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

Stem definitionDrug idCAS RN
antibacterials, nalidixic acid derivatives 1981 82419-36-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • gailuoxian
  • ofloxacine
  • oxaldin
  • prifloxcin
  • prifloxin
  • ofloxacin
  • ofloxacin hydrochloride
  • ofloxacin HCl
A synthetic fluoroquinolone antibacterial agent that inhibits the supercoiling activity of bacterial DNA GYRASE, halting DNA REPLICATION.
  • Molecular weight: 361.37
  • Formula: C18H20FN3O4
  • CLOGP: -0.51
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 1
  • TPSA: 73.32
  • ALOGS: -2.40
  • ROTB: 2

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
0.40 g O
0.40 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 3.54 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 64 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 31.62 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 1.60 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 2.50 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.75 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 8.90 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Dec. 28, 1990 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 resistance 107.07 38.55 23 515 2601 2354946
Toxic anterior segment syndrome 103.60 38.55 16 522 277 2357270
Confusional state 81.62 38.55 30 508 24314 2333233
Drug hypersensitivity 59.72 38.55 29 509 46614 2310933
Tendonitis 55.13 38.55 13 525 2214 2355333
Encephalopathy 50.45 38.55 14 524 4547 2353000
Hepatitis 45.90 38.55 14 524 6323 2351224
Renal necrosis 44.42 38.55 6 532 37 2357510
Psychotic disorder due to a general medical condition 44.28 38.55 6 532 38 2357509
Drug reaction with eosinophilia and systemic symptoms 43.44 38.55 13 525 5505 2352042
Hypopyon 43.25 38.55 7 531 164 2357383
Pyrexia 41.85 38.55 24 514 53684 2303863
Seizure 39.79 38.55 18 520 24448 2333099
Corneal deposits 38.79 38.55 6 532 104 2357443

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
Type 2 lepra reaction 142.17 41.14 19 548 54 1746160
Tendonitis 113.92 41.14 24 543 1409 1744805
Drug reaction with eosinophilia and systemic symptoms 102.12 41.14 28 539 5042 1741172
Skin hyperpigmentation 71.65 41.14 14 553 557 1745657
Thrombocytopenia 62.84 41.14 28 539 21221 1724993
Hepatitis 62.29 41.14 19 548 4936 1741278
Haemolytic anaemia 60.15 41.14 15 552 1847 1744367
Cholestasis 58.90 41.14 17 550 3648 1742566
Hepatocellular injury 56.46 41.14 16 551 3215 1742999
Neuralgia 53.93 41.14 13 554 1389 1744825
Acute kidney injury 52.38 41.14 29 538 34915 1711299
Drug dependence 51.52 41.14 15 552 3312 1742902
Agranulocytosis 50.45 41.14 15 552 3561 1742653
Distal intestinal obstruction syndrome 50.07 41.14 7 560 30 1746184
Pyrexia 47.25 41.14 30 537 46370 1699844
Encephalopathy 47.21 41.14 15 552 4437 1741777
Motion sickness 44.25 41.14 7 560 78 1746136
Confusional state 44.17 41.14 22 545 21256 1724958
Drug resistance 43.17 41.14 13 554 3217 1742997
Tendon disorder 42.96 41.14 9 558 507 1745707
Eosinophilia 42.05 41.14 13 554 3514 1742700
Rash maculo-papular 41.42 41.14 13 554 3690 1742524

Pharmacologic Action:

SourceCodeDescription
ATC J01MA01 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
QUINOLONE ANTIBACTERIALS
Fluoroquinolones
ATC J01RA09 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
COMBINATIONS OF ANTIBACTERIALS
Combinations of antibacterials
ATC S01AE01 SENSORY ORGANS
OPHTHALMOLOGICALS
ANTIINFECTIVES
Fluoroquinolones
ATC S02AA16 SENSORY ORGANS
OTOLOGICALS
ANTIINFECTIVES
Antiinfectives
FDA EPC N0000175937 Quinolone Antimicrobial
FDA Chemical/Ingredient N0000007606 Quinolones
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000892 Anti-Infective Agents, Urinary
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
CHEBI has role CHEBI:35441 antiinfective agent
CHEBI has role CHEBI:36047 antibacterial drug
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
Lower respiratory tract infection indication 50417007
Pneumonia due to Escherichia coli indication 51530003
Bacterial pneumonia indication 53084003 DOID:874
Klebsiella cystitis indication 60867007
Acute gonococcal endometritis indication 65295003 DOID:7527
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
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
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
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
Streptococcus Pneumoniae Bronchitis indication
Complicated Klebsiella Peritonitis indication
Staphylococcus Cystitis indication
Morganella Morganii Urinary Tract Infection indication
Staphylococcus Aureus Bronchitis indication
Staphylococcus Saprophyticus Urinary Tract Infection indication
Haemophilus Influenzae Bronchitis indication
Enterococcus Urinary Tract Infection indication
Nosocomial Pneumonia due to Escherichia Coli indication
Skin and Skin Structure Citrobacter Infection indication
Skin and Skin Structure Pseudomonas Aeruginosa Infection indication
Synergy for Nosocomial Pneumonia due to Pseudomonas Aeruginosa indication
Chronic Enterococcus faecalis Prostatitis indication
Citrobacter Cystitis indication
Pseudomonas Aeruginosa Osteomyelitis indication
Colorectal Surgery Infection Prevention indication
Bacterial Corneal Ulcer Infection indication
Haemophilus Parainfluenzae Bronchitis indication
Enterococcus Complicated UTI indication
Legionella Pneumophila Pneumonia indication
Complicated E. Coli Peritonitis indication
Klebsiella Nosocomial Pneumonia indication
Nosocomial Pneumonia due to Methicillin-Sensitive Staphylococcus Aureus indication
Mixed Gonococcal and Chlamydia Infection of the Cervix indication
Complicated Skin and Skin Structure Staphylococcus Aureus Infection indication
Serratia Urinary Tract Infection indication
Staphylococcus Aureus Otitis Externa indication
Diarrhea due to E. Coli indication
Streptococcus Pneumoniae Chronic Bronchitis indication
Moraxella Catarrhalis Pneumonia indication
Skin and Skin Structure Proteus Infection indication
E. Coli Pyelonephritis indication
Serratia Osteomyelitis indication
Staphylococcus Epidermidis Urinary Tract Infection indication
E. Coli Cystitis indication
Citrobacter Complicated UTI indication
Citrobacter Urinary Tract Infection indication
Pseudomonas Aeruginosa Joint Infection indication
Complicated UTI with Pseudomonas Aeruginosa indication
Pseudomonas Aeruginosa Urinary Tract Infection indication
Chronic Escherichia coli Prostatitis indication
Complicated Skin and Skin Structure Streptococcus Pyogenes Infection indication
Chronic Staphylococcus epidermidis Prostatitis indication
Haemophilus Parainfluenzae Pneumonia indication
Moraxella Catarrhalis Chronic Bronchitis indication
Chronic Bacterial Prostatitis indication
Complicated Proteus UTI indication
Enterobacter Osteomyelitis indication
Complicated Skin and Skin Structure Proteus Infection indication
Haemophilus Influenzae Chronic Bronchitis indication
Providencia Urinary Tract Infection indication
Nosocomial Pneumonia due to Serratia Marcescens indication
Chlamydia Cervicitis indication
Pelvic Inflammatory Disease with Neisseria Gonorrhea indication
Complicated Bacterial Peritonitis indication
Enterobacter Cystitis indication
Gram-Negative Aerobic Bacillary Pneumonia indication
Proteus Prostatitis indication
Skin and Skin Structure Serratia Infection indication
Staphylococcus Epidermidis Skin and Skin Structure Infection indication
Complicated Skin and Skin Structure Enterococcus Faecalis Infection indication
Serratia Joint Infection indication
Pseudomonas Aeruginosa Cystitis indication
Complicated Bacteroides Peritonitis indication
Skin and Skin Structure Morganella Morganii Infection indication
Mixed Gonococcal and Chlamydia Infection of the Urethra indication
Enterobacter Pneumonia indication
Vaginal Hysterectomy Infection Prevention indication
Proteus Cystitis indication
Skin and Skin Structure Providencia Infection indication
Complicated Urinary Tract Infections indication
Nosocomial Pneumonia due to Haemophilus Influenzae indication
EnterobacterJoint Infection indication
Nosocomial Pneumonia due to Klebsiella Pneumoniae indication
Complicated Skin and Skin Structure Infection indication
Nosocomial Pneumonia due to Streptococcus Pneumoniae 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
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
Torsades de pointes contraindication 31722008
Transplantation of heart contraindication 32413006
Dehydration contraindication 34095006
Tendinitis contraindication 34840004 DOID:971
Hypokalemia contraindication 43339004
Bradycardia contraindication 48867003
Hepatic failure contraindication 59927004
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
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
Tremors contraindication
Shoulder Tendonitis contraindication
Severe Cerebral Arteriosclerosis contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 6.12 acidic
pKa2 8.29 Basic
pKa3 1.12 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
Muscarinic acetylcholine receptor M1 GPCR IC50 4.41 WOMBAT-PK
Sodium-dependent serotonin transporter Transporter IC50 4.54 WOMBAT-PK
Gamma-aminobutyric acid receptor subunit alpha-2 Ion channel IC50 4.23 WOMBAT-PK
Histamine H3 receptor GPCR IC50 4.55 WOMBAT-PK
DNA gyrase subunit A Enzyme INHIBITOR IC50 5.28 WOMBAT-PK CHEMBL
Gag-Pro-Pol polyprotein Polyprotein IC50 4.82 WOMBAT-PK
GABA-A receptor; anion channel Ion channel IC50 4.96 CHEMBL
Trypsin Unclassified AC50 5.03 CHEMBL
DNA gyrase subunit B Enzyme WOMBAT-PK
CAAX prenyl protease 1 Unclassified AC50 5.71 CHEMBL

External reference:

IDSource
4019567 VUID
N0000147667 NUI
C0028902 UMLSCUI
D00453 KEGG_DRUG
96086002 SNOMEDCT_US
4019567 VANDF
7623 RXNORM
387551000 SNOMEDCT_US
47400 MMSL
5197 MMSL
d00114 MMSL
003563 NDDF
A4P49JAZ9H UNII
5322 INN_ID
CHEMBL4 ChEMBL_ID
118120-51-7 SECONDARY_CAS_RN
DB01165 DRUGBANK_ID
CHEBI:7731 CHEBI
D015242 MESH_DESCRIPTOR_UI
4583 PUBCHEM_CID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Ofloxacin HUMAN PRESCRIPTION DRUG LABEL 1 0404-7189 SOLUTION/ DROPS 3 mg OPHTHALMIC ANDA 10 sections
Ofloxacin HUMAN PRESCRIPTION DRUG LABEL 1 0517-0760 SOLUTION/ DROPS 3 mg OPHTHALMIC ANDA 11 sections
Ofloxacin HUMAN PRESCRIPTION DRUG LABEL 1 0517-0761 SOLUTION/ DROPS 3 mg OPHTHALMIC ANDA 11 sections
OCUFLOX HUMAN PRESCRIPTION DRUG LABEL 1 11980-779 SOLUTION/ DROPS 3 mg OPHTHALMIC NDA 10 sections
Ofloxacin HUMAN PRESCRIPTION DRUG LABEL 1 13985-602 SOLUTION/ DROPS 3 mg OPHTHALMIC ANDA 11 sections
OFLOXACIN HUMAN PRESCRIPTION DRUG LABEL 1 16590-175 SOLUTION/ DROPS 3 mg OPHTHALMIC ANDA 10 sections
OFLOXACIN HUMAN PRESCRIPTION DRUG LABEL 1 16590-931 SOLUTION/ DROPS 3 mg AURICULAR (OTIC) ANDA 11 sections
Ofloxacin HUMAN PRESCRIPTION DRUG LABEL 1 17478-713 SOLUTION/ DROPS 3 mg OPHTHALMIC ANDA 11 sections
Ofloxacin HUMAN PRESCRIPTION DRUG LABEL 1 21695-439 SOLUTION/ DROPS 3 mg OPHTHALMIC ANDA 11 sections
Ofloxacin HUMAN PRESCRIPTION DRUG LABEL 1 21695-881 SOLUTION/ DROPS 3 mg AURICULAR (OTIC) ANDA 11 sections
Ofloxacin HUMAN PRESCRIPTION DRUG LABEL 1 24208-410 SOLUTION 3 mg AURICULAR (OTIC) ANDA 10 sections
Ofloxacin HUMAN PRESCRIPTION DRUG LABEL 1 24208-434 SOLUTION/ DROPS 3 mg OPHTHALMIC ANDA 11 sections
Ofloxacin HUMAN PRESCRIPTION DRUG LABEL 1 33261-737 SOLUTION 3 mg AURICULAR (OTIC) ANDA 10 sections
Ofloxacin HUMAN PRESCRIPTION DRUG LABEL 1 42254-257 SOLUTION 3 mg AURICULAR (OTIC) ANDA 10 sections
Ofloxacin HUMAN PRESCRIPTION DRUG LABEL 1 50090-0891 SOLUTION/ DROPS 3 mg OPHTHALMIC ANDA 11 sections
Ofloxacin Otic HUMAN PRESCRIPTION DRUG LABEL 1 50090-1090 SOLUTION 3 mg AURICULAR (OTIC) ANDA 11 sections
Ofloxacin HUMAN PRESCRIPTION DRUG LABEL 1 50090-1346 SOLUTION/ DROPS 3 mg OPHTHALMIC ANDA 11 sections
Ofloxacin HUMAN PRESCRIPTION DRUG LABEL 1 50090-1736 SOLUTION 3 mg AURICULAR (OTIC) ANDA 10 sections
Ofloxacin HUMAN PRESCRIPTION DRUG LABEL 1 50090-3836 SOLUTION/ DROPS 3 mg AURICULAR (OTIC) ANDA 11 sections
Ofloxacin HUMAN PRESCRIPTION DRUG LABEL 1 50383-024 SOLUTION/ DROPS 3 mg OPHTHALMIC ANDA 10 sections
Ofloxacin HUMAN PRESCRIPTION DRUG LABEL 1 50383-025 SOLUTION/ DROPS 3 mg AURICULAR (OTIC) ANDA 11 sections
Ofloxacin HUMAN PRESCRIPTION DRUG LABEL 1 50436-0713 SOLUTION/ DROPS 3 mg OPHTHALMIC ANDA 11 sections
Ofloxacin HUMAN PRESCRIPTION DRUG LABEL 1 50436-6112 SOLUTION/ DROPS 3 mg OPHTHALMIC ANDA 11 sections
ofloxacin HUMAN PRESCRIPTION DRUG LABEL 1 52959-763 SOLUTION 3 mg OPHTHALMIC ANDA 11 sections
Ofloxacin HUMAN PRESCRIPTION DRUG LABEL 1 53002-1324 SOLUTION/ DROPS 3 mg OPHTHALMIC ANDA 11 sections
Ofloxacin HUMAN PRESCRIPTION DRUG LABEL 1 53002-1604 SOLUTION 3 mg AURICULAR (OTIC) ANDA 10 sections
Ofloxacin Otic HUMAN PRESCRIPTION DRUG LABEL 1 53002-2604 SOLUTION 3 mg AURICULAR (OTIC) ANDA 11 sections
Ofloxacin HUMAN PRESCRIPTION DRUG LABEL 1 54868-6035 SOLUTION/ DROPS 3 mg AURICULAR (OTIC) ANDA 12 sections
Ofloxacin HUMAN PRESCRIPTION DRUG LABEL 1 54868-6112 SOLUTION/ DROPS 3 mg OPHTHALMIC ANDA 10 sections
Ofloxacin HUMAN PRESCRIPTION DRUG LABEL 1 55111-160 TABLET, COATED 200 mg ORAL ANDA 15 sections