NITROFURANTOIN

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Search structure


Trade Names	FURADANTIN FURALAN NITROFURANTOIN
Synonyms	Berkfurin Ceduran Dantafur Furadantin Furalan Genfura Ivadantin Macrobid Macrodantin NSC-2107 NSC-44150 Nitrofurantoin Nitrofurantoin (monohydrate/macrocrystals) Nitrofurantoin anhydrous Nitrofurantoin macrocrystal Nitrofurantoin macrocrystalline Nitrofurantoin, macrocrystalline Nitrofurantoin, macrocrystals Nitrofurantoinum anhydrous
Status
Molecule Category	Free-form
ATC	J01XE01
UNII	927AH8112L


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	NXFQHRVNIOXGAQ-YCRREMRBSA-N
Smiles	O=C1CN(/N=C/c2ccc([N+](=O)[O-])o2)C(=O)N1
InChI	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+

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C8H6N4O5
Molecular Weight	238.16
AlogP	0.07
Hydrogen Bond Acceptor	6.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	3.0
Polar Surface Area	118.05
Molecular species	NEUTRAL
Aromatic Rings	1.0
Heavy Atoms	17.0

Bioactivity

Mechanism of Action	Action	Reference
DNA inhibitor	INHIBITOR	FDA

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Oxidoreductase	-	-	-	-	41
Enzyme Protease Serine protease Serine protease PA clan Serine protease S1A subfamily	-	-	-	-	91
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides	-	-	-	-	-2-101
Transporter Primary active transporter ATP-binding cassette ABCC subfamily	-	20900	-	-	-
Unclassified protein	-	19100	-	816	-

Assay Description	Organism	Bioactivity	Reference
Inhibition of beta-lactamase at 100 uM	None	5.0 %
Inhibition of chymotrypsin at 250 uM	unidentified	91.0 %
Inhibition of malate dehydrogenase (MDH) at 400 uM	None	97.0 %
Anti-Herpes simplex virus type-1 activity in vero cells using plaque inhibition assay	Chlorocebus sabaeus	0.9 nM
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting	Homo sapiens	23.3 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting	Homo sapiens	-1.5 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting	Homo sapiens	23.1 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	97.62 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	100.8 %
Inhibition of COX-2 (unknown origin) using arachidonic acid as substrate assessed as formation of prostanoid products at 500 uM preincubated for 10 mins prior to substrate addition measured after 2 mins by Ellman's method relative to control	Homo sapiens	41.0 %
Inhibition of COX-1 (unknown origin) using arachidonic acid as substrate assessed as formation of prostanoid products at 500 uM preincubated for 10 mins prior to substrate addition measured after 2 mins by Ellman's method relative to control	Homo sapiens	66.0 %
DNDI: HAT in Vitro, 72 hour	Trypanosoma brucei rhodesiense	500.0 nM
Permeability in human Caco2 cells assessed as 11 uM BCRP inhibitor Ko134-mediated inhibition of nitrofurantoin at 5 uM by liquid scintillation counting	Homo sapiens	78.0 %
Displacement of [3H]rosiglitazone from recombinant human C-terminal His-tagged MitoNEET cytosolic domain (32 to 108 residues) expressed in Escherichia coli BL21 by Cheng-Prusoff analysis	Homo sapiens	816.0 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	21.5 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	14.81 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.2 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.2 %
Antibacterial activity against Escherichia coli assessed as reduction in bacterial growth by serial dilution method	Escherichia coli	690.0 nM

Cross References

Resources	Reference
ChEBI	71415
ChEMBL	CHEMBL572
DrugBank	DB00698
DrugCentral	1949
FDA SRS	927AH8112L
Guide to Pharmacology	10917
KEGG	C07268
PDB	U6Z
PubChem	6604200
SureChEMBL	SCHEMBL29470
ZINC	ZINC000003875368

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).