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    Chemistry

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    Also known as: 82419-36-1, Floxin, Tarivid, Ofloxacine, Oxaldin, Ocuflox
    Molecular Formula
    C18H20FN3O4
    Molecular Weight
    361.4  g/mol
    InChI Key
    GSDSWSVVBLHKDQ-UHFFFAOYSA-N
    FDA UNII
    A4P49JAZ9H
    Ofloxacin
    A synthetic fluoroquinolone antibacterial agent that inhibits the supercoiling activity of bacterial DNA GYRASE, halting DNA REPLICATION.
    Ofloxacin is a Quinolone Antimicrobial.
    1 2D Structure

    Ofloxacin

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylic acid
    2.1.2 InChI
    InChI=1S/C18H20FN3O4/c1-10-9-26-17-14-11(16(23)12(18(24)25)8-22(10)14)7-13(19)15(17)21-5-3-20(2)4-6-21/h7-8,10H,3-6,9H2,1-2H3,(H,24,25)
    2.1.3 InChI Key
    GSDSWSVVBLHKDQ-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1COC2=C3N1C=C(C(=O)C3=CC(=C2N4CCN(CC4)C)F)C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    A4P49JAZ9H
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Dl 8280

    2. Dl-8280

    3. Dl8280

    4. Dr 3355

    5. Dr-3355

    6. Dr3355

    7. Hoe 280

    8. Hoe-280

    9. Hoe280

    10. Ofloxacin Hydrochloride

    11. Ofloxacine

    12. Orf 28489

    13. Orf-28489

    14. Orf28489

    15. Ru 43280

    16. Ru-43280

    17. Ru43280

    18. Tarivid

    2.3.2 Depositor-Supplied Synonyms

    1. 82419-36-1

    2. Floxin

    3. Tarivid

    4. Ofloxacine

    5. Oxaldin

    6. Ocuflox

    7. Hoe-280

    8. Oflx

    9. Dl-8280

    10. Ofloxacino

    11. Ofloxacinum

    12. Exocin

    13. Hoe 280

    14. Floxin Otic

    15. Dextrofloxacin

    16. 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7h-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic Acid

    17. 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-3,7-dihydro-2h-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic Acid

    18. Chebi:7731

    19. Oflocet

    20. Visiren

    21. Chembl4

    22. J01ma01

    23. Nsc-727071

    24. Nsc-758178

    25. A4p49jaz9h

    26. Mls000028749

    27. Ofloxacina

    28. Ofloxacin Otic

    29. Ofloxacina [dcit]

    30. Ofloxacine [french]

    31. Ofloxacinum [latin]

    32. Exocine

    33. Flobacin

    34. Ofloxacin 100 Microg/ml In Acetonitrile

    35. Smr000058192

    36. Zanocin

    37. Floxil

    38. Ofloxacino [spanish]

    39. Dsstox_cid_21085

    40. Dsstox_rid_79623

    41. Dsstox_gsid_41085

    42. 8-fluoro-3-methyl-9-(4-methyl-piperazin-1-yl)-6-oxo-2,3-dihydro-6h-1-oxa-3a-aza-phenalene-5-carboxylic Acid

    43. Ofx

    44. Floxin In Dextrose 5%

    45. Dl 8280

    46. Pt 01

    47. Orf 18489

    48. (-)-(s)-9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7h-pyrido[1,2,3-de]-1;(-)-(s)-9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7h-pyrido[1,2,3-de]-1

    49. 9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7h-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic Acid

    50. Floxin (tn)

    51. Ccris 5233

    52. (+/-)-floxin

    53. Sr-01000076050

    54. Mfcd00226105

    55. Unii-a4p49jaz9h

    56. Floxin In Dextrose 5% In Plastic Container

    57. Brn 3657947

    58. Monoflocet

    59. Dl-ofloxacin

    60. Hsdb 8030

    61. Ofloxacin,(s)

    62. Ncgc00016948-01

    63. Ofloxacin (floxin)

    64. Cas-82419-36-1

    65. Dl8280

    66. Exocin (eye Drops)

    67. Ofloxacin [usan:usp:inn:ban:jan]

    68. (+-)-9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7h-pyrido(1,2,3-de)-1,4-benzoxazine-6-carboxylic Acid

    69. 83380-47-6

    70. Wp-0405

    71. Spectrum_001186

    72. Ofloxacin [inn]

    73. Ofloxacin [jan]

    74. Ofloxacin [mi]

    75. (r)-ofloxacin-[d3]

    76. Ofloxacin [usan]

    77. Opera_id_1114

    78. Prestwick0_000237

    79. Prestwick1_000237

    80. Prestwick2_000237

    81. Prestwick3_000237

    82. Spectrum2_001464

    83. Spectrum3_001499

    84. Spectrum4_000324

    85. Spectrum5_001063

    86. Ofloxacin [vandf]

    87. Epitope Id:116889

    88. Ofloxacin [mart.]

    89. O 8757

    90. Ofloxacin [usp-rs]

    91. Ofloxacin [who-dd]

    92. Lopac0_000904

    93. Oprea1_242882

    94. Schembl24373

    95. Bspbio_000313

    96. Bspbio_003117

    97. Kbiogr_000667

    98. Kbioss_001666

    99. Fluoro-methyl-(4-methylpiperazin-1-yl)-oxo-[?]carboxylic Acid

    100. Mls001074203

    101. Mls006011774

    102. Divk1c_000721

    103. Spectrum1502044

    104. Spbio_001387

    105. Spbio_002234

    106. (s)-ofloxacin;levaquin;quixin

    107. Ofloxacin (jp17/usp/inn)

    108. Bpbio1_000345

    109. Ofloxacin [orange Book]

    110. Dtxsid3041085

    111. Ofloxacin [ep Monograph]

    112. Schembl14163982

    113. Gtpl10918

    114. Hms502e03

    115. Kbio1_000721

    116. Kbio2_001666

    117. Kbio2_004234

    118. Kbio2_006802

    119. Kbio3_002617

    120. Ofloxacin [usp Monograph]

    121. Chebi:194135

    122. Ninds_000721

    123. Hms1568p15

    124. Hms1921h12

    125. Hms2090f07

    126. Hms2092b10

    127. Hms2095p15

    128. Hms2235c05

    129. Hms3259g07

    130. Hms3262f10

    131. Hms3369b01

    132. Hms3393k06

    133. Hms3604b17

    134. Hms3712p15

    135. Pharmakon1600-01502044

    136. (3r)-9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7h-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic Acid

    137. (s)-9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-3,7-dihydro-2h-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic Acid

    138. Amy22220

    139. Bcp14346

    140. Bcp22048

    141. Hy-b0125

    142. Rkl10083

    143. Ofloxacin, Fluoroquinolone Antibiotic

    144. Tox21_110703

    145. Tox21_500904

    146. Bbl005605

    147. Bdbm50045004

    148. Ccg-39210

    149. Nsc727071

    150. Nsc758178

    151. S1463

    152. Stk256723

    153. Ofloxacin 100 Microg/ml In Methanol

    154. Akos001033517

    155. Akos016042783

    156. Ofloxacine; Dl-8280; Hoe-280

    157. Tox21_110703_1

    158. Ac-7616

    159. Bcp9000851

    160. Cs-1891

    161. Db01165

    162. Ks-5011

    163. Lp00904

    164. Nc00466

    165. Nsc 727071

    166. Nsc 758178

    167. Sdccgsbi-0050879.p004

    168. Idi1_000721

    169. Ncgc00015772-02

    170. Ncgc00015772-03

    171. Ncgc00015772-04

    172. Ncgc00015772-05

    173. Ncgc00015772-06

    174. Ncgc00015772-07

    175. Ncgc00015772-08

    176. Ncgc00015772-09

    177. Ncgc00015772-10

    178. Ncgc00015772-12

    179. Ncgc00015772-13

    180. Ncgc00015772-22

    181. Ncgc00094219-01

    182. Ncgc00094219-02

    183. Ncgc00094219-03

    184. Ncgc00094219-04

    185. Ncgc00094219-05

    186. Ncgc00094219-06

    187. Ncgc00178284-01

    188. Ncgc00178284-02

    189. Ncgc00261589-01

    190. (+-)-9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7h-pyrido(1,2,3-de)(1,4)benzoxazin-6-carbonsaeure

    191. (+/-)-9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7h-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic Acid

    192. 7h-pyrido(1,2,3-de)-1,4-benzoxazine-6-carboxylic Acid, 2,3-dihydro-9-fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-, (+-)-

    193. 7h-pyrido(1,2,3-de)-1,4-benzoxazine-6-carboxylic Acid, 9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-, (+-)-

    194. 9-fluoro-3,7-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2h-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic Acid

    195. Sy007392

    196. Sbi-0050879.p003

    197. Db-056608

    198. Ab00513820

    199. Eu-0100904

    200. Ft-0627808

    201. Ft-0630905

    202. Ft-0670773

    203. Ft-0673216

    204. O0403

    205. Ofloxacin, Vetranal(tm), Analytical Standard

    206. Vu0243192-7

    207. 86o854

    208. C07321

    209. D00453

    210. O-2800

    211. Ab00052263-12

    212. Ab00052263-13

    213. Ab00052263_14

    214. Ab00052263_15

    215. Ofloxacin, Antibiotic For Culture Media Use Only

    216. A864414

    217. Q411447

    218. Sr-01000076050-1

    219. Sr-01000076050-4

    220. Sr-01000076050-7

    221. Brd-a24228527-001-05-9

    222. Brd-a24228527-001-19-0

    223. Sr-01000076050-16

    224. Z56761309

    225. F0020-0095

    226. F0472-0226

    227. 7-chloro-4-hydroxy-8-methylquinoline-3-carboxylicethylester

    228. Ofloxacin, European Pharmacopoeia (ep) Reference Standard

    229. Ofloxacin, United States Pharmacopeia (usp) Reference Standard

    230. (+/-)-9-fluoro-2,2,3-de)-1,4-benzoxazine-6-carboxylic Acid

    231. 8-methyl-2,3-dihydrofuro[3,2-e]imidazo-[1,2-c]pyrimidine-9-carboxylicacid

    232. Ofloxacin, Pharmaceutical Secondary Standard; Certified Reference Material

    233. (+/-)-9-fluoro-2, 3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7h-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic Acid

    234. 7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^{5,13}]trideca-5(13),6,8,11-tetraene-11-carboxylic Acid

    235. 7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5,7,9(13),11-tetraene-11-carboxylic Acid

    236. 7h-pyrido(1,2,3-de)-1,4-benzoxazine-6-carboxylic Acid, 9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-

    237. 7h-pyrido(1,2,3-de)-1,4-benzoxazine-6-carboxylic Acid, 9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-, (+/-)-

    238. 9-fluoro-10-(4-methylpiperazino)-3-methyl-7-oxo-2,3-dihydro-7h-pyrido[1,2,3-de]-1,4-benzooxazine-6-carboxylic Acid

    239. 9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7h-pyrido(1,2,3-de)(1,4)benzoxazine-6-carboxylic Acid, Dl-

    240. 9-fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7h-pyrido [1,2,3-de]-1,4-benzoxazin-6-carboxylic Acid

    241. 9-fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7h-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic Acid

    242. 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-3,7-dihydro-2h-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylicacid

    243. 9-fluoro-3-methyl-10-(4-methylpiperazino)-7-oxo-2,3-dihydro-7h-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic Acid

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 361.4 g/mol
    Molecular Formula C18H20FN3O4
    XLogP3-0.4
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count2
    Exact Mass361.14378429 g/mol
    Monoisotopic Mass361.14378429 g/mol
    Topological Polar Surface Area73.3 Ų
    Heavy Atom Count26
    Formal Charge0
    Complexity634
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 6  
    Drug NameFloxin otic
    PubMed HealthOfloxacin (Into the ear)
    Drug ClassesAntibacterial
    Drug LabelOCUFLOX (ofloxacin ophthalmic solution) 0.3% is a sterile ophthalmic solution. It is a fluorinated carboxyquinolone anti-infective for topical ophthalmic use....
    Active IngredientOfloxacin
    Dosage FormSolution/drops
    RouteOtic
    Strength0.3%
    Market StatusPrescription
    CompanyDaiichi

    2 of 6  
    Drug NameOcuflox
    PubMed HealthOfloxacin (Into the eye)
    Drug ClassesAntibiotic
    Drug LabelTo reduce the development of drug-resistant bacteria and maintain the effectiveness of ofloxacin tablets and other antibacterial drugs, ofloxacin tablets should be used only to treat or prevent infections that are proven or strongly suspected to be c...
    Active IngredientOfloxacin
    Dosage FormSolution/drops
    RouteOphthalmic
    Strength0.3%
    Market StatusPrescription
    CompanyAllergan

    3 of 6  
    Drug NameOfloxacin
    PubMed HealthOfloxacin
    Drug ClassesAntibacterial, Antibiotic
    Active IngredientOfloxacin
    Dosage FormSolution/drops; Tablet
    RouteOphthalmic; Oral; Otic
    Strength200mg; 400mg; 300mg; 0.3%
    Market StatusPrescription
    CompanyTeva; Cadila Pharms; Apotex; Altaire Pharms; Hi Tech Pharma; Bausch And Lomb; Alcon Pharms; Fera Pharms; Dr Reddys Labs; Fdc; Akorn

    4 of 6  
    Drug NameFloxin otic
    PubMed HealthOfloxacin (Into the ear)
    Drug ClassesAntibacterial
    Drug LabelOCUFLOX (ofloxacin ophthalmic solution) 0.3% is a sterile ophthalmic solution. It is a fluorinated carboxyquinolone anti-infective for topical ophthalmic use....
    Active IngredientOfloxacin
    Dosage FormSolution/drops
    RouteOtic
    Strength0.3%
    Market StatusPrescription
    CompanyDaiichi

    5 of 6  
    Drug NameOcuflox
    PubMed HealthOfloxacin (Into the eye)
    Drug ClassesAntibiotic
    Drug LabelTo reduce the development of drug-resistant bacteria and maintain the effectiveness of ofloxacin tablets and other antibacterial drugs, ofloxacin tablets should be used only to treat or prevent infections that are proven or strongly suspected to be c...
    Active IngredientOfloxacin
    Dosage FormSolution/drops
    RouteOphthalmic
    Strength0.3%
    Market StatusPrescription
    CompanyAllergan

    6 of 6  
    Drug NameOfloxacin
    PubMed HealthOfloxacin
    Drug ClassesAntibacterial, Antibiotic
    Active IngredientOfloxacin
    Dosage FormSolution/drops; Tablet
    RouteOphthalmic; Oral; Otic
    Strength200mg; 400mg; 300mg; 0.3%
    Market StatusPrescription
    CompanyTeva; Cadila Pharms; Apotex; Altaire Pharms; Hi Tech Pharma; Bausch And Lomb; Alcon Pharms; Fera Pharms; Dr Reddys Labs; Fdc; Akorn

    4.2 Therapeutic Uses

    Anti-Bacterial Agents; Anti-Infective Agents, Urinary; Nucleic Acid Synthesis Inhibitors

    National Library of Medicine's Medical Subject Headings online file (MeSH, 2012)

    Ofloxacin is used in the treatment of acute pelvic inflammatory disease (PID) caused by susceptible C. trachomatis or N. gonorrhoeae, but should not be used if QRNG may be involved or if in vitro susceptibility cannot be tested. /Included in US product label/

    American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 407

    Ofloxacin is used in adults for the treatment of nongonococcal urethritis and cervicitis caused by Chlamydia trachomatis. /Included in US product label/

    American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 407

    Ofloxacin is used in adults for the treatment of uncomplicated urinary tract infections (UTIs) (cystitis) caused by susceptible gram-negative bacteria, including Citrobacter diversus, ... Enterobacter aerogenes, ... Escherichia coli, Klebsiella pneumoniae, ... Proteus mirabilis, or Pseudomonas aeruginosa. /Included in US product label/

    American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 406

    For more Therapeutic Uses (Complete) data for Ofloxacin (36 total), please visit the HSDB record page.

    4.3 Drug Warning

    /BOXED WARNING/ WARNING: Fluoroquinolones, including ofloxacin, are associated with an increased risk of tendinitis and tendon rupture in all ages. This risk is further increased in older patients usually over 60 years of age, in patients taking corticosteroid drugs, and in patients with kidney, heart or lung transplants.

    US Natl Inst Health; DailyMed. Current Medication Information for OFLOXACIN tablet, film coated (January 2012). Available from, as of February 28, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=95b9fc17-9c94-4762-910c-df0bb0b2aa85

    /BOXED WARNING/ WARNING: Fluoroquinolones, including ofloxacin, may exacerbate muscle weakness in persons with myasthenia gravis. Avoid ofloxacin in patients with known history of myasthenia gravis.

    US Natl Inst Health; DailyMed. Current Medication Information for OFLOXACIN tablet, film coated (January 2012). Available from, as of February 28, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=95b9fc17-9c94-4762-910c-df0bb0b2aa85

    Some quinolones, including ofloxacin, have been associated with prolongation of the QT interval on the electrocardiogram and infrequent cases of arrhythmia. Rare cases of torsade de pointes have been spontaneously reported during postmarketing surveillance in patients receiving quinolones, including ofloxacin.

    US Natl Inst Health; DailyMed. Current Medication Information for OFLOXACIN tablet, film coated (January 2012). Available from, as of February 28, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=95b9fc17-9c94-4762-910c-df0bb0b2aa85

    Rare cases of sensory or sensorimotor axonal polyneuropathy affecting small and/or large axons resulting in paresthesias, hypoesthesias, dysesthesias and weakness have been reported in patients receiving quinolones, including ofloxacin. Ofloxacin should be discontinued if the patient experiences symptoms of neuropathy including pain, burning, tingling, numbness, and/or weakness or other alterations of sensation including light touch, pain, temperature, position sense, and vibratory sensation in order to prevent the development of an irreversible condition.

    US Natl Inst Health; DailyMed. Current Medication Information for OFLOXACIN tablet, film coated (January 2012). Available from, as of February 28, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=95b9fc17-9c94-4762-910c-df0bb0b2aa85

    For more Drug Warnings (Complete) data for Ofloxacin (28 total), please visit the HSDB record page.

    4.4 Drug Indication

    For the treatment of infections (respiratory tract, kidney, skin, soft tissue, UTI), urethral and cervical gonorrhoea.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Ofloxacin is a quinolone/fluoroquinolone antibiotic. Ofloxacin is bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase, which allows the untwisting required to replicate one DNA double helix into two. Notably the drug has 100 times higher affinity for bacterial DNA gyrase than for mammalian. Ofloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria.

    5.2 MeSH Pharmacological Classification

    Anti-Infective Agents, Urinary

    Substances capable of killing agents causing urinary tract infections or of preventing them from spreading. (See all compounds classified as Anti-Infective Agents, Urinary.)

    Anti-Bacterial Agents

    Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

    Topoisomerase II Inhibitors

    Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II. (See all compounds classified as Topoisomerase II Inhibitors.)

    Cytochrome P-450 CYP1A2 Inhibitors

    Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP1A2. (See all compounds classified as Cytochrome P-450 CYP1A2 Inhibitors.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    OFLOXACIN
    5.3.2 FDA UNII
    A4P49JAZ9H
    5.3.3 Pharmacological Classes
    Quinolones [CS]; Quinolone Antimicrobial [EPC]
    5.4 ATC Code

    J01MA01

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01M - Quinolone antibacterials

    J01MA - Fluoroquinolones

    J01MA01 - Ofloxacin

    S - Sensory organs

    S01 - Ophthalmologicals

    S01A - Antiinfectives

    S01AE - Fluoroquinolones

    S01AE01 - Ofloxacin

    S - Sensory organs

    S02 - Otologicals

    S02A - Antiinfectives

    S02AA - Antiinfectives

    S02AA16 - Ofloxacin

    5.5 Absorption, Distribution and Excretion

    Absorption

    Bioavailability of ofloxacin in the tablet formulation is approximately 98%

    Route of Elimination

    Ofloxacin is mainly eliminated by renal excretion, where between 65% and 80% of an administered oral dose of ofloxacin is excreted unchanged via urine within 48 hours of dosing. About 4-8% of an ofloxacin dose is excreted in the feces and the drug is minimally subject to biliary excretion.

    Ofloxacin is distributed into bone, cartilage, bile, skin, sputum, bronchial secretions, pleural effusions, tonsils, saliva, gingival mucosa, nasal secretions, aqueous humor, tears, sweat, lung, blister fluid, pancreatic fluid, ascitic fluid, peritoneal fluid, gynecologic tissue, vaginal fluid, cervix, ovary, semen, prostatic fluid, and prostatic tissue. For most of these tissues and fluids, ofloxacin concentrations are approximately 0.5-1.7 times concurrent serum concentrations. Ofloxacin is concentrated within neutrophils, achieving concentrations in these cells that may be up to 8 times greater than extracellular concentrations.

    American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 417

    Ofloxacin is widely distributed into body tissues and fluids following oral administration. In healthy adults, the apparent volume of distribution of ofloxacin averages 1-2.5 L/kg. Impaired renal function does not appear to affect the volume of distribution of ofloxacin; the apparent volume of distribution of the drug averages 1.1-2 L/kg in patients with impaired renal function, including those with severe renal failure undergoing hemodialysis.

    American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 417

    Pharmacokinetic parameters in geriatric patients receiving ofloxacin generally are similar to those in younger adults. Although results of pharmacokinetic studies in geriatric individuals 65-81 years of age indicate that the rate of absorption, volume of distribution, and route of excretion in geriatric individuals are similar to those in younger adults, peak serum concentrations are slightly higher (9-21% higher) and half-life more prolonged in geriatric patients than in younger adults. There also is evidence that peak plasma concentration are higher in geriatric women than geriatric men (114% higher following single doses or 54% higher following multiple doses).

    American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 417

    The oral bioavailability of ofloxacin is 85-100% in healthy, fasting adults, and peak serum concentrations of the drug generally are attained within 0.5-2 hours. In patients with normal renal and hepatic function, peak serum concentrations and AUCs increase in proportion to the dose over the oral dosage range of 100-600 mg and generally are unaffected by age. Following oral administration of a single 100-, 200-, 300-, or 400-mg dose of ofloxacin in healthy, fasting adults, peak serum concentrations average 1-1.3, 1.5-2.7, 2.4-4.6, or 2.9-5.6 ug/mL, respectively. Some accumulation occurs following multiple doses. Steady-state serum concentrations of ofloxacin are achieved after 4 doses of the drug and are approximately 40% higher than concentrations achieved following single oral doses.

    American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 417

    For more Absorption, Distribution and Excretion (Complete) data for Ofloxacin (18 total), please visit the HSDB record page.

    5.6 Metabolism/Metabolites

    Hepatic

    Less than 10% of a single dose of ofloxacin is metabolized; approximately 3-6% of the dose is metabolized to desmethyl ofloxacin and 1-5% is metabolized to ofloxacin N-oxide. Desmethyl ofloxacin is microbiologically active, but is less active against susceptible organisms than is ofloxacin; ofloxacin N-oxide has only minimal antibacterial activity.

    American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 417

    Seven patients with end-stage renal disease on regular hemodialysis were treated orally with a loading dose of 200 mg ofloxacin and multiple maintenance doses of 100 mg per 24 hr for 10 days. The pharmacokinetics of ofloxacin and its metabolites were studied at the end of the treatment period. Plasma and dialysate concentrations of ofloxacin and ofloxacin metabolites were measured by HPLC. Peak (3.1 mg.L-1) and trough levels (1.6 mg.L-1) and the AUC of ofloxacin were comparable to the values in healthy volunteers given 300 to 400 mg ofloxacin p.o. The mean half-life, determined in the dialysis-free interval (t1/2 beta) and during the haemodialysis session (t1/2 HD), was 38.5 h and 9.9 h, respectively. Extrarenal clearance (32.7 mL.min-1) was unchanged as compared to that reported in healthy volunteers after a single dose of ofloxacin. The fractional removal by haemodialysis amounted to 21.5%. Two metabolites, ofloxacin-N-oxide and demethyl-ofloxacin, were detected in plasma. Despite prolonged t1/2 beta of both metabolites (66.1 and 50.9 hr) and multiple doses of ofloxacin the peak concentrations of the metabolites reached only 14% and 5% of that of the parent drug, respectively. It is concluded that in patients on regular hemodialysis treatment the dosage adjustment employed resulted in safe and therapeutically favourable plasma concentrations. The observed accumulation of ofloxacin metabolites does not appear to have any toxic or therapeutic significance.

    PMID:1541323 Kampf D et al; Eur J Clin Pharmacol 42 (1): 95-9 (1992)

    5.7 Biological Half-Life

    9 hours

    In adults with creatinine clearances of 10-50 mL/minute, half-life of the drug averages 16.4 hours (range: 11-33.5 hours); in adults with creatinine clearances less than 10 mL/minute, half-life averages 21.7 hours (range: 16.9-28.4 hours). In patients with end-stage renal failure, half-life of the drug may range from 25-48 hours.

    American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 417

    In healthy adults with normal renal function, the elimination half-life of ofloxacin in the distribution phase averages 0.5-0.6 hours and the elimination half-life in the terminal phase averages 4-8 hours.In healthy geriatric adults 64-86 years of age with renal function normal for their age, half-life of the drug averages 6.4-8.5 hours.

    American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 417

    Following ocular instillation of 1 drop of ofloxacin 0.3% 4 times daily for 12 doses in healthy individuals, the elimination half-life of drug in tear film was approximately 226 minutes. In a study in rabbits, the terminal elimination half-life of ofloxacin in tear film following topical application to the eye was approximately 210 minutes. In adults with normal renal function, the serum elimination half-life of ofloxacin in the terminal phase averages 4-8 hours.

    American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011

    5.8 Mechanism of Action

    Ofloxacin acts on DNA gyrase and toposiomerase IV, enzymes which, like human topoisomerase, prevents the excessive supercoiling of DNA during replication or transcription. By inhibiting their function, the drug thereby inhibits normal cell division.

    Quinolone(s) (QNs) is widely used in infection therapy due to its good antimicrobial characteristics. However, QNs-induced arthropathy of immature animals has led to restrictions on the therapeutic use of these antimicrobial agents. The exact mechanism(s) of QNs-induced chondrotoxicity remain unknown. In the present study, .../the authors/ investigated the possible mechanism of ofloxacin (one typical QNs)-induced injuries of chondrocytes. Juvenile rabbit joint chondrocytes cultured in alginate microspheres were incubated with ofloxacin at concentrations of 0, 2, 5, 10, 20, and 40 microg/mL for up to 96 hr. Concentration of 10 microg/mL ofloxacin induced apoptosis of chondrocyte with visible apoptotic signs, including degradation of poly(ADP-ribose) polymerase, caspase-3 activation, and DNA ladder formation. Furthermore, extracellular signal-regulated kinase 1/2 (phospho-ERK1/2) and growth factor receptor-bound protein 2 (Grb2) were significantly reduced, and similar changes were also observed in the beta(1)-integrin receptor as assessed by immunoblotting. However, the mRNA level of beta(1)-integrin obtained from reverse transcription-polymerase chain reaction remained unchanged. Results of beta(1)-integrin immunoprecipitation have also shown that beta(1)-integrin did not interact with activated intracellular signaling proteins. In addition, ofloxacin did not induce apoptosis and decrease beta(1)-integrin expression in chondrocytes supplemented with Mg(2+), and the ofloxacin-induced apoptosis was caspase-8-dependent, inhibition of which did not affect the expression mode of phospho-ERK1/2 and beta(1)-integrin. Our results demonstrate that ofloxacin affects beta(1)-integrin receptor functions and the ERK mitogen-activated protein kinase signaling pathway, causing caspase-8-dependent apoptosis after exposure of 48 hr.

    PMID:17400890 Sheng ZG et al; J Pharmacol Exp Ther 322 (1): 155-65 (2007)

    Quinolones are widely used in infection therapy due to their good antimicrobial characteristics. However, there potential joint chondrotoxicity on immature animals has stood in the way of the therapeutic application of these agents, the exact mechanism of which is still unclear. This study was undertaken to investigate the role of oxidative damage in ofloxacin (one typical quinolones)-induced arthropathy. Chondrocytes from juvenile rabbit joints were incubated with ofloxacin at concentrations of 0, 5, 10, 20, 40 and 80 ug/mL, respectively. The extent of oxidative damage was assessed by measuring the reactive oxygen species level, activities of antioxidant enzymes, and oxidative damage to some macromolecules. It was observed that ofloxacin induced a concentration-dependent increase in intracellular reactive oxygen species production, which may be an early mediator of ofloxacin cytotoxicity. Similarly, ofloxacin resulted in a significant lipid peroxidation, revealed by a concentration-dependent increase in the level of thiobarbituric acid reactive substances. At the same time, ofloxacin induced DNA damage in a concentration-dependent manner for 24 hr measured by comet assay, which may be a cause for overproduction of reactive oxygen species. Furthermore, antioxidant enzyme activities, such as glutathione peroxidase (GPx), catalase and superoxide dismutase (SOD), were rapidly decreased after treatment with ofloxacin. In addition, SOD decline and reactive oxygen species production were strongly inhibited, and the loss in cell viability was partly abated by additional glutathione (GSH), N-acetylcysteine (NAC) and dithiothreitol (DTT). In conclusion, these results clearly demonstrated that ofloxacin could induce oxidative stress, lipid peroxidation and DNA oxidative damage to chondrocytes.

    PMID:19818344 Li Q et al; Eur J Pharmacol 626 (2-3): 146-53 (2010)

    Ofloxacin is a quinolone antimicrobial agent. The mechanism of action of ofloxacin and other fluoroquinolone antimicrobials involves inhibition of bacterial topoisomerase IV and DNA gyrase (both of which are type II topoisomerases), enzymes required for DNA replication, transcription, repair and recombination. Ofloxacin has in vitro activity against a wide range of gram-negative and gram-positive microorganisms. Ofloxacin is often bactericidal at concentrations equal to or slightly greater than inhibitory concentrations. Fluoroquinolones, including ofloxacin, differ in chemical structure and mode of action from aminoglycosides, macrolides and beta-lactam antibiotics, including penicillins. Fluoroquinolones may, therefore, be active against bacteria resistant to these antimicrobials. Resistance to ofloxacin due to spontaneous mutation in vitro is a rare occurrence (range: 10(-9) to 10(-11)). Although cross-resistance has been observed between ofloxacin and some other fluoroquinolones, some microorganisms resistant to other fluoroquinolones may be susceptible to ofloxacin.

    US Natl Inst Health; DailyMed. Current Medication Information for OFLOXACIN tablet, film coated (January 2012). Available from, as of February 28, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=95b9fc17-9c94-4762-910c-df0bb0b2aa85

    Fluoroquinolones prolong the QT interval by blocking voltage-gated potassium channels, especially the rapid component of the delayed rectifier potassium current I(Kr), expressed by HERG (the human ether-a-go-go-related gene). According to the available case reports and clinical studies, moxifloxacin carries the greatest risk of QT prolongation from all available quinolones in clinical practice and it should be used with caution in patients with predisposing factors for Torsades de pointes (TdP).

    PMID:22156660 Briasoulis A et al; Cardiology 120 (2): 103-10 (2011)

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    02-Jan-2021
    29-Nov-2024
    KGS
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