nitrofurantoin Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
NO2 - derivatives 1949 67-20-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • nitrofurantoin sodium
  • nitrofurantoin
  • furadantin
  • furadantoin
  • nitrofurantoin, macrocrystalline
  • nitrofurantoin monohydrate
A urinary anti-infective agent effective against most gram-positive and gram-negative organisms. Although sulfonamides and antibiotics are usually the agents of choice for urinary tract infections, nitrofurantoin is widely used for prophylaxis and long-term suppression.
  • Molecular weight: 238.16
  • Formula: C8H6N4O5
  • CLOGP: -0.47
  • LIPINSKI: 0
  • HAC: 9
  • HDO: 1
  • TPSA: 120.73
  • ALOGS: -2.76
  • ROTB: 3

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.20 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 4 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.19 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 47 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 24 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 87 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.57 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 9.70 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.17 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 0.97 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Feb. 6, 1953 FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug hypersensitivity 928.13 40.37 276 1169 46367 2310273
Autoimmune hepatitis 371.54 40.37 71 1374 1624 2355016
Jaundice 238.17 40.37 61 1384 5447 2351193
Pulmonary fibrosis 238.14 40.37 53 1392 2587 2354053
Drug-induced liver injury 235.95 40.37 56 1389 3643 2352997
Dyspnoea 209.06 40.37 110 1335 78623 2278017
Rash 180.10 40.37 91 1354 59467 2297173
Interstitial lung disease 150.61 40.37 46 1399 7766 2348874
Nausea 140.79 40.37 97 1348 112092 2244548
Vomiting 137.19 40.37 81 1364 71521 2285119
Pyrexia 122.04 40.37 68 1377 53640 2303000
Liver injury 116.47 40.37 29 1416 2285 2354355
Hepatitis 112.25 40.37 35 1410 6302 2350338
Hepatic fibrosis 107.28 40.37 21 1424 537 2356103
Malaise 101.22 40.37 61 1384 55524 2301116
Hepatic cirrhosis 101.14 40.37 26 1419 2327 2354313
Acute hepatic failure 93.40 40.37 25 1420 2617 2354023
Drug reaction with eosinophilia and systemic symptoms 83.30 40.37 27 1418 5491 2351149
Pulmonary toxicity 79.66 40.37 17 1428 672 2355968
Respiratory failure 79.47 40.37 33 1412 13495 2343145
Urinary tract infection 79.07 40.37 42 1403 29900 2326740
Liver function test abnormal 79.01 40.37 28 1417 7462 2349178
Chills 78.30 40.37 34 1411 15518 2341122
Alanine aminotransferase increased 71.67 40.37 31 1414 14001 2342639
Cough 69.68 40.37 40 1405 33077 2323563
International normalised ratio increased 68.26 40.37 25 1420 7311 2349329
Maternal exposure during pregnancy 66.75 40.37 30 1415 14833 2341807
Hepatotoxicity 64.82 40.37 20 1425 3461 2353179
Coagulopathy 63.98 40.37 19 1426 2890 2353750
Hepatic necrosis 61.29 40.37 15 1430 1095 2355545
Liver transplant 59.50 40.37 13 1432 574 2356066
Aspartate aminotransferase increased 58.34 40.37 26 1419 12586 2344054
Abdominal pain 57.91 40.37 36 1409 34338 2322302
Hypersensitivity pneumonitis 57.17 40.37 12 1433 437 2356203
Fatigue 56.90 40.37 51 1394 84822 2271818
Leukocytosis 55.98 40.37 18 1427 3558 2353082
Hepatic failure 55.18 40.37 20 1425 5669 2350971
Chronic hepatitis 54.34 40.37 10 1435 181 2356459
Pneumonitis 53.83 40.37 18 1427 4021 2352619
Hepatitis acute 51.74 40.37 14 1431 1521 2355119
Cholestasis 51.25 40.37 17 1428 3704 2352936
Eosinophilia 50.82 40.37 16 1429 2954 2353686
Systemic inflammatory response syndrome 50.55 40.37 12 1433 769 2355871
Toxicity to various agents 49.40 40.37 32 1413 32722 2323918
Blood bilirubin increased 48.89 40.37 18 1427 5327 2351313
Transaminases increased 47.76 40.37 17 1428 4570 2352070
Clostridium difficile colitis 47.54 40.37 14 1431 2065 2354575
Rales 46.12 40.37 12 1433 1121 2355519
Vasculitis 46.03 40.37 14 1431 2304 2354336
Acute febrile neutrophilic dermatosis 45.66 40.37 10 1435 446 2356194
Decreased appetite 45.46 40.37 29 1416 28862 2327778
Diarrhoea 44.05 40.37 44 1401 83520 2273120
Pruritus 43.51 40.37 33 1412 43307 2313333
Myalgia 43.24 40.37 26 1419 23307 2333333
Dizziness 42.69 40.37 37 1408 58628 2298012
Wheezing 42.29 40.37 17 1428 6367 2350273
Blood alkaline phosphatase increased 41.88 40.37 17 1428 6528 2350112
Exposure during pregnancy 41.37 40.37 26 1419 25193 2331447
Acute kidney injury 41.21 40.37 27 1418 28095 2328545
Hypersensitivity 40.40 40.37 25 1420 23568 2333072

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Pulmonary fibrosis 78.21 51.21 17 252 2487 1744025
Drug hypersensitivity 67.80 51.21 22 247 15113 1731399
Dyspnoea 53.36 51.21 26 243 52033 1694479
Pulmonary toxicity 51.48 51.21 10 259 829 1745683
Melanocytic naevus 51.36 51.21 9 260 422 1746090

Pharmacologic Action:

SourceCodeDescription
ATC J01XE01 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
OTHER ANTIBACTERIALS
Nitrofuran derivatives
ATC J01XE51 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
OTHER ANTIBACTERIALS
Nitrofuran derivatives
FDA EPC N0000175494 Nitrofuran Antibacterial
FDA CS M0014892 Nitrofurans
CHEBI has role CHEBI:35441 antiinfective agent
CHEBI has role CHEBI:36047 antibacterial drug
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000892 Anti-Infective Agents, Urinary

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Klebsiella cystitis indication 60867007
Escherichia coli urinary tract infection indication 301011002
Staphylococcus Saprophyticus Urinary Tract Infection indication
Enterobacter Cystitis indication
Enterococcus Urinary Tract Infection indication
Staphylococcus Aureus Urinary Tract Infection indication
Prevention of Bacterial Urinary Tract Infection off-label use
Anuria contraindication 2472002 DOID:2983
Acute hepatitis contraindication 37871000
Vitamin B deficiency contraindication 47903000
Fibrosis of lung contraindication 51615001 DOID:3770
Obstructive hyperbilirubinemia contraindication 59848001
Interstitial pneumonia contraindication 64667001
Optic neuritis contraindication 66760008 DOID:1210
Diabetes mellitus contraindication 73211009 DOID:9351
Chronic hepatitis contraindication 76783007 DOID:2237
Oliguria contraindication 83128009
Cholestatic hepatitis contraindication 95556007
Anemia due to enzyme deficiency contraindication 111577008
Deficiency of glucose-6-phosphate dehydrogenase contraindication 124134002 DOID:2862
Cobalamin deficiency contraindication 190634004
Impaired renal function disorder contraindication 197663003
Drug-induced hepatitis contraindication 235876009
Peripheral nerve disease contraindication 302226006
Pseudomembranous enterocolitis contraindication 397683000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.28 acidic
pKa2 0.0 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Glucose-6-phosphate 1-dehydrogenase Enzyme WOMBAT-PK

External reference:

IDSource
4018849 VUID
N0000147151 NUI
C0028156 UMLSCUI
D00439 KEGG_DRUG
85343003 SNOMEDCT_US
4018849 VANDF
7454 RXNORM
373543005 SNOMEDCT_US
5179 MMSL
d00112 MMSL
181427 MMSL
002852 NDDF
927AH8112L UNII
488 INN_ID
6604200 PUBCHEM_CID
CHEBI:71415 CHEBI
CHEMBL572 ChEMBL_ID
DB00698 DRUGBANK_ID
17140-81-7 SECONDARY_CAS_RN
CHEMBL1201000 ChEMBL_ID
D009582 MESH_DESCRIPTOR_UI

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Nitrofurantoin Macrocrystals HUMAN PRESCRIPTION DRUG LABEL 1 0115-1643 CAPSULE 50 mg ORAL ANDA 14 sections
Nitrofurantoin Macrocrystals HUMAN PRESCRIPTION DRUG LABEL 1 0115-1645 CAPSULE 100 mg ORAL ANDA 14 sections
Nitrofurantoin (monohydrate/macrocrystals) HUMAN PRESCRIPTION DRUG LABEL 2 0185-0122 CAPSULE 25 mg ORAL ANDA 14 sections
Nitrofurantoin (monohydrate/macrocrystals) HUMAN PRESCRIPTION DRUG LABEL 2 0185-0122 CAPSULE 75 mg ORAL ANDA 14 sections
Nitrofurantoin Monohydrate/Macrocrystals HUMAN PRESCRIPTION DRUG LABEL 2 0378-3422 CAPSULE 25 mg ORAL ANDA 13 sections
Nitrofurantoin Monohydrate/Macrocrystals HUMAN PRESCRIPTION DRUG LABEL 2 0378-3422 CAPSULE 75 mg ORAL ANDA 13 sections
Nitrofurantoin Macrocrystals HUMAN PRESCRIPTION DRUG LABEL 1 0440-1866 CAPSULE 100 mg ORAL ANDA 14 sections
Nitrofurantoin HUMAN PRESCRIPTION DRUG LABEL 1 0472-1992 SUSPENSION 25 mg ORAL ANDA 11 sections
Nitrofurantoin HUMAN PRESCRIPTION DRUG LABEL 1 0591-3684 CAPSULE 25 mg ORAL ANDA 12 sections
Nitrofurantoin HUMAN PRESCRIPTION DRUG LABEL 1 0591-3685 CAPSULE 50 mg ORAL ANDA 12 sections
Nitrofurantoin HUMAN PRESCRIPTION DRUG LABEL 1 0591-3686 CAPSULE 100 mg ORAL ANDA 12 sections
nitrofurantoin macrocrystals HUMAN PRESCRIPTION DRUG LABEL 1 0904-7025 CAPSULE 100 mg ORAL ANDA 13 sections
nitrofurantoin macrocrystals HUMAN PRESCRIPTION DRUG LABEL 1 0904-7026 CAPSULE 50 mg ORAL ANDA 13 sections
Nitrofurantoin Monohydrate/ Macrocrystalline HUMAN PRESCRIPTION DRUG LABEL 2 10544-086 CAPSULE 25 mg ORAL NDA 14 sections
Nitrofurantoin Monohydrate/ Macrocrystalline HUMAN PRESCRIPTION DRUG LABEL 2 10544-086 CAPSULE 75 mg ORAL NDA 14 sections
Nitrofurantoin Macrocrystals HUMAN PRESCRIPTION DRUG LABEL 1 10544-601 CAPSULE 100 mg ORAL ANDA 13 sections
Nitrofurantion Macrocrystals HUMAN PRESCRIPTION DRUG LABEL 1 12634-415 CAPSULE 100 mg ORAL NDA 11 sections
Nitrofurantoin HUMAN PRESCRIPTION DRUG LABEL 2 13811-719 CAPSULE 25 mg ORAL ANDA 13 sections
Nitrofurantoin HUMAN PRESCRIPTION DRUG LABEL 2 13811-719 CAPSULE 75 mg ORAL ANDA 13 sections
NITROFURANTOIN MACROCRYSTALS HUMAN PRESCRIPTION DRUG LABEL 1 16590-380 CAPSULE 100 mg ORAL ANDA 13 sections
Nitrofurantoin (monohydrate/macrocrystals) HUMAN PRESCRIPTION DRUG LABEL 2 16714-439 CAPSULE 25 mg ORAL ANDA 14 sections
Nitrofurantoin (monohydrate/macrocrystals) HUMAN PRESCRIPTION DRUG LABEL 2 16714-439 CAPSULE 75 mg ORAL ANDA 14 sections
Nitrofurantoin (monohydrate/macrocrystals) HUMAN PRESCRIPTION DRUG LABEL 2 21695-300 CAPSULE 75 mg ORAL ANDA 14 sections
Nitrofurantoin (monohydrate/macrocrystals) HUMAN PRESCRIPTION DRUG LABEL 2 21695-300 CAPSULE 25 mg ORAL ANDA 14 sections
Nitrofurantoin Monohydrate/ Macrocrystalline HUMAN PRESCRIPTION DRUG LABEL 2 33261-160 CAPSULE 75 mg ORAL NDA 13 sections
Nitrofurantoin Monohydrate/ Macrocrystalline HUMAN PRESCRIPTION DRUG LABEL 2 33261-160 CAPSULE 25 mg ORAL NDA 13 sections
Nitrofurantion Macrocrystals HUMAN PRESCRIPTION DRUG LABEL 1 33261-226 CAPSULE 100 mg ORAL NDA 11 sections
Nitrofurantoin HUMAN PRESCRIPTION DRUG LABEL 1 40032-450 SUSPENSION 25 mg ORAL ANDA 13 sections
Nitrofurantoin macrocrystals HUMAN PRESCRIPTION DRUG LABEL 1 40032-641 CAPSULE 50 mg ORAL ANDA 13 sections
Nitrofurantoin macrocrystals HUMAN PRESCRIPTION DRUG LABEL 1 40032-642 CAPSULE 100 mg ORAL ANDA 13 sections