Details of the Drug

General Information of Drug (ID: DM7PQIK)

Drug Name

Nitrofurantoin

Synonyms

Alfuran; Benkfuran; Berkfuran; Berkfurin; Ceduran; Chemiofuran; Cistofuran; Cyantin; Cystit; Dantafur; Furabid; Furachel; Furadantin; Furadantine; Furadantoin; Furadoine; Furadonin; Furadonine; Furadoninum; Furadontin; Furalan; Furaloid; Furantoin; Furatoin; Furedan; Furina; Furobactina; Furodantin; Furophen; Gerofuran; Ituran; Macpac; Macrobid; Macrodantin; Macrodantina; Macrofuran; Macrofurin; NITROFURANTION; Nierofu; Nifurantin; Nifuretten; Nitoin; Nitrex; Nitrofuradantin; Nitrofurantoina; Nitrofurantoine; Nitrofurantoinum; Novofuran; Orafuran; Parfuran; Phenurin; PiyEloseptyl; Siraliden; Trantoin; Uerineks; Urantoin; Urizept; Urodil; Urodin; Urofuran; Urofurin; Urolisa; Urolong; Welfurin; Zoofurin; Fua Med; Furadantin Retard; Furadantina MC; Furadantine mc; Furophen T; NITROFURANTOIN MACROCRYSTALLINE; Nitrofurantoina [DCIT]; Fua-med; Fur-ren; Furadantin (TN); Furadantine-MC; Macrobid (TN); Macrodantin (TN); N-Toin; ND-3320; ND-7248; NITROFURANTOIN, MACROCRYSTALLINE; Nitro Macro (TN); Nitrofur-C; Nitrofurantoine [INN-French]; Nitrofurantoinum [INN-Latin]; Ro-Antoin; Urantoin (TN); Uro-Selz; Uro-Tablinen; Uro-tablineu; Usaf ea-2; Nitrofurantoin (JAN/USP/INN); Nitrofurantoin [USAN:INN:BAN:JAN]; N-(5-Nitrofurfurylidene)-1-aminohydantoin; N-(5-Nitro-2-furfurylidene)-1-aminohydantoin; N-(5-Nitro-2-furfurylideno)-1-aminohydantoina; N-(5-Nitro-2-furfurylideno)-1-aminohydantoina [Polish]; N-(5-nitro-2-furfurylidene)-1-aminohyda ntoin; 1-(((5-nitro-2-furanyl)methylene)amino)-2,4-imidazolidinedione; 1-((5-Nitrofurfurylidene)amino)hydantoin; 1-(5-Nitro-2-furfurylidenamino)hydantoin; 1-(5-Nitro-2-furfurylideneamino)hydantoin; 1-[(5-:nitrofurfurylidene)amino]hydantoin; 1-[(5-Nitrofurfurylidene)amino]hydantoin; 1-[(E)-(5-nitrofuran-2-yl)methylideneamino]imidazolidine-2,4-dione; 1-[[(5-Nitro-2-furanyl)methylene]amino]-2,4-imidazolidinedione; 1-{[(1E)-(5-nitro-2-furyl)methylene]amino}imidazolidine-2,4-dione; 1-{[(1E)-(5-nitrofuran-2-yl)methylidene]amino}imidazolidine-2,4-dione; 5-Nitrofurantoin

Indication

Disease Entry	ICD 11	Status	REF
Urinary tract infection	GC08	Approved	[1]
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Therapeutic Class

Antiinfective Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

238.16

Logarithm of the Partition Coefficient (xlogp)

-0.5

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption AUC: The area under the plot of plasma concentration (AUC) of drug is 2.21-2.42 mgh/L [2]
Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 0.875-0.963 mg/L [2]
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 4: low solubility and low permeability [3]
Bioavailability: 87% of drug becomes completely available to its intended biological destination(s) [4]
Clearance: The clearance of drug is 16.7-19.4 L/h [2]
Elimination: 27-50% of an oral dose is excreted in the urine as unchanged nitrofurantoin [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 0.72 - 0.78 hours [2]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 24 micromolar/kg/day [5]
Unbound Fraction: The unbound fraction of drug in plasma is 0.17% [6]
Vd: The volume of distribution (Vd) of drug is 0.46 L/kg [7]
Water Solubility: The ability of drug to dissolve in water is measured as 0.19 mg/mL [3]

Chemical Identifiers

Formula: C8H6N4O5
IUPAC Name: 1-[(E)-(5-nitrofuran-2-yl)methylideneamino]imidazolidine-2,4-dione
Canonical SMILES: C1C(=O)NC(=O)N1/N=C/C2=CC=C(O2)[N+](=O)[O-]
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+
InChIKey: NXFQHRVNIOXGAQ-YCRREMRBSA-N

Cross-matching ID

PubChem CID: 6604200
ChEBI ID: CHEBI:71415
CAS Number: 67-20-9
DrugBank ID: DB00698
TTD ID: D0R0BX
VARIDT ID: DR00886
INTEDE ID: DR1169
ACDINA ID: D00475

Combinatorial Drugs (CBD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Bacterial Deoxyribonucleic acid (Bact DNA)	TTS1W4A	NOUNIPROTAC	Breaker	[8]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Breast cancer resistance protein (ABCG2)	DTI7UX6	ABCG2_HUMAN	Substrate	[9]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
NADPH-cytochrome P450 reductase (CPR)	DE3N2FM	NCPR_HUMAN	Substrate	[10]
NADPH-dependent oxidoreductase (nfrA)	DE82GV7	NRFA_STAA8	Substrate	[11], [12]
NADPH-dependent nitroreductase (nfrA1)	DE21PLI	NFRA1_BACSU	Substrate	[13], [14]
Nitroreductase (NTR)	DEUW4J0	A0A376H6M5_ENTGA	Substrate	[15]
Nitroreductase (NTR)	DEP7ECA	B1R7B9_CLOPF	Substrate	[16]
Nitroreductase (NTR)	DE5LYXF	A0A2X3BKF5_CLOSG	Substrate	[17], [16]
Nitroreductase (NTR)	DE3U2Y6	A0A377KR04_ENTCA	Substrate	[15]
Nitroreductase (NTR)	DEAVXGM	A0A412R9E4_9FIRM	Substrate	[16]
Nitroreductase (NTR)	DE7XBKW	A0A174SJF2_9CLOT	Substrate	[16]
Nitroreductase (NTR)	DEH3ABM	A0A351QTB1_CLOSP	Substrate	[16]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Bile salt export pump (ABCB11)	OTRU7THO	ABCBB_HUMAN	Gene/Protein Processing	[18]
Broad substrate specificity ATP-binding cassette transporter ABCG2 (ABCG2)	OTW8V2V1	ABCG2_HUMAN	Regulation of Drug Effects	[19]
Glutamate--cysteine ligase catalytic subunit (GCLC)	OTESDI4D	GSH1_HUMAN	Gene/Protein Processing	[20]
Heat shock factor protein 1 (HSF1)	OTYNJ4KP	HSF1_HUMAN	Gene/Protein Processing	[21]
NAD(P)H dehydrogenase 1 (NQO1)	OTZGGIVK	NQO1_HUMAN	Drug Response	[22]
Phosphatidylcholine translocator ABCB4 (ABCB4)	OTE6PY83	MDR3_HUMAN	Gene/Protein Processing	[23]
Transmembrane protease serine 2 (TMPRSS2)	OTN44YQ5	TMPS2_HUMAN	Gene/Protein Processing	[24]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Nitrofurantoin (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Remdesivir	DMBFZ6L	Moderate	Increased risk of hepatotoxicity by the combination of Nitrofurantoin and Remdesivir.	1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019]	[25]
Scopolamine	DMOM8AL	Minor	Altered absorption of Nitrofurantoin due to GI dynamics variation caused by Scopolamine.	Addictive disorder [6C50-6C5Z]	[26]
Bedaquiline	DM3906J	Moderate	Increased risk of hepatotoxicity by the combination of Nitrofurantoin and Bedaquiline.	Antimicrobial drug resistance [MG50-MG52]	[27]
Pexidartinib	DMS2J0Z	Major	Increased risk of hepatotoxicity by the combination of Nitrofurantoin and Pexidartinib.	Bone/articular cartilage neoplasm [2F7B]	[28]
Mepenzolate	DM8YU2F	Minor	Altered absorption of Nitrofurantoin due to GI dynamics variation caused by Mepenzolate.	Digestive system disease [DE2Z]	[26]
Oxybutynine	DMJPBAX	Minor	Altered absorption of Nitrofurantoin due to GI dynamics variation caused by Oxybutynine.	Discovery agent [N.A.]	[26]
Ethotoin	DMXWOCP	Moderate	Increased metabolism of Nitrofurantoin caused by Ethotoin mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[29]
Cannabidiol	DM0659E	Moderate	Increased risk of hepatotoxicity by the combination of Nitrofurantoin and Cannabidiol.	Epileptic encephalopathy [8A62]	[30]
Solifenacin	DMG592Q	Minor	Altered absorption of Nitrofurantoin due to GI dynamics variation caused by Solifenacin.	Functional bladder disorder [GC50]	[26]
Tolterodine	DMSHPW8	Minor	Altered absorption of Nitrofurantoin due to GI dynamics variation caused by Tolterodine.	Functional bladder disorder [GC50]	[26]
Propantheline	DM2EN6G	Minor	Altered absorption of Nitrofurantoin due to GI dynamics variation caused by Propantheline.	Gastric ulcer [DA60]	[26]
Brentuximab vedotin	DMWLC57	Moderate	Increased risk of peripheral neuropathy by the combination of Nitrofurantoin and Brentuximab vedotin.	Hodgkin lymphoma [2B30]	[31]
Mipomersen	DMGSRN1	Major	Increased risk of hepatotoxicity by the combination of Nitrofurantoin and Mipomersen.	Hyper-lipoproteinaemia [5C80]	[32]
Teriflunomide	DMQ2FKJ	Major	Increased risk of hepatotoxicity by the combination of Nitrofurantoin and Teriflunomide.	Hyper-lipoproteinaemia [5C80]	[33]
BMS-201038	DMQTAGO	Major	Increased risk of hepatotoxicity by the combination of Nitrofurantoin and BMS-201038.	Hyper-lipoproteinaemia [5C80]	[34]
Belladonna	DM2RBWK	Minor	Altered absorption of Nitrofurantoin due to GI dynamics variation caused by Belladonna.	Infectious gastroenteritis/colitis [1A40]	[26]
Clidinium	DMUMQZ0	Minor	Altered absorption of Nitrofurantoin due to GI dynamics variation caused by Clidinium.	Irritable bowel syndrome [DD91]	[26]
Dicyclomine	DMZSDGX	Minor	Altered absorption of Nitrofurantoin due to GI dynamics variation caused by Dicyclomine.	Irritable bowel syndrome [DD91]	[26]
Calaspargase pegol	DMQZBXI	Moderate	Increased risk of hepatotoxicity by the combination of Nitrofurantoin and Calaspargase pegol.	Malignant haematopoietic neoplasm [2B33]	[35]
Idelalisib	DM602WT	Moderate	Increased risk of hepatotoxicity by the combination of Nitrofurantoin and Idelalisib.	Mature B-cell leukaemia [2A82]	[36]
Thalidomide	DM70BU5	Moderate	Increased risk of peripheral neuropathy by the combination of Nitrofurantoin and Thalidomide.	Multiple myeloma [2A83]	[37]
Prilocaine	DMI7DZ2	Major	Increased risk of methemoglobinemia by the combination of Nitrofurantoin and Prilocaine.	Pain [MG30-MG3Z]	[38]
Flavoxate	DMKV4NL	Minor	Altered absorption of Nitrofurantoin due to GI dynamics variation caused by Flavoxate.	Pain [MG30-MG3Z]	[26]
Biperiden	DME78OA	Minor	Altered absorption of Nitrofurantoin due to GI dynamics variation caused by Biperiden.	Parkinsonism [8A00]	[26]
Methylscopolamine	DM5VWOB	Minor	Altered absorption of Nitrofurantoin due to GI dynamics variation caused by Methylscopolamine.	Peptic ulcer [DA61]	[26]
Leflunomide	DMR8ONJ	Major	Increased risk of hepatotoxicity by the combination of Nitrofurantoin and Leflunomide.	Rheumatoid arthritis [FA20]	[33]
Trabectedin	DMG3Y89	Moderate	Increased risk of hepatotoxicity by the combination of Nitrofurantoin and Trabectedin.	Solid tumour/cancer [2A00-2F9Z]	[30]
Naltrexone	DMUL45H	Moderate	Increased risk of hepatotoxicity by the combination of Nitrofurantoin and Naltrexone.	Substance abuse [6C40]	[39]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Allura red AC dye	E00338	33258	Colorant
D&C red no. 33	E00261	19116	Colorant
FD&C blue no. 1	E00263	19700	Colorant
FD&C blue no. 2	E00446	2723854	Colorant
Quinoline yellow WS	E00309	24671	Colorant
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Sunset yellow FCF	E00255	17730	Colorant
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Butyl alcohol	E00011	263	Flavoring agent; Solvent
Eisenoxyd	E00585	56841934	Colorant
Ferric hydroxide oxide yellow	E00539	23320441	Colorant
Ferrosoferric oxide	E00231	14789	Colorant
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Potassium hydroxide	E00233	14797	Alkalizing agent
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
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⏷ Show the Full List of 19 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Nitrofurantoin 100 mg capsule	100 mg	Oral Capsule	Oral
Nitrofurantoin 50 mg capsule	50 mg	Oral Capsule	Oral
Nitrofurantoin 25 mg capsule	25 mg	Oral Capsule	Oral

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References

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2	Pharmacological properties of oral antibiotics for the treatment of uncomplicated urinary tract infections. J Chemother. 2017 Dec;29(sup1):10-18. doi: 10.1080/1120009X.2017.1380357.
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