1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

• ChemBase编号: 659
• 分子式: C12H12N2O3
• 平均质量: 232.23528
• 单一同位素质量: 232.08479225
• SMILES: O=c1c2c(n(CC)cc1C(=O)O)nc(cc2)C
• Canonical SMILES: CCn1cc(C(=O)O)c(=O)c2c1nc(C)cc2
• 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

名称和登记号

名称

• IUPAC标准名: 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
• IUPAC传统名: nalidixic acid; 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
• 商标名: Cybis; Dixiben; Dixinal; Eucistin; Innoxalon; Jicsron; Nalidic acid; Nalidixan; Nalidixate; Nalidixic acid USP27; Nalidixin; Nalidixinic acid; Nalitucsan; Nalix; Nalurin; Naxuril; NegGram; Negram; Nevigramon; Nogram; Sicmylon; Unaserus; Urisal; Uronidix; Wintomylon; Wintron; naladixic acid
• 别名: 萘啶酮酸; 1,4-二氢-1-乙基-7-甲基-1,8-萘啶-4-酮-3-羧酸; 1-乙基-1,4-二氢-7-甲基-4-氧代-1,8-萘啶-3-羧酸; 萘啶酸; 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid; NALDIXIC ACID; Nalidixic Acid; NegGram; Nevigramon; Nalidixin; Uronidix; 1,4-Dihydro-1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic Acid; Betaxina; Cybis; Dixiben; Eucistin; Nelidix; Win 18320; Wintomylon; 1,4-Dihydro-1-ethyl-7-methyl-1,8-naphthyridin-4-one-3-carboxylic acid; 1-Ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid; Negram; Nalidixanum; Nalidixic acid; Nalidixic acid; 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

登记号

• CAS号: 389-08-2
• EC号: 206-864-7
• MDL号: MFCD00006884
• Beilstein号: 750515
• 默克索引号: 146359
• PubChem SID: 46507401; 24897719; 24897864; 160964122
• PubChem CID: 4421

理论计算性质

JChem

• Acid pKa: 5.950253
• 质子受体: 5
• 质子供体: 1
• LogD (pH = 5.5): 1.0300463
• LogD (pH = 7.4): -0.25419375
• Log P: 1.0082526
• 摩尔折射率: 62.8245 cm^3
• 极化性: 23.020437 Å^3
• 极化表面积: 70.5 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.95
• LOG S: -2.0
• 溶解度: 2.30e+00 g/l

分子性质

理化性质

• 溶解度: 100 mg/L; Chloroform; chloroform: soluble20 mg/mL, clear; Ethanol; Methanol; Toluene
• 外观: Pale Yellow Solid
• 熔点: 227-229 °C(lit.); 227-229°C; 228-230 °C; 228-230°C; 229-230°C
• 疏水性(logP): 2.1

安全信息

• 保存条件: -20°C; Refrigerator
• 保存注意事项: Harmful
• RTECS编号: QN2885000
• 欧盟危险性物质标志: X; 有害性(Harmful) (Xn)
• 德国WGK号: 2
• 危险公开号: 22; 42/43
• 安全公开号: 22-36/37-45; 36
• TSCA收录: 否
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Danger
• GHS危险声明: H302; H334
• GHS警示性声明: P261-P342 + P311; P264-P270-P301+P312-P330-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves; Eyeshields, Faceshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

药理学性质

• 生物活性机理: DNA polymerase inhibitor

产品相关信息

• 纯度: ≥98%; ≥99.0% (T); 99%
• 成盐信息: Free Base
• 适用性: meets USP testing specifications
• 应用领域: Antibacterial agent; Antibiotic; Antiseptic
• Empirical Formula (Hill Notation): C12H12N2O3

详细说明

MP Biomedicals - 05224670

MP Biomedicals Rare Chemical collection

DrugBank - DB00779

• Drug Groups: approved
• Description: 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]
• 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.
• Pharmacology: 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.
• 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
• Biotransformation: 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.
• 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.
• Half Life: 1.1 to 2.5 hours in healthy adult patients, and up to 21 hours in patients with impaired renal function.
• Protein Binding: Nalidixic acid is 93% bound to protein in the blood, and the active metabolite, hydroxynalidixic acid is 63% bound.
• 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.
• External Links: RxList; Drugs.com

Selleck Chemicals - S2328

Research Area: Infection
Biological Activity:
Nalidixic acid(NegGram) is a synthetic 1,8-naphthyridine antimicrobial agent with a limited bacteriocidal spectrum. It is an inhibitor of the A subunit of bacterial DNA gyrase. Evidence exists that the active metabolite, hydroxynalidixic acid, binds strongly, but reversibly, to DNA, interfering with synthesis of RNA and, consequently, with protein synthesis. [1]

Sigma Aldrich - 70162

Other Notes
细菌 DNA 合成抑制剂1

Sigma Aldrich - N5035

Biochem/physiol Actions
Used to modulate (inhibit) bacterial DNA gyrase-dependent processes such as DNA polymerization, (ATP-dependen)t DNA supercoiling, and chromosome fragmentation.

Sigma Aldrich - N8878

Application
Used to modulate (inhibit) bacterial DNA gyrase-dependent processes such as DNA polymerization, (ATP-dependen)t DNA supercoiling, and chromosome fragmentation.
包装
5, 25, 100 g in poly bottle

Toronto Research Chemicals - N275600

Antibacterial.

参考文献

• http://www.drugbank.ca/drugs/DB00779
• Bourguignon, G.J., et al.: Antimicrob. Agents Chemother., 4, 479 (1973)
• Grubb, P.E., et al.: Anal. Profiles Drug Subs., 8, 371 (1973)
• Wright, H.T., et al.: Science, 213, 455 (1973)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, EID000
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 473B, (nmr)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 889B, (ir)
• Lesher, G.Y. et al., J. Med. Chem., 1962, 5, 1063
• Santielli, A.A. et al., J. Med. Chem., 1975, 18, 1038, (synth)
• Lesher, G.Y., Kirk-Othmer Encycl. Chem. Technol., 3rd edn., Wiley, 1978, 2, 782, (rev)
• Grubb, P.E., Anal. Profiles Drug Subst., 1979, 8, 371, (rev)
• Huber, C.P. et al., Acta Cryst. B, 1980, 36, 497, (cryst struct)
• Koch, H. et al., Pharm. Int., 1980, 1, 108, (rev, pharmacol)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 2267
• Morrissey, R.E. et al., Drug Chem. Toxicol., 1991, 14, 45, (tox)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 184