Abstract
Penicillium adametzi and seven other species convert nalidixic acid, 1,4-dihydro-1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid, to 1,4-dihydro-1-ethyl-7-hydroxymethyl-4-oxo-1,8-naphthyridine-3-carboxylic acid. Forty-seven other species from six orders of fungi seem to achieve the same conversion as judged by chromatographic and spectral evidence. Under special conditions, P. adametzi also produces a second metabolite which was identified as the corresponding 7-carboxylic acid. The metabolic attack on the ring substituent is identical with the pathway previously established with humans. No evidence was obtained for metabolic attack on the naphthyridine nucleus itself.
Full text
PDFSelected References
These references are in PubMed. This may not be the complete list of references from this article.
- Alexander M. Biodegradation: problems of molecular recalcitrance and microbial fallibility. Adv Appl Microbiol. 1965;7:35–80. doi: 10.1016/s0065-2164(08)70383-6. [DOI] [PubMed] [Google Scholar]
- DULANEY E. L., MCALEER W. J., KOSLOWSKI M., STAPLEY E. O., JAGLOM J. Hydroxylation of progesterone and 11-desoxy-17-hydroxycorticosterone by Aspergillus and Penicillium. Appl Microbiol. 1955 Nov;3(6):336–340. doi: 10.1128/am.3.6.336-340.1955. [DOI] [PMC free article] [PubMed] [Google Scholar]
- GOSS W. A., DEITZ W. H., COOK T. M. MECHANISM OF ACTION OF NALIDIXIC ACID ON ESCHERICHIA COLI.II. INHIBITION OF DEOXYRIBONUCLEIC ACID SYNTHESIS. J Bacteriol. 1965 Apr;89:1068–1074. doi: 10.1128/jb.89.4.1068-1074.1965. [DOI] [PMC free article] [PubMed] [Google Scholar]
- LESHER G. Y., FROELICH E. J., GRUETT M. D., BAILEY J. H., BRUNDAGE R. P. 1,8-NAPHTHYRIDINE DERIVATIVES. A NEW CLASS OF CHEMOTHERAPEUTIC AGENTS. J Med Pharm Chem. 1962 Sep;91:1063–1065. doi: 10.1021/jm01240a021. [DOI] [PubMed] [Google Scholar]
- MCCHESNEY E. W., FROELICH E. J., LESHER G. Y., CRAIN A. V., ROSI D. ABSORPTION, EXCRETION, AND METABOLISM OF A NEW ANTIBACTERIAL AGENT, NALIDIXIC ACID. Toxicol Appl Pharmacol. 1964 May;6:292–309. doi: 10.1016/0041-008x(64)90070-5. [DOI] [PubMed] [Google Scholar]
- Portmann G. A., McChesney E. W., Stander H., Moore W. E. Pharmacokinetic model for nalidixic acid in man. I. Kinetic pathways for hydroxynalidixic acid. J Pharm Sci. 1966 Jan;55(1):59–62. doi: 10.1002/jps.2600550113. [DOI] [PubMed] [Google Scholar]
- Rosi D., Lewis T. R., Lorenz R., Freele H., Berberian D. A., Archer S. Preparation and schistosomicidal activity of some 4-hydroxymethyl-3-chloroanilines. J Med Chem. 1967 Sep;10(5):877–880. doi: 10.1021/jm00317a026. [DOI] [PubMed] [Google Scholar]
- Rosi D., Peruzzotti G., Dennis E. W., Berberian D. A., Freele H., Tullar B. F., Archer S. Hycanthone, a new active metabolite of lucanthone. J Med Chem. 1967 Sep;10(5):867–876. doi: 10.1021/jm00317a025. [DOI] [PubMed] [Google Scholar]
- SENECA H. CURRENT THERAPY OF INFECTIONS OF THE RENAL EXCRETORY SYSTEM. J Am Geriatr Soc. 1964 Dec;12:1100–1127. doi: 10.1111/j.1532-5415.1964.tb00670.x. [DOI] [PubMed] [Google Scholar]
- ZAFFARONI A., BURTON R. B., KEUTMANN E. H. Adrenal cortical hormones; analysis by paper partition chromatography and occurrence in the urine of normal persons. Science. 1950 Jan 6;111(2871):6–8. doi: 10.1126/science.111.2871.6. [DOI] [PubMed] [Google Scholar]