Cadrofloxacin
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MedKoo CAT#: 326632

CAS#: 153808-85-6 (free base)

Description: Cadrofloxacin, also known as Caderofloxacin and CS-940, is a novel fluoroquinolone antibacterial. The activities of CS-940 against gram-positive cocci and gram-negative rods, including methicillin-susceptible Staphylococcus aureus and penicillin-resistant Streptococcus pneumoniae, were comparable to those of tosufloxacin, with MICs at which 90% of the strains were inhibited (MIC90s) of 0.5 microg/ml or less. Against methicillin-resistant S. aureus, CS-940 was as active as tosufloxacin, with a MIC90 of 16 microg/ml. The efficacy of CS-940 against murine respiratory infections due to S. pneumoniae or Haemophilus influenzae was better than those of tosufloxacin and sparfloxacin. The efficacy of oral doses of CS-940 reflected not only potent in vitro activity but also a high transmigration ratio from the bloodstream to lung tissues.


Chemical Structure

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Cadrofloxacin
CAS# 153808-85-6 (free base)

Theoretical Analysis

MedKoo Cat#: 326632
Name: Cadrofloxacin
CAS#: 153808-85-6 (free base)
Chemical Formula: C19H20F3N3O4
Exact Mass: 411.1406
Molecular Weight: 411.3812
Elemental Analysis: C, 55.47; H, 4.90; F, 13.85; N, 10.21; O, 15.56

Price and Availability

Size Price Availability Quantity
1.0mg USD 120.0 Ready to ship
5.0mg USD 450.0 Ready to ship
10.0mg USD 750.0 Ready to ship
25.0mg USD 1650.0 Ready to ship
50.0mg USD 2650.0 Ready to ship
100.0mg USD 3850.0 Ready to ship
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Related CAS #: 128427-55-4 (HCl)   153808-85-6 (free base)  

Synonym: CS-940; CS 940; CS940; Cadrofloxacin; Caderofloxacin; Cadrofloxacin hydrochloride; Cadrofloxacin HCl.

IUPAC/Chemical Name: (S)-1-cyclopropyl-8-(difluoromethoxy)-6-fluoro-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

InChi Key: QBDBUKJBJJWZMG-VIFPVBQESA-N

InChi Code: InChI=1S/C19H20F3N3O4/c1-9-7-24(5-4-23-9)15-13(20)6-11-14(17(15)29-19(21)22)25(10-2-3-10)8-12(16(11)26)18(27)28/h6,8-10,19,23H,2-5,7H2,1H3,(H,27,28)/t9-/m0/s1

SMILES Code: O=C(C1=CN(C2CC2)C3=C(C=C(F)C(N4C[C@H](C)NCC4)=C3OC(F)F)C1=O)O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Biological target: Cadrofloxacin (Caderofloxacin; CS-940), an active fluoroquinolone, is effective against aerobic/anaerobic Gram-positive and Gram-negative bacteria.
In vitro activity: The in vitro activities of CS-940, a new fluoroquinolone, were compared with those of a group of other drugs. The activities of CS-940 against gram-positive cocci and gram-negative rods, including methicillin-susceptible Staphylococcus aureus and penicillin-resistant Streptococcus pneumoniae, were comparable to those of tosufloxacin, with MICs at which 90% of the strains were inhibited (MIC90s) of 0.5 microg/ml or less. Against methicillin-resistant S. aureus, CS-940 was as active as tosufloxacin, with a MIC90 of 16 microg/ml. Reference: Antimicrob Agents Chemother. 1997 Nov;41(11):2582-5. https://pubmed.ncbi.nlm.nih.gov/9371375/
In vivo activity: The in vivo activities of CS-940, a new 6-fluoro-8-difluoromethoxy quinolone, were compared with those of ciprofloxacin, tosufloxacin, sparfloxacin, and levofloxacin. CS-940 showed potent bactericidal activity against S. aureus, Escherichia coli, Klebsiella pneumoniae, and Pseudomonas aeruginosa. In oral treatment of mouse systemic infections caused by S. aureus, Streptococcus pneumoniae, Streptococcus pyogenes, E. coli, K. pneumoniae, Serratia marcescens, and P. aeruginosa, CS-940 was more effective than ciprofloxacin, sparfloxacin, and levofloxacin against all strains tested. Against experimental pneumonia with K. pneumoniae in mice, CS-940 was the most effective of all the quinolones tested. These results suggest that CS-940 may be effective in the therapy of various bacterial infections. Reference: Antimicrob Agents Chemother. 1996 May;40(5):1201-7. https://pubmed.ncbi.nlm.nih.gov/8723467/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 10.0 24.31

Preparing Stock Solutions

The following data is based on the product molecular weight 411.3812 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Biedenbach DJ, Sutton LD, Jones RN. Antimicrobial activity of CS-940, a new trifluorinated quinolone. Antimicrob Agents Chemother. 1995 Oct;39(10):2325-30. doi: 10.1128/AAC.39.10.2325. PMID: 8619590; PMCID: PMC162937. 2. Miyazaki S, Domon H, Tateda K, Ohno A, Ishii Y, Matsumoto T, Furuya N, Yamaguchi K. In vitro and in vivo antibacterial activities of CS-940, a new fluoroquinolone, against isolates from patients with respiratory infections. Antimicrob Agents Chemother. 1997 Nov;41(11):2582-5. doi: 10.1128/AAC.41.11.2582. PMID: 9371375; PMCID: PMC164170. 3. Masuda N, Takahashi Y, Otsuki M, Ibuki E, Miyoshi H, Nishino T. In vitro and in vivo antibacterial activities of CS-940, a new 6-fluoro-8-difluoromethoxy quinolone. Antimicrob Agents Chemother. 1996 May;40(5):1201-7. doi: 10.1128/AAC.40.5.1201. PMID: 8723467; PMCID: PMC163292.
In vitro protocol: 1. Biedenbach DJ, Sutton LD, Jones RN. Antimicrobial activity of CS-940, a new trifluorinated quinolone. Antimicrob Agents Chemother. 1995 Oct;39(10):2325-30. doi: 10.1128/AAC.39.10.2325. PMID: 8619590; PMCID: PMC162937. 2. Miyazaki S, Domon H, Tateda K, Ohno A, Ishii Y, Matsumoto T, Furuya N, Yamaguchi K. In vitro and in vivo antibacterial activities of CS-940, a new fluoroquinolone, against isolates from patients with respiratory infections. Antimicrob Agents Chemother. 1997 Nov;41(11):2582-5. doi: 10.1128/AAC.41.11.2582. PMID: 9371375; PMCID: PMC164170.
In vivo protocol: 1. Biedenbach DJ, Sutton LD, Jones RN. Antimicrobial activity of CS-940, a new trifluorinated quinolone. Antimicrob Agents Chemother. 1995 Oct;39(10):2325-30. doi: 10.1128/AAC.39.10.2325. PMID: 8619590; PMCID: PMC162937. 2. Masuda N, Takahashi Y, Otsuki M, Ibuki E, Miyoshi H, Nishino T. In vitro and in vivo antibacterial activities of CS-940, a new 6-fluoro-8-difluoromethoxy quinolone. Antimicrob Agents Chemother. 1996 May;40(5):1201-7. doi: 10.1128/AAC.40.5.1201. PMID: 8723467; PMCID: PMC163292.

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1: Ma RL, Zhou HH, Liu R, Wang EH, Sheng LS. [Analysis of impurity in caderofloxacin]. Yao Xue Xue Bao. 2003 Dec;38(12):950-2. Chinese. PubMed PMID: 15040093.

2: Kawahara S, Tada A, Nagare H. [Clinical evaluation of new quinolones as antituberculosis drugs]. Kekkaku. 1999 Jan;74(1):71-5. Review. Japanese. PubMed PMID: 10067058.

3: Namba K. [View of development of fluoroquinolones]. Kekkaku. 1999 Jan;74(1):47-52. Review. Japanese. PubMed PMID: 10067055.

4: Kawahara S. [Chemotherapeutic agents under study]. Nihon Rinsho. 1998 Dec;56(12):3096-9. Review. Japanese. PubMed PMID: 9883617.

5: Miyazaki S, Domon H, Tateda K, Ohno A, Ishii Y, Matsumoto T, Furuya N, Yamaguchi K. In vitro and in vivo antibacterial activities of CS-940, a new fluoroquinolone, against isolates from patients with respiratory infections. Antimicrob Agents Chemother. 1997 Nov;41(11):2582-5. PubMed PMID: 9371375; PubMed Central PMCID: PMC164170.

6: Schmitz FJ, Jones ME. Antibiotics for treatment of infections caused by MRSA and elimination of MRSA carriage. What are the choices? Int J Antimicrob Agents. 1997 Jun;9(1):1-19. PubMed PMID: 18611815.

7: Mizutani S. [Chemotherapy of pulmonary Mycobacterium kansasii infection]. Kekkaku. 1996 Sep;71(9):527-31. Japanese. PubMed PMID: 8914388.

8: Takenouchi T, Tabata F, Iwata Y, Hanzawa H, Sugawara M, Ohya S. Hydrophilicity of quinolones is not an exclusive factor for decreased activity in efflux-mediated resistant mutants of Staphylococcus aureus. Antimicrob Agents Chemother. 1996 Aug;40(8):1835-42. PubMed PMID: 8843290; PubMed Central PMCID: PMC163426.

9: Yamane N, Chilima BZ, Tosaka M, Okazawa Y, Tanno K. [Determination of antimycobacterial activities of fluoroquinolones against clinical isolates of Mycobacterium tuberculosis: comparative determination with egg-based Ogawa and agar-based Middlebrook 7H10 media]. Kekkaku. 1996 Aug;71(8):453-8. Japanese. PubMed PMID: 8831190.

10: Masuda N, Takahashi Y, Otsuki M, Ibuki E, Miyoshi H, Nishino T. In vitro and in vivo antibacterial activities of CS-940, a new 6-fluoro-8-difluoromethoxy quinolone. Antimicrob Agents Chemother. 1996 May;40(5):1201-7. PubMed PMID: 8723467; PubMed Central PMCID: PMC163292.

11: Biedenbach DJ, Sutton LD, Jones RN. Antimicrobial activity of CS-940, a new trifluorinated quinolone. Antimicrob Agents Chemother. 1995 Oct;39(10):2325-30. PubMed PMID: 8619590; PubMed Central PMCID: PMC162937.



Additional Information

Related CAS#
153808-85-6 (free base); 128427-55-4 (HCl).