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

Stem definitionDrug idCAS RN
antibacterials, nalidixic acid derivatives 1967 70458-96-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • floxacin
  • norfloxacine
  • norphloxacine
  • norfloxacin
A synthetic fluoroquinolone (FLUOROQUINOLONES) with broad-spectrum antibacterial activity against most gram-negative and gram-positive bacteria. Norfloxacin inhibits bacterial DNA GYRASE.
  • Molecular weight: 319.34
  • Formula: C16H18FN3O3
  • CLOGP: -0.78
  • LIPINSKI: 0
  • HAC: 6
  • HDO: 2
  • TPSA: 72.88
  • ALOGS: -2.50
  • ROTB: 3

  • Status: OFM

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

Drug dosage:

DoseUnitRoute
0.80 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 4 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.75 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 29 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 35.79 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 35 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 1.88 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 6.96 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.13 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 4.45 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Oct. 31, 1986 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
International normalised ratio fluctuation 380.91 57.72 44 124 287 2357630
Drug intolerance 217.14 57.72 44 124 13673 2344244
Infection 210.98 57.72 45 123 17984 2339933
Therapeutic product effect incomplete 209.82 57.72 41 127 10490 2347427
Drug hypersensitivity 153.86 57.72 42 126 46601 2311316
Bloody discharge 114.92 57.72 14 154 135 2357782
Lyme disease 100.55 57.72 14 154 402 2357515
Tendonitis 64.15 57.72 12 156 2215 2355702

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

Pharmacologic Action:

SourceCodeDescription
ATC J01MA06 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
QUINOLONE ANTIBACTERIALS
Fluoroquinolones
ATC J01RA13 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
COMBINATIONS OF ANTIBACTERIALS
Combinations of antibacterials
ATC S01AE02 SENSORY ORGANS
OPHTHALMOLOGICALS
ANTIINFECTIVES
Fluoroquinolones
FDA EPC N0000175937 Quinolone Antimicrobial
FDA CS M0023650 Quinolones
CHEBI has role CHEBI:36047 antibacterial drug
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000970 Antineoplastic Agents
MeSH PA D065609 Cytochrome P-450 CYP1A2 Inhibitors
MeSH PA D065607 Cytochrome P-450 Enzyme Inhibitors
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D065606 Metabolic Side Effects of Drugs and Substances
MeSH PA D059005 Topoisomerase II Inhibitors

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Otitis externa indication 3135009
Typhoid fever indication 4834000 DOID:13258
Septicemia due to Escherichia coli indication 9323009
Prostatitis indication 9713002 DOID:14654
Infection due to Pseudomonas aeruginosa indication 11218009
Gonorrhea indication 15628003 DOID:7551
Enteric campylobacteriosis indication 18081009
Infectious diarrheal disease indication 19213003 DOID:13250
Infection of skin AND/OR subcutaneous tissue indication 19824006
Acute gonococcal cervicitis indication 20943002 DOID:10615
Staphylococcal pneumonia indication 22754005
Acute gonococcal urethritis indication 29864006
Acute bacterial peritonitis indication 31860008
Bronchitis indication 32398004 DOID:6132
Postoperative infection indication 33910007
Pneumonia due to Streptococcus indication 34020007
Shigellosis indication 36188001
Cystitis indication 38822007 DOID:1679
Pneumonia due to Pseudomonas indication 41381004
Gonorrhea of rectum indication 42746002
Pyelonephritis indication 45816000 DOID:11400
Pneumonia due to Mycoplasma pneumoniae indication 46970008
Peritonitis indication 48661000
Lower respiratory tract infection indication 50417007
Pneumonia due to Escherichia coli indication 51530003
Bacterial pneumonia indication 53084003 DOID:874
Klebsiella cystitis indication 60867007
Pneumonia due to Klebsiella pneumoniae indication 64479007
Acute gonococcal endometritis indication 65295003 DOID:7527
Miscarriage with sepsis indication 67465009
Acute maxillary sinusitis indication 68272006 DOID:2050
Urinary tract infectious disease indication 68566005
Haemophilus influenzae pneumonia indication 70036007
Infection due to Escherichia coli indication 71057007
Rhinoscleroma indication 72409005 DOID:11336
Abdominal abscess indication 75100008
Acute bacterial sinusitis indication 75498004
Nongonococcal urethritis indication 84619001
Infective otitis externa indication 86981007 DOID:9463
Chronic tubotympanic suppurative otitis media indication 87665008 DOID:14435
Endomyometritis indication 88027004
Infection of bone indication 111253001
Female genital tract infection indication 125585007
Infectious disease of abdomen indication 128070006
Bacterial conjunctivitis indication 128350005 DOID:9700
Infection due to Enterobacteriaceae indication 128945009
Postnatal infection indication 178280004
Urethritis due to Chlamydia trachomatis indication 179101003
Bacterial infection due to Klebsiella pneumoniae indication 186435004
Chlamydial pelvic inflammatory disease indication 188463006
Acute Moraxella catarrhalis bronchitis indication 195722003
Proteus pneumonia indication 195888009
Malignant otitis externa due to Pseudomonas aeruginosa indication 232230009
Acute bacterial bronchitis indication 233598009
Pneumonia indication 233604007 DOID:552
Pneumococcal pneumonia indication 233607000
Chlamydial pneumonia indication 233609002
Infective cystitis indication 236620008
Chancroid indication 266143009 DOID:13778
Female pelvic cellulitis indication 280486004
Escherichia coli urinary tract infection indication 301011002
Proteus urinary tract infection indication 301012009
Streptococcus pyogenes infection indication 302809008
Bacterial urinary infection indication 312124009
Infective otitis media indication 312218008
Infectious disorder of joint indication 363162000
Infection due to Staphylococcus aureus indication 406602003
Anthrax indication 409498004 DOID:7427
Acute osteomyelitis indication 409780002
Nosocomial pneumonia indication 425464007
Acute exacerbation of chronic bronchitis indication 425748003
Urinary tract infection caused by Klebsiella indication 369001000119100
Enterococcus Urinary Tract Infection indication
Klebsiella Pneumoniae Chronic Bronchitis indication
Pseudomonas Aeruginosa Cystitis indication
Haemophilus Parainfluenzae Chronic Bronchitis indication
Complicated Urinary Tract Infections indication
Prevotella Postpartum Infection indication
Complicated Bacterial Peritonitis indication
E. Coli Cystitis indication
Complicated Skin and Skin Structure Streptococcus Pyogenes Infection indication
Streptococcal Pelvic Cellulitis indication
Enterobacter Osteomyelitis indication
Staphylococcus Cystitis indication
Citrobacter Urinary Tract Infection indication
Bacterial Corneal Ulcer Infection indication
Enterobacter Pneumonia indication
Providencia Urinary Tract Infection indication
Complicated Skin and Skin Structure Staphylococcus Aureus Infection indication
Chlamydia Pneumoniae Bronchitis indication
Morganella Morganii Urinary Tract Infection indication
Skin and Skin Structure Morganella Morganii Infection indication
Complicated Klebsiella Peritonitis indication
Bacteroides Pelvic Cellulitis indication
Moraxella Catarrhalis Chronic Bronchitis indication
Gardnerella Septic Abortion indication
Staphylococcus Epidermidis Urinary Tract Infection indication
Haemophilus Influenzae Chronic Bronchitis indication
EnterobacterJoint Infection indication
E. Coli Endomyometritis indication
Legionella Pneumophila Pneumonia indication
Bacteroides Endomyometritis indication
Chronic Enterococcus faecalis Prostatitis indication
Gardnerella Endomyometritis indication
Pseudomonas Aeruginosa Osteomyelitis indication
Nosocomial Pneumonia due to Methicillin-Sensitive Staphylococcus Aureus indication
Enterococcus Pelvic Cellulitis indication
Serratia Joint Infection indication
Proteus Prostatitis indication
Complicated E. Coli Peritonitis indication
Skin and Skin Structure Citrobacter Infection indication
Skin and Skin Structure Proteus Infection indication
Serratia Urinary Tract Infection indication
Pseudomonas Aeruginosa Urinary Tract Infection indication
Gardnerella Postpartum Infection indication
Enterococcus Postpartum Infection indication
Bacteroides Septic Abortion indication
Prevotella Septic Abortion indication
Skin and Skin Structure Providencia Infection indication
Prevention of Infection in Transrectal Prostate Biopsy indication
Chronic Escherichia coli Prostatitis indication
Gardnerella Pelvic Cellulitis indication
Complicated Skin and Skin Structure Streptococcus Agalactiae Infection indication
Enterococcus Complicated UTI indication
Prevotella Pelvic Cellulitis indication
Diarrhea due to E. Coli indication
Complicated Proteus UTI indication
Streptococcal Endomyometritis indication
Streptococcus Pneumoniae Chronic Bronchitis indication
E. Coli Septic Abortion indication
Haemophilus Influenzae Bronchitis indication
Complicated Streptococcus Peritonitis indication
Complicated Skin and Skin Structure Infection indication
Nosocomial Pneumonia due to Escherichia Coli indication
E. Coli Pyelonephritis indication
Vaginal Hysterectomy Infection Prevention indication
Peptostreptococcus Postpartum Infection indication
Enterobacter Cloacae Bronchitis indication
Mixed Gonococcal and Chlamydia Infection of the Urethra indication
Peptostreptococcus Endomyometritis indication
Gram-Negative Aerobic Bacillary Pneumonia indication
Citrobacter Complicated UTI indication
Colorectal Surgery Infection Prevention indication
Klebsiella Nosocomial Pneumonia indication
Chlamydia Cervicitis indication
Chronic Staphylococcus epidermidis Prostatitis indication
Mixed Gonococcal and Chlamydia Infection of the Cervix indication
Nosocomial Pneumonia due to Serratia Marcescens indication
Enterococcus Endomyometritis indication
Skin and Skin Structure Streptococcus Infection indication
Nosocomial Pneumonia due to Streptococcus Pneumoniae indication
Synergy for Nosocomial Pneumonia due to Pseudomonas Aeruginosa indication
Streptococcal Septic Abortion indication
Prevotella Endomyometritis indication
Staphylococcus Aureus Otitis Externa indication
Proteus Cystitis indication
Skin and Skin Structure Serratia Infection indication
Complicated Skin and Skin Structure Proteus Infection indication
Peptostreptococcus Septic Abortion indication
Pseudomonas Aeruginosa Joint Infection indication
Moraxella Catarrhalis Pneumonia indication
Complicated Skin and Skin Structure Enterococcus Faecalis Infection indication
Pelvic Inflammatory Disease with Neisseria Gonorrhea indication
Citrobacter Cystitis indication
Serratia Osteomyelitis indication
E. Coli Postpartum Infection indication
Prevention of Infection from Transurethral Surgery indication
Bacteroides Postpartum Infection indication
Staphylococcus Aureus Bronchitis indication
Enterobacter Cystitis indication
Complicated UTI with Pseudomonas Aeruginosa indication
Streptococcal Postpartum Infection indication
E. Coli Pelvic Cellulitis indication
Complicated Skin and Skin Structure Pseudomonas Aeruginosa Infection indication
Haemophilus Parainfluenzae Bronchitis indication
Nosocomial Pneumonia due to Klebsiella Pneumoniae indication
Haemophilus Parainfluenzae Pneumonia indication
Skin and Skin Structure Pseudomonas Aeruginosa Infection indication
Staphylococcus Epidermidis Skin and Skin Structure Infection indication
Complicated Skin and Skin Structure E. Coli Infection indication
Nosocomial Pneumonia due to Haemophilus Influenzae indication
Peptostreptococcus Pelvic Cellulitis indication
Streptococcus Pneumoniae Bronchitis indication
Staphylococcus Chronic Bronchitis indication
Complicated Bacteroides Peritonitis indication
Chronic Bacterial Prostatitis indication
Enterococcus Septic Abortion indication
Staphylococcus Saprophyticus Urinary Tract Infection indication
Inhalational anthrax off-label use 11389007
Traveler's diarrhea off-label use 11840006
Acute tuberculosis off-label use 25629007
Salmonella septicemia off-label use 49786009
Cutaneous anthrax off-label use 84980006 DOID:7426
Gastrointestinal anthrax off-label use 111798006 DOID:13386
Pulmonary tuberculosis off-label use 154283005 DOID:2957
Diverticulitis of gastrointestinal tract off-label use 271366000
Bacterial gastroenteritis off-label use 274080003
Ventilator-acquired pneumonia off-label use 429271009
Prevention of Meningococcal Meningitis off-label use
Diabetic Foot Infection off-label use
Hallucinations contraindication 7011001
Achilles tendinitis contraindication 11654001
Agranulocytosis contraindication 17182001 DOID:12987
Lowered convulsive threshold contraindication 19260006
Cirrhosis of liver contraindication 19943007 DOID:5082
Torsades de pointes contraindication 31722008
Transplantation of heart contraindication 32413006
Dehydration contraindication 34095006
Tendinitis contraindication 34840004 DOID:971
Depressive disorder contraindication 35489007
Hypokalemia contraindication 43339004
Conduction disorder of the heart contraindication 44808001
Bradycardia contraindication 48867003
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Psychotic disorder contraindication 69322001
Transplant of kidney contraindication 70536003
Diabetes mellitus contraindication 73211009 DOID:9351
Epilepsy contraindication 84757009 DOID:1826
Leukopenia contraindication 84828003 DOID:615
Transplant of lung contraindication 88039007
Kidney disease contraindication 90708001 DOID:557
Myasthenia gravis contraindication 91637004 DOID:437
Prolonged QT interval contraindication 111975006
Pancytopenia contraindication 127034005 DOID:12450
Liver function tests abnormal contraindication 166603001
Hypomagnesemia contraindication 190855004
Superimposed infection contraindication 193198003
Impaired renal function disorder contraindication 197663003
Disease of liver contraindication 235856003 DOID:409
Drug-induced hepatitis contraindication 235876009
Rhabdomyolysis contraindication 240131006
Anemia contraindication 271737000 DOID:2355
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Peripheral nerve disease contraindication 302226006
Viral ear infection contraindication 312137007
Pseudomembranous enterocolitis contraindication 397683000
Myocardial ischemia contraindication 414795007 DOID:3393
Traumatic rupture of tendon contraindication 415749005
Congenital long QT syndrome contraindication 442917000
Shoulder Tendonitis contraindication
Tremors contraindication
Severe Cerebral Arteriosclerosis contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 5.98 acidic
pKa2 8.54 Basic
pKa3 1.37 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
Gamma-aminobutyric acid receptor subunit alpha-1 Ion channel IC50 6.29 WOMBAT-PK
Gamma-aminobutyric acid receptor subunit alpha-5 Ion channel IC50 6.29 WOMBAT-PK
Gamma-aminobutyric acid receptor subunit alpha-3 Ion channel IC50 6.29 WOMBAT-PK
Gamma-aminobutyric acid receptor subunit alpha-2 Ion channel IC50 6.29 WOMBAT-PK
Gamma-aminobutyric acid receptor subunit alpha-4 Ion channel IC50 6.29 WOMBAT-PK
DNA topoisomerase 2-beta Enzyme IC50 6.22 WOMBAT-PK
Gamma-aminobutyric acid receptor subunit alpha-6 Ion channel IC50 6.29 WOMBAT-PK
Multidrug and toxin extrusion protein 1 Transporter IC50 4.75 CHEMBL
DNA topoisomerase 4 subunit A Enzyme INHIBITOR IC50 5.29 WOMBAT-PK CHEMBL
DNA gyrase subunit A Enzyme INHIBITOR IC50 6.05 WOMBAT-PK CHEMBL
DNA topoisomerase 4 subunit A Enzyme IC50 5.46 CHEMBL
DNA gyrase subunit A Enzyme IC50 4.28 CHEMBL
GABA-A receptor; anion channel Ion channel IC50 7.70 CHEMBL
Multidrug resistance protein mdtK Unclassified Kd 4.01 CHEMBL

External reference:

IDSource
4019503 VUID
N0000147623 NUI
C0028365 UMLSCUI
D00210 KEGG_DRUG
49485009 SNOMEDCT_US
4019503 VANDF
7517 RXNORM
387271008 SNOMEDCT_US
5189 MMSL
d00113 MMSL
002881 NDDF
CHEMBL9 ChEMBL_ID
CHEMBL33 ChEMBL_ID
DB01059 DRUGBANK_ID
N0F8P22L1P UNII
5105 INN_ID
CHEBI:100246 CHEBI
4539 PUBCHEM_CID
D009643 MESH_DESCRIPTOR_UI

Pharmaceutical products:

None