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Synopsis

Chemistry

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Also known as: 85721-33-1, Ciprofloxacine, Ciprobay, Cipro, Ciproxan, Ciprofloxacina
Molecular Formula
C17H18FN3O3
Molecular Weight
331.34  g/mol
InChI Key
MYSWGUAQZAJSOK-UHFFFAOYSA-N
FDA UNII
5E8K9I0O4U

Ciprofloxacin
A broad-spectrum antimicrobial carboxyfluoroquinoline.
Ciprofloxacin is a Quinolone Antimicrobial.
1 2D Structure

Ciprofloxacin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid
2.1.2 InChI
InChI=1S/C17H18FN3O3/c18-13-7-11-14(8-15(13)20-5-3-19-4-6-20)21(10-1-2-10)9-12(16(11)22)17(23)24/h7-10,19H,1-6H2,(H,23,24)
2.1.3 InChI Key
MYSWGUAQZAJSOK-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1CC1N2C=C(C(=O)C3=CC(=C(C=C32)N4CCNCC4)F)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
5E8K9I0O4U
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Anhydrous, Ciprofloxacin Hydrochloride

2. Bay 09867

3. Bay-09867

4. Bay09867

5. Ciprinol

6. Cipro

7. Ciprofloxacin Hydrochloride

8. Ciprofloxacin Hydrochloride Anhydrous

9. Ciprofloxacin Monohydrochloride Monohydrate

10. Hydrochloride Anhydrous, Ciprofloxacin

11. Hydrochloride, Ciprofloxacin

12. Monohydrate, Ciprofloxacin Monohydrochloride

13. Monohydrochloride Monohydrate, Ciprofloxacin

2.3.2 Depositor-Supplied Synonyms

1. 85721-33-1

2. Ciprofloxacine

3. Ciprobay

4. Cipro

5. Ciproxan

6. Ciprofloxacina

7. Cipro Iv

8. Ciprofloxacinum

9. Bay Q 3939

10. Ciprofloxacino

11. Ciproflox

12. Ciproxina

13. Otiprio

14. 1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic Acid

15. 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic Acid

16. Cetraxal

17. Cipro Xr

18. Bay-09867

19. Cpfx

20. 1-cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydro-3-quinolinecarboxylic Acid

21. Bayq3939

22. 1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic Acid

23. Ciproxin

24. Ciflox

25. Ciprofloxacin (cipro)

26. Chembl8

27. Bay O 9867

28. 1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,4-dihydroquinoline-3-carboxylic Acid

29. 3-quinolinecarboxylic Acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-

30. Nsc-758467

31. 5e8k9i0o4u

32. Ciprocinol

33. Cipromycin

34. Ciproquinol

35. Bacquinor

36. Bernoflox

37. Cifloxin

38. Ciprinol

39. Ciprodar

40. Septicide

41. Bay O 9867 Free Base

42. Bay-o-9867 Free Base

43. Chebi:100241

44. Bay-q-3939

45. Velmonit

46. Ciprofloxacin Monohydrochloride

47. Ciprecu

48. Ciprogis

49. Ciprolin

50. Ciprolon

51. Ciprowin

52. Ciproxine

53. Citopcin

54. Corsacin

55. Fimoflox

56. Ipiflox

57. Italnik

58. Probiox

59. Proflaxin

60. Quinolid

61. Quintor

62. Roxytal

63. Spitacin

64. Superocin

65. Zumaflox

66. Baflox

67. Ciplus

68. Ciriax

69. Rancif

70. Cilab

71. Cixan

72. Cycin

73. Loxan

74. Unex

75. Sophixin Ofteno

76. Ciprobay Uro

77. Alcon Cilox

78. Bi-cipro

79. Cipro (tn)

80. 3-quinolinecarboxylic Acid, 1,4-dihydro-1-cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-

81. Proksi 250

82. Proksi 500

83. Cyprobay

84. Auripro

85. Eni

86. 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline-carboxylic Acid

87. 1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,4-dihydro-quinoline-3-carboxylic Acid

88. 1-cyclopropyl-6-fluoro-7-hexahydro-1-pyrazinyl-4-oxo-1,4-dihydro-3-quinolinecarboxylic Acid

89. Bay-o 9867

90. Ciprofloxacine [inn-french]

91. Ciprofloxacinum [inn-latin]

92. 1-cyclopropyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic Acid

93. Smr000471901

94. Ciprofloxacino [inn-spanish]

95. Ccris 5241

96. Nsc620634

97. Hsdb 6987

98. Sr-05000001863

99. Ciprofloxacin 100 Microg/ml In Methanol

100. Ncgc00016959-01

101. Cas-93107-08-5

102. Cipro In Dextrose 5% In Plastic Container

103. Brn 3568352

104. Rubrum

105. Unii-5e8k9i0o4u

106. Ciprine

107. Linhaliq

108. Bay 09867

109. Cipro In Sodium Chloride 0.9% In Plastic Container

110. Ciprofloxacin,(s)

111. Ciprofloxacin [usan:usp:inn:ban]

112. Mfcd00185755

113. Spectrum_000162

114. 3-quinolinecarboxylic Acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-, Hydrochloride

115. Prestwick0_000113

116. Prestwick1_000113

117. Prestwick2_000113

118. Prestwick3_000113

119. Spectrum2_001567

120. Spectrum3_001872

121. Spectrum4_000874

122. Spectrum5_001089

123. Cipro (*hydrochloride*)

124. Cbmicro_048498

125. Ciprofloxacin [mi]

126. Ciloxan (*hydrochloride*)

127. Ciprofloxacin [inn]

128. Ciprofloxacin [jan]

129. Schembl2900

130. Ciprofloxacin [hsdb]

131. Ciprofloxacin [usan]

132. Oprea1_008239

133. Oprea1_313572

134. Bspbio_000126

135. Bspbio_003344

136. Ciprofloxacin [vandf]

137. Kbiogr_001567

138. Kbioss_000642

139. Anhydrous Ciprofloxacin

140. Mls001336035

141. Mls006011837

142. Bidd:gt0205

143. Ciprofloxacin [mart.]

144. Divk1c_000095

145. Spectrum1503614

146. Spbio_001474

147. Spbio_002065

148. Ciprofloxacin [usp-rs]

149. Ciprofloxacin [who-dd]

150. Ciprofloxacin [who-ip]

151. Bpbio1_000140

152. Dtxsid8022824

153. Bay-o9867

154. Bdbm21690

155. Gtpl10902

156. Hms500e17

157. Kbio1_000095

158. Kbio2_000642

159. Kbio2_003210

160. Kbio2_005778

161. Kbio3_002846

162. Linhaliq [liposomal Formulation]

163. Zinc20220

164. Ciprofloxacin (jp17/usp/inn)

165. Ninds_000095

166. Bay O 9867 (*hydrochloride*)

167. Hms1922e18

168. Hms2090o07

169. Hms2093i03

170. Pharmakon1600-01503614

171. Ciprofloxacin [orange Book]

172. Albb-015909

173. Bcp28586

174. Hy-b0356

175. Rkl10073

176. Ciprofloxacin [ep Monograph]

177. Bbl005612

178. Ccg-39345

179. Ciprofloxacin [usp Monograph]

180. Ciprofloxacin Extended Release

181. Ciprofloxacin, >=98.0% (hplc)

182. Nsc758467

183. Nsc759028

184. S2027

185. Stk021082

186. 1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-yl-quinoline-3-carboxylic Acid

187. 1-cyclopropyl-6-fluoro-4-oxo-7-piperazinylhydroquinoline-3-carboxylic Acid

188. Akos000269653

189. Ciprodex Component Ciprofloxacin

190. Ciprofloxacinum [who-ip Latin]

191. Ac-7613

192. Db00537

193. Ks-5006

194. Nsc 758467

195. Nsc-759028

196. Idi1_000095

197. Smp1_000125

198. Ncgc00016959-02

199. Ncgc00016959-03

200. Ncgc00016959-04

201. Ncgc00016959-05

202. Ncgc00016959-07

203. Ncgc00095058-01

204. Ncgc00095058-02

205. Ncgc00178128-01

206. Ciprofloxacin Component Of Ciprodex

207. Sbi-0048462.p003

208. Ft-0601635

209. C-6350

210. C05349

211. Ciprofloxacin 100 Microg/ml In Methanol:water

212. D00186

213. 721c331

214. A841426

215. Ciprofloxacin, Vetranal(tm), Analytical Standard

216. Q256602

217. Ciprofloxacin, Antibiotic For Culture Media Use Only

218. Sr-05000001863-1

219. Sr-05000001863-3

220. Brd-k04804440-311-02-3

221. Z56933707

222. Ciprofloxacin, European Pharmacopoeia (ep) Reference Standard

223. Enrofloxacin For Veterinary Use Impurity B [ep Impurity]

224. Ciprofloxacin, United States Pharmacopeia (usp) Reference Standard

225. 1-cyclopropyl-6-fluoro-1,4-dihydro 4-oxo-7-[1-piperazinyl)-quinoline-3-carboxylic Acid

226. 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7- (1-piperazinyl)-3-quinoline-carboxylic Acid

227. 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-quinoline -3-carboxylic Acid

228. 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-quinoline-3-carboxylic Acid

229. 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)quinoline-3-carboxylic Acid

230. 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1piperazinyl)-3quinolinecarboxylic Acid

231. 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(piperazin-1-yl)-quinoline-3-carboxylic Acid

232. 1-cyclopropyl-6-fluoro-1,4-dihydro-7-(1-piperazinyl)-4-oxo-3-quinoline Carboxylic Acid

233. 1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylicacid

234. 1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-4-ium-1-yl-quinoline-3-carboxylate;ciprofloxacin

235. 1-cyclopropyl-6-fluoro-7-(piperazin-1-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic Acid

236. Ciprofloxacin, Pharmaceutical Secondary Standard; Certified Reference Material

237. 1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,4-dihydroquinoline-3-carboxylic Acid Hydrochloride

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 331.34 g/mol
Molecular Formula C17H18FN3O3
XLogP3-1.1
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count3
Exact Mass331.13321961 g/mol
Monoisotopic Mass331.13321961 g/mol
Topological Polar Surface Area72.9 Ų
Heavy Atom Count24
Formal Charge0
Complexity571
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 14  
Drug NameCetraxal
PubMed HealthCiprofloxacin (Into the ear)
Drug ClassesAntibacterial
Drug LabelCETRAXAL (ciprofloxacin otic solution) 0.2% contains the synthetic antimicrobial agent ciprofloxacin hydrochloride. CETRAXAL is a sterile, preservative-free solution for otic use. Each single use container of CETRAXAL delivers 0.25 mL of solution equ...
Active IngredientCiprofloxacin hydrochloride
Dosage FormSolution/drops
RouteOtic
Strengtheq 0.2% base
Market StatusPrescription
CompanyWraser Pharms

2 of 14  
Drug NameCiloxan
PubMed HealthCiprofloxacin (Into the eye)
Drug ClassesAntibiotic
Drug LabelCILOXAN (ciprofloxacin HCl ophthalmic solution) is a synthetic, sterile, multiple dose, antimicrobial for topical ophthalmic use. Ciprofloxacin is a fluoroquinolone antibacterial active against a broad spectrum of gram-positive and gram-negative oc...
Active IngredientCiprofloxacin hydrochloride
Dosage FormSolution/drops; Ointment
RouteOphthalmic
Strengtheq 0.3% base
Market StatusPrescription
CompanyAlcon Pharms

3 of 14  
Drug NameCipro
PubMed HealthCiprofloxacin/Dexamethasone (Into the ear)
Drug ClassesAnti-Infective/Anti-Inflammatory Combination, Antibacterial
Drug LabelCiprofloxacin Tablets, USPis a synthetic broad spectrum antimicrobial agent for oral administration. Ciprofloxacin hydrochloride, USP, a fluoroquinolone, is the monohydrochloride monohydrate salt of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-pip...
Active IngredientCiprofloxacin hydrochloride; Ciprofloxacin
Dosage FormInjectable; Tablet; For suspension
RouteInjection; Oral
Strengtheq 750mg base; eq 100mg base; 400mg/40ml (10mg/ml); 200mg/20ml (10mg/ml); 500mg/5ml; eq 500mg base; eq 250mg base; 250mg/5ml
Market StatusPrescription
CompanyBayer Hlthcare

4 of 14  
Drug NameCipro xr
PubMed HealthCiprofloxacin Betaine/Ciprofloxacin Hydrochloride (By mouth)
Drug ClassesAntibacterial
Drug LabelCiprofloxacin Tablets, USPis a synthetic broad spectrum antimicrobial agent for oral administration. Ciprofloxacin hydrochloride, USP, a fluoroquinolone, is the monohydrochloride monohydrate salt of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-pip...
Active IngredientCiprofloxacin; ciprofloxacin hydrochloride
Dosage FormTablet, extended release
Routeoral
Strengtheq 287.5mg base; 425.2mg; eq 574.9mg base; 212.6mg
Market StatusPrescription
CompanyBayer Pharms

5 of 14  
Drug NameCiprofloxacin
PubMed HealthCiprofloxacin
Drug ClassesAntibacterial, Antibiotic, Antitubercular
Active IngredientCiprofloxacin
Dosage FormInjectable; Tablet; For suspension
Routeoral; Injection; Oral
Strength400mg/40ml (10mg/ml); 200mg/20ml (10mg/ml); 250mg; 500mg/5ml; 100mg; 250mg/5ml
Market StatusTentative Approval; Prescription
CompanyIvax Sub Teva Pharms; Hospira; Claris Lifesciences; Hikma Farmaceutica; Lupin; Sandoz; Carlsbad; Hikma

6 of 14  
Drug NameCiprofloxacin extended release
PubMed HealthCiprofloxacin Betaine/Ciprofloxacin Hydrochloride (By mouth)
Drug ClassesAntibacterial
Drug LabelCiprofloxacin Tablets, USPis a synthetic broad spectrum antimicrobial agent for oral administration. Ciprofloxacin hydrochloride, USP, a fluoroquinolone, is the monohydrochloride monohydrate salt of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-pip...
Active IngredientCiprofloxacin; ciprofloxacin hydrochloride
Dosage FormTablet, extended release
RouteOral
Strength425.2mg; eq 287.5mg base; 212.6mg; eq 574.9mg base
Market StatusPrescription
CompanyMylan Pharms; Anchen Pharms; Actavis Labs Fl; Dr Reddys Labs

7 of 14  
Drug NameCiprofloxacin hydrochloride
Active IngredientCiprofloxacin hydrochloride
Dosage FormSolution/drops; Tablet
RouteOphthalmic; Oral
Strengtheq 100mg base; eq 750mg base; eq 500mg base; eq 0.3% base; eq 250mg base
Market StatusPrescription
CompanyWatson Labs; Nexus Pharms; Ranbaxy; Ivax Sub Teva Pharms; Apotex; Bausch And Lomb; Aurobindo Pharma; Taro; Dr Reddys Labs; Unique Pharm Labs; Carlsbad; Pharmaforce; Fdc; Mylan; Hikma; Akorn

8 of 14  
Drug NameCetraxal
PubMed HealthCiprofloxacin (Into the ear)
Drug ClassesAntibacterial
Drug LabelCETRAXAL (ciprofloxacin otic solution) 0.2% contains the synthetic antimicrobial agent ciprofloxacin hydrochloride. CETRAXAL is a sterile, preservative-free solution for otic use. Each single use container of CETRAXAL delivers 0.25 mL of solution equ...
Active IngredientCiprofloxacin hydrochloride
Dosage FormSolution/drops
RouteOtic
Strengtheq 0.2% base
Market StatusPrescription
CompanyWraser Pharms

9 of 14  
Drug NameCiloxan
PubMed HealthCiprofloxacin (Into the eye)
Drug ClassesAntibiotic
Drug LabelCILOXAN (ciprofloxacin HCl ophthalmic solution) is a synthetic, sterile, multiple dose, antimicrobial for topical ophthalmic use. Ciprofloxacin is a fluoroquinolone antibacterial active against a broad spectrum of gram-positive and gram-negative oc...
Active IngredientCiprofloxacin hydrochloride
Dosage FormSolution/drops; Ointment
RouteOphthalmic
Strengtheq 0.3% base
Market StatusPrescription
CompanyAlcon Pharms

10 of 14  
Drug NameCipro
PubMed HealthCiprofloxacin/Dexamethasone (Into the ear)
Drug ClassesAnti-Infective/Anti-Inflammatory Combination, Antibacterial
Drug LabelCiprofloxacin Tablets, USPis a synthetic broad spectrum antimicrobial agent for oral administration. Ciprofloxacin hydrochloride, USP, a fluoroquinolone, is the monohydrochloride monohydrate salt of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-pip...
Active IngredientCiprofloxacin hydrochloride; Ciprofloxacin
Dosage FormInjectable; Tablet; For suspension
RouteInjection; Oral
Strengtheq 750mg base; eq 100mg base; 400mg/40ml (10mg/ml); 200mg/20ml (10mg/ml); 500mg/5ml; eq 500mg base; eq 250mg base; 250mg/5ml
Market StatusPrescription
CompanyBayer Hlthcare

11 of 14  
Drug NameCipro xr
PubMed HealthCiprofloxacin Betaine/Ciprofloxacin Hydrochloride (By mouth)
Drug ClassesAntibacterial
Drug LabelCiprofloxacin Tablets, USPis a synthetic broad spectrum antimicrobial agent for oral administration. Ciprofloxacin hydrochloride, USP, a fluoroquinolone, is the monohydrochloride monohydrate salt of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-pip...
Active IngredientCiprofloxacin; ciprofloxacin hydrochloride
Dosage FormTablet, extended release
Routeoral
Strengtheq 287.5mg base; 425.2mg; eq 574.9mg base; 212.6mg
Market StatusPrescription
CompanyBayer Pharms

12 of 14  
Drug NameCiprofloxacin
PubMed HealthCiprofloxacin
Drug ClassesAntibacterial, Antibiotic, Antitubercular
Active IngredientCiprofloxacin
Dosage FormInjectable; Tablet; For suspension
Routeoral; Injection; Oral
Strength400mg/40ml (10mg/ml); 200mg/20ml (10mg/ml); 250mg; 500mg/5ml; 100mg; 250mg/5ml
Market StatusTentative Approval; Prescription
CompanyIvax Sub Teva Pharms; Hospira; Claris Lifesciences; Hikma Farmaceutica; Lupin; Sandoz; Carlsbad; Hikma

13 of 14  
Drug NameCiprofloxacin extended release
PubMed HealthCiprofloxacin Betaine/Ciprofloxacin Hydrochloride (By mouth)
Drug ClassesAntibacterial
Drug LabelCiprofloxacin Tablets, USPis a synthetic broad spectrum antimicrobial agent for oral administration. Ciprofloxacin hydrochloride, USP, a fluoroquinolone, is the monohydrochloride monohydrate salt of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-pip...
Active IngredientCiprofloxacin; ciprofloxacin hydrochloride
Dosage FormTablet, extended release
RouteOral
Strength425.2mg; eq 287.5mg base; 212.6mg; eq 574.9mg base
Market StatusPrescription
CompanyMylan Pharms; Anchen Pharms; Actavis Labs Fl; Dr Reddys Labs

14 of 14  
Drug NameCiprofloxacin hydrochloride
Active IngredientCiprofloxacin hydrochloride
Dosage FormSolution/drops; Tablet
RouteOphthalmic; Oral
Strengtheq 100mg base; eq 750mg base; eq 500mg base; eq 0.3% base; eq 250mg base
Market StatusPrescription
CompanyWatson Labs; Nexus Pharms; Ranbaxy; Ivax Sub Teva Pharms; Apotex; Bausch And Lomb; Aurobindo Pharma; Taro; Dr Reddys Labs; Unique Pharm Labs; Carlsbad; Pharmaforce; Fdc; Mylan; Hikma; Akorn

4.2 Therapeutic Uses

Anti-Infective Agents; Nucleic Acid Synthesis Inhibitors

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


Ciprofloxacin (IV, conventional tablets, oral suspension) is used in adults for the treatment of bone and joint infections, including osteomyelitis, caused by susceptible E. cloacae, ... Ps. aeruginosa, or S. marcescens. ... /Included in US product label/

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 358


Ciprofloxacin (IV, conventional tablets, oral suspension) is used in adults for the treatment of bone and joint infections, including osteomyelitis, caused by susceptible E. aerogenes, ... E. coli, K. pneumoniae, M. morganii, P. mirabilis, ... . The drug also has been used in adults for the treatment of bone and joint infections caused by susceptible S. aureus, S. epidermidis, other coagulase-negative staphylococci, or Enterococcus faecalis (formerly S. faecalis), but other anti-infectives generally are preferred for these infections. Although resistance to ciprofloxacin has been reported in some strains of oxacillin-resistant S. aureus, oral ciprofloxacin may be a useful alternative to parenteral anti-infectives for the treatment of infections caused by susceptible oxacillin-resistant staphylococci. /NOT included in US product label/

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 358


Although only limited experience is available to date, ciprofloxacin is recommended by the American Heart Association (AHA) and Infectious Diseases Society of America (IDSA) as an alternative agent for the treatment of native or prosthetic valve endocarditis caused by fastidious gram-negative bacilli known as the HACEK group (Actinobacillus actinomycetemcomitans, Cardiobacterium hominis, Eikenella corrodens, Haemophilus aphrophilus, H. influenzae, H. parainfluenzae, H. paraphrophilus, Kingella denitrificans, K. kingae). /NOT included in US product label/

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 358


For more Therapeutic Uses (Complete) data for CIPROFLOXACIN (53 total), please visit the HSDB record page.


4.3 Drug Warning

/BOXED WARNING/ WARNING: Fluoroquinolones, including Cipro, 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 CIPRO (ciprofloxacin hydrochloride) tablet, film coated CIPRO (ciprofloxacin) kit (November 2011). Available from, as of February 28, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=888dc7f9-ad9c-4c00-8d50-8ddfd9bd27c0


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

US Natl Inst Health; DailyMed. Current Medication Information for CIPRO (ciprofloxacin hydrochloride) tablet, film coated CIPRO (ciprofloxacin) kit (November 2011). Available from, as of February 28, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=888dc7f9-ad9c-4c00-8d50-8ddfd9bd27c0


In 4 corneal transplantation patients treated preoperatively with ciprofloxacin ophthalmic drops, microprecipitates associated with damaged corneal epithelium were noted in 2 patients. Another patient developed a large macroprecipitate in a corneal ulcer. All specimens were examined by electron microscopy & high-pressure liquid chromatography. The crystalline precipitates were pure ciprofloxacin. The macroprecipitate demonstrated a large zone of inhibition on agar plates seeded with a susceptible organism at 24 & 48 hr. It was bioactive & bioavailable in vitro.

PMID:11687375 Eiferman RA et al; J Cataract Refract Surg 27 (10): 1701-1702 (2001)


Serious and occasionally fatal hypersensitivity (anaphylactic) reactions, some following the first dose, have been reported in patients receiving quinolone therapy. Some reactions were accompanied by cardiovascular collapse, loss of consciousness, tingling, pharyngeal or facial edema, dyspnea, urticaria, and itching. Only a few patients had a history of hypersensitivity reactions. Serious anaphylactic reactions require immediate emergency treatment with epinephrine. Oxygen, intravenous steroids, and airway management, including intubation, should be administered as indicated.

US Natl Inst Health; DailyMed. Current Medication Information for CIPRO (ciprofloxacin hydrochloride) tablet, film coated CIPRO (ciprofloxacin) kit (November 2011). Available from, as of February 28, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=888dc7f9-ad9c-4c00-8d50-8ddfd9bd27c0


For more Drug Warnings (Complete) data for CIPROFLOXACIN (41 total), please visit the HSDB record page.


4.4 Drug Indication

Ciprofloxacin is only indicated in infections caused by susceptible bacteria. Ciprofloxacin immediate release tablets, oral suspensions, and intravenous injections are indicated for the treatment of skin and skin structure infections, bone and joint infections, complicated intra-abdominal infections, nosocomial pneumonia, febrile neutropenia, adults who have inhaled anthrax, plague, chronic bacterial prostatitis, lower respiratory tract infections including acute exacerbations of chronic bronchitis, urinary tract infections, complicated urinary tract infections in pediatrics, complicated pyelonephritis in pediatrics, and acute sinusitis. A ciprofloxacin otic solution and otic suspension with hydrocortisone are indicated for acute otitis externa. Ciprofloxacin suspension with dexamethasone is indicated for acute otitis media in pediatric patients with tympanostomy tubes or acute otitis externa. A ciprofloxacin intratympanic injection is indicated for pediatric patients with bilateral otitis media with effusion who are having tympanostomy tubes placed or pediatric patients 6 months or older with acute otitis externa. A ciprofloxacin eye drop is indicated for bacterial corneal ulcers and conjunctivitis. A ciprofloxacin eye ointment is indicated for bacterial conjunctivitis. A ciprofloxacin extended release tablet is indicated for uncomplicated urinary tract infections, complicated urinary tract infections, and acute uncomplicated pyelonephritis.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Ciprofloxacin is a second generation fluoroquinolone that is active against many Gram negative and Gram positive bacteria. It produces its action through inhibition of bacterial DNA gyrase and topoisomerase IV. Ciprofloxacin binds to bacterial DNA gyrase with 100 times the affinity of mammalian DNA gyrase. There is no cross resistance between fluoroquinolones and other classes of antibiotics, so it may be of clinical value when other antibiotics are no longer effective. Ciprofloxain and its derivatives are also being investigated for its action against malaria, cancers, and AIDS.


5.2 MeSH Pharmacological Classification

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
CIPROFLOXACIN
5.3.2 FDA UNII
5E8K9I0O4U
5.3.3 Pharmacological Classes
Quinolones [CS]; Quinolone Antimicrobial [EPC]
5.4 ATC Code

S01AE03

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

J01MA02 - Ciprofloxacin


S - Sensory organs

S01 - Ophthalmologicals

S01A - Antiinfectives

S01AE - Fluoroquinolones

S01AE03 - Ciprofloxacin


S - Sensory organs

S02 - Otologicals

S02A - Antiinfectives

S02AA - Antiinfectives

S02AA15 - Ciprofloxacin


S - Sensory organs

S03 - Ophthalmological and otological preparations

S03A - Antiinfectives

S03AA - Antiinfectives

S03AA07 - Ciprofloxacin


5.5 Absorption, Distribution and Excretion

Absorption

A 250mg oral dose of ciprofloxacin reaches an average maximum concentration of 0.94mg/L in 0.81 hours with an average area under the curve of 1.013L/h\*kg. The FDA reports an oral bioavailability of 70-80% while other studies report it to be approximately 60%. An early review of ciprofloxacin reported an oral bioavailability of 64-85% but recommends 70% for all practical uses.


Route of Elimination

27% of an oral dose was recovered unmetabolized in urine compared to 46% of an intravenous dose. Collection of radiolabelled ciprofloxacin resulted in 45% recovery in urine and 62% recovery in feces.


Volume of Distribution

Cirpofloxacin follws a 3 compartment distribution model with a central compartment volume of 0.161L/kg and a total volume of distribution of 2.00-3.04L/kg.


Clearance

The average renal clearance after a 250mg oral dose is 5.08mL/min\*kg. Following a 100mg intravenous dose, the average total clearance is 9.62mL/min\*kg, average renal clearance is 4.42mL/min\*kg, and average non renal clearance is 5.21mL/min\*kg.


Based on population pharmacokinetics, bioavailability of ciprofloxacin oral suspension in children is approximately 60%. Following a single oral dose of 10 mg/kg of ciprofloxacin given as the oral suspension to children 4 months to 7 years of age, the mean peak plasma concentration was 2.4 ug/mL. There was no apparent age dependence and no increase in peak plasma concentrations following multiple doses.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 379


When extended-release tablets containing ciprofloxacin hydrochloride (ProQuin XR) are administered with food, approximately 87% of the drug is gradually released from the tablet over a 6- hour period. When administered following a meal, peak plasma concentrations are attained approximately 4.5-7 hours after the dose. Bioavailability is substantially lower if ProQuin XR tablets are given while fasting. In healthy adults receiving ProQuin XR extended-release tablets in a dosage of 500 mg once daily given following a standardized meal, peak plasma concentrations at steady state (day 3) average 0.82 mcg/mL and are attained 6.1 hours after the dose. /Ciprofloxacin hydrochloride/

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 379


Following oral administration of extended-release tablets containing ciprofloxacin hydrochloride and base (Cipro XR), peak plasma concentrations of ciprofloxacin are attained within 1-4 hours. Cipro XR tablets contain approximately 35% of the dose within an immediate-release component; the remaining 65% of the dose is contained in a slow-release matrix. Oral administration of ciprofloxacin 500 mg daily as Cipro XR extended-release tablets or 250 mg twice daily as conventional tablets results in steady-state mean peak plasma concentrations of 1.59 or 1.14 ug/mL, respectively; however, the area under the concentration-time curve (AUC) is similar with both regimens. /Ciprofloxacin hydrochloride/

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 379


Peak serum concentrations of ciprofloxacin and AUCs of the drug are slightly higher in geriatric patients than in younger adults; this may occur because of increased bioavailability, reduced volume of distribution, and/or reduced renal clearance in these patients. Single-dose oral studies using ciprofloxacin conventional tablets and single- and multiple-dose IV studies indicate that, compared with younger adults, peak plasma concentrations are 16-40% higher, mean AUC is approximately 30% higher, and elimination half-life is prolonged approximately 20% in individuals older than 65 years of age. These differences can be at least partially attributed to decreased renal clearance in this age group and are not clinically important.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 379


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


5.6 Metabolism/Metabolites

Ciprofloxacin is primarily metabolized by CYP1A2. The primary metabolites oxociprofloxacin and sulociprofloxacin make up 3-8% of the total dose each. Ciprofloxacin is also converted to the minor metabolites desethylene ciprofloxacin and formylciprofloxacin. These 4 metabolites account for 15% of a total oral dose. There is a lack of available data on the enzymes and types of reactions involved in forming these metabolites.


The drug is partially metabolized in the liver by modification of the piperazinyl group to at least 4 metabolites. These metabolites, which have been identified as desethyleneciprofloxacin (M1), sulfociprofloxacin (M2), oxociprofloxacin (M3), and N-formylciprofloxacin (M4), have microbiologic activity that is less than that of the parent drug but may be similar to or greater than that of some other quinolones (e.g., M3 and M4 are comparable to norfloxacin for certain organisms).

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 380


5.7 Biological Half-Life

The average half life following a 250mg oral dose was 4.71 hours and 3.65 hours following a 100mg intravenous dose. Generally the half life is reported as 4 hours.


The serum elimination half-life of ciprofloxacin in adults with normal renal function is 3-7 hours. Following IV administration in healthy adults, the distribution half-life of ciprofloxacin averages 0.18-0.37 hours and the elimination half-life averages 3-4.8 hours. The elimination half-life of the drug is slightly longer in geriatric adults than in younger adults, and ranges from 3.3-6.8 hours in adults 60-91 years of age with renal function normal for their age. Based on population pharmacokinetic analysis of pediatric patients with various infections, the predicted mean half-life of ciprofloxacin in children is approximately 4-5 hours. In patients with impaired renal function, serum concentrations of ciprofloxacin are higher and the half-life prolonged. In adults with creatinine clearances of 30 mL/minute or less, half-life of the drug ranges from 4.4-12.6 hours.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 380


t1/2 for ciprofloxacin- normal: 4 (hr), anephric: 8.5 (hr) /from table/

Young, L.Y., M.A. Koda-Kimble (eds.). Applied Therapeutics. The Clinical Use of Drugs. 6th ed. Vancouver, WA., Applied Therapeutics, Inc. 1995., p. 32-7


5.8 Mechanism of Action

Ciprofloxacin acts on bacterial topoisomerase II (DNA gyrase) and topoisomerase IV. Ciprofloxacin's targeting of the alpha subunits of DNA gyrase prevents it from supercoiling the bacterial DNA which prevents DNA replication.


The mechanism by which ciprofloxacin's inhibition of DNA gyrase or topoisomerase IV results in death in susceptible organisms has not been fully determined. Unlike beta-lactam anti-infectives, which are most active against susceptible bacteria when they are in the logarithmic phase of growth, studies using Escherichia coli and Pseudomonas aeruginosa indicate that ciprofloxacin can be bactericidal during both logarithmic and stationary phases of growth; this effect does not appear to occur with gram-positive bacteria (e.g., Staphylococcus aureus). In vitro studies indicate that ciprofloxacin concentrations that approximate the minimum inhibitory concentration (MIC) of the drug induce filamentation in susceptible organisms; high concentrations of the drug result in enlarged or elongated cells that may not be extensively filamented. Although the bactericidal effect of some fluoroquinolones (e.g., norfloxacin) evidently requires competent RNA and protein synthesis in the bacterial cell, and concurrent use of anti-infectives that affect protein synthesis (e.g., chloramphenicol, tetracyclines) or RNA synthesis (e.g., rifampin) inhibit the in vitro bactericidal activity of these drugs, the bactericidal effect of ciprofloxacin is only partially reduced in the presence of these anti-infectives. This suggests that ciprofloxacin has an additional mechanism of action that is independent of RNA and protein synthesis.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 375


Ciprofloxacin usually is bactericidal in action. Like other fluoroquinolone anti-infectives, ciprofloxacin inhibits DNA synthesis in susceptible organisms via inhibition of the enzymatic activities of 2 members of the DNA topoisomerase class of enzymes, DNA gyrase and topoisomerase IV. DNA gyrase and topoisomerase IV have distinct essential roles in bacterial DNA replication. DNA gyrase, a type II DNA topoisomerase, was the first identified quinolone target; DNA gyrase is a tetramer composed of 2 GyrA and 2 GyrB subunits. DNA gyrase introduces negative superhelical twists in DNA, an activity important for initiation of DNA replication. DNA gyrase also facilitates DNA replication by removing positive super helical twists. Topoisomerase IV, another type II DNA topoisomerase, is composed of 2 ParC and 2 ParE subunits. DNA gyrase and topoisomerase IV are structurally related; ParC is homologous to GyrA and ParE is homologous to GyrB. Topoisomerase IV acts at the terminal states of DNA replication by allowing for separation of interlinked daughter chromosomes so that segregation into daughter cells can occur. Fluoroquinolones inhibit these topoisomerase enzymes by stabilizing either the DNA-DNA gyrase complex or the DNA-topoismerase IV complex; these stabilized complexes block movement of the DNA replication fork and thereby inhibit DNA replication resulting in cell death.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 375


... Ciprofloxacin is cytotoxic to a variety of cultured mammalian cell lines at concn that deplete cells of mtDNA. The IC50 values for ciprofloxacin varied from 40-80 ug/ml depending on the cell line tested. Cytotoxicity required continuous exposure of cells to drug for 2-4 days, which corresponded to approx three or four cell doublings. Shorter times of drug exposure did not cause significant cytotoxicity. In addition, cells became drug resistant when they were grown under conditions that bypassed the need for mitochondrial respiration. Resistance was not due to a decr in cellular drug accumulation, ... /indicating/ that ciprofloxacin cytotoxicity is caused by the loss of mtDNA encoded functions. Analysis of mtDNA from ciprofloxacin treated cells revealed the presence of site specific, double stranded DNA breaks. ... Exonuclease protection studies indicated that the 5'-, but not the 3', ends of the drug induced DNA breaks were tightly associated with protein. These results suggest that ciprofloxacin may be causing cytotoxicity by interfering with a mitochondrial topoisomerase II like activity, resulting in a loss of mtDNA.

PMID:8913349 Lawrence JW, et al; Mol Pharmacol 50 (5): 1178-88 (1996)


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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04-Jan-2021
29-Aug-2024
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DOSAGE - INJECTABLE;INJECTION - 200MG/100ML *...DOSAGE - INJECTABLE;INJECTION - 200MG/100ML **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 19857

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DOSAGE - INJECTABLE;INJECTION - 400MG/200ML *...DOSAGE - INJECTABLE;INJECTION - 400MG/200ML **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 19857

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DOSAGE - INJECTABLE, SUSPENSION;OTIC - 6% (60...DOSAGE - INJECTABLE, SUSPENSION;OTIC - 6% (60MG/ML)

USFDA APPLICATION NUMBER - 207986

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DOSAGE - SUSPENSION/DROPS;OTIC - 0.3%;0.1%

USFDA APPLICATION NUMBER - 21537

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