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药品详细

Nalidixic Acid(萘啶酸)

化学结构式图
中文名
萘啶酸
英文名
Nalidixic Acid
分子式
C12H12N2O3
化学名
1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
分子量
Average: 232.2353
Monoisotopic: 232.08479226
CAS号
389-08-2
ATC分类
J01M 未知
药物类型
small molecule
阶段
approved
商品名
Cybis;Dixiben;Dixinal;Eucistin;Innoxalon;Jicsron;naladixic acid;Nalidic acid;Nalidixan;Nalidixate;Nalidixic acid USP27;Nalidixin;Nalidixinic acid;Nalitucsan;Nalix;Nalurin;Naxuril;NegGram;Negram;Nevigramon;Nogram;Sicmylon;Unaserus;Urisal;Uronidix;Wintomylon;Wintron;
同义名
基本介绍

A synthetic 1,8-naphthyridine antimicrobial agent with a limited bacteriocidal spectrum. It is an inhibitor of the A subunit of bacterial DNA gyrase. [PubChem]

生产厂家
  • Mutual pharmaceutical co inc
  • Sanofi aventis us llc
  • Watson laboratories inc
封装厂家
参考
Synthesis Reference Not Available
General Reference Not Available
剂型
规格
化合物类型
Type small molecule
Classes
  • Fluoroquinolones and Quinolones
Substructures
  • Hydroxy Compounds
  • Acetates
  • Fluoroquinolones and Quinolones
  • Pyridines and Derivatives
  • Carboxylic Acids and Derivatives
  • Heterocyclic compounds
  • Aromatic compounds
  • Imines
  • Cyanamides
适应症
antibacterials 抗细菌;
药理
Indication For the treatment of urinary tract infections caused by susceptible gram-negative microorganisms, including the majority of E. Coli, Enterobacter species, Klebsiella species, and Proteus species.
Pharmacodynamics Nalidixic acid is a quinolone antibacterial agent for oral administration. Nalidixic acid has marked antibacterial activity against gram-negative bacteria including Enterobacter species, Escherichia coli, Morganella Morganii; Proteus Mirabilis, Proteus vulgaris, and Providencia rettgeri. Pseudomonas species are generally resistant to the drug. Nalidixic acid is bactericidal and is effective over the entire urinary pH range. Conventional chromosomal resistance to nalidixic acid taken in full dosage has been reported to emerge in approximately 2 to 14 percent of patients during treatment; however, bacterial resistance to nalidixic acid has not been shown to be transferable via R factor.
Mechanism of action Evidence exists for Nalidixic acid that its active metabolite, hydroxynalidixic acid, binds strongly, but reversibly, to DNA, interfering with synthesis of RNA and, consequently, with protein synthesis.
Absorption Following oral administration, nalidixic acid is rapidly absorbed from the gastrointestinal tract. Bioavailability is approximately 96%. Absorption may be delayed if taken with antacids.
Volume of distribution Not Available
Protein binding Nalidixic acid is 93% bound to protein in the blood, and the active metabolite, hydroxynalidixic acid is 63% bound.
Metabolism
Hepatic. 30% of administered dose is metabolized to the active metabolite, hydroxynalidixic acid. Rapid conjugation of parent drug and active metabolite to inactive metabolites. Metabolism may vary widely among individuals. In the urine, hydroxynalidixic acid represents 80 to 85% of the antibacterial activity.

Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us.

Substrate Enzymes Product
Nalidixic Acid
    		Hydroxynalidixic acid Details
    Route of elimination Following oral administration, NegGram is rapidly absorbed from the gastrointestinal tract, partially metabolized in the liver, and rapidly excreted through the kidneys. Approximately four percent of NegGram is excreted in the feces.
    Half life 1.1 to 2.5 hours in healthy adult patients, and up to 21 hours in patients with impaired renal function.
    Clearance Not Available
    Toxicity ORAL (LD50): Acute: 1160 mg/kg [Rat]. 572 mg/kg [Mouse]. Toxic psychosis, convulsions, increased intracranial pressure, or metabolic acidosis may occur in patients taking more than the recommended dosage. Vomiting, nausea, and lethargy may also occur following overdosage.
    Affected organisms
    • Enteric bacteria and other eubacteria
    Pathways Not Available
    理化性质
    Properties
    State solid
    Experimental Properties
    Property Value Source
    melting point 229.5 °C PhysProp
    water solubility 100 mg/L (at 23 °C) MERCK INDEX (1996)
    logP 1.59 BIOBYTE (1995)
    logS -3.37 ADME Research, USCD
    pKa 8.6 OSOL,A & HOOVER,JE (1975)
    Predicted Properties
    Property Value Source
    water solubility 2.30e+00 g/l ALOGPS
    logP 0.95 ALOGPS
    logP 1.01 ChemAxon
    logS -2 ALOGPS
    pKa (strongest acidic) 5.95 ChemAxon
    pKa (strongest basic) 4.68 ChemAxon
    physiological charge -1 ChemAxon
    hydrogen acceptor count 5 ChemAxon
    hydrogen donor count 1 ChemAxon
    polar surface area 70.5 ChemAxon
    rotatable bond count 2 ChemAxon
    refractivity 62.82 ChemAxon
    polarizability 23.65 ChemAxon
    药物相互作用
    Drug Interaction
    Acenocoumarol The quinolone antibiotic, nalidixic acid, may increase the anticoagulant effect of acenocoumarol.
    Anisindione The quinolone antibiotic, nalidixic acid, may increase the anticoagulant effect of anisindione.
    Calcium Acetate Calcium salts such as calcium acetate may decrease the absorption of quinolone antibiotics such as nalidixic acid. Of concern only with oral administration of both agents. Interactions can be minimized by administering oral quinolone at least 2 hours before, or 6 hours after, the dose of an oral calcium supplement. Monitor for decreased therapeutic effects of oral quinolones if administered with oral calcium supplements.
    Dicumarol The quinolone antibiotic, nalidixic acid, may increase the anticoagulant effect of dicumarol.
    Warfarin The quinolone antibiotic, nalidixic acid, may increase the anticoagulant effect of warfarin.
    食物相互作用
    • Take with food to reduce irritation. Drink liberally.

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