Furazolidone

Furazolidone: Furazolidone

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

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 eMolecules & PubChem

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

N(what is this?) (verify)

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 Protozoan

1.2 Bacterial

2 Mechanism

3 Side effects

4 References

Uses

It is used to treat diarrhoea and enteritis caused by bacteria or protozoan infections.

It has also been used in aquaculture.^[1]

Protozoan

Furazolidone is also used for giardiasis (due to Giardia lamblia), though it is not a first line treatment.^[2]

Bacterial

Furazolidone is also used to treat traveler's diarrhoea, cholera, and bacteremic salmonellosis.

As a veterinary medicine, furazolidone has been used with some success to treat salmonids for Myxobolus cerebralis infections.

Use in treating Helicobacter pylori infections has been proposed.^[3]

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

^ 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.

^ 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.

^ 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.

^ "DrugBank: Showing Furazolidone (DB00614)". http://www.drugbank.ca/drugs/DB00614. Retrieved 2008-12-19.

^ http://caraga.da.gov.ph/services/banmed-Nitrofurans.htm

v · d · eGynecological anti-infectives and antiseptics (G01)

Antibiotics
polyene antimycotic (Nystatin, Natamycin, Amphotericin B) • Candicidin • Chloramphenicol • Hachimycin • Oxytetracycline • Carfecillin • Mepartricin • Clindamycin • Pentamycin

Arsenic compounds
Acetarsol

Quinoline derivatives
Diiodohydroxyquinoline • Clioquinol • Chlorquinaldol • Dequalinium • Broxyquinoline • Oxyquinoline

Organic acids
Lactic acid • Acetic acid • Ascorbic acid

Sulfonamides
Sulfatolamide

Imidazole derivatives
Metronidazole • Clotrimazole • Miconazole • Econazole • Ornidazole • Isoconazole • Tioconazole • Ketoconazole • Fenticonazole • Azanidazole • Propenidazole • Butoconazole • Omoconazole • Oxiconazole • Flutrimazole

Triazole derivatives
Terconazole

Other
Clodantoin • Inosine • Policresulen • Nifuratel • Furazolidone • Methylrosaniline • Povidone-iodine • Ciclopirox • Protiofate • Lactobacillus fermentum • Copper usnate

M: ♀ FRS

anat/phys/devp

noco/cong/npls, sysi/epon

proc/asst, drug (G1/G2B/G3CD)

v · d · eAntiparasitics – antiprotozoal agents – Excavata antiparasitics (P01)

Discicristata

Trypanosomiasis

African trypanosomiasis: ornithine (Eflornithine^#) • arsenical (Melarsoprol^#) • benzamidine (Pentamidine^#) • naphthalenesulfonate (Suramin^#)
Chagas disease: nitroimidazole (Benznidazole^#) • nitrofuran (Nifurtimox^#)

Leishmaniasis

macrolide (Amphotericin B^#)

Pentavalent antimonials (Meglumine antimoniate^#, Sodium stibogluconate)
benzamidine (Pentamidine^#) • phosphorylcholine (Miltefosine) • neomycin (Paromomycin)

PAM

macrolide (Amphotericin B)

Trichozoa

Giardiasis

nitroimidazole (Metronidazole^#, Tinidazole) • benzimidazole (Albendazole)

thiazole (Nitazoxanide) • nitrofuran (Furazolidone)
aminoacridine (Quinacrine)

Trichomoniasis

nitroimidazole (Metronidazole^#, Tinidazole)

Dientamoebiasis

nitroimidazole (Metronidazole, Secnidazole)
oxyquinoline (Iodoquinol) • tetracycline (Doxycycline) • neomycin (Paromomycin)

^#WHO-EM. ^‡Withdrawn from market. Clinical trials: ^†Phase III. ^§Never to phase III

M: PRO

ambz, excv, chrm (strc)

ambz, excv, chrm

ambz, excv, chrm

v · d · eAntibacterials: nucleic acid inhibitors (J01E, J01M)

Antifolates
(inhibits
purine metabolism,
thereby inhibiting
DNA and RNA synthesis)

DHFR inhibitor

2,4-Diaminopyrimidine (Trimethoprim^#, Brodimoprim, Tetroxoprim, Iclaprim^†)

Sulfonamides
(DHPS inhibitor)

Short-
acting

Sulfaisodimidine • Sulfamethizole • Sulfadimidine • Sulfapyridine • Sulfafurazole • Sulfanilamide (Prontosil) • Sulfathiazole • Sulfathiourea

Intermediate-
acting

Sulfamethoxazole • Sulfadiazine^# • Sulfamoxole

Long-
acting

Sulfadimethoxine • Sulfalene • Sulfametomidine • Sulfametoxydiazine • Sulfamethoxypyridazine • Sulfaperin • Sulfamerazine • Sulfaphenazole • Sulfamazone

Other/ungrouped

sulfanilamide (Sulfacetamide, Sulfametrole)

Combinations

Trimethoprim/sulfamethoxazole^#

Topoisomerase
inhibitors/
quinolones/
(inhibits
DNA replication)

1st g.

Cinoxacin^‡ • Flumequine • Nalidixic acid • Oxolinic acid • Pipemidic acid • Piromidic acid • Rosoxacin

Fluoro-
quinolones

2nd g.

Ciprofloxacin^# • Enoxacin^‡ • Fleroxacin^‡ • Lomefloxacin • Nadifloxacin • Ofloxacin • Norfloxacin • Pefloxacin • Rufloxacin

3rd g.

Balofloxacin • Grepafloxacin^‡ • Levofloxacin • Pazufloxacin • Sparfloxacin^‡ • Temafloxacin^‡ • Tosufloxacin

4th g.

Besifloxacin • Clinafloxacin^† • Garenoxacin • Gemifloxacin • Moxifloxacin • Gatifloxacin^‡ • Sitafloxacin • Trovafloxacin^‡/Alatrofloxacin^‡ • Prulifloxacin

Vet.

Danofloxacin • Difloxacin • Enrofloxacin • Ibafloxacin • Marbofloxacin • Orbifloxacin • Pradofloxacin • Sarafloxacin

Related (DG)

Aminocoumarins: Novobiocin

Anaerobic DNA
inhibitors

Nitro- imidazole derivatives

Metronidazole^# • Tinidazole • Ornidazole

Nitrofuran derivatives

Nitrofurantoin^# • Furazolidone^‡ • Nifurtoinol

RNA synthesis

Rifamycins/
RNA polymerase

Rifampicin • Rifabutin • Rifapentine • Rifaximin

^#WHO-EM. ^‡Withdrawn from market. Clinical trials: ^†Phase III. ^§Never to phase III

M: BAC

bact (clas)

gr+f/gr+a(t)/gr-p(c)/gr-o

drug(J1p, w, n, m, vacc)

Categories:
Antibiotics
Antiprotozoal agents
Nitrofurans
Monoamine oxidase inhibitors
Oxazolidinones
Hydrazones

Furazolidone

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
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	eMolecules & PubChem
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
N(what is this?) (verify)

Игры ⚽ Поможем сделать НИР

Look at other dictionaries:

furazolidone — Has antibacterial and antiprotozoal activity against enteric organisms; used in the treatment of bacterial enteritis and diarrhea. * * * fu·ra·zol·i·done .fyu̇r ə zäl ə .dōn n an antimicrobial drug C8H7N3O5 used against bacteria and some… … Medical dictionary
furazolidone — noun Etymology: furfural + azole + ide + one Date: 1955 an antimicrobial drug C8H7N3O5 used against bacteria and some protozoa especially in infections of the gastrointestinal tract … New Collegiate Dictionary
furazolidone — /fyoor euh zol i dohn /, n. Pharm. a nitrofuran, C8H7N3O5, that is used in the treatment of giardiasis, and bacterial gastroenteritis and dysentery. [1950 55; prob. fur(anyl) + (ox)azolid(in)one, two of its chemical components] * * * … Universalium
furazolidone — noun An antibacterial agent used to treat diarrhoea and enteritis caused by bacteria or protozoan infections … Wiktionary
furazolidone — fu·ra·zol·i·done … English syllables
furazolidone — ˌfyu̇rəˈzälə̇ˌdōn, zȯl noun ( s) Etymology: fur + azole + ide + one : an antimicrobial drug C8H7N3O5 used against bacteria and some protozoa especially in infections of the gastrointestinal tract * * * /fyoor euh zol i dohn /, n. Pharm. a… … Useful english dictionary
Monoamine oxidase inhibitor — MAOI redirects here. For the Easter Island statues, see Moai. Monoamine oxidase Monoamine oxidase inhibitors (MAOIs) are a class of antidepressant drugs prescribed for the treatment of depression. They are particularly effective in treating… … Wikipedia
Nitrofurantoin — Systematic (IUPAC) name (E) 1 [(5 nitro 2 furyl)methylideneamino]imidazolidine 2,4 dione Clinical data AHFS/Drugs.com … Wikipedia
Dimethyltryptamine — Systematic (IUPAC) name 2 (1H indol 3 yl) N … Wikipedia
Phenothiazine — Phenothiazine … Wikipedia

Academic Dictionaries and Encyclopedias

Furazolidone

Contents

Uses

Protozoan

Bacterial

Mechanism

Side effects

References

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Academic Dictionaries and Encyclopedias

Wikipedia

Furazolidone

Contents

Uses

Protozoan

Bacterial

Mechanism

Side effects

References

Look at other dictionaries:

Share the article and excerpts

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