Search References Drug Actions/Targets About Access data Feedback
Sign In
mitontu@gmail.com
2021 MitoTox | (CC BY-NC 4.0)
Drug

D0377 | Nitrofurantoin

Molecular Formula C8H6N4O5
Molecular Weight 238.16
Structure
State solid
Clearance The clearance of nitrofurantoin is 16.7-19.4L/h.[A179830]
Volume of distribution Data regarding the volume of distribution in humans is scarce but it has been reported as 0.46L/kg in dogs.[A179857]
Route of elimination 27-50% of an oral dose is excreted in the urine as unchanged nitrofurantoin.[A179830] 90% of the total dose is eliminated in the urine.[A179836]
Protein binding Nitrofurantoin could be up to 90% protein bound in plasma.[A179806]
Half life The half life of nitrofurantoin is 0.72-0.78h.[A179830]
Absorption Nitrofurantoin reaches a C<sub>max</sub> of 0.875-0.963mg/L with an AUC of 2.21-2.42mg\*h/L.[A179830] It is 38.8-44.3% bioavailable.[A179830] Taking nitrofurantoin with food increases the absorption and duration of therapeutic concentrations in the urine.[A179854]
Trade names Macrobid, Macrodantin
Description nitrofuran antibiotic; Nitrofurantoin is converted by bacterial nitroreductases to electrophilic intermediates which inhibit the citric acid cycle as well as synthesis of DNA, RNA, and protein.

J

J01XE51 Nitrofurantoin, combinations


[J01XE] Nitrofuran derivatives


[J01X] OTHER ANTIBACTERIALS


[J01] ANTIBACTERIALS FOR SYSTEMIC USE


[J] Antiinfectives for systemic use

J01XE01 Nitrofurantoin


[J01XE] Nitrofuran derivatives


[J01X] OTHER ANTIBACTERIALS


[J01] ANTIBACTERIALS FOR SYSTEMIC USE


[J] Antiinfectives for systemic use

Toxicity Dose Time Species Model Method Action Positive criterion Reference
UNCOUPLING increase 36
MEMBRANE POTENTIAL 26.31±6.35 human qHTS-HepG2 MMP assay decrease IC50 163
MEMBRANE POTENTIAL 8.69 human HepG2 MMP assay decrease IC50 163
MEMBRANE POTENTIAL 7.26±6.35 rat hepatocytes MMP assay decrease IC50 163
MEMBRANE POTENTIAL 442.5 µM 30 mins mouse liver mitochondria Rh123 fluorescence (excitation 485 nm, emission 535 nm) are recorded using a fluorescence multi-well plate reader (mCICCP (20 µM) treatments was considered as the 100% baseline for ΔΨm loss) decrease EC20 36
RESPIRATION 232.3 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Rotenone (2µM) was used as 100% baseline for complex I inhibition. decrease EC20 36
RESPIRATION 8.7 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Oligomycin A (1µM) was used as 100% baseline for complex II inhibition. decrease EC20 36
STATE 3 RESPIRATION 1 mM mouse; C57B/6J liver mitochondria Measurement of oxygen uptake; used glutamate as substrate decrease p < 0.05; 61% inhibition 13
STATE 3 RESPIRATION 50 μM mouse; C57B/6J liver mitochondria Measurement of oxygen uptake; used glutamate as substrate decrease p < 0.05; 72% inhibition 13
STATE 3 RESPIRATION 5 μM mouse; C57B/6J liver mitochondria Measurement of oxygen uptake; used glutamate as substrate decrease p < 0.05; 38% inhibition 13
STATE 3 RESPIRATION 1 mM mouse; C57B/6J liver mitochondria Measurement of oxygen uptake; used β-hydroxybutyrate as substrate decrease p < 0.05 13
STATE 3 RESPIRATION 50 μM mouse; C57B/6J liver mitochondria Measurement of oxygen uptake; used β-hydroxybutyrate as substrate decrease p < 0.05; 60% inhibition 13
STATE 3 RESPIRATION 5 μM mouse; C57B/6J liver mitochondria Measurement of oxygen uptake; used β-hydroxybutyrate as substrate decrease p < 0.05 13
STATE 3 RESPIRATION 1 mM mouse; C57B/6J liver mitochondria Measurement of oxygen uptake; used α-ketoghttarate as substrate decrease p < 0.05 13
STATE 3 RESPIRATION 50 μM mouse; C57B/6J liver mitochondria Measurement of oxygen uptake; used α-ketoghttarate as substrate decrease p < 0.05; 70% inhibition 13
STATE 3 RESPIRATION 5 μM mouse; C57B/6J liver mitochondria Measurement of oxygen uptake; used α-ketoghttarate as substrate decrease p < 0.05 13
ELECTRON TRANSPORT CHAIN decrease 35
DNP-UNCOUPLED RESPIRATION 1 mM mouse; C57B/6J liver mitochondria Measurement of oxygen uptake decrease p < 0.05 13
DNP-UNCOUPLED RESPIRATION 0.05mM mouse; C57B/6J liver mitochondria Measurement of oxygen uptake Negative p < 0.05 13
DNP-UNCOUPLED RESPIRATION 0.005mM mouse; C57B/6J liver mitochondria Measurement of oxygen uptake decrease p < 0.05 13
DNP-UNCOUPLED RESPIRATION 1 mM mouse; C57B/6J liver mitochondria Measurement of oxygen uptake decrease p < 0.05 13
DNP-UNCOUPLED RESPIRATION 0.05mM mouse; C57B/6J liver mitochondria Measurement of oxygen uptake decrease p < 0.05 13
DNP-UNCOUPLED RESPIRATION 1 mM mouse; C57B/6J liver mitochondria Measurement of oxygen uptake decrease p < 0.05 13
DNP-UNCOUPLED RESPIRATION 0.05mM mouse; C57B/6J liver mitochondria Measurement of oxygen uptake decrease p < 0.05 13
GLUCOSE GALACTOSE IC50 RATIO permeabilized LUHMES cells Assessment of the function of individual mitochondrial complexes using Agilent Seahorse XFe24 Negative EC25(NA) [Glc/Gal] 326
SWELLING > 800 µM 30 mins mouse liver mitochondria swelling assay: Absorbance at 545 nm using a fluorescence multi-well plate reader (CaCl2 (50 µM) was considered as the 100% baseline for the swelling ) increase EC20 36

Target Dose Time Species Model Method Action Positive criterion Reference
NADH:ubiquinone reductase inhibitor 35
NADH:ubiquinone reductase 232.3 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Rotenone (2µM) was used as 100% baseline for complex I inhibition. inhibit EC20 36
Succinate dehydrogenase 8.7 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Oligomycin A (1µM) was used as 100% baseline for complex II inhibition. inhibit EC20 36
Cytochrome c > 400 µM 30 mins mouse liver mitochondria Cytochrome c release was evaluated using ELISA kit ( 20 µg/ml Alamethicin was used as 100% baseline) release EC20 36

Pictogram Signal Statements Precautionary Statement Codes
Danger

Aggregated GHS information provided by 91 companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


H302 (93.41%): Harmful if swallowed [Warning Acute toxicity, oral]


H317 (58.24%): May cause an allergic skin reaction [Warning Sensitization, Skin]


H334 (59.34%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]


H361 (10.99%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]


Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.


 P201, P202, P261, P264, P270, P272, P280, P281, P285, P301+P312, P302+P352, P304+P341, P308+P313, P321, P330, P333+P313, P342+P311, P363, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

Organism Test type Route Dose (normalized dose) Effect Source
rat LD50 oral 1493mg/kg (1493mg/kg) Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
rat LD50 subcutaneous 178mg/kg (178mg/kg) Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.

  • Abscess

  • Angioedema

  • Arthralgia

  • Asthma

  • Bacteriuria

  • Bladder pain

  • Body temperature increased

  • Cystitis noninfective

  • Dermatitis

  • Drug hypersensitivity

  • Infection

  • Musculoskeletal discomfort

  • Pancreatitis

  • Pruritus

  • Pyelonephritis

  • Rash

  • Sialoadenitis

  • Urinary tract infection

  • Urticaria

  • Flatulence (0.00015)

  • Headache (6e-04)

  • Nausea (8e-04)

    • (E)-1-(((5-Nitrofuran-2-yl)methylene)amino)imidazolidine-2,4-dione (E)-1-[(5-nitro-2-furyl)methylideneamino]imidazolidine-2,4-dione 1-(((5-Nitrofuran-2-yl)methylene)-amino)imidazolidine-2,4-dione
    1-(((5-Nitrofuran-2-yl)methylene)amino)imidazolidine-2,4-dione 1-(((5-nitro-2-furanyl)methylene)amino)-2,4-imidazolidinedione 1-((5-Nitrofurfurylidene)amino)hydantoin
    1-((5-nitro-2-furanyl)methylene)amino-2,4-imidazolidenedione 1-((5-nitrofurfurylidene)amino)-hydantoin 1-(5-Nitro-2-furfurylidenamino)hydantoin
    1-(5-Nitro-2-furfurylideneamino)hydantoin 1-([(5-Nitro-2-furyl)methylidene]amino)-2,4-imidazolidinedione # 1-[(1E)-2-(5-nitro(2-furyl))-1-azavinyl]-1,3-diazolidine-2,4-dione
    1-[(5-:nitrofurfurylidene)amino]hydantoin 1-[(5-Nitrofurfurylidene)amino]hydantoin 1-[(E)-(5-nitro-2-furanyl)methylideneamino]imidazolidine-2,4-dione
    1-[(E)-(5-nitro-2-furyl)methyleneamino]imidazolidine-2,4-dione 1-[(E)-(5-nitrofuran-2-yl)methylideneamino]imidazolidine-2,4-dione 1-[[(5-Nitro-2-furanyl)methylene]amino]-2,4-imidazolidinedione
    1-[[(5-nitrofuran-2-yl)methylene]amino]imidazolidine-2,4-dione 1-{[(1E)-(5-nitro-2-furyl)methylene]amino}imidazolidine-2,4-dione 1-{[(1E)-(5-nitrofuran-2-yl)methylidene]amino}imidazolidine-2,4-dione
    1-{[(5-nitro-2-furyl)methylene]amino}imidazolidine-2,4-dione 1-{[(5-nitrofuran-2-yl)methylidene]amino}imidazolidine-2,4-dione 1-{[(E)-(5-nitrofuran-2-yl)methylidene]amino}imidazolidine-2,4-dione
    1-{[(E)-1-(5-nitro-2-furyl)methylidene]amino}-1H-imidazole-2,4(3H,5H)-dione 178170-37-1 2,4-Imidazolidenedione, 1-(((5-nitro-2-furanyl)methylene)amino)-
    2,4-Imidazolidinedione, 1-(((5-nitro-2-furanyl)methylene)amino)- 2,4-Imidazolidinedione, 1-[[(5-nitro-2-furanyl)methylene]amino]- 4-hydroxy-1-{[(E)-(5-nitrofuran-2-yl)methylidene]amino}-1,5-dihydro-2H-imidazol-2-one
    5-Nitrofurantoin 5-Nitrofurantoindorn 67-20-9
    927AH8112L A16008 A835659
    AB00052052_03 AB00513815 AI3-26388
    AKOS001678301 ARONIS27199 Alfuran
    BDBM57045 BIDD:GT0181 BPBio1_000039
    BRD-K76927775-001-05-0 BSPBio_000035 BSPBio_002073
    Benkfuran Berkfuran Berkfurin
    C07268 C8H6N4O5 CCG-40108
    CCRIS 1192 CHEBI:71415 CHEBI:95222
    CHEMBL572 CPD000058271 Ceduran
    Certified Reference Material Chemiofuran Cistofuran
    Cyantin Cystit D00439
    DB00698 Dantafur EINECS 200-646-5
    Fua Med Fuamed Fur-ren
    Furabid Furachel Furadantin
    Furadantin (TN) Furadantin Retard Furadantina MC
    Furadantine Furadantine mc Furadantine-MC
    Furadantoin Furadoin Furadoine
    Furadonin Furadonine Furadoninum
    Furadontin Furadoxyl Furalan
    Furaloid Furantoin Furantoina
    Furatoin Furedan Furina
    Furobactina Furodantin Furophen T
    Furophen T-Caps Gerofuran HMS1568B17
    HMS1920P21 HMS2091H16 HMS2095B17
    HMS3712B17 HMS500L06 HSDB 3135
    HY-A0090 Hydantoin, 1-((5-nitrofurfurylidene)amino)- Hydantoin, 1-[(5-nitrofurfurylidene)amino]-
    Hydantoin, 1-[(5-nitrofurfurylidene)amino]- (7CI,8CI) Hydantoin, n-(5-nitro-2-furfurylidene)-1-amino- IDI1_000224
    Ituran Ivadantin J01XE01
    J10193 LS-1560 MFCD00003224
    MLS000028500 Macpac Macrobid
    Macrodantin Macrodantina Macrofuran
    Macrofurin 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-furfurylidine)-1-aminohydantoin N-(5-Nitrofurfurylidene)-1-aminohydantoin
    N-(5-Nitrofurfurylidene)-1aminohydantoin N-(5-nitro-2-furfurylidene)-1-aminohyda ntoin N-Toin
    N0883 NCGC00091505-01 NCGC00091505-03
    NCGC00091505-04 NCGC00091505-05 NCGC00091505-06
    NCGC00091505-07 NCGC00091505-08 NCGC00091505-09
    NCGC00091505-10 NCI-C55196 ND-3320
    ND-7248 NITROFURANTION NITROFURANTOIN MACROCRYSTALLINE
    NITROFURANTOIN, MACROCRYSTALLINE NSC 2107 NSC 44150
    NSC-2107 NSC-757243 NSC2107
    NSC44150 NSC757243 NXFQHRVNIOXGAQ-YCRREMRBSA-N
    Nierofu Nifurantin Nifuretten
    Nitoin Nitrex Nitrofur-C
    Nitrofuradantin Nitrofurantoin (JAN/USP/INN) Nitrofurantoin Macro
    Nitrofurantoin Macrocrystals Nitrofurantoin [USAN:INN:BAN:JAN] Nitrofurantoin [USP:INN:BAN:JAN]
    Nitrofurantoin anhydrous Nitrofurantoin macrocrystal Nitrofurantoin, 97%
    Nitrofurantoin, 98% Nitrofurantoin, Antibiotic for Culture Media Use Only Nitrofurantoin, Pharmaceutical Secondary Standard
    Nitrofurantoin, United States Pharmacopeia (USP) Reference Standard Nitrofurantoin, VETRANAL(TM), analytical standard Nitrofurantoin, crystalline
    Nitrofurantoin, macrocrystals Nitrofurantoina Nitrofurantoina [DCIT]
    Nitrofurantoine Nitrofurantoine [INN-French] Nitrofurantoinum
    Nitrofurantoinum [INN-Latin] Nitrofurantoinum anhydrous Novofuran
    Orafuran Parfuran Pharmakon1600-01500433
    Phenurin PiyEloseptyl Prestwick2_000168
    Prestwick3_000168 Prestwick_358 PubChem6954
    Q-201479 RTR-022602 Ro-Antoin
    SAM002554913 SBB056985 SBI-0051457.P003
    SC-06194 SCHEMBL29470 SCHEMBL29472
    SMR000058271 SPECTRUM1500433 SR-05000001681
    SR-05000001681-1 SR-05000001681-2 SR-05000001681-3
    SR-05000001681-4 ST24031483 STK009471
    STL454163 Siraliden Spectrum5_001367
    TR-022602 Trantoin UNII-927AH8112L
    Uerineks Urantoin Urizept
    Uro-Selz Uro-Tablinen Urodin
    Urofuran Urofurin Urolisa
    Urolong Usaf ea-2 Uvamin
    Welfurin Z-1941 ZINC7997568
    Zoofurin cid_4509 fua-med
    furophen nitrofurantoin s4536
    uro-tablineu urodil

    DrugBank Name Nitrofurantoin
    DrugBank DB00698
    CAS Number 178170-37-1, 54-87-5, 67-20-9
    PubChem Compound 6604200
    KEGG Compound ID C07268
    KEGG Drug D00439
    PubChem.Substance 46504447
    ChEBI 71415
    PharmGKB PA450640
    ChemSpider 5036498
    BindingDB 57045.0
    TTD DAP000998
    Wikipedia Nitrofurantoin
    DPD 10196