Grepafloxacin

Names

[ CAS No. ]:
119914-60-2

[ Name ]:
Grepafloxacin

[Synonym ]:
1-cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid
1-cyclopropyl-5-methyl-6-fluoro-7-(3-methylpiperazin-1-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
1-Cyclopropyl-6-fluoro-7-(3-methyl-1-piperazinyl)-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
MFCD00865116

Biological Activity

[Description]:

Grepafloxacin (OPC-17116) is an oral actively fluoroquinolone antibiotic with potent activity against community-acquired respiratory pathogens including Streptococcus pneumonia. Grepafloxacin has high tissue penetration and a promising pharmacodynamic profile[1][2][3].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Bacterial

[In Vitro]

Grepafloxacin is a once-daily fluoroquinolone[2]. Grepafloxacin exhibits potent in vitro antibacterial activity against Gram-positive bacteria such as Streptococcus pneumoniae and high in vivo efficacy on the experimental systemic infections caused by the Gram-positive and -negative bacteria tested[4].

[In Vivo]

Grepafloxacin (OPC-17116) (200 mg/kg; p.o.; Balb/c mice) displays good safety profile in terms of phototoxicity[2]. Grepafloxacin (p.o.; 25, 50, 100, and 200 mg/kg; 5 days/week for 4 weeks; Female C57BL6/J-Lyst bg-J/ mice/beige mice) has modest activities in both intranasal (IN) infection and intravenous (IV) Mycobacterium avium infection models[3].

[References]

[1]. Efthymiopoulos C. Pharmacokinetics of grepafloxacin. J Antimicrob Chemother. 1997;40 Suppl A:35-43.

[2]. Owen K. Comparative grepafloxacin phototoxicity in mouse skin. J Antimicrob Chemother. 1998;42(2):261-264.

[3]. Cynamon MH, et al. The activity of grepafloxacin in two murine models of Mycobacterium avium infection. J Infect Chemother. 2004;10(3):185-188.

[4]. Miyamoto H, et al. Synthesis and biological properties of substituted 1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acids. Bioorg Med Chem. 1995;3(12):1699-1706.

Chemical & Physical Properties

[ Density]:
1.366

[ Boiling Point ]:
610ºC at 760mmHg

[ Melting Point ]:
189-192ºC

[ Molecular Formula ]:
C₁₉H₂₂FN₃O₃

[ Molecular Weight ]:
359.39500

[ Flash Point ]:
322.7ºC

[ Exact Mass ]:
359.16500

[ PSA ]:
74.57000

[ LogP ]:
2.67400

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VB1993785

CHEMICAL NAME :: 3-Quinolinecarboxylic acid, 1,4-dihydro-1-cyclopropyl-6-fluoro-5-methyl-7-(3-meth yl- 1-piperazinyl)-4-oxo-

CAS REGISTRY NUMBER :: 119914-60-2

LAST UPDATED :: 199606

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C19-H22-F-N3-O3

MOLECULAR WEIGHT :: 359.44

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 78 mg/kg

SEX/DURATION :: female 6-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 22,4531,1994

Safety Information

[ Hazard Codes ]:
Xi

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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