Mebendazole hydrochloride (5-benzoyl-1H-benzimidazole-2-yl)-carbamic
acid methyl ester hydrochloride, MBZ.HCl, a new stable salt of
mebendazole (MBZ), has been synthesized and characterized. It can easily
be obtained from recrystallization of forms A, B, or C of MBZ in diverse
solvents with the addition of hydrochloric acid solution.
Crystallographic data reveals that the particular conformation adopted
by the carbamic group contributes to the stability of the network. The
crystal packing is stabilized by the presence of three N-H...Cl
intermolecular interactions that form chains along the b axis. The XRD
analyses of the three crystalline habits found in the crystallization
process (square-based pyramids, pseudohexagonal plates, and prismatic)
show equivalent diffraction patterns. The vibrational behavior is
consistent with crystal structure. The most important functional groups
show shifts to lower or higher frequencies in relation to the MBZ
polymorphs. The thermal study on MBZ center dot HCI indicates that the
compound is stable up to 160 degrees C approximately. Decomposition
occurs in four steps. In the first step the HCl group is eliminated, and
after that the remaining MBZ polymorph A decomposes in three steps, as
happens with polymorphs B and C. (C) 2007 Wiley-Liss, Inc. and the
American Pharmacists Association J Pharm Sci 97:542-552, 2008.
%0 Journal Article
%1 WOS:000252127000038
%A Brusau, E V
%A Cami, G E
%A Narda, G E
%A Cuffini, S
%A Ayala, A P
%A Ellena, J
%C 111 RIVER ST, HOBOKEN 07030-5774, NJ USA
%D 2008
%I WILEY
%J JOURNAL OF PHARMACEUTICAL SCIENCES
%K FTIR; Raman crystal formation; hydrochloride; polymorphism; salt spectroscopy; stability} structure; thermal {mebendazole
%N 1
%P 542-552
%R 10.1002/jps.21164
%T Synthesis and characterization of a new mebendazole salt: Mebendazole
hydrochloride
%V 97
%X Mebendazole hydrochloride (5-benzoyl-1H-benzimidazole-2-yl)-carbamic
acid methyl ester hydrochloride, MBZ.HCl, a new stable salt of
mebendazole (MBZ), has been synthesized and characterized. It can easily
be obtained from recrystallization of forms A, B, or C of MBZ in diverse
solvents with the addition of hydrochloric acid solution.
Crystallographic data reveals that the particular conformation adopted
by the carbamic group contributes to the stability of the network. The
crystal packing is stabilized by the presence of three N-H...Cl
intermolecular interactions that form chains along the b axis. The XRD
analyses of the three crystalline habits found in the crystallization
process (square-based pyramids, pseudohexagonal plates, and prismatic)
show equivalent diffraction patterns. The vibrational behavior is
consistent with crystal structure. The most important functional groups
show shifts to lower or higher frequencies in relation to the MBZ
polymorphs. The thermal study on MBZ center dot HCI indicates that the
compound is stable up to 160 degrees C approximately. Decomposition
occurs in four steps. In the first step the HCl group is eliminated, and
after that the remaining MBZ polymorph A decomposes in three steps, as
happens with polymorphs B and C. (C) 2007 Wiley-Liss, Inc. and the
American Pharmacists Association J Pharm Sci 97:542-552, 2008.
@article{WOS:000252127000038,
abstract = {Mebendazole hydrochloride [(5-benzoyl-1H-benzimidazole-2-yl)-carbamic
acid methyl ester hydrochloride, MBZ.HCl], a new stable salt of
mebendazole (MBZ), has been synthesized and characterized. It can easily
be obtained from recrystallization of forms A, B, or C of MBZ in diverse
solvents with the addition of hydrochloric acid solution.
Crystallographic data reveals that the particular conformation adopted
by the carbamic group contributes to the stability of the network. The
crystal packing is stabilized by the presence of three N-H...Cl
intermolecular interactions that form chains along the b axis. The XRD
analyses of the three crystalline habits found in the crystallization
process (square-based pyramids, pseudohexagonal plates, and prismatic)
show equivalent diffraction patterns. The vibrational behavior is
consistent with crystal structure. The most important functional groups
show shifts to lower or higher frequencies in relation to the MBZ
polymorphs. The thermal study on MBZ center dot HCI indicates that the
compound is stable up to 160 degrees C approximately. Decomposition
occurs in four steps. In the first step the HCl group is eliminated, and
after that the remaining MBZ polymorph A decomposes in three steps, as
happens with polymorphs B and C. (C) 2007 Wiley-Liss, Inc. and the
American Pharmacists Association J Pharm Sci 97:542-552, 2008.},
added-at = {2022-05-23T20:00:14.000+0200},
address = {111 RIVER ST, HOBOKEN 07030-5774, NJ USA},
author = {Brusau, E V and Cami, G E and Narda, G E and Cuffini, S and Ayala, A P and Ellena, J},
biburl = {https://www.bibsonomy.org/bibtex/20cac59d18e153fe36b8e5c94b32e1611/ppgfis_ufc_br},
doi = {10.1002/jps.21164},
interhash = {4927009de0e2e1fc34e2ab86a12a0d07},
intrahash = {0cac59d18e153fe36b8e5c94b32e1611},
issn = {0022-3549},
journal = {JOURNAL OF PHARMACEUTICAL SCIENCES},
keywords = {FTIR; Raman crystal formation; hydrochloride; polymorphism; salt spectroscopy; stability} structure; thermal {mebendazole},
number = 1,
pages = {542-552},
publisher = {WILEY},
pubstate = {published},
timestamp = {2022-05-23T20:00:14.000+0200},
title = {Synthesis and characterization of a new mebendazole salt: Mebendazole
hydrochloride},
tppubtype = {article},
volume = 97,
year = 2008
}