Isonicotinic acid hydrazide – a reinvestigation

Bhat, T.R.; Singh, T. R.; Vijayan, M.

doi:10.1107/s0567740874008521

Cited by 43 publications

(31 citation statements)

References 3 publications

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“…The crystal structures of isoniazid 56 were prepared according to the procedure described in the previous sections immediately before solid-state NMR analysis. The materials were packed in zirconia rotors and placed in the NMR probe immediately after the sample preparation to avoid any impact of environmental changes.…”

Section: Methodsmentioning

confidence: 99%

Mechanistic and Kinetic Insight into Spontaneous Cocrystallization of Isoniazid and Benzoic Acid

et al. 2015

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Solid-state cocrystallization is of contemporary interest because it offers an easy and efficient way to produce cocrystals, which are recognized as prospective pharmaceutical materials. Research explaining solid-state cocrystallization mechanisms is important but still too scarce to give a broad understanding of factors governing and limiting these reactions. Here we report an investigation of the mechanism and kinetics of isoniazid cocrystallization with benzoic acid. This reaction is spontaneous; however, its rate is greatly influenced by environmental conditions (humidity and temperature) and pretreatment (milling) of the sample. The acceleration of cocrystallization in the presence of moisture is demonstrated by kinetic studies at elevated humidity. The rate dependence on humidity stems from moisture facilitated rearrangements on the surface of isoniazid crystallites, which lead to cocrystallization in the presence of benzoic acid vapor. Furthermore, premilling the mixture of the cocrystal ingredients eliminated the induction time of the reaction and considerably increased its rate.

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Section: Methodsmentioning

confidence: 99%

Mechanistic and Kinetic Insight into Spontaneous Cocrystallization of Isoniazid and Benzoic Acid

et al. 2015

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“…The corresponding values for INH in the complexes with CcP, APX, W41A, and H42A are 35.2, 50.5, 25.1, and 9.0°, respectively. In the crystals of native INH, the angle between the two planes was reported to be 18.1° (19). When the aromatic rings are located in the proximity of the hydrophilic center, the planes are relatively more parallel than those when it is located away from the hydrophilic center.…”

Section: Resultsmentioning

confidence: 99%

“…1). The initial coordinates of the isoniazid structure were taken from the studies of Bhat et al (19) and were fitted into the very characteristic observed electron density in the ͉F o Ϫ F c ͉ difference Fourier map. Further rigid body refinement and several rounds of positional and restrained individual B-factor refinement were carried out.…”

Section: Methodsmentioning

confidence: 99%

Mode of Binding of the Tuberculosis Prodrug Isoniazid to Heme Peroxidases

Singh

Kumar

Pandey

et al. 2010

Journal of Biological Chemistry

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“…In the solid state, INH molecules form specific hydrogen bonds, composed by interactions between hydrazide and pyridine groups through N-H···N interactions [8]. There are also some reported structures with INH coordinated to transition metal ions [9][10][11][12]; the hydrogen bond networks are different to those observed in the INH structure, mainly due to coordination and the presence of counter ions which contain acceptor atoms for hydrogen bonds, like ClO 4 , and/or water molecules in the structure.…”

Section: Introductionmentioning

confidence: 96%

“…The objective in this work is to study isonicotinohydrazide (INH) [figure 1(a)]. This compound was first reported in 1952, and it is a potent agent in tuberculosis treatment [6]; its crystalline structure is already reported and this molecule is well known [7,8].…”

Section: Introductionmentioning

confidence: 98%

Isonicotinohydrazide conformation in a supramolecular system with 1,4-benzenedicarboxylic acid and Zn²⁺ and Mn²⁺

Almeida

Silva

Abreu

et al. 2015

Journal of Coordination Chemistry

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2015) Isonicotinohydrazide conformation in a supramolecular system with 1,4-benzenedicarboxylic acid and Zn 2+ and MnAn anti-tuberculosis drug, isonicotinohydrazide (INH), is studied concerning its conformation in different crystalline environments. In the present work, compounds with zinc (1) and manganese (2) ions are reported where INH has different conformations, caused by hydrogen bonds with 1,4-benzenedicarboxylic acid (H 2 BDC) and water molecules and by coordination bonds involving its functional groups. In 1, INH is coordinated to two zinc ions, where H 2 BDC and crystallization water molecules form several hydrogen bonds giving rise to a complex three-dimensional (3-D) network. In 2, both INH and H 2 BDC molecules are coordinated to manganese as well as four water molecules. The complex formed interacts by hydrogen bonds forming a 2-D arrangement. A 3-D network extension arises from other hydrogen bonds generated by crystallization water. In these two compounds, the presence of BDC ion and water molecules is very important in the stabilization of the complexes and in INH conformation. This work is focused on the structural description of formed compounds.

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Isonicotinic acid hydrazide – a reinvestigation

Cited by 43 publications

References 3 publications

Mechanistic and Kinetic Insight into Spontaneous Cocrystallization of Isoniazid and Benzoic Acid

Mechanistic and Kinetic Insight into Spontaneous Cocrystallization of Isoniazid and Benzoic Acid

Mode of Binding of the Tuberculosis Prodrug Isoniazid to Heme Peroxidases

Isonicotinohydrazide conformation in a supramolecular system with 1,4-benzenedicarboxylic acid and Zn²⁺ and Mn²⁺

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Isonicotinic acid hydrazide – a reinvestigation

Cited by 43 publications

References 3 publications

Mechanistic and Kinetic Insight into Spontaneous Cocrystallization of Isoniazid and Benzoic Acid

Mechanistic and Kinetic Insight into Spontaneous Cocrystallization of Isoniazid and Benzoic Acid

Mode of Binding of the Tuberculosis Prodrug Isoniazid to Heme Peroxidases

Isonicotinohydrazide conformation in a supramolecular system with 1,4-benzenedicarboxylic acid and Zn2+ and Mn2+

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Isonicotinohydrazide conformation in a supramolecular system with 1,4-benzenedicarboxylic acid and Zn²⁺ and Mn²⁺