Ciprofloxacin

Inquiry

Cat Number

API85721331

CAS Number

85721-33-1

For research use only. We do not supply to patients.

For pharmaceutical-grade products or other inquiries, please contact our experts.

Product Detail Description Scientific Support Advanced Innovations Customer Q&A

CAS Number

85721-33-1

EINECS

617-751-0

Storage

Store at room temperature

Synonyms

Ciprofloxacine; Ciprobay; Cipro; Ciprofloxacina; 1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid; Ciprofloxacino; Ciprofloxacinum

Molecular Formula

C17H18FN3O3

Molecular Weight

331.34

Smiles

C1CC1N2C=C(C(=O)C3=CC(=C(C=C32)N4CCNCC4)F)C(=O)O

Appearance

White to slightly yellow powder

Melting Point

255-257°C

Boiling Point

581.8±50.0°C at 760 mmHg (Predicted)

Relative Density

1.461±0.06 (Predicted)

General Description

Ciprofloxacin is a fluoroquinolone antibiotic with a cyclopropyl group at position 1 and a fluorine atom at position 6, along with a piperazinyl substituent at position 7. The molecule is a synthetic derivative of nalidixic acid, with dramatically improved potency and spectrum. Ciprofloxacin is a zwitterion with both basic (piperazine) and acidic (carboxylic acid) functional groups.

Mechanism of Action

Ciprofloxacin inhibits bacterial DNA gyrase (topoisomerase II) and topoisomerase IV, enzymes required for DNA supercoiling, replication, and decatenation. By stabilizing the cleaved complex, it generates double-strand DNA breaks that are lethal to the bacterium. Ciprofloxacin has preferential activity against gram-negative bacteria due to higher affinity for gyrase over topoisomerase IV. The drug exhibits concentration-dependent bactericidal activity and a post-antibiotic effect.

Application

Ciprofloxacin is indicated for a broad range of infections including urinary tract infections, prostatitis, respiratory tract infections, skin and soft tissue infections, bone and joint infections, and gastrointestinal infections (including typhoid fever). It is also the drug of choice for anthrax post-exposure prophylaxis and for plague. Its excellent penetration into bone, prostate, and lung tissue makes it valuable in these settings.

Both type II topoisomerases Top2α and Top2β are present in mammalian mitochondria, with Top2β regulating mtDNA supercoiling. Loss of Top2β or its inhibition by ciprofloxacin leads to accumulation of positively supercoiled mtDNA, halting mitochondrial transcription and replication initiation, and depleting mtDNA copy number. These effects block cell proliferation and differentiation, possibly explaining some side effects of fluoroquinolone antibiotics. Topology is critical for mtDNA homeostasis.

Fig. 1 Topoisomerase 2α and 2β co-localize with replicating mitochondrial DNA nucleoids. (Hangas A, et al., 2018)

References

Hangas A, et al. Ciprofloxacin impairs mitochondrial DNA replication initiation through inhibition of Topoisomerase 2. Nucleic Acids Res. 2018;46(18):9625-9636.

Two ciprofloxacin‑loaded mesoporous silica nanoparticle formulations were prepared: MSN‑[Ch][Cip] (ciprofloxacin as counter‑ion of choline derivative) and MSN‑Cip (covalently linked via amide bond). Both showed no cytotoxicity to 3T3 fibroblasts. They exhibited promising antimicrobial activity against Staphylococcus aureus, and against Bacillus subtilis and Klebsiella pneumoniae they performed better than the precursor or free ciprofloxacin. These nanomaterials offer potential for treating bacterial infections.

Fig. 2 Ciprofloxacin immobilized in mesoporous silica nanoparticles (by functionalization of choline derivative cation, MSN-[Ch][Cip]) or by direct functionalization of ciprofloxacin drug MSN-Cip. (de Juan Mora B, et al., 2021)

References

de Juan Mora B, et al. Boosting Antimicrobial Activity of Ciprofloxacin by Functionalization of Mesoporous Silica Nanoparticles. Pharmaceutics. 2021;13(2):218.

Does Ciprofloxacin require protection from light during long-term storage?

Yes, it is photosensitive. UV exposure can cause photodegradation and formation of the ethylenediamine impurity. Store in light-resistant containers, preferably original opaque packaging.

What is the recommended storage humidity for Ciprofloxacin?

It is slightly hygroscopic. Under high humidity (>75% RH), it may absorb moisture and clump. Store in tightly sealed containers with desiccant.

Is Ciprofloxacin stable in intravenous solution formulations?

Reconstituted solutions are stable for up to 24 hours at room temperature when protected from light.

How is the impurity ciprofloxacin desfluoro (a process-related impurity) monitored?

This impurity is quantified using a stability-indicating HPLC method, ensuring it remains below USP/EP limits.