Identifying the intermolecular hydrogen-bonding supramolecular synthons in an indomethacin–nicotinamide cocrystal by solid-state NMR

Maruyoshi, Keisuke; Iuga, Dinu; Antzutkin, Oleg N.; Alhalaweh, Amjad; Velaga, Sitaram P.; Brown, Steven P.

doi:10.1039/c2cc36094b

Cited by 77 publications

(73 citation statements)

References 35 publications

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“…The composition of the different tablets studied is shown in Table 2. Nicotinamide forms hydrogen bonded complexes with indomethacin, resulting in potential physicochemical interactions between the readily and poorly soluble materials (Bogdanova et al, 1998;Maruyoshi et al, 2012). Provided that these intermolecular interactions are maintained during the dissolution process, the more readily soluble drug acts as a carrier and thus increases the release of the poorly water-soluble drug into the surrounding solution.…”

Section: Methodsmentioning

confidence: 99%

“…In certain molar ratios there are different intermolecular interactions competing within the formulation. The indomethacin-nicotinamide interactions have been described by Maruyoshi et al (2012) and are characterised as a result of hydrogen bonds forming between the carbonyl group (COOH) in the indomethacin and the aromatic functional group in the nicotinamide (Maruyoshi et al, 2012). It has been reported that the different structural forms of indomethacin (amorphous, a-and g-forms) are also a result of intermolecular interactions between two indomethacin molecules (Taylor and Zografi, 1997).…”

Section: Compact Identificationmentioning

confidence: 97%

“…Changing the physical state of indomethacin to the amorphous form is commonly employed as a means to increase the rate of release of the drug into the system and factors that prevent crystallisation and stabilise the amorphous form are of great interest (Ewing et al, 2014;Kaminska et al, 2014;Karmwar et al, 2011;Surwase et al, 2013). Indomethacin has been used as a model poorly watersoluble drug in a number of investigations where co-complexes between the drug and carrier have been achieved via hydrogen bonded interactions (Majumder et al, 2013;Maruyoshi et al, 2012). Indomethacin with various hydrotropes such as sodium benzoate, nicotinamide, resorcinol and urea were studied, which enhanced the solubility for aqueous injections (Jain, 2008).…”

Section: Introductionmentioning

confidence: 99%

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Comparison of pharmaceutical formulations: ATR-FTIR spectroscopic imaging to study drug-carrier interactions

Ewing

Biggart

Hale

et al. 2015

International Journal of Pharmaceutics

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Section: Methodsmentioning

confidence: 99%

Section: Compact Identificationmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Comparison of pharmaceutical formulations: ATR-FTIR spectroscopic imaging to study drug-carrier interactions

Ewing

Biggart

Hale

et al. 2015

International Journal of Pharmaceutics

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“…40 Specifically, Figure 9 The 1 H DQ MAS spectrum in Figure 9(a) reveals a key pair of cross-peaks at a DQ frequency of 26 SQ refocused INEPT spectrum in Figure 9(d) shows that this could be assigned to an aromatic proton, only the 14 N-1 H spectra prove that it is not a NH 2 proton. Consider the 14 N-1 H HMQC spectrum in Figure 9(b), where the use of a short recoupling time ensures that only one-bond N-H correlations are observed, thus allowing the determination of the two NIC NH 2 1 H chemical shifts as 7.3 and 9.0 ppm.…”

Section: Application Of 14 N-1 H Nmr To Pharmaceuticalsmentioning

confidence: 99%

Nitrogen-Proton Correlation Experiments of Organic Solids at Natural Isotopic Abundance

Brown

2014

eMagRes

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Solid-state NMR methods for recording two-dimensional nitrogen-proton correlation spectra at natural isotopic abundance are presented. There are two isotopes of nitrogen: the spin I = 1 14 N (99.6% natural abundance) and the spin I = 1/2 15 N (0.4% natural abundance). The reduced natural abundance and smaller magnetogyric ratio as compared to 13 C explain the comparative scarcity of nitrogen-proton spectra for 15 N in the literature. While this article describes these few examples of 1 H-15 N and 15 N-1 H experiments, including the first applications of DNP to increase sensitivity, the focus is on 14 N-1 H heteronuclear multiple-quantum coherence (HMQC) MAS NMR spectroscopy using inverse (i.e., 1 H) detection. Specifically, HMQC can be created following free evolution under heteronuclear through-bond 14 N-1 H J-couplings as well as residual second-order quadrupolar-dipolar couplings that are not removed by MAS or by recoupling of 14 N-1 H dipolar couplings using n = 2 rotary resonance recoupling (R 3 ) or symmetry-based sequences. The quadrupolar interaction for 14 N causes anisotropic broadening and an isotropic second-order quadrupolar shift and affects the optimization of 14 N RF irradiation, for which high 14 N nutation frequencies are important. Fast MAS improves sensitivity by narrowing 1 H resonances and lengthening 1 H coherence lifetimes. The creation of double-quantum or overtone 14 N coherence has the advantage of insensitivity (compared to 14 N single-quantum coherence) to motion and small deviations away from the perfect setting of the magic angle. Applications to supramolecular chemistry and pharmaceuticals are presented; changing the recoupling duration allows longer range N· · ·H proximities to be identified, thus identifying specific intermolecular hydrogen bonding arrangements.

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“…Indomethacin (IMC) is a typical BCS class II drug with poorly water-soluble property and has been chosen as a model drug in numerous studies of co-crystal formation to improve the solubility of IMC [25][26][27][28][29][30][31][32][33][34]. In our previous studies, IMC-saccharin (SAC) and IMC-nicotinamide (NIC) co-crystals via intermolecular hydrogen bonding had been successfully prepared using solvent evaporation, neat grinding process, or thermal stress in the solid or liquid state [30,33,[35][36].…”

Section: Introductionmentioning

confidence: 99%

Effect of Povacoat or Soluplus on Solid-State Characterization of Indomethacin-Nicotinamide Co-Crystal Formation

Lin¹,

Lin²,

Hung³

et al. 2015

Pharm Anal Acta

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Novel pharmaceutical polymers named Povacoat and Soluplus were used to investigate whether both polymers could influence the co-crystal formation between indomethacin (IMC) and nicotinamide (NIC) or the solid-state characterization of IMC-NIC mixture after co-grinding or solvent evaporation. Different weight ratios of Povacoat or Soluplus to IMC-NIC (molar ratio = 1:1) were respectively co-ground or dissolved in different solvents via ultrasonication, and then co-evaporated under a hood at ambient temperature. All the samples were determined by thermo analytical and FTIR spectroscopic studies. The results indicate that Povacoat or Soluplus added did not induce any interaction among Povacoat or Soluplus, IMC and NIC after co-grinding process. It is also found that Povacoat did not induce the IMC-NIC co-crystal formation but only caused the amorphous formation of IMC in the Povacoat/IMC-NIC evaporates prepared by 4:1 (w/w) weight ratio of Povacoat to IMC:NIC (1:1 molar ratio) with final volume ratio of 1:9 (v/v) water to ethanol via ultrasonication and evaporation. On the other hand, the Soluplus/IMC-NIC evaporates after co-evaporation from acetone solution exhibited either IMC-NIC co-crystal or amorphous IMC formation, which was dependent on the amounts of Soluplus added. The former IMC-NIC co-crystal was prepared in the formulations with less amount of Soluplus, implies that Soluplus did not interfere the IMC-NIC co-crystal formation after co-evaporation. While a large amount of Soluplus added might directly interrupt the IMC-NIC cocrystal formation but cause the amorphous IMC formed in the Soluplus solid dispersion.

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Identifying the intermolecular hydrogen-bonding supramolecular synthons in an indomethacin–nicotinamide cocrystal by solid-state NMR

Cited by 77 publications

References 35 publications

Comparison of pharmaceutical formulations: ATR-FTIR spectroscopic imaging to study drug-carrier interactions

Comparison of pharmaceutical formulations: ATR-FTIR spectroscopic imaging to study drug-carrier interactions

Nitrogen-Proton Correlation Experiments of Organic Solids at Natural Isotopic Abundance

Effect of Povacoat or Soluplus on Solid-State Characterization of Indomethacin-Nicotinamide Co-Crystal Formation

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