Structure of the 1:1 complex between 4-amino-N-(4,6-dimethyl-2-pyrimidinyl)benzenesulfonamide (sulfadimidine) and 2-hydroxybenzoic acid (salicylic acid)

Patel, Urmila H.; Haridas, M.; Singh, T.P.

doi:10.1107/s0108270188003579

Cited by 20 publications

(12 citation statements)

References 5 publications

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“…The 1:1 cocrystal was synthesized using solvent drop grinding as described in a previous publication . The solid materials were characterized by X-ray powder diffraction (XRPD) using an Empyrean diffractometer (PANalytical, Philips) with Cu Kα 1,2 radiation at 40 kV and 40 mA and verified to be identical with the only previously described crystalline phases of the respective compounds ,, (XRPD patterns are provided as Supporting Information). A 1:1 molar ratio physical mixture of the two pure solid coformers (SMT and SA) was prepared by careful weighing and gentle mixing of equimolar amounts of separately ground crystal powders.…”

Section: Experimental Workmentioning

confidence: 99%

Calorimetric Determination of Cocrystal Thermodynamic Stability: Sulfamethazine–Salicylic Acid Case Study

Svärd

Ahuja

Rasmuson

2020

Crystal Growth & Design

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This work demonstrates how the thermodynamics of cocrystal formation from the pure, solid coformers can be directly determined from experimentally obtained calorimetric data, without involving solubility data or approximations of ideal solution. For the 1:1 cocrystal between the drug API sulfamethazine and salicylic acid, the melting temperatures and associated enthalpies of fusion have been determined for the coformers in their respective pure solid state and as an equimolar physical mixture and for the cocrystal, using differential scanning calorimetry. Heat capacities have been determined for the respective solid forms and their supercooled melts. The Gibbs energy for cocrystal formation and the enthalpic and entropic components have been determined as functions of temperature through a thermodynamic cycle. The Gibbs energy, enthalpy, and entropy of mixing have been estimated from the thermodynamic functions for cocrystal formation and fusion of the solid phases. The results show that the Gibbs energy for cocrystal formation is negative, i.e. the cocrystal is the stable solid phase in relation to a 1:1 mixture of the coformers throughout the temperature interval from room temperature to the cocrystal melting point, and becomes increasingly negative with increasing temperature. Cocrystal formation is an endothermic process, driven by the favorable entropy increase, and is accompanied by a 6% increase in molecular volume. At room temperature, liquid mixing of coformers is found to be weakly exothermic. The results qualitatively align with a previously reported analysis based on solubility data.

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Section: Experimental Workmentioning

confidence: 99%

Calorimetric Determination of Cocrystal Thermodynamic Stability: Sulfamethazine–Salicylic Acid Case Study

Svärd

Ahuja

Rasmuson

2020

Crystal Growth & Design

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“…In all carboxylic acid-cocrystal structures of the related sulfa drug sulfamethazine reported to date preferential H-bonding between the carboxyl group and the amidine group was observed. [78][79][80][81][82][83][84][85][86] This has been attributed to the empirical rule "the best donor bonds to the best acceptor." 67,87 It should be noted that in contrast to other sulfonamides, X-ray structures of cocrystals of SMZ are surprisingly rare.…”

Section: Formation and Structure Of The Smz/oxalic Acid Cocrystalmentioning

confidence: 99%

Effects of Ball-Milling and Cryomilling on Sulfamerazine Polymorphs: A Quantitative Study

MacFhionnghaile

Gniado

et al. 2014

Journal of Pharmaceutical Sciences

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The effects of ball-milling and cryomilling on sulfamerazine forms I and II (SMZ FI, FII) were investigated using X-ray powder diffraction, IR and NIR spectroscopy. Cryomilling resulted in the complete amorphization of both polymorphs. Milling at room temperature gave mixtures of amorphous SMZ (FA) and FII. Calibration models were developed for the quantitative analysis of binary (FI/FII, FI/FA and FII/FA) and ternary (FI/FII/FA) mixtures using NIR spectroscopy combined with partial least-squares (PLS) regression. The PLS models for binary (0 -100 %), ternary (0 -100 %) and low level (0 -10 %) binary mixtures had root-mean-square errors of prediction of 1.8, 5.1 and 0.80 %, respectively. The calibration models were used to obtain a detailed quantitative picture of solid-state transformations during milling and any subsequent recrystallizations. FA prepared by cryomilling FI for less than 60 min. recrystallized to mixtures of FI and FII, while samples milled for more than 60 min. crystallized to pure FII. The effect of co-milling SMZ with stoichiometric amounts of additives was investigated. SMZ formed amorphous materials with oxalic, DL-tartaric and citric acids that were more stable towards recrystallization than FA.Amorphous SMZ/oxalic acid was found to recrystallize to a 2:1 co-crystal during storage.

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“…This is similar to the case of the SMT-salicylic acid co-crystal, where the difference between the two C-O bond lengths is 0.049 Å (GEYSAE). 23 For salts, this difference is usually less than 0.03 Å as the carboxylate ion, formed after proton loss goes into resonance. 24 Using 2.65 25 as pK 1 value for the conjugate acid form of the basic SMT and 2.95 26 as pK 1 value for 3mSA, ΔpK a becomes −0.3, which according to the pK a rule also suggests that SMT-3mSA should form a co-crystal as opposed to a salt.…”

Section: Solid Phase and Crystal Structure Analysismentioning

confidence: 99%

Solution and calorimetric thermodynamic study of a new 1 : 1 sulfamethazine–3-methylsalicylic acid co-crystal

et al. 2020

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Structure of the 1:1 complex between 4-amino-N-(4,6-dimethyl-2-pyrimidinyl)benzenesulfonamide (sulfadimidine) and 2-hydroxybenzoic acid (salicylic acid)

Cited by 20 publications

References 5 publications

Calorimetric Determination of Cocrystal Thermodynamic Stability: Sulfamethazine–Salicylic Acid Case Study

Calorimetric Determination of Cocrystal Thermodynamic Stability: Sulfamethazine–Salicylic Acid Case Study

Effects of Ball-Milling and Cryomilling on Sulfamerazine Polymorphs: A Quantitative Study

Solution and calorimetric thermodynamic study of a new 1 : 1 sulfamethazine–3-methylsalicylic acid co-crystal

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