Nitroxoline
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| Non-proprietary name | Nitroxoline | ||||||||||||||||||
| other names |
5-nitroquinolin-8-ol ( IUPAC ) |
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| Molecular formula | C 9 H 6 N 2 O 3 | ||||||||||||||||||
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| Molar mass | 190.16 g · mol -1 | ||||||||||||||||||
| Physical state |
firmly |
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| Melting point |
179.5-181.5 ° C |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | |||||||||||||||||||
Nitroxoline is a 1967 introduced into the market antibiotic and antimycotic from the group of 8-hydroxyquinoline - derivatives intended for the treatment of acute and chronic infectious diseases of the efferent urinary tract , which by nitroxoline-sensitive bacteria and yeasts , is used are caused. These urinary tract infections include cystitis (inflammation of the bladder) and urethritis (inflammation of the urethra). The drug is also to relapse - prevention applied. Nitroxoline is in Germany under the trade name Cysto-saar ® MIP Pharma GmbH and Generic nitroxoline midi / -Forte Rosen Pharma GmbH commercially. In the current S3 guideline for the treatment of uncomplicated urinary tract infections, nitroxoline is recommended as the first choice for the treatment of uncomplicated cystitis due to its excellent resistance, the high eradication rate and the favorable side effect profile.
Stomach discomfort, nausea and vomiting are relatively common undesirable side effects. The usual intake time is between seven and ten days. In contrast to other antibiotics, the data on efficacy and tolerability are comparatively low, also because their use is essentially limited to Germany and the drug is rarely used internationally. Randomized studies comparing it with other antibiotics have not yet been published. Nitroxoline is more expensive than the control antibiotics and has slightly more common undesirable side effects.
synthesis
For the synthesis of nitroxoline, 8-hydroxyquinoline can be reacted with sodium nitrite and hydrochloric acid to form 8-hydroxy-5-nitrosoquinoline . This in turn can be oxidized to nitroxoline with nitric acid .
Individual evidence
- ↑ Entry on nitroxoline. In: Römpp Online . Georg Thieme Verlag, accessed on May 30, 2014.
- ↑ a b Data sheet 8-Hydroxy-5-nitroquinoline from Sigma-Aldrich , accessed on April 16, 2011 ( PDF ).
- ^ Entry on nitroxoline in the ChemIDplus database of the United States National Library of Medicine (NLM) .
- ↑ C. Pelletier et al: Roles of divalent cations and pH in mechanism of action of nitroxoline against Escherichia coli strains. In: Antimicrob Agents Chemother 39, 1995, pp. 707-713; PMID 7793877 ; PMC 162609 (free full text, PDF).
- ↑ DGU guideline program: interdisciplinary S3 guideline: epidemiology, diagnosis, therapy, prevention and management of uncomplicated, bacterial, community-acquired urinary tract infections in adult patients. Long version 1.1-2. German Society for Urology, 2017, pp. 78, 88, 99, 105 , accessed on November 23, 2017 .
- ↑ a b (Without author) Therapy review: Nitroxolin (Nitroxolin forte) against uncomplicated cystitis in women? Medicinal Telegram 2018; 49:36 (April 13, 2018)
- ↑ Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dietmar Reichert: Pharmaceutical Substances, 4th edition (2000), 2 volumes published by Thieme-Verlag Stuttgart, ISBN 978-1-58890-031-9 .
further reading
- A. Amgar et al .: Activity in vitro of urine samples from patients treated by nitroxoline against mycoplasmas. In: J Chemother 4, 1989, pp. 226-228, PMID 16312380 .
