Nalidixic Acid
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MedKoo CAT#: 318300

CAS#: 389-08-2

Description: Nalidixic Acid is the first of the synthetic quinolone antibiotics. Nalidixic 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.

Chemical Structure

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Nalidixic Acid
CAS# 389-08-2
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318300
Name: Nalidixic Acid
CAS#: 389-08-2
Chemical Formula: C12H12N2O3
Exact Mass: 232.08
Molecular Weight: 232.235
Elemental Analysis: C, 62.06; H, 5.21; N, 12.06; O, 20.67

Price and Availability

Size Price Availability Quantity
10g USD 150
100g USD 450
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Synonym: Nalidixic Acid, Nevigramon, Neggram, Wintomylon, WIN 18,320

IUPAC/Chemical Name: 1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid

InChi Key: MHWLWQUZZRMNGJ-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: O=C(C1=CN(CC)C2=C(C=CC(C)=N2)C1=O)O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
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Biological target: Nalidixic acid, a quinolone antibiotic, is effective against both gram-positive and gram-negative bacteria.
In vitro activity: Sodium nalidixate inhibited the cell growth and division of several respiratory competent strains of Saccharomyces cerevisiae. Reference: Mol Gen Genet. 1976 Jul 5;146(1):95-100. https://pubmed.ncbi.nlm.nih.gov/785214/
In vivo activity: Nalidixic acid preferentially suppressed growth in soft agar of transformed Balb/3T3 mouse cells induced by methylcholanthrene. Nalidixic acid suppressed growth in soft agar of NIH/3T3 mouse cells transformed by an activated c-Ha-ras, without affecting the amount of ras p21 proteins as detected by an immunoblotting analysis using a monoclonal antibody. Reference: Br J Cancer. 1989 Dec;60(6):880-6. https://pubmed.ncbi.nlm.nih.gov/2690912/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 6.0 25.84
Water 5.0 21.53

Preparing Stock Solutions

The following data is based on the product molecular weight 232.24 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Chadha J, Khullar L. Subinhibitory concentrations of nalidixic acid alter bacterial physiology and induce anthropogenic resistance in a commensal strain of Escherichia coli in vitro. Lett Appl Microbiol. 2021 Nov;73(5):623-633. doi: 10.1111/lam.13550. Epub 2021 Aug 24. PMID: 34376018. 2. Carnevali F, Sarcoe LE, Whittaker PA. Differential effects of nalidixate on the cell growth of respiratory competent strains and cytoplasmic petite mutants of Saccharomyces cerevisiae. Mol Gen Genet. 1976 Jul 5;146(1):95-100. doi: 10.1007/BF00267988. PMID: 785214. 3. Kaneko M, Horikoshi J. Reversible suppression by nalidixic acid of anchorage-independent growth of mouse cells transformed by 3-methylcholanthrene or an activated c-Ha-ras gene. Br J Cancer. 1989 Dec;60(6):880-6. doi: 10.1038/bjc.1989.384. PMID: 2690912; PMCID: PMC2247252. 4. McQueen CA, Rosado RR, Williams GM. Effect of nalidixic acid on DNA repair in rat hepatocytes. Cell Biol Toxicol. 1989 Jun;5(2):201-6. doi: 10.1007/BF00122653. PMID: 2504447.
In vitro protocol: 1. Chadha J, Khullar L. Subinhibitory concentrations of nalidixic acid alter bacterial physiology and induce anthropogenic resistance in a commensal strain of Escherichia coli in vitro. Lett Appl Microbiol. 2021 Nov;73(5):623-633. doi: 10.1111/lam.13550. Epub 2021 Aug 24. PMID: 34376018. 2. Carnevali F, Sarcoe LE, Whittaker PA. Differential effects of nalidixate on the cell growth of respiratory competent strains and cytoplasmic petite mutants of Saccharomyces cerevisiae. Mol Gen Genet. 1976 Jul 5;146(1):95-100. doi: 10.1007/BF00267988. PMID: 785214.
In vivo protocol: 1. Kaneko M, Horikoshi J. Reversible suppression by nalidixic acid of anchorage-independent growth of mouse cells transformed by 3-methylcholanthrene or an activated c-Ha-ras gene. Br J Cancer. 1989 Dec;60(6):880-6. doi: 10.1038/bjc.1989.384. PMID: 2690912; PMCID: PMC2247252. 2. McQueen CA, Rosado RR, Williams GM. Effect of nalidixic acid on DNA repair in rat hepatocytes. Cell Biol Toxicol. 1989 Jun;5(2):201-6. doi: 10.1007/BF00122653. PMID: 2504447.

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1: Gu B, Cao Y, Pan S, Zhuang L, Yu R, Peng Z, Qian H, Wei Y, Zhao L, Liu G, Tong M. Comparison of the prevalence and changing resistance to nalidixic acid and ciprofloxacin of Shigella between Europe-America and Asia-Africa from 1998 to 2009. Int J Antimicrob Agents. 2012 Jul;40(1):9-17. doi: 10.1016/j.ijantimicag.2012.02.005. Epub 2012 Apr 5. Review. PubMed PMID: 22483324.

2: Shakespeare WA, Davie D, Tonnerre C, Rubin MA, Strong M, Petti CA. Nalidixic acid-resistant Salmonella enterica serotype Typhi presenting as a primary psoas abscess: case report and review of the literature. J Clin Microbiol. 2005 Feb;43(2):996-8. Review. PubMed PMID: 15695728; PubMed Central PMCID: PMC548044.

3: Singh H, Sachdev HP. Nalidixic acid. Indian Pediatr. 1988 Mar;25(3):279-81. Review. PubMed PMID: 3069738.

4: Albrecht R. Development of antibacterial agents of the nalidixic acid type. Prog Drug Res. 1977;21:9-104. Review. PubMed PMID: 339272.

5: Zinsser HH. Nalidixic acid in acute and chronic urinary tract infections. Med Clin North Am. 1970 Sep;54(5):1347-50. Review. PubMed PMID: 4248514.

6: Pagnini G. [Nalidixic acid]. Antibiotica. 1967 Jun;5(2):134-59. Review. Multiple languages. PubMed PMID: 4389549.

7: Parry CM. The treatment of multidrug-resistant and nalidixic acid-resistant typhoid fever in Viet Nam. Trans R Soc Trop Med Hyg. 2004 Jul;98(7):413-22. Review. PubMed PMID: 15138078.

8: Petersen U. [The evolution of quinolone: from nalidixic acid to the quinolones of the third generation]. Pharm Unserer Zeit. 2001;30(5):376-81. Review. German. PubMed PMID: 11575173.

9: Gleckman R, Alvarez S, Joubert DW, Matthews SJ. Drug therapy reviews: nalidixic acid. Am J Hosp Pharm. 1979 Aug;36(8):1071-6. Review. PubMed PMID: 384787.

10: Bauernfeind A. Mode of action of nalidixic acid. Antibiot Chemother (1971). 1971;17:122-36. Review. PubMed PMID: 4950999.

11: Finegold SM, Ziment I. Sulfonamides, nitrofurans and nalidixic acid. Pediatr Clin North Am. 1968 Feb;15(1):95-105. Review. PubMed PMID: 4866909.