U6Z

1-[(~{E})-(5-nitrofuran-2-yl)methylideneamino]imidazolidine-2,4-dione

Created:	2021-01-25
Last modified:	2021-07-21

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1 entries where U6Z is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	23
Chiral Atom Count	0
Bond Count	24
Aromatic Bond Count	5

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Chemical Component Summary
Name	1-[(~{E})-(5-nitrofuran-2-yl)methylideneamino]imidazolidine-2,4-dione
Synonyms	Nitrofurantoin
Systematic Name (OpenEye OEToolkits)	1-[(~{E})-(5-nitrofuran-2-yl)methylideneamino]imidazolidine-2,4-dione
Formula	C₈ H₆ N₄ O₅
Molecular Weight	238.157
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	CACTVS	3.385	O=C1CN(N=Cc2oc(cc2)[N](=O)=O)C(=O)N1
SMILES	OpenEye OEToolkits	2.0.7	c1cc(oc1C=NN2CC(=O)NC2=O)N(=O)=O
Canonical SMILES	CACTVS	3.385	O=C1CN(/N=C/c2oc(cc2)[N](=O)=O)C(=O)N1
Canonical SMILES	OpenEye OEToolkits	2.0.7	c1cc(oc1/C=N/N2CC(=O)NC2=O)N(=O)=O
InChI	InChI	1.03	InChI=1S/C8H6N4O5/c13-6-4-11(8(14)10-6)9-3-5-1-2-7(17-5)12(15)16/h1-3H,4H2,(H,10,13,14)/b9-3+
InChIKey	InChI	1.03	NXFQHRVNIOXGAQ-YCRREMRBSA-N

Drug Info: DrugBank

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License

DrugBank ID	DB00698
Name	Nitrofurantoin
Groups	approved vet_approved
Description	Nitrofurantoin is a nitrofuran antibiotic used to treat uncomplicated urinary tract infections.[L6856,L6859,L6862] Nitrofurantoin is converted by bacterial nitroreductases to electrophilic intermediates which inhibit the citric acid cycle as well as synthesis of DNA, RNA, and protein.[A179824] This drug is more resistant to the development of bacterial resistance because it acts on many targets at once.[A179824] Nitrofurantoin is a second line treatment to [trimethoprim]/[sulfamethoxazole].[A179830] Nitrofurantoin was granted FDA approval on 6 February 1953.[L6895]
Synonyms	nitrofurantoina Nitrofurantoin sodium Nitrofurantoin macrocrystal Nitrofurantoin anhydrous Nitrofurantoin, macrocrystals Nitrofurantoin monohydrate Nitrofurantoinum anhydrous 1-((5-nitro-2-furanyl)methylene)amino-2,4-imidazolidenedione N-(5-Nitrofurfurylidene)-1-aminohydantoin nitrofurantoine 5-Nitrofurantoin Nitrofurantoin macrocrystalline nitrofurantoinum Nitrofurantoin Nitrofurantoin, macrocrystalline 1-((5-nitrofurfurylidene)amino)hydantoin
Brand Names	Nitrofurantoin (macrocrystals) Jamp Nitrofurantoin Bid Nitrofurantoin 50 Tab 50mg Nephronex Tab 50mg Macrodantin Cap 25mg Nitrofurantion Nitrofurantoin Monohydrate/Macrocrystals Teva-nitrofurantoin Nitrofurantoin Mono Nitrofurantoin Oral Suspension Nitrofurantoin Monohydrate/ Macrocrystalline Nitrofurantoin Nitrofurantoin Monohydrate Macrocrystalline Nitrofurantoin (monohydrate/macrocrystals) Auro-nitrofurantoin Bid Macrodantin NITROFURANTOIN (monohydrate/macrocrystals) Nitrofurantoin Monohydrate/Macrocrystalline Novo-furan Tab 50mg Macrodantin Cap 100mg PMS-nitrofurantoin Bid Novo-furan 100mg Nu-nitrofurantoin Tablets Nitrofurantoine 100 Tab 100mg Furadantin Novo-furan Sus 25mg/5ml Nitrofurantoin Monohydrate/Macrocrystal Nitrofurantoin monohydrate/macrocrystals (monohydrate/macrocrystals) Nitrofurantoin Macrocrystals Macrodantin (100 Mg) Macrobid Macrodantin Cap 50mg Nitrofurantoin monohydrate macrocrystals Macrodantin (50 Mg) Nitrofurantion Macrocrystals Nitrofurantoin macrocrystals Jamp Nitrofurantoin
Indication	Nitrofurantoin is indicated to treat acute uncomplicated urinary tract infections.[L6856,L6859,L6862]
Categories	Agents causing hyperkalemia Anti-Bacterial Agents Anti-Infective Agents Anti-Infective Agents, Urinary Antibacterials for Systemic Use Antiinfectives for Systemic Use BCRP/ABCG2 Substrates BSEP/ABCB11 Substrates Drugs that are Mainly Renally Excreted Furans Methemoglobinemia Associated Agents Nitro Compounds Nitrofuran Antibacterial Nitrofuran Derivatives Nitrofurans P-glycoprotein substrates Renal Agents Thyroxine-binding globulin substrates
ATC-Code	J01XE01 J01XE51
CAS number	67-20-9

Drug Targets

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License

Name	Target Sequence	Pharmacological Action	Actions
Probable pyruvate-flavodoxin oxidoreductase	MITIDGNGAVASVAFRTSEVIAIYPITPSSTMAEQADAWAGNGLKNVWGD...	unknown	potentiator
Oxygen-insensitive NADPH nitroreductase	MTPTIELICGHRSIRHFTDEPISEAQREAIINSARATSSSSFLQCSSIIR...	unknown	potentiator
30S ribosomal protein S10	MQNQRIRIRLKAFDHRLIDQATAEIVETAKRTGAQVRGPIPLPTRKERFT...	unknown	inhibitor
NADPH--cytochrome P450 reductase	MGDSHVDTSSTVSEAVAEEVSLFSMTDMILFSLIVGLLTYWFLFRKKKEE...	unknown	substrate
Broad substrate specificity ATP-binding cassette transporter ABCG2	MSSSNVEVFIPVSQGNTNGFPATASNDLKAFTEGAVLSFHNICYRVKLKS...	unknown	substrate
Bile salt export pump	MSDSVILRSIKKFGEENDGFESDKSYNNDKKSRLQDEKKGDGVRVGFFQL...	unknown	substrate
ATP-dependent translocase ABCB1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate
ATP-binding cassette sub-family C member 2	MLEKFCNSTFWNSSFLDSPEADLPLCFEQTVLVWIPLGYLWLLAPWQLLH...	unknown
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682