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Merck

17850

Ciprofloxacin

≥98% (HPLC)

Synonym(s):

1-Cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid, Ciprobay

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About This Item

Empirical Formula (Hill Notation):
C17H18FN3O3
CAS Number:
85721-33-1
Molecular Weight:
331.34
UNSPSC Code:
41116105
NACRES:
NA.21
PubChem Substance ID:
329751572
MDL number:
MFCD00185755
Beilstein/REAXYS Number:
3568352

Product Name

Ciprofloxacin, ≥98% (HPLC)

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)

SMILES string

OC(=O)C1=CN(C2CC2)c3cc(N4CCNCC4)c(F)cc3C1=O

InChI key

MYSWGUAQZAJSOK-UHFFFAOYSA-N

agency

EPA 1694

assay

≥98% (HPLC)

form

powder or crystals

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

application(s)

environmental

mode of action

DNA synthesis | interferes
enzyme | inhibits

Quality Level

200

Gene Information

human ... CYP1A2(1544), KCNH1(3756)
rat ... Gabra1(29705)

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Application

Ciprofloxacin is widely used in clinical practices against Gram-positive and Gram-negative bacteria and the treatment of a broad range of infections, including those of the skin, eyes, urinary tract, lower respiratory tract, gastrointestinal tract, et cetera. It can also be combined with various antimicrobial agents to combat bacterial biofilms as well as multidrug-resistant microorganisms. Its derivatives have been developed to synthesize novel antibacterials with enhanced potency and diverse antimicrobial effects including antibacterial, antifungal, anti-HIV, anti-tumor, and anti-TB properties.

Biochem/physiol Actions

The mechanism of action of Ciprofloxacin is the inhibition of bacterial DNA synthesis by blocking the subunit A of DNA gyrase enzyme as well as by affecting the bacterial cell wall.

General description

Ciprofloxacin is a second-generation broad-spectrum fluoroquinolone antibiotic with extensive antimicrobial and pharmacokinetic properties that is widely used to combat bacterial infections. Its chemical name is 1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid.

Chemical structure: fluoroquinolone

Storage Class

11 - Combustible Solids

wgk

WGK 2

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000488016
0000488016
0000488015
0000488015
0000369395

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. What is the solubility of Product 17850, Ciprofloxacin?

    17850 is the free base of ciprofloxacin. It is soluble in 0.1N HCl at 25 mg/ml.  Ciprofloxacin is poorly soluble in DMSO. For HPLC, dissolve the sample material in a mixture ofAcetonitril/Phosphoric acid pH 2.4 by ultrasonification (5 mg/10 ml solvent).

  4. Can Product 17850, Ciprofloxacin, be used in cell culture?

    We have not done cell culture testing with this product.

  5. What is the potency of Product 17850, Ciprofloxacin?

    The potency of this product has not been determined by our Quality Control or by our supplier.

  6. Can Product 17850, Ciprofloxacin, be used to remove Mycoplasma contaminations?

    We have not tested the product for that application. However, there is a reference in Roche's Biochemica Newsletter Issue 1 from 1996 that describes using Ciprofloxacin in mycoplasma contamination.

  7. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  8. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  9. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

The resistance mechanisms of bacteria against ciprofloxacin and new approaches for enhancing the efficacy of this antibiotic
Shariati et al.
Frontiers in public health, 10 (2022)
Gui-Fu Zhang et al.
European journal of medicinal chemistry, 146, 599-612 (2018-02-07)
Bacterial infections represent a significant health threat globally, and are responsible for the majority of hospital-acquired infections, leading to extensive mortality and burden on global healthcare systems. The second generation fluoroquinolone ciprofloxacin which exhibits excellent antimicrobial activity and pharmacokinetic properties
Athina Andrea et al.
Microorganisms, 7(3) (2019-03-22)
Among non-mammalian infection model organisms, the larvae of the greater wax moth Galleria mellonella have seen increasing popularity in recent years. Unlike other invertebrate models, these larvae can be incubated at 37 °C and can be dosed relatively precisely. Despite
Orjan Samuelsen et al.
Antimicrobial agents and chemotherapy, 54(1), 346-352 (2009-11-04)
Scandinavia is considered a region with a low prevalence of antimicrobial resistance. However, the number of multidrug-resistant (MDR) Gram-negative bacteria is increasing, including metallo-beta-lactamase (MBL)-producing Pseudomonas aeruginosa. In this study MBL-producing P. aeruginosa isolates identified in Norway (n = 4)
Dongeun Yong et al.
Antimicrobial agents and chemotherapy, 53(12), 5046-5054 (2009-09-23)
A Swedish patient of Indian origin traveled to New Delhi, India, and acquired a urinary tract infection caused by a carbapenem-resistant Klebsiella pneumoniae strain that typed to the sequence type 14 complex. The isolate, Klebsiella pneumoniae 05-506, was shown to
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