publication . Article . 2018

Mechanochemical Synthesis and Crystal Structure of the Lidocaine-Phloroglucinol Hydrate 1:1:1 Complex

Nancy Magaña-Vergara; Porfirio de la Cruz-Cruz; Ana Peraza-Campos; Francisco Martínez-Martínez; Juan González-González;
Open Access English
  • Published: 09 Mar 2018 Journal: Crystals (issn: 2073-4352, Copyright policy)
  • Publisher: MDPI AG
Abstract
Molecular complexation is a strategy used to modify the physicochemical or biopharmaceutical properties of an active pharmaceutical ingredient. Solvent assisted grinding is a common method used to obtain solid complexes in the form of cocrystals. Lidocaine is a drug used as an anesthetic and for the treatment of chronic pain, which bears in its chemical structure an amide functional group able to form hydrogen bonds. Polyphenols are used as cocrystal coformers due to their ability to form O–H···X (X = O, N) hydrogen bond interactions. The objective of this study was to exploit the ability of phloroglucinol to form molecular complexes with lidocaine by liquid ass...
Subjects
free text keywords: lidocaine, phloroglucinol, crystal structure, hydrogen bond, hydration, molecular complex, Crystallography, QD901-999, Inorganic Chemistry, General Materials Science, General Chemical Engineering, Condensed Matter Physics, Chemistry, Cocrystal, Molecule, Amide, chemistry.chemical_compound, Infrared spectroscopy, Chemical structure, Hydrate, Solvent
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31 references, page 1 of 3

9th ed.; Lippincott & Wilkins: Baltimore, MD, USA, 2011; pp. 90-92.

A special emphasis on cocrystals. Adv. Drug Deliv. Rev. 2017, 117, 25-46. [CrossRef] [PubMed]

Chem. Pharm. Bull. 2007, 55, 832-836. [CrossRef] [PubMed]

Steed, J.W.; Atwood, J.L. Supramolecular Chemistry, 2nd ed.; John Wiley & Sons Ltd: Wiltshire, UK, 2009;

pp. 2-9.

A literature review. Rev. Bras. Reumatol. 2014, 54, 386-392.

Badawi, H.M.; Förner, W.; Ali, S.A. The molecular structure and vibrational, 1H and 13C NMR spectra of

lidocaine hydrochloride monohydrate. Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 2016, 152, 92-100.

7. Rajendiran, N.; Mohandoss, T.; Saravanan, J. Guest: Host interactions of lidocaine and prilocaine with natural cyclodextrins: Spectral and molecular modeling studies. Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 2014, 132, 387-396. [CrossRef] [PubMed] [OpenAIRE]

8. Umeda, Y.; Nagase, H.; Makimura, M.; Tomono, K.; Shiro, M.; Ueda, H. Crystal Structure of a 2:1 Complex of Indomethacin and Lidocaine. Anal. Sci. 2007, 23, x15-x16. [CrossRef]

9. Corvis, Y.; Négrier, P.; Lazerges, M.; Massip, S.; Léger, J.M.; Espeau, P. Lidocaine/L-Menthol Binary System: Cocrystallization versus Solid-State Immiscibility. J. Phys. Chem. B 2010, 114, 5420-5426. [CrossRef] [PubMed] [OpenAIRE]

10. Lebedyeva, I.O.; Oliferenko, A.A.; Oliferenko, P.V.; Hromas, R.A.; Neubert, J.K.; Caudle, R.M.; Wickersham, J.; Castleman, W.L.; Altschuler, G.I.; Ostrov, D.A.; et al. Ionic conjugates of lidocaine and sweeteners as better tasting local anesthetics for dentistry. J. Mater. Chem. B 2015, 3, 8492-8498. [CrossRef] [OpenAIRE]

11. Berton, P.; Di Bona, K.R.; Yancey, D.; Rizvi, S.A.A.; Gray, M.; Gurau, G.; Shamshina, J.L.; Rasco, J.F.; Rogers, R.D. Transdermal Bioavailability in Rats of Lidocaine in the Forms of Ionic Liquids, Salts, and Deep Eutectic. ACS Med. Chem. Lett. 2017, 8, 498-503. [CrossRef] [PubMed]

12. Khan, M.; Enkelmann, V.; Brunklaus, G. O-H N Heterosynthon: A Robust Supramolecular Unit for Crystal Engineering. Cryst. Growth Des. 2009, 9, 2354-2362. [CrossRef]

13. Mukherjee, A.; Grobelny, P.; Thakur, T.S.; Desiraju, G.R. Polymorphs, Pseudopolymorphs, and Co-Crystals of Orcinol: Exploring the Structural Landscape with High Throughput Crystallography. Cryst. Growth Des. 2011, 11, 2637-2653. [CrossRef]

31 references, page 1 of 3
Abstract
Molecular complexation is a strategy used to modify the physicochemical or biopharmaceutical properties of an active pharmaceutical ingredient. Solvent assisted grinding is a common method used to obtain solid complexes in the form of cocrystals. Lidocaine is a drug used as an anesthetic and for the treatment of chronic pain, which bears in its chemical structure an amide functional group able to form hydrogen bonds. Polyphenols are used as cocrystal coformers due to their ability to form O–H···X (X = O, N) hydrogen bond interactions. The objective of this study was to exploit the ability of phloroglucinol to form molecular complexes with lidocaine by liquid ass...
Subjects
free text keywords: lidocaine, phloroglucinol, crystal structure, hydrogen bond, hydration, molecular complex, Crystallography, QD901-999, Inorganic Chemistry, General Materials Science, General Chemical Engineering, Condensed Matter Physics, Chemistry, Cocrystal, Molecule, Amide, chemistry.chemical_compound, Infrared spectroscopy, Chemical structure, Hydrate, Solvent
Download fromView all 2 versions
Crystals
Article . 2018
Crystals
Article . 2018
Provider: Crossref
Crystals
Article
Provider: UnpayWall
31 references, page 1 of 3

9th ed.; Lippincott & Wilkins: Baltimore, MD, USA, 2011; pp. 90-92.

A special emphasis on cocrystals. Adv. Drug Deliv. Rev. 2017, 117, 25-46. [CrossRef] [PubMed]

Chem. Pharm. Bull. 2007, 55, 832-836. [CrossRef] [PubMed]

Steed, J.W.; Atwood, J.L. Supramolecular Chemistry, 2nd ed.; John Wiley & Sons Ltd: Wiltshire, UK, 2009;

pp. 2-9.

A literature review. Rev. Bras. Reumatol. 2014, 54, 386-392.

Badawi, H.M.; Förner, W.; Ali, S.A. The molecular structure and vibrational, 1H and 13C NMR spectra of

lidocaine hydrochloride monohydrate. Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 2016, 152, 92-100.

7. Rajendiran, N.; Mohandoss, T.; Saravanan, J. Guest: Host interactions of lidocaine and prilocaine with natural cyclodextrins: Spectral and molecular modeling studies. Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 2014, 132, 387-396. [CrossRef] [PubMed] [OpenAIRE]

8. Umeda, Y.; Nagase, H.; Makimura, M.; Tomono, K.; Shiro, M.; Ueda, H. Crystal Structure of a 2:1 Complex of Indomethacin and Lidocaine. Anal. Sci. 2007, 23, x15-x16. [CrossRef]

9. Corvis, Y.; Négrier, P.; Lazerges, M.; Massip, S.; Léger, J.M.; Espeau, P. Lidocaine/L-Menthol Binary System: Cocrystallization versus Solid-State Immiscibility. J. Phys. Chem. B 2010, 114, 5420-5426. [CrossRef] [PubMed] [OpenAIRE]

10. Lebedyeva, I.O.; Oliferenko, A.A.; Oliferenko, P.V.; Hromas, R.A.; Neubert, J.K.; Caudle, R.M.; Wickersham, J.; Castleman, W.L.; Altschuler, G.I.; Ostrov, D.A.; et al. Ionic conjugates of lidocaine and sweeteners as better tasting local anesthetics for dentistry. J. Mater. Chem. B 2015, 3, 8492-8498. [CrossRef] [OpenAIRE]

11. Berton, P.; Di Bona, K.R.; Yancey, D.; Rizvi, S.A.A.; Gray, M.; Gurau, G.; Shamshina, J.L.; Rasco, J.F.; Rogers, R.D. Transdermal Bioavailability in Rats of Lidocaine in the Forms of Ionic Liquids, Salts, and Deep Eutectic. ACS Med. Chem. Lett. 2017, 8, 498-503. [CrossRef] [PubMed]

12. Khan, M.; Enkelmann, V.; Brunklaus, G. O-H N Heterosynthon: A Robust Supramolecular Unit for Crystal Engineering. Cryst. Growth Des. 2009, 9, 2354-2362. [CrossRef]

13. Mukherjee, A.; Grobelny, P.; Thakur, T.S.; Desiraju, G.R. Polymorphs, Pseudopolymorphs, and Co-Crystals of Orcinol: Exploring the Structural Landscape with High Throughput Crystallography. Cryst. Growth Des. 2011, 11, 2637-2653. [CrossRef]

31 references, page 1 of 3
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publication . Article . 2018

Mechanochemical Synthesis and Crystal Structure of the Lidocaine-Phloroglucinol Hydrate 1:1:1 Complex

Nancy Magaña-Vergara; Porfirio de la Cruz-Cruz; Ana Peraza-Campos; Francisco Martínez-Martínez; Juan González-González;