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Furazolidone
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Systematic (IUPAC) name |
3-{[(5-nitro-2-furyl)methylene]amino}-1,3-oxazolidin-2-one |
Clinical data |
AHFS/Drugs.com |
Micromedex Detailed Consumer Information |
Pregnancy cat. |
? |
Legal status |
? |
Routes |
Oral-Local |
Identifiers |
CAS number |
67-45-8 Y |
ATC code |
G01AX06 QJ01XE90 |
PubChem |
CID 3435 |
DrugBank |
DB00614 |
ChemSpider |
3317 Y |
UNII |
5J9CPU3RE0 Y |
KEGG |
C07999 N |
ChEMBL |
CHEMBL1103 N |
Chemical data |
Formula |
C8H7N3O5 |
Mol. mass |
225.16 |
SMILES
- [O-][N+](=O)c2oc(C=NN1C(=O)OCC1)cc2
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InChI
-
InChI=1S/C8H7N3O5/c12-8-10(3-4-15-8)9-5-6-1-2-7(16-6)11(13)14/h1-2,5H,3-4H2 Y
Key:PLHJDBGFXBMTGZ-UHFFFAOYSA-N Y
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N (what is this?) (verify)
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Furazolidone is a nitrofuran antibacterial. It is marketed by Roberts Laboratories under the brand name Furoxone and by GlaxoSmithKline as Dependal-M.
Contents
- 1 Uses
- 1.1 Use in humans
- 1.2 Use in animals
- 1.3 Use in laboratory
- 2 Mechanism
- 3 Side effects
- 4 References
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Uses
Furazolidone has been used in human and veterinary medicine. It has a broad spectrum of activity being active against
- Gram positive
- Clostridium perfringens
- Corynebacterium pyogenes
- Streptococci
- Staphylococci
- Gram negative
- E coli
- Salmonella dublin
- Salmonella typhimurium
- Protozoa
- Giardia lamblia
- Eimeria species
- Histomonas meleagridis
Use in humans
In humans it has used to treat diarrhoea and enteritis caused by bacteria or protozoan infections. It has been used to treat traveler's diarrhoea, cholera and bacteremic salmonellosis. Use in treating Helicobacter pylori infections has also been proposed.[1]
Furazolidone is also used for giardiasis (due to Giardia lamblia), though it is not a first line treatment.[2]
As for all medicines the most recent local recommendations for its use should be always be followed. The usual dose is:
- Adult: 100 mg 4 times daily. Usual duration: 2-5 days, up to 7 days in some patients or 10 days for giardiasis.
- Child: 1.25 mg/kg 4 times daily, usually given for 2-5 days or up to 10 days for giardiasis.
Use in animals
As a veterinary medicine, furazolidone has been used with some success to treat salmonids for Myxobolus cerebralis infections.
It has also been used in aquaculture.[3]
Use in laboratory
It is used to differentiate micrococci and staphylococci.
Mechanism
It is believed to work by crosslinking of DNA.[4]
Side effects
Furazolidone is no longer available in the US. Though an effective antibiotic when all others fail, against extremely drug resistant infections, it has many side effects, and as with other nitrofurans generally, minimum inhibitory concentrations also produce systemic toxicity (tremors, convulsions, peripheral neuritis, gastrointestinal disturbances, depression of spermatogenesis.) Nitrofurans are recognized by FDA as mutagens/carcinogens, and can no longer be used since 1991.[5]
References
- ^ Machado RS, Silva MR, Viriato A (2008). "Furazolidone, tetracycline and omeprazole: a low-cost alternative for Helicobacter pylori eradication in children". Jornal de pediatria 84 (2): 160–5. doi:10.2223/JPED.1772. PMID 18372934.
- ^ Petri WA (February 2005). "Treatment of Giardiasis" ([dead link]). Curr Treat Options Gastroenterol 8 (1): 13–17. doi:10.1007/s11938-005-0047-3. PMID 15625030. http://www.treatment-options.com/1092-8472/8/13.
- ^ Meng J, Mangat SS, Grudzinski IP, Law FC (1998). "Evidence of 14C-furazolidone metabolite binding to the hepatic DNA of trout". Drug Metabol Drug Interact 14 (4): 209–19. PMID 10694929.
- ^ "DrugBank: Showing Furazolidone (DB00614)". http://www.drugbank.ca/drugs/DB00614. Retrieved 2008-12-19.
- ^ http://caraga.da.gov.ph/services/banmed-Nitrofurans.htm
Gynecological anti-infectives and antiseptics (G01)
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Antibiotics |
- Candicidin
- Chloramphenicol
- Hachimycin
- Oxytetracycline
- Carfecillin
- Mepartricin
- Clindamycin
- Pentamycin
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Arsenic compounds |
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Quinoline derivatives |
- Diiodohydroxyquinoline
- Clioquinol
- Chlorquinaldol
- Dequalinium
- Broxyquinoline
- Oxyquinoline
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Organic acids |
- Lactic acid
- Acetic acid
- Ascorbic acid
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Sulfonamides |
|
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Antifungals |
Imidazoles
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- Metronidazole
- Clotrimazole
- Miconazole
- Econazole
- Ornidazole
- Isoconazole
- Tioconazole
- Ketoconazole
- Fenticonazole
- Azanidazole
- Propenidazole
- Butoconazole
- Omoconazole
- Oxiconazole
- Flutrimazole
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Triazoles
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Polyenes
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- Nystatin
- Natamycin
- Amphotericin B
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Other
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- Ciclopirox
- Methylrosaniline
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Other |
- Clodantoin
- Inosine
- Policresulen
- Nifuratel
- Furazolidone
- Povidone-iodine
- Protiofate
- Lactobacillus fermentum
- Copper usnate
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noco/cong/npls, sysi/epon
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proc/asst, drug (G1/G2B/G3CD)
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Antiparasitics – antiprotozoal agents – Excavata antiparasitics (P01)
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Discicristata |
Trypanosomiasis
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- African trypanosomiasis: ornithine (Eflornithine#)
- arsenical (Melarsoprol#)
- benzamidine (Pentamidine#)
- naphthalenesulfonate (Suramin#)
Chagas disease: nitroimidazole (Benznidazole#)
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Leishmaniasis
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- macrolide (Amphotericin B#)
Pentavalent antimonials (Meglumine antimoniate#, Sodium stibogluconate)
- benzamidine (Pentamidine#)
- phosphorylcholine (Miltefosine)
- neomycin (Paromomycin)
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PAM
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- macrolide (Amphotericin B)
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Trichozoa |
Giardiasis
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- nitroimidazole (Metronidazole#, Tinidazole)
- benzimidazole (Albendazole)
- thiazole (Nitazoxanide)
- nitrofuran (Furazolidone)
- aminoacridine (Quinacrine)
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Trichomoniasis
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- nitroimidazole (Carnidazole, Metronidazole#, Tinidazole)
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Dientamoebiasis
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- nitroimidazole (Metronidazole
- Secnidazole)
- oxyquinoline (Iodoquinol)
- tetracycline (Doxycycline)
- neomycin (Paromomycin)
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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Antibacterials: nucleic acid inhibitors (J01E, J01M)
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Antifolates
(inhibits
purine metabolism,
thereby inhibiting
DNA and RNA synthesis) |
DHFR inhibitor |
- 2,4-Diaminopyrimidine
- Trimethoprim#
- Brodimoprim
- Tetroxoprim
- Iclaprim†
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Sulfonamides
(DHPS inhibitor) |
Short-
acting |
- Sulfaisodimidine
- Sulfamethizole
- Sulfadimidine
- Sulfapyridine
- Sulfafurazole
- Sulfanilamide
- Sulfathiazole
- Sulfathiourea
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Intermediate-
acting |
- Sulfamethoxazole
- Sulfadiazine#
- Sulfamoxole
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Long-
acting |
- Sulfadimethoxine
- Sulfadoxine
- Sulfalene
- Sulfametomidine
- Sulfametoxydiazine
- Sulfamethoxypyridazine
- Sulfaperin
- Sulfamerazine
- Sulfaphenazole
- Sulfamazone
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Other/ungrouped |
- sulfanilamide
- Sulfacetamide
- Sulfametrole
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Combinations |
- Trimethoprim/sulfamethoxazole#
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Topoisomerase
inhibitors/
quinolones/
(inhibits
DNA replication) |
1st g. |
- Cinoxacin‡
- Flumequine
- Nalidixic acid
- Oxolinic acid
- Pipemidic acid
- Piromidic acid
- Rosoxacin
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Fluoro-
quinolones |
2nd g. |
- Ciprofloxacin#
- Enoxacin‡
- Fleroxacin‡
- Lomefloxacin
- Nadifloxacin
- Ofloxacin
- Norfloxacin
- Pefloxacin
- Rufloxacin
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3rd g. |
- Balofloxacin
- Grepafloxacin‡
- Levofloxacin
- Pazufloxacin
- Sparfloxacin‡
- Temafloxacin‡
- Tosufloxacin
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4th g. |
- Besifloxacin
- Clinafloxacin†
- Garenoxacin
- Gemifloxacin
- Moxifloxacin
- Gatifloxacin‡
- Sitafloxacin
- Trovafloxacin‡/Alatrofloxacin‡
- Prulifloxacin
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Vet. |
- Danofloxacin
- Difloxacin
- Enrofloxacin
- Ibafloxacin
- Marbofloxacin
- Orbifloxacin
- Pradofloxacin
- Sarafloxacin
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Related (DG) |
- Aminocoumarins: Novobiocin
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Anaerobic DNA
inhibitors |
Nitro- imidazole derivatives |
- Metronidazole#
- Tinidazole
- Ornidazole
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Nitrofuran derivatives |
- Nitrofurantoin#
- Furazolidone‡
- Nifurtoinol
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RNA synthesis |
Rifamycins/
RNA polymerase |
- Rifampicin#
- Rifabutin
- Rifapentine
- Rifaximin
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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gr+f/gr+a (t)/gr-p (c)/gr-o
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drug (J1p, w, n, m, vacc)
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UpToDate Contents
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English Journal
- The Problem of Helicobacter pylori Resistance to Antibiotics: A Systematic Review in Latin America.
- Camargo MC1, García A2, Riquelme A3, Otero W4, Camargo CA5, Hernandez-García T2, Candia R3, Bruce MG6, Rabkin CS1.Author information 1Division of Cancer Epidemiology and Genetics, National Cancer Institute, Rockville, Maryland, USA.2Department of Microbiology, Universidad de Concepcion, Concepcion, Chile.3Department of Gastroenterology, School of Medicine, Pontificia Universidad Católica, Santiago, Chile.41] Department of Gastroenterology, School of Medicine, Universidad Nacional, Bogota, Colombia [2] Clinica Fundadores, Bogotá, Colombia.5Secretaría de Salud, México City, México.6Division of Preparedness and Emerging Infections, Artic Investigations Program, Centers for Disease Control and Prevention, Anchorage, Alaska, USA.AbstractOBJECTIVES:Latin America has a high prevalence of Helicobacter pylori infection and associated diseases, including gastric cancer. Antibiotic therapy can eradicate the bacterial infection and decrease associated morbidity and mortality. To tailor recommendations for optimal treatments, we summarized published literature and calculated region- and country-specific prevalences of antibiotic resistance.METHODS:Searches of PubMed and regional databases for observational studies evaluating H. pylori antibiotic resistance yielded a total of 59 independent studies (56 in adults, 2 in children, and 1 in both groups) published up to October 2013 regarding H. pylori isolates collected between 1988 and 2011. Study-specific prevalences of primary resistance to commonly prescribed antibiotics were summarized using random-effects models. Between-study heterogeneity was assessed by meta-regression. As a sensitivity analysis, we extended our research to studies of patients with prior H. pylori-eradication therapy.RESULTS:Summary prevalences of antimicrobial primary resistance among adults varied by antibiotic, including 12% for clarithromycin (n=35 studies), 53% for metronidazole (n=34), 4% for amoxicillin (n=28), 6% for tetracycline (n=20), 3% for furazolidone (n=6), 15% for fluoroquinolones (n=5), and 8% for dual clarithromycin and metronidazole (n=10). Resistance prevalence varied significantly by country, but not by year of sample collection. Analyses including studies of patients with prior therapy yielded similar estimates. Pediatric reports were too few to be summarized by meta-analysis.CONCLUSIONS:Resistance to first-line anti-H. pylori antibiotics is high in Latin American populations. In some countries, the empirical use of clarithromycin without susceptibility testing may not be appropriate. These findings stress the need for appropriate surveillance programs, improved antimicrobial regulations, and increased public awareness.Am J Gastroenterol advance online publication, 4 March 2014; doi:10.1038/ajg.2014.24.
- The American journal of gastroenterology.Am J Gastroenterol.2014 Mar 4. doi: 10.1038/ajg.2014.24. [Epub ahead of print]
- OBJECTIVES:Latin America has a high prevalence of Helicobacter pylori infection and associated diseases, including gastric cancer. Antibiotic therapy can eradicate the bacterial infection and decrease associated morbidity and mortality. To tailor recommendations for optimal treatments, we summarized
- PMID 24589670
- Performance evaluation of commercial ELISA kits for screening of furazolidone and furaltadone residues in fish.
- Jester EL1, Abraham A, Wang Y, El Said KR, Plakas SM.Author information 1FDA, Division of Seafood Science and Technology, Gulf Coast Seafood Laboratory, Dauphin Island, AL 36528, United States. Electronic address: Edward.Jester@fda.hhs.gov.AbstractRegulatory monitoring for nitrofuran drug residues in aquaculture products has largely focused on LC-MS/MS. In addition, there is a need for facile and high-throughput screening methods for monitoring programs. We evaluated the performance of Ridascreen (R-Biopharm) ELISA kits for nitrofuran drug residues in fish muscle, with verification by LC-MS/MS. Kits were available for 3-amino-2-oxazolidinone (AOZ) and 3-amino-5-morpholino-methyl-2-oxazolidinone (AMOZ) side-chains of furazolidone and furaltadone, respectively. We found good repeatability in fortified and incurred muscle samples, with RSDs ranging from 1.8% to 7.6%. Recoveries of AOZ and AMOZ from muscle fortified at levels of 0.5-2 ng/g ranged from 98% to 114%. Excellent selectivity was demonstrated. The minimum detection limits (MDLs) for AOZ and AMOZ in muscle were 0.05 and 0.2 ng/g, respectively. ELISA data were highly correlated with those of LC-MS/MS. Results of this study support the use of these kits as screening assays for nitrofuran residues in fish muscle.
- Food chemistry.Food Chem.2014 Feb 15;145:593-8. doi: 10.1016/j.foodchem.2013.08.090. Epub 2013 Sep 3.
- Regulatory monitoring for nitrofuran drug residues in aquaculture products has largely focused on LC-MS/MS. In addition, there is a need for facile and high-throughput screening methods for monitoring programs. We evaluated the performance of Ridascreen (R-Biopharm) ELISA kits for nitrofuran drug re
- PMID 24128519
- Triple Therapy with High-Dose Proton-Pump Inhibitor, Amoxicillin, and Doxycycline Is Useless for Helicobacter pylori Eradication: A Proof-of-Concept Study.
- Almeida N1, Romãozinho JM, Donato MM, Luxo C, Cardoso O, Cipriano MA, Marinho C, Sofia C.Author information 1Gastroenterology Department, Coimbra University Hospital, Coimbra, Portugal.AbstractINTRODUCTION: Helicobacter pylori resistance to antibiotics is steadily increasing and multidrug-resistant strains are common and difficult to eliminate, mainly in countries where bismuth, tetracycline, furazolidone, and rifabutin are unavailable.
- Helicobacter.Helicobacter.2014 Apr;19(2):90-7. doi: 10.1111/hel.12106. Epub 2014 Feb 10.
- INTRODUCTION: Helicobacter pylori resistance to antibiotics is steadily increasing and multidrug-resistant strains are common and difficult to eliminate, mainly in countries where bismuth, tetracycline, furazolidone, and rifabutin are unavailable.AIM: To evaluate the efficacy and safety of a triple
- PMID 24506175
Japanese Journal
- Outbreak of Cholera Caused by Vibrio cholerae O1 El Tor Variant Strain in Bihar, India
- Koley Hemanta,Ray Nivedita,Chowdhury Goutam,Barman Soumik,Mitra Soma,Ramamurthy T.,Mukhopadhyay Asish K.,Sarkar B. L.,Katyal Rakesh,Das Pradeep,Panda Samiran,Ghosh Subrata
- Japanese Journal of Infectious Diseases 67(3), 221-226, 2014
- … These isolates were resistant to several drugs, including ampicillin, streptomycin, tetracycline, nalidixic acid, and furazolidone. …
- NAID 130004757086
- Repeated Treatment with Furazolidone Induces Multiple Cytochrome P450-Related Activities in Chicken Liver, but Not in Rat Liver
- SASAKI Nobuo,MATUMOTO Tomoyuki,IKENAKA Yoshinori [他],NAKAYAMA Shouta M. M.,ISHIZUKA Mayumi,KAZUSAKA Akio,FUJITA Shoichi
- Journal of Veterinary Medical Science 75(11), 1497-1502, 2013
- … The nitrofuran antimicrobial agent, furazolidone (FZ), is still used in veterinary medicine in some countries in the Middle and Far Eastern countries. …
- NAID 130003362235
- Furazolidone induces the activity of microsomal enzymes that metabolize furazolidone in chickens
- Pesticide Biochemistry and Physiology 100(2), 135-139, 2011-06
- … The nitrofuran antibacterial agent furazolidone (FZ) is still used in veterinary medicine in some countries in the Middle and Far East. …
- NAID 80021797020
Related Links
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