Ciprofloxacin
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| Category | Antibiotics |
| Catalog number | BBF-04539 |
| CAS | 85721-33-1 |
| Molecular Weight | 331.34 |
| Molecular Formula | C17H18FN3O3 |
| Purity | >98% |
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Description
Ciprofloxacin is a fluoroquinolone antibiotic, shows broad and potent antibacterial activity, with MIC90 of 0.024-6 μM. It is active against a variety of Gram-positive and Gram-negative bacteria in vitro, including S. aureus, L. monocytogenes, P. aeruginosa, Legionella, N. gonorrhoeae and H. pylori.
Specification
| Related CAS | 93107-08-5 (hydrochloride) |
| Synonyms | 1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic Acid; Bay q 3939; Ciflafin; Ciprine; Cipro IV; Ciprofloxacillin; Ciprobay; Fimoflox; Ipiflox; Probiox |
| Storage | Store at -20°C |
| IUPAC Name | 1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid |
| Canonical SMILES | C1CC1N2C=C(C(=O)C3=CC(=C(C=C32)N4CCNCC4)F)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) |
| InChI Key | MYSWGUAQZAJSOK-UHFFFAOYSA-N |
| Source | Synthetic |
Properties
| Appearance | White Solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 581.8±50.0°C (Predicted) |
| Melting Point | 253-255°C (dec.) |
| Density | 1.461±0.06 g/cm3 (Predicted) |
| Solubility | Slightly soluble in DMSO (Heated), Methanol (Heated) |
| LogP | 0.28 |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | The bactericidal action of ciprofloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV, which are required for bacterial DNA replication, transcription, repair, strand supercoiling repair, and recombination. |
Reference Reading
1.Urinary tract physiological conditions promote ciprofloxacin resistance in low-level quinolone resistant Escherichia coli.
Martín-Gutiérrez G1, Rodríguez-Beltrán J2, Rodríguez-Martínez JM3, Costas C2, Aznar J1, Pascual Á4, Blázquez J5. Antimicrob Agents Chemother. 2016 May 2. pii: AAC.00602-16. [Epub ahead of print]
Escherichia coli isolates carrying chromosomally-encoded low-level quinolone resistant (LLQR) determinants are frequently found in urinary tract infections (UTI). LLQR mutations are considered the first step in the evolutionary pathway producing high-level fluoroquinolone resistance. Therefore, their evolution and dissemination might influence the outcome of fluoroquinolone treatments of UTI. Previous studies support the notion that low urine pH decreases susceptibility to ciprofloxacin in E. coli However, the effect of the urinary tract physiological parameters on the activity of ciprofloxacin against LLQR E. coli strains has received little attention. We have studied the activity of ciprofloxacin under physiological urinary tract conditions against a set of well-characterized isogenic E. coli derivatives carrying the most prevalent chromosomal mutations (ΔmarR, gyrA-S83L, gyrA-D87N and parC-S80R and some combinations). The results presented here demonstrate that all the LLQR strains studied become resistant to ciprofloxacin (according to CLSI) under physiological conditions whereas the control strain lacking LLQR mutations does not.
2.Involvement of antibiotic efflux machinery in glutathione-mediated decreased ciprofloxacin activity in Escherichia coli.
Goswami M1, Subramanian M2, Kumar R3, Jass J3, Jawali N4. Antimicrob Agents Chemother. 2016 May 2. pii: AAC.00414-16. [Epub ahead of print]
We have analyzed the contribution of different efflux components towards glutathione-mediated abrogation of ciprofloxacin's activity in Escherichia coli and underlying potential mechanism(s) behind this phenomenon. The results indicated that glutathione increased the total active efflux thereby partially contributing towards glutathione-mediated neutralization of ciprofloxacin's antibacterial action in E. coli. However, the role of glutathione-mediated increased efflux becomes evident in the absence of functional TolC-AcrAB efflux pump.
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C17H18FN3O3
Molecular Weight (Monoisotopic Mass): 331.1332 Da
Molecular Weight (Avergae Mass): 331.3415 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C17H18FN3O3
Molecular Weight (Monoisotopic Mass): 331.1332 Da
Molecular Weight (Avergae Mass): 331.3415 Da
LC-MS/MS Spectrum - LC-ESI-qTof , Positive
Experimental Conditions
Instrument Type: LC-ESI-qTof
Ionization Mode: Positive
Ionization Mode: Positive
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C17H18FN3O3
Molecular Weight (Monoisotopic Mass): 331.1332 Da
Molecular Weight (Avergae Mass): 331.3415 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C17H18FN3O3
Molecular Weight (Monoisotopic Mass): 331.1332 Da
Molecular Weight (Avergae Mass): 331.3415 Da
13C NMR Spectrum
Experimental Conditions
Solvent: D2O
Nucleus: 13C
Frequency: 100
Nucleus: 13C
Frequency: 100
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
