Ciprofloxacin

"Cipro" redirects here. For the Rome Metro station, see Cipro (Rome Metro).
Not to be confused with Ciproxifan.

Ciprofloxacin
ciprofloxacin molecule
structure
ciprofloxacin zwitterion molecule
3D model of ciprofloxacin zwitterion
Clinical data
Trade namesCiloxan, Cipro, Neofloxin, 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%[4]
Protein binding30%[4]
MetabolismLiver
Elimination half-life3.5 hours[4]
ExcretionKidney
Identifiers
  • 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 Edit this at Wikidata
Chemical and physical data
FormulaC17H18FN3O3
Molar mass331.347 g·mol−1
3D model (JSmol)
  • C1CNCCN1c(c2)c(F)cc3c2N(C4CC4)C=C(C3=O)C(=O)O
  • 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) checkY
  • Key:MYSWGUAQZAJSOK-UHFFFAOYSA-N checkY
  (verify)

Ciprofloxacin is a fluoroquinolone antibiotic used to treat a number of bacterial infections.[5] 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.[5] For some infections it is used in addition to other antibiotics.[5] It can be taken by mouth, as eye drops, as ear drops, or intravenously.[5][6]

Common side effects include nausea, vomiting, and diarrhea.[5] Severe side effects include an increased risk of tendon rupture, hallucinations, and nerve damage.[5] In people with myasthenia gravis, there is worsening muscle weakness.[5] Rates of side effects appear to be higher than some groups of antibiotics such as cephalosporins but lower than others such as clindamycin.[7] Studies in other animals raise concerns regarding use in pregnancy.[8] No problems were identified, however, in the children of a small number of women who took the medication.[8] It appears to be safe during breastfeeding.[5] It is a second-generation fluoroquinolone with a broad spectrum of activity that usually results in the death of the bacteria.[5][9][10]

Ciprofloxacin was patented in 1980 and introduced by Bayer in 1987.[11][12] It is on the World Health Organization's List of Essential Medicines.[13][14] The World Health Organization classifies ciprofloxacin as critically important for human medicine.[15] It is available as a generic medication.[5][16] In 2022, it was the 181st most commonly prescribed medication in the United States, with more than 2 million prescriptions.[17][18]

  1. ^ "Ciprofloxacin Use During Pregnancy". Drugs.com. 7 January 2019. Retrieved 19 December 2019.
  2. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  3. ^ "Cipro- ciprofloxacin hydrochloride tablet, film coated; Cipro- ciprofloxacin kit". DailyMed. 31 January 2023. Retrieved 9 February 2024.
  4. ^ 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.
  5. ^ 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.
  6. ^ "Ciprofloxacin Hcl Drops". WebMD. 22 February 2018. Retrieved 22 February 2018.
  7. ^ Heidelbaugh JJ, Holmstrom H (April 2013). "The perils of prescribing fluoroquinolones". The Journal of Family Practice. 62 (4): 191–197. PMID 23570031.
  8. ^ a b "Prescribing medicines in pregnancy database". Government of Australia. 23 August 2015. Archived from the original on 8 April 2014.
  9. ^ 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.
  10. ^ 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.
  11. ^ 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.
  12. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 500. ISBN 978-3-527-60749-5.
  13. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  14. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  15. ^ 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.
  16. ^ 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.
  17. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  18. ^ "Ciprofloxacin Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.