An Unusual Case of Nitrofurantoin-Associated Hepatotoxicity

Ramadas, Poornima; Krishnan, Prathik; Frechette, Vincent

doi:10.1097/mjt.0000000000000556

Cited by 5 publications

(3 citation statements)

References 4 publications

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“…The first published report of nitrofurantoin-induced liver injury was in 1961, 6 with an appreciable number of reports since then. [7][8][9][10][11][12][13][14][15] Nitrofurantoin has been shown to cause a spectrum of hepatic injury ranging from mild hepatitis to fulminant liver failure and death. 9,10 Despite this, the overall incidence of liver injury is very rare, reported at 0.0003%.…”

Section: Discussionmentioning

confidence: 99%

Nitrofurantoin-induced liver failure

Luk¹,

Edwards

Bates

et al. 2021

Can Fam Physician

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Section: Discussionmentioning

confidence: 99%

Nitrofurantoin-induced liver failure

Luk¹,

Edwards

Bates

et al. 2021

Can Fam Physician

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“…Compared with other antimicrobial drugs, there are few drug-resistant cases of NFT reported in clinic, promoting its continuous application (Guay, 2001;Araújo et al, 2011). However, the longterm use of NFT would trigger adverse drug reactions with different levels, such as diarrhea, dizziness, serious lung toxicity, neurotoxicity and hepatotoxicity (Tan et al, 2012;Stock, 2014;Ramadas et al, 2018;Batzlaff and Koroscil, 2020).…”

Section: Nitrofurantoinmentioning

confidence: 99%

Metabolic Activation and Hepatotoxicity of Furan-Containing Compounds

2022

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Furan-containing compounds are abundant in nature, of which many but not all have been found to be hepatotoxic and carcinogenic. The furan ring present in the chemical structures may be one of the domineering factors to bring about the toxic response resulting from the generation of reactive epoxide or cis-enedial intermediates which are of the potential to react with biomacromolecules. This review sets out to explore the relationship between the metabolic activation and hepatotoxicity of furan-containing compounds on the strength of scientific reports on several typical alkylated furans, synthetic pharmaceuticals and components extracted from herbal medicines. The pharmacological activities as well as concrete evidence of their liver injuries are described, and the potential toxic mechanisms were discussed partly based on our previous work. Efforts were made to understand the development of liver injury and seek solutions to prevention and interference of the adverse effects.

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“…As a 5-nitrofuran derivative, nitrofurantoin (NFT), (1-{[(5-nitro-2-furanyl)methylene]amino}-2,4-imidazolidinedione), is an antimicrobial agent and has been widely used for almost 7 decades in the first-line treatment of uncomplicated urinary tract infections (UTIs). , However, various adverse effects have been observed arising from the long-term use of NFT, including hepatotoxicity which was characterized by acute hepatitis, granulomatous reaction, cholestasis, autoimmune-mediated hepatitis, and chronic active hepatitis. , NFT-associated liver injury is also known as one of the most common causes of drug induced liver injury (DILI) . Numerous liver injury cases due to NFT use have been reported, even including a number of deaths. − Thus, clarifying the mechanisms is very urgent for assessment of its adverse effects for its safe use.…”

Section: Introductionmentioning

confidence: 99%

Electron Deficiency of Nitro Group Determines Hepatic Cytotoxicity of Nitrofurantoin

Zhang

Yang

et al. 2019

Chem. Res. Toxicol.

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Nitrofurantoin (NFT) is a widely used antimicrobial agent in the treatment of specific urinary tract infections (UTIs). Many adverse effects associated with NFT use have been reported, including hepatotoxicity. A structure−toxicity relationship study was performed to gain the insight into the mechanisms of toxic action of NFT. The toxic effects of NFT and its nine analogues or constituent moieties (1−9) designed and synthesized by structural manipulation of NFT were evaluated in rat liver microsomes and primary rat hepatocytes. A decrease in ability to deplete glutathione (GSH) was found in the following order: nitrofuran-containing compounds (NFT and 1−3) > nitrobenzene-containing compounds (4 and 5) > nitro-free compounds (6−9). A similar pattern was observed in the cytotoxicity of these compounds as that of GSH depletion. The potential for reduction (electron deficiency) of nitro groups of the nitro-containing test compounds (NFT, 1−5) decreased with the decrease in the ability to deplete GSH and the intensity of their cytotoxicity. The corresponding nitroso and hydroxylamine intermediates resulting from metabolic reduction of NFT were found to be reactive to GSH for the first time. Additionally, nitro-containing compound 4 (a model compound) was much more cytotoxic than the corresponding analine (4a). The findings allowed us not only to define the mechanism of toxic action of NFT but also to provide medicinal chemists with instructive guidance for rational design of nitro-containing pharmaceutical agents.

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An Unusual Case of Nitrofurantoin-Associated Hepatotoxicity

Cited by 5 publications

References 4 publications

Nitrofurantoin-induced liver failure

Nitrofurantoin-induced liver failure

Metabolic Activation and Hepatotoxicity of Furan-Containing Compounds

Electron Deficiency of Nitro Group Determines Hepatic Cytotoxicity of Nitrofurantoin

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