R Major Increased risk of tendinitis/tendon rupture by the combination of Nalidixic acid and Bempedoic acid. Hyper-lipoproteinaemia [5C80] [16]
Quinapril DMR8H31 Moderate Decreased absorption of Nalidixic acid due to formation of complexes caused by Quinapril. Hypertension [BA00-BA04] [14]
Givosiran DM5PFIJ Moderate Increased risk of nephrotoxicity by the combination of Nalidixic acid and Givosiran. Inborn porphyrin/heme metabolism error [5C58] [8]
Probenecid DMMFWOJ Moderate Decreased elimination of Nalidixic acid caused by Probenecid mediated competitive inhibition of renal tubular secretion. Inborn purine/pyrimidine/nucleotide metabolism error [5C55] [17]
Meclofenamic acid DM05FXR Moderate Additive CNS stimulant effects by the combination of Nalidixic acid and Meclofenamic acid. Inflammatory spondyloarthritis [FA92] [18]
Ramelteon DM7IW9J Moderate Decreased metabolism of Nalidixic acid caused by Ramelteon mediated inhibition of CYP450 enzyme. Insomnia [7A00-7A0Z] [19]
Melatonin DMKWFBT Minor Decreased metabolism of Nalidixic acid caused by Melatonin mediated inhibition of CYP450 enzyme. Insomnia [7A00-7A0Z] [8]
Tasimelteon DMLOQ1V Moderate Decreased metabolism of Nalidixic acid caused by Tasimelteon mediated inhibition of CYP450 enzyme. Insomnia [7A00-7A0Z] [20]
Iron DMAP8MV Moderate Decreased absorption of Nalidixic acid due to formation of complexes caused by Iron. Iron deficiency anaemia [3A00] [21]
Polyethylene glycol DM4I1JP Moderate Increased risk of lowers seizure threshold by the combination of Nalidixic acid and Polyethylene glycol. Irritable bowel syndrome [DD91] [22]
Alosetron DML2A03 Moderate Decreased metabolism of Nalidixic acid caused by Alosetron mediated inhibition of CYP450 enzyme. Irritable bowel syndrome [DD91] [23]
Lurbinectedin DMEFRTZ Minor Decreased absorption of Nalidixic acid due to intestinal mucosa variation caused by Lurbinectedin. Lung cancer [2C25] [9]
Fludarabine DMVRLT7 Minor Decreased absorption of Nalidixic acid due to intestinal mucosa variation caused by Fludarabine. Malignant haematopoietic neoplasm [2B33] [9]
Mercaptopurine DMTM2IK Minor Decreased absorption of Nalidixic acid due to intestinal mucosa variation caused by Mercaptopurine. Mature B-cell lymphoma [2A85] [9]
Cytarabine DMZD5QR Minor Decreased absorption of Nalidixic acid due to intestinal mucosa variation caused by Cytarabine. Mature B-cell lymphoma [2A85] [9]
Ethinyl estradiol DMODJ40 Moderate Decreased absorption of Nalidixic acid due to formation of complexes caused by Ethinyl estradiol. Menopausal disorder [GA30] [12]
Lanthanum carbonate DMMJQSH Moderate Decreased absorption of Nalidixic acid due to formation of complexes caused by Lanthanum carbonate. Mineral absorption/transport disorder [5C64] [24]
Deflazacort DMV0RNS Major Increased risk of tendinitis/tendon rupture by the combination of Nalidixic acid and Deflazacort. Muscular dystrophy [8C70] [25]
Hydroxyurea DMOQVU9 Minor Decreased absorption of Nalidixic acid due to intestinal mucosa variation caused by Hydroxyurea. Myeloproliferative neoplasm [2A20] [9]
Bupropion DM5PCS7 Major Increased risk of lowers seizure threshold by the combination of Nalidixic acid and Bupropion. Nicotine use disorder [6C4A] [26]
Naproxen DMZ5RGV Moderate Additive CNS stimulant effects by the combination of Nalidixic acid and Naproxen. Osteoarthritis [FA00-FA05] [11]
Carboplatin DMG281S Minor Decreased absorption of Nalidixic acid due to intestinal mucosa variation caused by Carboplatin. Ovarian cancer [2C73] [9]
Topotecan DMP6G8T Minor Decreased absorption of Nalidixic acid due to intestinal mucosa variation caused by Topotecan. Ovarian cancer [2C73] [9]
Aspirin DM672AH Moderate Additive CNS stimulant effects by the combination of Nalidixic acid and Aspirin. Pain [MG30-MG3Z] [27]
Diflunisal DM7EN8I Moderate Additive CNS depression effects by the combination of Nalidixic acid and Diflunisal. Pain [MG30-MG3Z] [11]
Ibuprofen DM8VCBE Moderate Additive CNS depression effects by the combination of Nalidixic acid and Ibuprofen. Pain [MG30-MG3Z] [11]
Rasagiline DM3WKQ4 Major Decreased metabolism of Nalidixic acid caused by Rasagiline mediated inhibition of CYP450 enzyme. Parkinsonism [8A00] [8]
Choline salicylate DM8P137 Moderate Additive CNS stimulant effects by the combination of Nalidixic acid and Choline salicylate. Postoperative inflammation [1A00-CA43] [18]
Salsalate DM13P4C Moderate Additive CNS stimulant effects by the combination of Nalidixic acid and Salsalate. Rheumatoid arthritis [FA20] [11]
Meloxicam DM2AR7L Moderate Additive CNS stimulant effects by the combination of Nalidixic acid and Meloxicam. Rheumatoid arthritis [FA20] [11]
Oxaprozin DM9UB0P Moderate Additive CNS stimulant effects by the combination of Nalidixic acid and Oxaprozin. Rheumatoid arthritis [FA20] [11]
Dexamethasone DMMWZET Major Increased risk of tendinitis/tendon rupture by the combination of Nalidixic acid and Dexamethasone. Rheumatoid arthritis [FA20] [25]
Asenapine DMSQZE2 Moderate Decreased metabolism of Nalidixic acid caused by Asenapine mediated inhibition of CYP450 enzyme. Schizophrenia [6A20] [28]
Dactinomycin DM2YGNW Minor Decreased absorption of Nalidixic acid due to intestinal mucosa variation caused by Dactinomycin. Solid tumour/cancer [2A00-2F9Z] [9]
Methylprednisolone DM4BDON Major Increased risk of tendinitis/tendon rupture by the combination of Nalidixic acid and Methylprednisolone. Solid tumour/cancer [2A00-2F9Z] [25]
Docetaxel DMDI269 Minor Decreased absorption of Nalidixic acid due to intestinal mucosa variation caused by Docetaxel. Solid tumour/cancer [2A00-2F9Z] [9]
Mitoxantrone DMM39BF Minor Decreased absorption of Nalidixic acid due to intestinal mucosa variation caused by Mitoxantrone. Solid tumour/cancer [2A00-2F9Z] [9]
Prednisolone DMQ8FR2 Major Increased risk of tendinitis/tendon rupture by the combination of Nalidixic acid and Prednisolone. Solid tumour/cancer [2A00-2F9Z] [25]
Taxol DMUOT9V Minor Decreased absorption of Nalidixic acid due to intestinal mucosa variation caused by Taxol. Solid tumour/cancer [2A00-2F9Z] [9]
Doxorubicin DMVP5YE Minor Decreased absorption of Nalidixic acid due to intestinal mucosa variation caused by Doxorubicin. Solid tumour/cancer [2A00-2F9Z] [9]
Tacrolimus DMZ7XNQ Moderate Increased risk of nephrotoxicity by the combination of Nalidixic acid and Tacrolimus. Transplant rejection [NE84] [8]
⏷ Show the Full List of 52 DDI Information of This Drug

References

1 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 071919.
2 BDDCS applied to over 900 drugs
3 Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
6 Activity of fluoroquinolone antibiotics against Plasmodium falciparum in vitro. Antimicrob Agents Chemother. 1988 Aug;32(8):1182-6.
7 Contrasting effects of fluoroquinolone antibiotics on the expression of the collagenases, matrix metalloproteinases (MMP)-1 and -13, in human tendon-derived cells. Rheumatology (Oxford). 2005 Dec;44(12):1514-7. doi: 10.1093/rheumatology/kei087. Epub 2005 Sep 7.
8 Cerner Multum, Inc. "Australian Product Information.".
9 Johnson EJ, MacGowan AP, Potter MN, et al "Reduced absorption of oral ciprofloxacin after chemotherapy for haematological malignancy." J Antimicrob Chemother 25 (1990): 837-42. [PMID: 2373666]
10 Ball P "Ciprofloxacin: an overview of adverse experiences." J Antimicrob Chemother 18 (1986): 187-93. [PMID: 3542945]
11 Product Information. Factive (gemifloxacin). GeneSoft Inc, San Francisco, CA.
12 Friedman CI, Huneke AL, Kim MH, Powell J "The effect of ampicillin on oral contraceptive effectiveness." Obstet Gynecol 55 (1980): 33-7. [PMID: 7188714]
13 Product Information. CellCept (mycophenolate mofetil). Roche Laboratories, Nutley, NJ.
14 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
15 Deppermann KM, Lode H "Fluoroquinolones: interaction profile during enteral absorption." Drugs 45 Suppl 3 (1993): 65-72. [PMID: 7689454]
16 Product Information. Nexletol (bempedoic acid). Esperion Therapeutics, Ann Arbor, MI.
17 Dash H, Mills J "Letter: Severe metabolic acidosis associated with nalidixic acid overdose." Ann Intern Med 84 (1976): 570-1. [PMID: 1275361]
18 Davey PG "Overview of drug interactions with the quinolones." J Antimicrob Chemother 22(suppl c) (1988): 97-107. [PMID: 3053579]
19 Product Information. Rozerem (ramelteon). Takeda Pharmaceuticals America, Lincolnshire, IL.
20 Product Information. Hetlioz (tasimelteon). Vanda Pharmaceuticals Inc, Rockville, MD.
21 Product Information. NegGram (nalidixic acid). Sanofi Winthrop Pharmaceuticals, New York, NY.
22 Product Information. Suprep Bowel Prep Kit (magnesium/potassium/sodium sulfates). Braintree Laboratories, Braintree, MA.
23 Product Information. Lotronex (alosetron). Glaxo Wellcome, Research Triangle Park, NC.
24 Canadian Pharmacists Association.
25 FDA. U.S. Food and Drug Administration "Information for Healthcare Professionals. Fluoroquinolone Antimicrobial Drugs. FDA Alert [7/8/2008].".
26 Product Information. Wellbutrin XL (buPROPion). GlaxoSmithKline, Philadelphia, PA.
27 Product Information. Avelox (moxifloxacin) Bayer, West Haven, CT.
28 Product Information. Saphris (asenapine). Schering-Plough Corporation, Kenilworth, NJ.