An update on derivatisation and repurposing of clinical nitrofuran drugs

Zuma, Nonkululeko H.; Aucamp, J.L.; N’Da, David D.

doi:10.1016/j.ejps.2019.105092

Cited by 63 publications

(50 citation statements)

References 109 publications

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“…Hence, the development of NF-related compounds with low toxicity, and more cost-effective than NF, are required for anti-AAT treatment in domestic animals [ 1 ]. It is noteworthy to indicate that the collective ban of nitrofuran antibiotics is not due to the toxicity induced by the 5-nitrofuran moiety but rather the hydrazone metabolite [ 43 ]. Indeed, the chemotherapeutic effects of these drugs are linked to the 5-nitrofuran moiety present in their structures.…”

Section: Discussionmentioning

confidence: 99%

Therapeutic Efficacy of Orally Administered Nitrofurantoin against Animal African Trypanosomosis Caused by Trypanosoma congolense Infection

et al. 2022

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Animal African trypanosomosis (AAT) leads to emaciation and low productivity in infected animals. Only six drugs are commercially available against AAT; they have severe side effects and face parasite resistance. Thus, the development of novel trypanocidal drugs is urgently needed. Nitrofurantoin, an antimicrobial, is used for treating bacterial urinary tract infections. Recently, we reported the trypanocidal effects of nitrofurantoin and its analogs in vitro. Furthermore, a nitrofurantoin analog, nifurtimox, is currently used to treat Chagas disease and chronic human African trypanosomiasis. Thus, this study was aimed at evaluating the in vivo efficacy of nitrofurantoin in treating AAT caused by Trypanosoma congolense. Nitrofurantoin was orally administered for 7 consecutive days from 4 days post-infection in T. congolense-infected mice, and the animals were observed for 28 days. Compared to the control group, the treatment group showed significantly suppressed parasitemia at 6 days post-infection. Furthermore, survival was significantly prolonged in the group treated with at least 10 mg/kg nitrofurantoin. Moreover, 100% survival and cure was achieved with a dose of nitrofurantoin higher than 30 mg/kg. Thus, oral nitrofurantoin administration has potential trypanocidal efficacy against T. congolense-induced AAT. This preliminary data will serve as a benchmark when comparing future nitrofurantoin-related compounds, which can overcome the significant shortcomings of nitrofurantoin that preclude its viable use in livestock.

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Section: Discussionmentioning

confidence: 99%

Therapeutic Efficacy of Orally Administered Nitrofurantoin against Animal African Trypanosomosis Caused by Trypanosoma congolense Infection

et al. 2022

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“…[10][11][12] Nevertheless, NFX, which was frequently used for treatment of colitis and diarrhoea, showed low effect against those diseases due to poor absorption from the digestive tract (low burst effect) that resulted in fast removal from the body without being metabolized. 13 Some studies showed that improvement of the efficiency (faster dissolution rate and higher solubility) of low soluble drugs such as carvedilol, ibuprofen and silybin, can be achieved by integration with HAp. 5,6,14 It is assumed that the connection between HAp and drugs occurred mainly through establishment of hydrogen bonds between OH groups at HAp surface and some of the functional groups of the drug.…”

Section: Introductionmentioning

confidence: 99%

Hydroxyapatite/nifuroxazide conjugate: Characterization, drug release and antimicrobial activity

et al. 2021

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Synthetic hydroxyapatite (Ca10(PO4)6(OH)2, HAp) is very similar to the inorganic part of the bones and teeth of mammals. It is a well-known biomaterial with good biocompatibility, osteoconductivity and bioactivity. Nifuroxazide (C12H9N3O5, NFX) is a broad-spectrum antibacterial drug and poorly soluble in water. In order to increase the solubility of NFX, nanosized HAp powder and raw NFX drug were mixed giving, as a result, HAp/NFX conjugate. Characterization of the raw materials and the obtained conjugate confirmed the integration of NFX on the HAp surface. The in vitro study of drug release in simulated stomach acid and intestinal fluid showed a much faster release of NFX from HAp surface than those of raw drug. HAp/NFX conjugate showed an excellent inhibitory effect against Gram-positive bacterium Staphylococcus aureus, Gram-negative bacterium Escherichia coli and yeast Candida albicans, proving the nanosized HAp powder as a promising drug carrier.

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“… 4 − 6 These NF metabolite compounds have been proven to pose potential risk to human health because of their carcinogenic, teratogenic, and mutagenic potency. 5 , 7 Based on food safety needs, the use of NF drugs was banned by the European Union during the cultivation of animal products. 8 , 9 Since then, many countries have followed the suit, such as the United States, China, and Japan.…”

Section: Introductionmentioning

confidence: 99%

Determination of Nitrofuran Metabolites in Fish by Ultraperformance Liquid Chromatography-Photodiode Array Detection with Thermostatic Ultrasound-Assisted Derivatization

et al. 2020

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Nitrofuran (NF) is a class of broad-spectrum antibiotics that are used illegally in animal feeding. NF and its metabolites have proven to pose potential risk to human health. To address the current analytical needs to quantify low levels of NF metabolites in animal foods, a sensitive method was developed for simultaneous detection of four NF metabolites in fish products by an ultraperformance liquid chromatography-diode array detector (UPLC-DAD). With 2-nitrobenzaldehyde (2-NBA) as the derivatizing reagent, the metabolites were hydrolyzed and derivatized under the assistance of thermostatic ultrasound. Compared with the current detection methods, the time of the derivatization reaction has been shortened from 16 to 2 h. The relative coefficient of four NF metabolite derivatives reached more than 0.998, with excellent linear relationship. The limits of detection (LODs) and limits of quantification (LOQs) of six repeated determinations reached 0.25–0.33 and 0.80–1.10 μg/kg, respectively. For all four NF metabolites, the limit of detection of the method was below the minimum required performance limit (MRPL) of 1.0 μg/kg, which makes it compatible with the EU requirements. The recoveries ranging from 89.8 to 101.9% with relative standard deviation below 6.5% were obtained for all of the NF metabolites. What’s more, this method was successfully applied for the determination of four NF metabolites in the fish products. As a promising approach, this method could also be extended for the quantitation of NF metabolites in aquaculture and poultry products.

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An update on derivatisation and repurposing of clinical nitrofuran drugs

Cited by 63 publications

References 109 publications

Therapeutic Efficacy of Orally Administered Nitrofurantoin against Animal African Trypanosomosis Caused by Trypanosoma congolense Infection

Therapeutic Efficacy of Orally Administered Nitrofurantoin against Animal African Trypanosomosis Caused by Trypanosoma congolense Infection

Hydroxyapatite/nifuroxazide conjugate: Characterization, drug release and antimicrobial activity

Determination of Nitrofuran Metabolites in Fish by Ultraperformance Liquid Chromatography-Photodiode Array Detection with Thermostatic Ultrasound-Assisted Derivatization

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