Research Article: Marbofloxacin

Date Published: April 01, 2012

Publisher: International Union of Crystallography

Author(s): Jin Shen, Jing-Jing Qian, Jian-Ming Gu, Xiu-Rong Hu.


In the title compound, [systematic name: 9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl­piperazin-1-yl)-7-oxo-7H-pyrido[1,2,3-ij][1,2,4]benzoxadiazine-6-carb­oxy­lic acid], C17H19FN4O4, the carbonyl and carboxyl groups are coplanar with the quinoline ring, making a dihedral angle of 2.39 (2)°. The piperazine ring adopts a chair conformation and the oxadiazinane ring displays an envelope conformation with the CH2 group at the flap displaced by 0.650 (2) Å from the plane through the other five atoms. The mol­ecular structure exhibits an S(6) ring motif, owing to an intra­molecular O—H⋯O hydrogen bond. In the crystal, weak C—H⋯F hydrogen bonds link mol­ecules into layers parallel to the ab plane.

Partial Text

Marbofloxacin is a third-generation fluoro­quinolone for veterinary use, the anti­microbial activity of which depends upon its inhibition of DNA-gyrase and topoisomerase IV (Paradis et al., 2001 ▶; Thomas et al., 2001 ▶; Voermans et al., 2006 ▶). With a broad spectrum bactericidal activity and good efficacy, marbofloxacin is indicated for dermatological, respiratory and urinary tract infections resulting from both Gram-positive and Gram-negative bacteria (Lefebvre et al., 1998 ▶) and Mycoplasma (Spreng et al., 1995 ▶; Dossin et al., 1998 ▶; Carlotti et al., 1999 ▶; Ishak et al., 2008 ▶).