DT-Web

DB00614 - Furazolidone


Identification
Name Furazolidone
Accession Number DB00614 (APRD00988)
Type small molecule
Description A nitrofuran derivative with antiprotozoal and antibacterial activity. Furazolidone binds bacterial DNA which leads to the gradual inhibition of monoamine oxidase. (From Martindale, The Extra Pharmacopoeia, 30th ed, p514)
Structure
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 225.1583
Groups approved
Monoisotopic Weight 225.038570349
Pharmacology
Indication For the specific and symptomatic treatment of bacterial or protozoal diarrhea and enteritis caused by susceptible organisms.
Mechanism of action Furazolidone and its related free radical products are believed to bind DNA and induce cross-links. Bacterial DNA is particularly susceptible to this drug leading to high levels of mutations (transitions and transversions) in the bacterial chromosome.
Absorption Radiolabeled drug studies indicate that furazolidone is well absorbed following oral administration
Protein binding Not Available
Biotransformation Furazolidone is rapidly and extensively metabolized; the primary metabolic pathway identified begins with nitro-reduction to the aminofuran derivative. Two major metabolites are produced: 3-amino-2-oxazolidone (AOZ) or beta-hydroxyethylhydrazine (HEH). AOZ is responsible for monoamine oxidase inhibition. Detoxification and elimination of the drug is done primarily by conjugation with glutathione.
Route of elimination Not Available
Toxicity Reactions to Furoxone have been reported including a fall in blood pressure, urticaria, fever, arthralgia, and a vesicular morbilliform rash. Other adverse effects can include a brown discoloration of the urine; hemolysis can occur in G6PDH-deficient patients. The drug has a monoamine oxidase (MAO) inhibitory effect and should never be given concurrently to individuals already taking MAO inhibitors.
Affected organisms
  • Microbes (bacteria, parasites)
Interactions
Drug Interactions
Drug Mechanism of interaction
Milnacipran Increase serotonin levels. Combination therapy is contraindicated.
Tetrabenazine Tetrabenazine may increase the adverse/toxic effects of Furazolidine. Concomitant therapy is contraindicated.
Tolcapone Tolcapone and Furazolidone decrease the metabolism of endogenous catecholamines. Concomitant therapy may result in increased catecholamine effects. Consider alternate therapy or use cautiously and monitor for increased catecholamine effects.
Tramadol Tramadol increases the risk of serotonin syndrome and seizure induction by the MAO inhibitor, Furazolidone.
Tranylcypromine Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Trazodone Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Trimipramine Increased risk of serotonin syndrome. Ensure adequate washout period between therapies to avoid toxicity. Avoid combination or monitor for symptoms of serotonin syndrome and/or hypertensive crisis.
Venlafaxine Increased risk of serotonin syndrome. Ensure adequate washout period between therapies to avoid toxicity. Concurrent therapy should be avoided.
Zolmitriptan The MAO inhibitor, furazolidine, may increase the serum concentration of zolmitriptan by decreasing its metabolism. Concomitant therapy and use of zolmitriptan within two weeks of discontinuing furazolidine are contraindicated.
Food Interactions Not Available

Targets


DNA
Name DNA
Gene Name Not Available
Pharmacological action yes
Actions cross-linking/alkylation
References
  • Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. - Pubmed
  • Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. - Pubmed
  • Meng J, Mangat SS, Grudzinski IP, Law FC: Evidence of 14C-furazolidone metabolite binding to the hepatic DNA of trout. Drug Metabol Drug Interact. 1998;14(4):209-19. - Pubmed
DTHybrid score Not Available

Enzymes


Amine oxidase [flavin-containing] B
Name Amine oxidase [flavin-containing] B
Gene Name MAOB
Actions inhibitor
References
  • Timperio AM, Kuiper HA, Zolla L: Identification of a furazolidone metabolite responsible for the inhibition of amino oxidases. Xenobiotica. 2003 Feb;33(2):153-67. - Pubmed
  • Ali BH: Pharmacological, therapeutic and toxicological properties of furazolidone: some recent research. Vet Res Commun. 1999 Oct;23(6):343-60. - Pubmed
  • Hoogenboom LA, Tomassini O, Oorsprong MB, Kuiper HA: Use of pig hepatocytes to study the inhibition of monoamine oxidase by furazolidone. Food Chem Toxicol. 1991 Mar;29(3):185-91. - Pubmed
DTHybrid score 0.9484
Amine oxidase [flavin-containing] A
Name Amine oxidase [flavin-containing] A
Gene Name MAOA
Actions inhibitor
References
  • Timperio AM, Kuiper HA, Zolla L: Identification of a furazolidone metabolite responsible for the inhibition of amino oxidases. Xenobiotica. 2003 Feb;33(2):153-67. - Pubmed
  • Ali BH: Pharmacological, therapeutic and toxicological properties of furazolidone: some recent research. Vet Res Commun. 1999 Oct;23(6):343-60. - Pubmed
  • Hoogenboom LA, Tomassini O, Oorsprong MB, Kuiper HA: Use of pig hepatocytes to study the inhibition of monoamine oxidase by furazolidone. Food Chem Toxicol. 1991 Mar;29(3):185-91. - Pubmed
DTHybrid score 0.5416

Predictions


Id Partner name Gene Name Score
824 Sodium-dependent serotonin transporter SLC6A4 0.0598
713 Sodium-dependent dopamine transporter SLC6A3 0.0582
4200 Cytochrome P450 1A2 CYP1A2 0.0518
4119 Cytochrome P450 2D6 CYP2D6 0.0402
540 Sodium-dependent noradrenaline transporter SLC6A2 0.0389
131 Synaptic vesicular amine transporter SLC18A2 0.0348
511 5-hydroxytryptamine 1F receptor HTR1F 0.0325
6016 Cytochrome P450 2C19 CYP2C19 0.0297
3810 Catechol O-methyltransferase COMT 0.0289
4757 Cytochrome P450 2C9 CYP2C9 0.0271
725 5-hydroxytryptamine 1D receptor HTR1D 0.0262
885 5-hydroxytryptamine 1B receptor HTR1B 0.0258
318 Alpha-2A adrenergic receptor ADRA2A 0.024
2864 Penton protein PIII 0.0236
1588 Multidrug resistance protein 1 ABCB1 0.022
5841 Insulin-like growth factor IB IGF1 0.0206
556 Alpha-1A adrenergic receptor ADRA1A 0.0195
4512 Cytochrome P450 3A4 CYP3A4 0.017
146 Androgen receptor AR 0.0167
6013 Cytochrome P450 2E1 CYP2E1 0.0166
3811 Cytochrome P450 19A1 CYP19A1 0.0159
273 Apoptosis regulator Bcl-2 BCL2 0.0149
320 5-hydroxytryptamine 1A receptor HTR1A 0.0143
193 Beta-1 adrenergic receptor ADRB1 0.0137
5718 Cytochrome P450 2A6 CYP2A6 0.012
6147 Solute carrier family 22 member 3 SLC22A3 0.0115
1757 Myeloperoxidase MPO 0.0114
4924 Cytochrome P450 2C8 CYP2C8 0.0114
23 D(1A) dopamine receptor DRD1 0.0108
5698 Riboflavin synthase alpha chain ribE 0.0105
6030 Cytochrome P450 2B6 CYP2B6 0.0105
502 5-hydroxytryptamine 2A receptor HTR2A 0.0104
378 Alpha-2C adrenergic receptor ADRA2C 0.0102
408 Riboflavin kinase RFK 0.0101
629 Alpha-2B adrenergic receptor ADRA2B 0.01
1181 Alpha-1-acid glycoprotein 1 ORM1 0.01
118 Organic cation/carnitine transporter 2 SLC22A5 0.009
831 D(2) dopamine receptor DRD2 0.0087
6145 Solute carrier family 22 member 1 SLC22A1 0.0087
766 Beta-2 adrenergic receptor ADRB2 0.0083
1636 Trace amine-associated receptor 1 TAAR1 0.0081
3913 Glutamic acid decarboxylase GAD65 0.008
6144 Solute carrier family 22 member 2 SLC22A2 0.0079
1483 Membrane copper amine oxidase AOC3 0.0076
1656 CYP2B protein CYP2B 0.0075
654 Flavin reductase BLVRB 0.0075
1517 Beta-3 adrenergic receptor ADRB3 0.0072
789 Alpha-1D adrenergic receptor ADRA1D 0.0068
6031 Cytochrome P450 3A43 CYP3A43 0.0067
3917 Methylenetetrahydrofolate reductase MTHFR 0.0066
735 Alanine aminotransferase 1 GPT 0.0065
3904 Alanine aminotransferase 2 GPT2 0.0065
6164 POU domain, class 5, transcription factor 1 POU5F1 0.0061
632 Alpha-1B adrenergic receptor ADRA1B 0.0061
694 Matrix protein 2 M 0.0059
280 4-aminobutyrate aminotransferase, mitochondrial ABAT 0.0056
6014 Cytochrome P450 2A13 CYP2A13 0.0052
3876 Aromatic-L-amino-acid decarboxylase DDC 0.005
153 Dopamine beta-hydroxylase DBH 0.0047
6107 Cytochrome P450 3A7 CYP3A7 0.0042
6139 Solute carrier organic anion transporter family member 1A2 SLCO1A2 0.0041
706 Glutamate [NMDA] receptor subunit 3A GRIN3A 0.0041
6101 Dimethylaniline monooxygenase [N-oxide-forming] 3 FMO3 0.0041
1729 Solute carrier family 22 member 6 SLC22A6 0.0041
4118 Cytochrome P450 3A5 CYP3A5 0.004
1732 ATP-binding cassette sub-family G member 2 ABCG2 0.0039
6133 Sodium channel subunit beta-2 SCN2B 0.0038
6134 Sodium channel subunit beta-3 SCN3B 0.0038
6132 Sodium channel subunit beta-1 SCN1B 0.0038
6135 Sodium channel subunit beta-4 SCN4B 0.0038
6127 Carbonic anhydrase-related protein CA8 0.0038
6129 Carbonic anhydrase-related protein 11 CA11 0.0038
6128 Carbonic anhydrase-related protein 10 CA10 0.0038
948 Neuronal acetylcholine receptor subunit beta-2 CHRNB2 0.0038
6082 Neuronal acetylcholine receptor subunit beta-3 CHRNB3 0.0038
6080 Neuronal acetylcholine receptor subunit alpha-5 CHRNA5 0.0038
163 D(1B) dopamine receptor DRD5 0.0036
3803 Sodium channel protein type 3 subunit alpha SCN3A 0.0036
4097 Neuronal acetylcholine receptor subunit alpha-9 CHRNA9 0.0036
6130 Carbonic anhydrase 13 CA13 0.0036
436 5-hydroxytryptamine 2B receptor HTR2B 0.0036
6124 Carbonic anhydrase 5B, mitochondrial CA5B 0.0035
6081 Neuronal acetylcholine receptor subunit alpha-6 CHRNA6 0.0035
432 D(4) dopamine receptor DRD4 0.0035
833 Organic cation/carnitine transporter 1 SLC22A4 0.0034
638 D(3) dopamine receptor DRD3 0.0034
215 Sodium channel protein type 11 subunit alpha SCN11A 0.0032
6131 Carbonic anhydrase 14 CA14 0.0032
6078 Neuronal acetylcholine receptor subunit beta-4 CHRNB4 0.0032
590 5-hydroxytryptamine 2C receptor HTR2C 0.0031
1490 Solute carrier organic anion transporter family member 1B1 SLCO1B1 0.0031
6122 Carbonic anhydrase 3 CA3 0.0031
3802 Sodium channel protein type 2 subunit alpha SCN2A 0.0031
474 Acetylcholinesterase ACHE 0.003
6123 Carbonic anhydrase 5A, mitochondrial CA5A 0.003
1995 Sodium channel protein type 9 subunit alpha SCN9A 0.0029
6079 Neuronal acetylcholine receptor subunit alpha-3 CHRNA3 0.0029
3804 Sodium channel protein type 4 subunit alpha SCN4A 0.0029
458 Neuronal acetylcholine receptor subunit alpha-10 CHRNA10 0.0028
4205 Carbonic anhydrase 9 CA9 0.0028
3007 Carbonic anhydrase 12 CA12 0.0028
6024 Cytochrome P450 1A1 CYP1A1 0.0027
103 Muscarinic acetylcholine receptor M1 CHRM1 0.0027
15 Voltage-dependent T-type calcium channel subunit alpha-1I CACNA1I 0.0026
6126 Carbonic anhydrase 7 CA7 0.0026
158 Sodium channel protein type 1 subunit alpha SCN1A 0.0025
535 Voltage-dependent T-type calcium channel subunit alpha-1G CACNA1G 0.0025
964 Voltage-dependent T-type calcium channel subunit alpha-1H CACNA1H 0.0023
813 Neuronal acetylcholine receptor subunit alpha-2 CHRNA2 0.0022
4095 Neuronal acetylcholine receptor subunit alpha-7 CHRNA7 0.0022
947 Neuronal acetylcholine receptor subunit alpha-4 CHRNA4 0.0022
6020 Aldehyde oxidase AOX1 0.0022
592 Carbonic anhydrase 4 CA4 0.0021
295 Carbonic anhydrase 1 CA1 0.002
220 Sodium channel protein type 5 subunit alpha SCN5A 0.0019
4486 Phenol 2-hydroxylase component B pheA2 0.0018
4477 Dihydrolipoyl dehydrogenase lpdV 0.0018
5077 Dihydrolipoyl dehydrogenase Not Available 0.0018
5117 Dihydrolipoyl dehydrogenase lpd 0.0018
4439 Ferredoxin reductase bphA4 0.0018
5078 Amine oxidase, flavin-containing PSPTO1126 0.0018
526 Thioredoxin reductase trxB 0.0018
3767 Thioredoxin reductase trxB 0.0018
5122 Mersacidin decarboxylase mrsD 0.0017
5095 Putidaredoxin reductase camA 0.0017
5107 Alkyl hydroperoxide reductase subunit F ahpF 0.0017
5118 Alkyl hydroperoxide reductase subunit F ahpF 0.0017
5114 Putative acyl-CoA dehydrogenase TT_C0779 0.0017
5109 Outer membrane protein p64k or PM-6 m-6 0.0017
5115 FkbI fkbI 0.0017
3133 UDP-galactopyranose mutase glf 0.0017
5099 UDP-galactopyranose mutase glf 0.0017
5097 PROBABLE DIHYDROLIPOAMIDE DEHYDROGENASE LPDA lpdA 0.0017
3763 5,10-methylenetetrahydrofolate reductase metF 0.0017
3918 5,10-methylenetetrahydrofolate reductase MTHFR 0.0017
5094 5,10-methylenetetrahydrofolate reductase metF 0.0017
5102 4-cresol dehydrogenase [hydroxylating] flavoprotein subunit pchF 0.0017
5111 Phenylacetone monooxygenase pamO 0.0017
1329 Apoptosis-inducing factor 1, mitochondrial AIFM1 0.0017
5083 Cryptochrome DASH cry 0.0017
5100 Gamma-aminobutyrate metabolism dehydratase/isomerase abfD 0.0017
5081 L-aspartate oxidase nadB 0.0017
1410 Oxidoreductase HSD17B6 0.0017
4725 Oxidoreductase Not Available 0.0017
5124 Oxidoreductase Not Available 0.0017
5112 Benzoate 1,2-dioxygenase electron transfer component benC 0.0017
357 Carbonic anhydrase 2 CA2 0.0017
4440 NADH peroxidase npr 0.0015
5091 UDP-N-acetylenolpyruvoylglucosamine reductase murB 0.0015
5093 UDP-N-acetylenolpyruvoylglucosamine reductase murB 0.0015
3102 Flavohemoprotein hmp 0.0015
4969 Flavohemoprotein hmp 0.0015
3594 Deoxyribodipyrimidine photo-lyase phr 0.0015
5079 Deoxyribodipyrimidine photo-lyase phrB 0.0015
5080 Deoxyribodipyrimidine photo-lyase phr 0.0015
5072 N,N-dimethylglycine oxidase dmg 0.0015
2470 Pyruvate oxidase pox5 0.0015
5073 Ferredoxin--NADP reductase petH 0.0015
5076 Ferredoxin--NADP reductase fpr 0.0015
5119 Ferredoxin--NADP reductase petH 0.0015
5121 Ferredoxin--NADP reductase fpr 0.0015
5075 Sulfite reductase [NADPH] flavoprotein alpha-component cysJ 0.0015
440 Isovaleryl-CoA dehydrogenase, mitochondrial IVD 0.0015
667 Acyl-CoA dehydrogenase family member 8, mitochondrial ACAD8 0.0015
3506 Glutaryl-CoA dehydrogenase, mitochondrial GCDH 0.0015
5003 Acyl-CoA dehydrogenase, short-chain specific Not Available 0.0015
2268 Cholesterol oxidase choB 0.0015
2822 Cholesterol oxidase choA 0.0015
2526 NADPH-ferredoxin reductase fprA fprA 0.0015
6639 Peroxisomal acyl-coenzyme A oxidase 1 ACOX1 0.0015
3247 2-oxopropyl-CoM reductase, carboxylating xecC 0.0015
6689 TraN protein traN 0.0015
6672 Destrin DSTN 0.0015
6680 Cofilin-1 CFL1 0.0015
6670 Ig kappa chain V-I region Bi Not Available 0.0015
6671 Ig heavy chain V-III region VH26 Not Available 0.0015
4905 Cytochrome c2 Not Available 0.0015
4939 Cytochrome c2 cycA 0.0015
4964 Cytochrome c2 cycA 0.0015
4979 Cytochrome c2 cycA 0.0015
6673 Cytochrome c2 cycA 0.0015
6688 TraF protein traF 0.0015
6404 Rhomboid protease glpG glpG 0.0015
6797 Rhomboid protease glpG glpG 0.0015
3710 Acyl-CoA thioesterase 2 tesB 0.0015
6685 Outer membrane protein II porB 0.0015
6690 BenF-like porin PFL_1329 0.0015
6681 Probable N-acetylneuraminic acid outer membrane channel protein nanC nanC 0.0015
6687 TraO protein traO 0.0015
5793 Cytochrome c oxidase subunit 2 MT-CO2 0.0015
6559 Cytochrome c oxidase subunit 2 ctaC 0.0015
6669 Cytochrome c oxidase subunit 2 ctaC 0.0015
6668 Cytochrome c oxidase subunit 1-beta ctaDII 0.0015
6679 Colicin-Ia cia 0.0015
6676 Fe(3+)-pyochelin receptor fptA 0.0015
115 Penicillin-binding protein 2 mrdA 0.0015
6069 Penicillin-binding protein 2 mrdA 0.0015
6118 Penicillin-binding protein 2 penA 0.0015
6187 Penicillin-binding protein 2 pbpA 0.0015
6686 Penicillin-binding protein 2 pbp2 0.0015
6939 Penicillin-binding protein 2 mrdA 0.0015
7163 Penicillin-binding protein 2 pbpA 0.0015
6674 Nuclear factor erythroid 2-related factor 1 NFE2L1 0.0015
327 Glutathione reductase gor 0.0015
5110 Glutathione reductase GR2 0.0015
756 Sex hormone-binding globulin SHBG 0.0015
178 NADH-cytochrome b5 reductase 3 CYB5R3 0.0015
812 Dihydrolipoyl dehydrogenase, mitochondrial DLD 0.0015
126 D-lactate dehydrogenase dld 0.0014
3545 D-lactate dehydrogenase Not Available 0.0014
4510 D-lactate dehydrogenase ldhA 0.0014
6141 Sodium/bile acid cotransporter SLC10A1 0.0014
3185 Medium-chain specific acyl-CoA dehydrogenase, mitochondrial ACADM 0.0014
3254 Bifunctional protein putA [Includes: Proline dehydrogenase putA 0.0014
2893 Glycine oxidase thiO 0.0014
605 Fumarate reductase flavoprotein subunit frdA 0.0014
2709 Fumarate reductase flavoprotein subunit SO_0970 0.0014
3673 Fumarate reductase flavoprotein subunit fccA 0.0014
4912 Fumarate reductase flavoprotein subunit ifcA 0.0014
6549 Fumarate reductase flavoprotein subunit frdA 0.0014
6017 Cholesterol side-chain cleavage enzyme, mitochondrial CYP11A1 0.0014
3573 2,4-dienoyl-CoA reductase [NADPH] fadH 0.0013
2567 Thymidylate synthase thyX thyX 0.0013
2823 Trypanothione reductase TPR 0.0013
2769 P-hydroxybenzoate hydroxylase pobA 0.0013
2809 P-hydroxybenzoate hydroxylase pobA 0.0013
839 Short-chain specific acyl-CoA dehydrogenase, mitochondrial ACADS 0.0013
4760 Mll3241 protein mll3241 0.0013
3395 Iron(III) dicitrate transport protein fecA fecA 0.0013
6385 H subunit of photosynthetic reaction center complex puhA 0.0013
6474 Outer membrane protein W ompW 0.0013
6678 Colicin I receptor cirA 0.0013
3578 Protein crcA crcA 0.0013
6675 Colicin-E3 ceaC 0.0013
2925 Long-chain fatty acid transport protein fadL 0.0013
6480 Outer membrane usher protein papC papC 0.0013
6438 Outer membrane protein G ompG 0.0013
2447 Ammonia channel amtB 0.0013
2380 Monomeric sarcosine oxidase soxA 0.0012
1898 Cytochrome P450 1B1 CYP1B1 0.0012
3610 Thioredoxin reductase 1, cytoplasmic TXNRD1 0.0012
6645 D-amino-acid oxidase DAO 0.0012
6428 Light-harvesting protein B-800/850 beta chain Not Available 0.0012
6427 Light-harvesting protein B-800/850 alpha chain Not Available 0.0012
6533 Light-harvesting protein B-800/850 alpha chain A1 0.0012
6524 Protein tonB tonB 0.0012
2679 Vitamin B12 transporter btuB btuB 0.0012
6143 Solute carrier family 22 member 7 SLC22A7 0.0011
6677 Myelin P2 protein PMP2 0.0011
1302 Dihydropyrimidine dehydrogenase [NADP+] DPYD 0.0011
243 Ribosyldihydronicotinamide dehydrogenase [quinone] NQO2 0.001
714 Glutathione reductase, mitochondrial GSR 0.001
6142 Solute carrier family 22 member 8 SLC22A8 0.001
6352 Reaction center protein H chain puhA 0.001
6456 Reaction center protein H chain puhA 0.001
6682 Reaction center protein H chain puhA 0.001
6353 Reaction center protein L chain pufL 0.001
6454 Reaction center protein L chain pufL 0.001
6683 Reaction center protein L chain pufL 0.001
6354 Reaction center protein M chain pufM 0.001
6455 Reaction center protein M chain pufM 0.001
6684 Reaction center protein M chain pufM 0.001
6351 Photosynthetic reaction center cytochrome c subunit pufC 0.001
4120 NADPH--cytochrome P450 reductase POR 0.001
2828 Squalene--hopene cyclase shc 0.0009
2157 NAD(P)H dehydrogenase [quinone] 1 NQO1 0.0009
587 Serum albumin ALB 0.0009
76 Nitric-oxide synthase, brain NOS1 0.0009
2207 Rhodopsin RHO 0.0009
3947 Xanthine dehydrogenase/oxidase XDH 0.0008
424 Dihydroorotate dehydrogenase, mitochondrial DHODH 0.0008
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