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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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03-Jan-2021
31-Mar-2025
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ABOUT THIS PAGE

Looking for 82419-36-1 / Ofloxacin API manufacturers, exporters & distributors?

Ofloxacin manufacturers, exporters & distributors 1

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PharmaCompass offers a list of Ofloxacin API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Ofloxacin manufacturer or Ofloxacin supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Ofloxacin manufacturer or Ofloxacin supplier.

PharmaCompass also assists you with knowing the Ofloxacin API Price utilized in the formulation of products. Ofloxacin API Price is not always fixed or binding as the Ofloxacin Price is obtained through a variety of data sources. The Ofloxacin Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Ofloxacin

Synonyms

82419-36-1, Floxin, Tarivid, Ofloxacine, Oxaldin, Ocuflox

Cas Number

82419-36-1

Unique Ingredient Identifier (UNII)

A4P49JAZ9H

About Ofloxacin

A synthetic fluoroquinolone antibacterial agent that inhibits the supercoiling activity of bacterial DNA GYRASE, halting DNA REPLICATION.

Ofloxacin Manufacturers

A Ofloxacin manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Ofloxacin, including repackagers and relabelers. The FDA regulates Ofloxacin manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Ofloxacin API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Ofloxacin manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Ofloxacin Suppliers

A Ofloxacin supplier is an individual or a company that provides Ofloxacin active pharmaceutical ingredient (API) or Ofloxacin finished formulations upon request. The Ofloxacin suppliers may include Ofloxacin API manufacturers, exporters, distributors and traders.

click here to find a list of Ofloxacin suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Ofloxacin USDMF

A Ofloxacin DMF (Drug Master File) is a document detailing the whole manufacturing process of Ofloxacin active pharmaceutical ingredient (API) in detail. Different forms of Ofloxacin DMFs exist exist since differing nations have different regulations, such as Ofloxacin USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Ofloxacin DMF submitted to regulatory agencies in the US is known as a USDMF. Ofloxacin USDMF includes data on Ofloxacin's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Ofloxacin USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Ofloxacin suppliers with USDMF on PharmaCompass.

Ofloxacin JDMF

The Pharmaceuticals and Medical Devices Agency (PMDA) established the Japan Drug Master File (JDMF), also known as the Master File (MF), to permit Japanese and foreign manufacturers of drug substances, intermediates, excipients, raw materials, and packaging materials (‘Products’) to voluntarily register confidential information about the production and management of their products in Japan.

The Ofloxacin Drug Master File in Japan (Ofloxacin JDMF) empowers Ofloxacin API manufacturers to present comprehensive information (e.g., production methods, data, etc.) to the review authority, i.e., PMDA (Pharmaceuticals & Medical Devices Agency).

PMDA reviews the Ofloxacin JDMF during the approval evaluation for pharmaceutical products. At the time of Ofloxacin JDMF registration, PMDA checks if the format is accurate, if the necessary items have been included (application), and if data has been attached.

click here to find a list of Ofloxacin suppliers with JDMF on PharmaCompass.

Ofloxacin KDMF

In Korea, the Ministry of Food and Drug Safety (MFDS) is in charge of regulating pharmaceutical products and services.

Pharmaceutical companies submit a Ofloxacin Drug Master File in Korea (Ofloxacin KDMF) to the MFDS, which includes comprehensive information about the production, processing, facilities, materials, packaging, and testing of Ofloxacin. The MFDS reviews the Ofloxacin KDMF as part of the drug registration process and uses the information provided in the Ofloxacin KDMF to evaluate the safety and efficacy of the drug.

After submitting a Ofloxacin KDMF to the MFDS, the registered manufacturer can provide importers or distributors with the registration number without revealing confidential information to Korean business partners. Applicants seeking to register their Ofloxacin API can apply through the Korea Drug Master File (KDMF).

click here to find a list of Ofloxacin suppliers with KDMF on PharmaCompass.

Ofloxacin CEP

A Ofloxacin CEP of the European Pharmacopoeia monograph is often referred to as a Ofloxacin Certificate of Suitability (COS). The purpose of a Ofloxacin CEP is to show that the European Pharmacopoeia monograph adequately controls the purity of Ofloxacin EP produced by a given manufacturer. Suppliers of raw materials can prove the suitability of Ofloxacin to their clients by showing that a Ofloxacin CEP has been issued for it. The manufacturer submits a Ofloxacin CEP (COS) as part of the market authorization procedure, and it takes on the role of a Ofloxacin CEP holder for the record. Additionally, the data presented in the Ofloxacin CEP (COS) is managed confidentially and offers a centralized system acknowledged by numerous nations, exactly like the Ofloxacin DMF.

A Ofloxacin CEP (COS) is recognised by all 36 nations that make up the European Pharmacopoeia Convention. Ofloxacin CEPs may be accepted in nations that are not members of the Ph. Eur. at the discretion of the authorities there.

click here to find a list of Ofloxacin suppliers with CEP (COS) on PharmaCompass.

Ofloxacin WC

A Ofloxacin written confirmation (Ofloxacin WC) is an official document issued by a regulatory agency to a Ofloxacin manufacturer, verifying that the manufacturing facility of a Ofloxacin active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting Ofloxacin APIs or Ofloxacin finished pharmaceutical products to another nation, regulatory agencies frequently require a Ofloxacin WC (written confirmation) as part of the regulatory process.

click here to find a list of Ofloxacin suppliers with Written Confirmation (WC) on PharmaCompass.

Ofloxacin NDC

National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Ofloxacin as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for Ofloxacin API and other APIs are published in this directory by the FDA.

Unfinished drugs

The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

Pharmaceutical companies that manufacture Ofloxacin as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

Compounded drug products

The NDC directory also contains data on finished compounded human drug products that contain Ofloxacin and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Ofloxacin NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of Ofloxacin suppliers with NDC on PharmaCompass.

Ofloxacin GMP

Ofloxacin Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Ofloxacin GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Ofloxacin GMP manufacturer or Ofloxacin GMP API supplier for your needs.

Ofloxacin CoA

A Ofloxacin CoA (Certificate of Analysis) is a formal document that attests to Ofloxacin's compliance with Ofloxacin specifications and serves as a tool for batch-level quality control.

Ofloxacin CoA mostly includes findings from lab analyses of a specific batch. For each Ofloxacin CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Ofloxacin may be tested according to a variety of international standards, such as European Pharmacopoeia (Ofloxacin EP), Ofloxacin JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Ofloxacin USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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