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Ciprofloxacin information


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
  • US DailyMed: Ciprofloxacin
Pregnancy
category
  • AU: B3[1]
Routes of
administration
By mouth, intravenous, topical (ear drops, eye drops)
Drug classFluoroquinolone
ATC code
  • J01MA02 (WHO) S01AE03 (WHO) S02AA15 (WHO) S03AA07 (WHO) J01RA10 (WHO) J01RA11 (WHO) J01RA12 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: WARNING[2]Rx-only[3]
Pharmacokinetic data
Bioavailability70%[4]
Protein binding30%[4]
MetabolismLiver
Elimination half-life3.5 hours[4]
ExcretionKidney
Identifiers
IUPAC name
  • 1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-quinoline-3-carboxylic acid
CAS Number
  • 85721-33-1 checkY
PubChem CID
  • 2764
DrugBank
  • DB00537 checkY
ChemSpider
  • 2662 checkY
UNII
  • 5E8K9I0O4U
KEGG
  • D00186 checkY
  • as HCl: D02216 ☒N
ChEBI
  • CHEBI:100241 checkY
ChEMBL
  • ChEMBL8 checkY
NIAID ChemDB
  • 001992
CompTox Dashboard (EPA)
  • DTXSID8022824 Edit this at Wikidata
ECHA InfoCard100.123.026 Edit this at Wikidata
Chemical and physical data
FormulaC17H18FN3O3
Molar mass331.347 g·mol−1
3D model (JSmol)
  • Interactive image
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) 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 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 2021, it was the 141st most commonly prescribed medication in the United States, with more than 4 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 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  18. ^ "Ciprofloxacin - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

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narrow-spectrum antibiotics whenever possible. Broad-spectrum antibiotic: Ciprofloxacin, Doxycycline, Minocycline, Tetracycline, Imipenem, Azithromycin Extended-spectrum...

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include: Ciprodex ear drops containing ciprofloxacin and dexamethasone Ciproxin HC ear drops containing ciprofloxacin and hydrocortisone Kenacomb ear drops...

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