Ciprofloxacin

Not to be confused with Ciproxifan.

Ciprofloxacin
structure
3D model of ciprofloxacin
Clinical data
Trade namesCipro, others
AHFS/Drugs.comMonograph
MedlinePlusa688016
License data
Pregnancy
category
Routes of
administration		By mouth, intravenous, topical (ear drops, eye drops)
Drug classFluoroquinolone
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability70%[3]
Protein binding30%[3]
MetabolismLiver
Elimination half-life3.5 hours[3]
ExcretionKidney
Identifiers
IUPAC name
  • 1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-quinoline-3-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard100.123.026
Chemical and physical data
FormulaC17H18FN3O3
Molar mass331.347 g·mol−1
3D model (JSmol)
SMILES
  • C1CNCCN1c(c2)c(F)cc3c2N(C4CC4)C=C(C3=O)C(=O)O
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) Y
  • Key:MYSWGUAQZAJSOK-UHFFFAOYSA-N Y
  (verify)

Ciprofloxacin is a fluoroquinolone antibiotic used to treat a number of bacterial infections.[4] This includes bone and joint infections, intra-abdominal infections, certain types of infectious diarrhea, respiratory tract infections, skin infections, typhoid fever, and urinary tract infections, among others.[4] For some infections it is used in addition to other antibiotics.[4] It can be taken by mouth, as eye drops, as ear drops, or intravenously.[4][5]

Common side effects include nausea, vomiting, and diarrhea.[4] Severe side effects include tendon rupture, hallucinations, and nerve damage.[4] In people with myasthenia gravis, there is worsening muscle weakness.[4] Rates of side effects appear to be higher than some groups of antibiotics such as cephalosporins but lower than others such as clindamycin.[6] Studies in other animals raise concerns regarding use in pregnancy.[7] No problems were identified, however, in the children of a small number of women who took the medication.[7] It appears to be safe during breastfeeding.[4] It is a second-generation fluoroquinolone with a broad spectrum of activity that usually results in the death of the bacteria.[4][8][9]

Ciprofloxacin was patented in 1980 and introduced by Bayer in 1987.[10][11] It is on the World Health Organization's List of Essential Medicines.[12] The World Health Organization classifies ciprofloxacin as critically important for human medicine.[13] It is available as a generic medication.[4][14] In 2022, it was the 181st most commonly prescribed medication in the United States, with more than 2 million prescriptions.[15][16]

  1. ^ "Ciprofloxacin Use During Pregnancy". Drugs.com. 7 January 2019. Retrieved 19 December 2019.
  2. ^ "Cipro- ciprofloxacin hydrochloride tablet, film coated; Cipro- ciprofloxacin kit". DailyMed. 31 January 2023. Retrieved 9 February 2024.
  3. ^ a b c Zhanel GG, Fontaine S, Adam H, Schurek K, Mayer M, Noreddin AM, et al. (2006). "A Review of New Fluoroquinolones: Focus on their Use in Respiratory Tract Infections". Treatments in Respiratory Medicine. 5 (6): 437–465. doi:10.2165/00151829-200605060-00009. PMID 17154673. S2CID 26955572.
  4. ^ a b c d e f g h i j "Ciprofloxacin Hydrochloride". The American Society of Health-System Pharmacists. Archived from the original on 23 September 2015. Retrieved 23 August 2015.
  5. ^ "Ciprofloxacin (Ciloxan) ophthalmic - Uses, Side Effects, and More". WebMD. 22 February 2018. Retrieved 22 February 2018.
  6. ^ Heidelbaugh JJ, Holmstrom H (April 2013). "The perils of prescribing fluoroquinolones". The Journal of Family Practice. 62 (4): 191–197. PMID 23570031.
  7. ^ a b "Prescribing medicines in pregnancy database". Government of Australia. 23 August 2015. Archived from the original on 8 April 2014.
  8. ^ Ball P (July 2000). "Quinolone generations: natural history or natural selection?". The Journal of Antimicrobial Chemotherapy. 46 Suppl T1: 17–24. doi:10.1093/oxfordjournals.jac.a020889. PMID 10997595.
  9. ^ Oliphant CM, Green GM (February 2002). "Quinolones: a comprehensive review". American Family Physician. 65 (3): 455–464. doi:10.1016/s0022-5347(17)67120-9. PMID 1185862.
  10. ^ Oxford Handbook of Infectious Diseases and Microbiology. OUP Oxford. 2009. p. 56. ISBN 978-0-19-103962-1. Archived from the original on 8 September 2017.
  11. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 500. ISBN 978-3-527-60749-5.
  12. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  13. ^ World Health Organization (2019). Critically important antimicrobials for human medicine (6th revision ed.). Geneva: World Health Organization. hdl:10665/312266. ISBN 978-92-4-151552-8.
  14. ^ Hamilton RJ (2014). Tarascon pharmacopoeia (15th ed.). Jones & Bartlett Publishers. p. 85. ISBN 978-1-284-05671-6. Archived from the original on 8 September 2017.
  15. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  16. ^ "Ciprofloxacin Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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