Research Article: Clarithromycin monohydrate: a synchrotron X-ray powder study

Date Published: March 01, 2012

Publisher: International Union of Crystallography

Author(s): Shuji Noguchi, Sadahiro Fujiki, Yasunori Iwao, Keiko Miura, Shigeru Itai.


In the crystal structure of the title compound, clarithromycin (CAM) monohydrate, C38H69NO13·H2O, the water mol­ecule behaves as a proton donor and is hydrogen bonded to the hy­droxy O atom of the CAM cladinose ring. The hy­droxy O atom also behaves as a proton donor, forming an inter­molecular hydrogen bond with one of the hy­droxy groups of the 14-membered aglycone ring. The CAM mol­ecules are linked through these hydrogen bonds into chains running parallel to the c axis.

Partial Text

For background to the title compound, see Avrutov et al. (2003 ▶); Noguchi, Fujiki et al. (2012 ▶). For information relating to the pharmaceutical properties of CAM, see: Yajima et al. (1999 ▶, 2002 ▶); Fujiki et al. (2011 ▶); Liu et al. (1999 ▶). For related structures, see: Noguchi, Miura et al. (2012 ▶; form I, anhydrate); Jin et al. (2011 ▶; form 0, ethanol solvate); Stephenson et al. (1997 ▶; form II, anhydrate); Liang & Yao (2008 ▶; form III, acetonitrile solvate); Parvez et al. (2000 ▶; hydro­chloride salt); Iwasaki et al. (1993 ▶; methanol solvate).