Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Nitrofurazone: Difference between pages

{{short description|Chemical compound}}

| Watchedfields = changed

| verifiedrevid = 462261893

| IUPAC_name = (2''E'')-2-[(5-Nitro-2-furyl)methylene]hydrazine<br />carboxamide

| image = Nitrofural.svg

| alt = Skeletal formula of nitrofural

| width = 250

| image2 = Nitrofural 3D spacefill.png

| alt2 = Space-filling model of the nitrofural molecule

| width2 = 215

| tradename =Aldomycin, Amifur, Chemfuran, Coxistat, Furacin, Furan-2, Furacinetten, Furaplast, Furazol W, Furesol Furracoccid, Mammex, Nefco, Nifuzon, Nitrofural, Vabrocid

| pregnancy_US = C

| pregnancy_category =

| legal_status =US: Discontinued

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =5 hours

| excretion =

| CAS_supplemental =

| ATC_supplemental = {{ATC|D08|AF01}} {{ATC|D09|AA03}} (dressing) {{ATC|P01|CC02}} {{ATC|S01|AX04}} {{ATC|S02|AA02}} {{ATCvet|G01|AX90}} {{ATCvet|P51|AC02}}

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| UNII_Ref = {{fdacite|correct|FDA}}

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = C08042

| ChEBI = 44368

| chemical_formula =

| C=6 | H=6 | N=4 | O=4

|drug_name=|caption=|type=|MedlinePlus=|licence_EU=|licence_US=}}

'''Nitrofurazone''' ([[International Nonproprietary Name|INN]], trade name '''Furacin''') is an [[antimicrobial]] organic compound belonging to the [[nitrofuran]] class.<ref name=":0">{{Cite web|url=https://www.drugbank.ca/drugs/DB00336|title=Nitrofural|website=www.drugbank.ca|access-date=2018-03-14}}</ref> It is most commonly used as a topical [[antibiotic]] ointment.<ref name=":1" /> It is effective against [[gram-positive bacteria]], [[gram-negative bacteria]], and can be used in the treatment of [[trypanosomiasis]].<ref name=":0" /><ref>{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/nitrofurazone#section=Top|title=Nitrofurazone| work = Pubchem | publisher = U.S. National Library of Medicine |access-date=2018-03-14}}</ref><ref>{{Cite web |url= https://www.glowm.com/resources/glowm/cd/pages/drugs/n026.html |title=nitrofurazone|website=www.glowm.com|access-date=2018-03-14}}</ref> Its use in medicine has become less frequent, as safer and more effective products have become available.<ref name=":2">{{Cite web |url=http://adpen.com/2010/05/nitrofurans/ |title= Nitrofuran Analyses |last=Perez |first=Steven | name-list-style = vanc |date=26 May 2010|website=Adpen Laboratories|access-date=14 March 2018}}</ref> Nitrofurazone is listed under [[California Proposition 65 (1986)|California Prop 65]], and has demonstrated clear evidence to be [[mutagen]]ic and [[carcinogen]]ic during animal studies, and has been discontinued for human use in the USA.<ref name=":1">{{cite web | work = Drugs.com | url = https://www.drugs.com/cons/nitrofurazone-topical.html | title = Nitrofurazone (Topical route) }}</ref><ref name=":2" /><ref name=":3">{{Cite news | url= https://oehha.ca.gov/chemicals/nitrofurazone |title=Nitrofurazone |date=2015-03-22|work=Office of Environmental Health Hazard Assessment |access-date=2018-03-14}}</ref><ref name=":4">{{Cite journal|last=National Toxicology Program|date=June 1988|others=NIH Publication No. 88-2593|title=NTP Toxicology and Carcinogenesis Studies of Nitrofurazone in F344/N Rats and B6C3F1 Mice (Feed Studies)|url=https://ntp.niehs.nih.gov/ntp/htdocs/lt_rpts/tr337.pdf|journal=National Toxicology Program Technical Report Series|series=337|publisher=National Institute of Health|pages=1–186 }}</ref> The substance is pale yellow and crystalline. It was once widely used as an antibiotic for livestock.<ref>{{cite journal|title=Nitrofuran antibiotics: a review on the application, prohibition and residual analysis| vauthors = Vass M, Hruska K, Franek M |journal=Veterinarni Medicina|year=2008|volume=53| issue = 9 |pages=469–500|doi=10.17221/1979-VETMED|doi-access=free}}</ref><ref name=":5">{{Cite news |url= https://www.drugs.com/vet/nitrofurazone-ointment.html |title= Nitrofurazone Ointment for Animal Use - Drugs.com|work=Drugs.com|access-date=2018-03-14|language=en-US}}</ref>

== Medical uses ==

[[File:Раствор Фурацилина.JPG|thumb|left|Drugstore-made ~400 mL aqueous solution of Furacilin ({{Lang-ru|Фурацилин}}, nitrofural), 1 : 5000 (0.2 mg/mL or 0.02%), ready for topical use.]]

=== Human use ===

Nitrofurazone was previously available as a prescription in the U.S., and was indicated as a topical solution, topical cream, or topical ointment for the treatment of bacterial skin infections, wounds, burns, and ulcers.<ref name=":1" /> It was also used as a prophylactic measure to prevent infection that could potentially result in [[Skin grafting|skin graft]] rejection.<ref name=":0" /><ref>{{Cite web |url= http://www.minclinic.ru/drugs/drugs_eng/A/Aldomycin.html |title=Aldomycin | work = Minimally Invasive Neurosurgery Clinic |access-date=2018-03-14}}</ref> Nitrofurazone is still very popular as a topical solution for the treatment of tonsillitis in Russia.{{cn|date=December 2022}}

=== Animal use ===

Nitrofurazone is indicated for topical use in dogs, cats, and horses, for the treatment or [[Prophylactic|prophylactic treatment]] of superficial bacterial infections, burns, and cutaneous ulcers.<ref name=":5" /> Preparations for treating infections, such as [[fin rot]], in [[ornamental fish]] are also still commercially available.<ref name=":6">{{cite web |url= http://edis.ifas.ufl.edu/fa084|title=Use of Antibiotics in Ornamental Fish Aquaculture|last=Yanong|first=Roy P. E. | name-list-style = vanc |date=2017-01-05|website=edis.ifas.ufl.edu |access-date=2018-03-14}}</ref><ref>{{Cite book |url=https://books.google.com/books?id=GykB84HU6LoC&pg=PA71|title=Discus Fish |last=Giovanetti |first=Thomas A. | name-list-style = vanc |date=1991|publisher=Barron's Educational Series |isbn=9780812046694 }}</ref> The use of nitrofurazone, or related compounds, in animals raised for human consumption has been strictly banned.<ref name=":6" /><ref>{{Cite web|url=https://www.fda.gov/downloads/Food/GuidanceRegulation/UCM251970.pdf|title=Fish and Fishery Products Hazards and Controls Guidance|last=Center for Food Safety and Applied Nutrition|first=U.S. Department of Health and Human Services|date=April 2011|website=www.fda.gov|publisher=Food and Drug Administration|pages=183–208|language=en|access-date=2018-03-14|edition=Fourth}}</ref>

== Pharmacokinetics ==

The mechanism of action is not fully understood, but nitrofurazone's antimicrobial properties are suspected to be due to the interference of [[DNA synthesis]] in the microorganism by inhibiting certain enzymes that are involved with [[glycolysis]].<ref name=":0" /><ref name=":2" /> Other enzymes this may affect include, [[pyruvate dehydrogenase]], citrate synthetase, [[malate dehydrogenase]], [[glutathione reductase]], and [[pyruvate decarboxylase]].<ref name=":0" />

The metabolism of topically applied nitrofurazone is thought to be by 5-nitro reduction and cleavage of the -CH=N- linkage to generate a reactive species which can [[Covalent bond|covalently bond]] to cellular macromolecules, none of the end products are thought to be antimicrobial.<ref name=":0" /><ref>{{cite book |url= https://books.google.com/books?id=2IepBlgVqZcC&pg=PA107 |title=Residues of Some Veterinary Drugs in Animals and Foods: Monographs Prepared by the Fortieth Meeting of the Joint FAO/WHO Expert Committee on Food Additives, Geneva, 9-18 June 1992| work = Joint FAO/WHO Expert Committee on Food Additives Meeting |date=1993 |publisher= Food and Agriculture Organization of the United Nations |isbn=9789251032886 }}</ref>

== Adverse effects ==

Adverse effects for topical use are generally mild and include, [[erythema]], [[pruritus]], [[dermatitis]], rash, [[edema]] or [[inflammation]].<ref name=":0" /><ref name=":1" />

== Contraindications ==

People with [[chronic kidney disease]] and large [[Total body surface area|total body surface area (TBSA)]] [[burn]]s should not use nitrofurazone, as topical preparations commonly contain [[polyethylene glycol]], which is readily absorbed through the skin. Rapid absorption of the medication induces increased serum [[Osmolality|osmolalities]] and [[anion gap]], leading to death.<ref name=":7">{{Cite journal|date=2017-12-29|title=Thermal Burns: Overview, Pathophysiology, Quantifying Burn Severity|url=https://emedicine.medscape.com/article/1278244-overview#a7}}</ref> Symptoms are similar to [[ethylene glycol poisoning]], in that increased serum calcium levels occur concurrently with decreased ionized calcium.<ref name=":7" />

Nitrofurans have been found in honey, meat and seafood. In people who have [[glucose-6-phosphate dehydrogenase deficiency]] (G-6-PD deficiency), ingestion of fish, poultry, or other foodstuff that has been treated with nitrofurans, will likely suffer from [[hemolysis]] of [[red blood cell]]s as a result of eating the contaminated food.<ref name=":2" />

== Toxicities ==

Nitrofurazone is suspected to be a human carcinogen and is included in California's list of toxic chemicals as defined by [[1986 California Proposition 65|Proposition 65]].<ref name=":3" /><ref name=":4" /><ref>{{cite journal | vauthors = Ryan A, Kaplan E, Laurieri N, Lowe E, Sim E | title = Activation of nitrofurazone by azoreductases: multiple activities in one enzyme | language = En | journal = Scientific Reports | volume = 1 | issue = 1 | pages = 63 | date = 2011-08-12 | pmid = 22355582 | pmc = 3216550 | doi = 10.1038/srep00063 | bibcode = 2011NatSR...1E..63R }}</ref> Studies demonstrate that nitrofurazone induces mammary tumors ([[fibroadenoma]] and [[adenocarcinoma]]) in rats and ovarian tumors in mice.<ref name=":4" /> In addition, animal studies demonstrated an increased incidence in convulsive seizures, ovarian atrophy, testicular degeneration, and degeneration of articular cartilage.<ref name=":4" /><ref>{{Cite web|url=https://ntp.niehs.nih.gov/results/pubs/longterm/reports/longterm/tr300399/abstracts/tr337/index.html|title=Abstract for TR-337|website=ntp.niehs.nih.gov|language=en|access-date=2018-03-14}}</ref> Proper personal protective equipment should be utilized when handling nitrofurazone.<ref name=":5" />

== References ==

{{reflist}}

{{Agents against leishmaniasis and trypanosomiasis}}

{{Otologicals}}

[[Category:Antibiotics]]

[[Category:Nitrofurans]]

[[Category:Antiprotozoal agents]]

[[Category:Otologicals]]

[[Category:Semicarbazones]]