Synthesis and Characterization of a New Mebendazole Salt: Mebendazole Hydrochloride

Brusau, Elena V.; Camí, Gerardo Enrique; Narda, Griselda E.; Cuffini, Silvia Lucía; Ayala, A. P.; Ellena, Javier

doi:10.1002/jps.21164

Cited by 40 publications

(45 citation statements)

References 11 publications

(14 reference statements)

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“…They also reported that a polymorph of albendazole with C tautomer is relatively more preferable, over a polymorph with B tautomer for albendazole. Mebendazole is known to exist in three polymorphic forms (A, B, and C), with polymorph C being most efficacious [19,68,69]. Polymorph B is reported to be toxic.…”

Section: Intermolecular Interactions In Carbendazim Dimers and Their mentioning

confidence: 99%

“…Low aqueous solubility (\6 mg/mL) of these molecules has restricted their formulation development in the forms of suspensions, paste, powder, or intraruminal bolus, which compels the administration in larger doses to achieve the desired therapeutic response [16][17][18][19][20]. Solid-state researchers working in the molecular pharmaceutics are fascinated to understand the polymorphism in the BC molecules, so as to improve the bioavailability profile of these molecules.…”

Section: Introductionmentioning

confidence: 99%

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Tautomerism in drugs with benzimidazole carbamate moiety: an electronic structure analysis

Kasetti

Bharatam

2012

Theor Chem Acc

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Several medicinally important compounds carry benzimidazole carbamate moiety. In the scientific literature, these molecules are represented in different tautomeric forms. In this report, conformational and tautomeric preferences were analyzed on the model benzimidazole carbamate (carbendazim), so as to understand the potential energy surface of the title compounds. Quantum chemical calculations have been performed using HF, B3LYP, and MP2 methods in gas phase and solvent phase on model benzimidazole carbamate to understand the conformational and tautomeric preferences. (1) PE surface of amide-imide tautomers, (2) electron distribution, (3) AIM analysis, (4) NBO charges, (5) 1,3-H shift, etc., have been investigated for carbendazim and its conformers. The molecular electrostatic potential (MESP) surfaces of carbendazim have been studied. Further to understand the polymorphism in benzimidazole carbamate, analysis of dimers of carbendazim has been carried out. The results indicate that a neglected tautomer is important and the tautomeric equilibrium is quite subtle in these systems and it should be extensively considered in all studies related to these drugs.

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Section: Intermolecular Interactions In Carbendazim Dimers and Their mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Tautomerism in drugs with benzimidazole carbamate moiety: an electronic structure analysis

Kasetti

Bharatam

2012

Theor Chem Acc

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“…Complete crystal structure data of MBZ polymorphs are not found in the literature because single crystals seem to be hard to obtain. In an attempt to obtain adequate crystals for single crystal X‐ray diffraction we have recently reported a new stable salt, mebendazole hydrochloride which was also fully characterized by structural, vibrational and thermal analysis 14…”

Section: Introductionmentioning

confidence: 99%

Intermolecular contacts influencing the conformational and geometric features of the pharmaceutically preferred mebendazole polymorph C

Martins

Neves

Ellena

et al. 2009

Journal of Pharmaceutical Sciences

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“…Therefore, some derivatives, such as the hydrochloride salt [9], and crystal engineering [10] alternatives have been recently proposed to promote polymorph conversion or improve drug solubility and bioavailability.…”

Section: Introductionmentioning

confidence: 99%

Mebendazole crystal forms in tablet formulations. An ATR-FTIR/chemometrics approach to polymorph assignment

Calvo

Kaufman

Maggio

2016

Journal of Pharmaceutical and Biomedical Analysis

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a b s t r a c tStructural polymorphism of active pharmaceutical ingredients (API) is a relevant concern for the modern pharmaceutical industry, since different polymorphic forms may display dissimilar properties, critically affecting the performance of the corresponding drug products. Mebendazole (MEB) is a widely used broad spectrum anthelmintic drug of the benzimidazole class, which exhibits structural polymorphism (Forms A-C). Form C, which displays the best pharmaceutical profile, is the recommended one for clinical use. The polymorphs of MEB were prepared and characterized by spectroscopic, calorimetric and microscopic means. The polymorphs were employed to develop a suitable chemometrics-assisted sample display model based on the first two principal components of their ATR-FTIR spectra in the 4000-600 cm −1 region. The model was internally and externally validated employing the leave-one-out procedure and an external validation set, respectively. Its suitability for revealing the polymorphic identity of MEB in tablets was successfully assessed analyzing commercial tablets under different physical forms (whole, powdered, dried, sieved and aged). It was concluded that the ATR-FTIR/PCA (principal component analysis) association is a fast, efficient and non-destructive technique for assigning the solid-state forms of MEB in its drug products, with minimum sample pre-treatment.

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Synthesis and Characterization of a New Mebendazole Salt: Mebendazole Hydrochloride

Cited by 40 publications

References 11 publications

Tautomerism in drugs with benzimidazole carbamate moiety: an electronic structure analysis

Tautomerism in drugs with benzimidazole carbamate moiety: an electronic structure analysis

Intermolecular contacts influencing the conformational and geometric features of the pharmaceutically preferred mebendazole polymorph C

Mebendazole crystal forms in tablet formulations. An ATR-FTIR/chemometrics approach to polymorph assignment

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