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Ibuprofen and Paracetamol when They Meet: Quantum Theory of Atoms in Molecules Perspective

Year 2023, , 188 - 196, 26.03.2023

Cemal Parlak , Özgür Alver , Özge Bağlayan , Onur Demirel

https://doi.org/10.17776/csj.1112531
Cited By: 1

Abstract

Ibuprofen (IBP) and paracetamol (PCM) are widely used and prescribed two drugs for particularly their effects in reducing pain and fever. For enhanced pain relief, combinations of IBP and PCM are considered another option rather than taken each drug alone. In the scope of this work, the possible structural interaction edges, some important electronic properties and the binding energy evaluations of the IBP&PCM system were examined with density functional theory (DFT) and quantum theory of atoms in molecules (QTAIM). Further, all the configurations were subjected to biological activity evaluations. It was observed that hydrogen bonding interactions are possible for the examined drug couple and configuration 4 is the most stable form whereas C1 and C6 are better inhibitors. Therefore, possible advantages and disadvantages or possible side effects must be taken into account before combining these two important drug molecules.

Keywords

Ibuprofen Paracetamol DFT Hydrogen bonding QTAIM

Supporting Institution

Eskişehir Technical University

Project Number

20ADP133

References

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  • [4] Anderson B.J., Paracetamol (acetaminophen): mechanisms of action, Paediatr Anaesth., 18(10) (2008) 915-921.
  • [5] Langhendries J.P., Allegaert K., Van Den Anker J.N., Veyckemans F., Smets F., Possible effects of repeated exposure to ibuprofen and acetaminophen on the intestinal immune response in young infants, Med. Hypotheses, 87 (2016) 90-96.
  • [6] Derry C.J., Derry S., Moore R.A., Single dose oral ibuprofen plus paracetamol (acetaminophen) for acute postoperative pain, Cochrane Database Syst. Rev., (6) CD010210 (2013).
  • [7] Doherty M., Hawkey C., Goulder M., Gibb I., Hill N., Aspley S., Reader S., A randomised controlled trial of ibuprofen, paracetamol or a combination tablet of ibuprofen/paracetamol in community-derived people with knee pain, Ann. Rheum. Dis., 70(9) (2011) 1534-1541.
  • [8] Eccles R., Holbrook A., Jawad M., A double-blind, randomised, crossover study of two doses of a single-tablet combination of ibuprofen/paracetamol and placebo for primary dysmenorrhoea, Curr. Med. Res. Opin., 26 (11) (2010) 2689-2699.
  • [9] Mehlisch D.R., Aspley S., Daniels S.E., Bandy D. P., Comparison of the analgesic efficacy of concurrent ibuprofen and paracetamol with ibuprofen or paracetamol alone in the management of moderate to severe acute postoperative dental pain in adolescents and adults: a randomized, double-blind, placebo-controlled, parallel-group, single-dose, two-center, modified factorial study, Clin. Ther., 32(5) (2010) 882-895.
  • [10] Merry A.F., Gibbs R.D., Edwards J., Ting G.S., Frampton C., Davies E., Anderson B.J., Combined acetaminophen and ibuprofen for pain relief after oral surgery in adults: a randomized controlled trial, Br. J. Anaesth., 104(1) (2010) 80-88.
  • [11] Kawakami J., Kakinami H., Matsushima N., Nakane A., Kitahara H., Nagaki M., Ito S., Structure-activity relationship analysis for antimicrobial activities of tryptanthrin derivatives using quantum chemical calculations, J. Comput. Chem. Jpn., 12(2) (2013) 109-112.
  • [12] Venkataramanan N.S., Suvitha A., Kawazoe Y., Intermolecular interaction in nucleobases and dimethylsulfoxide/water molecules: A DFT, NBO, AIM and NCI analysis, J. Mol. Graph. Model., 78 (2017) 48–60.
  • [13] Ravaei I., Haghighat M., Azami S.M., A DFT, AIM and NBO study of isoniazid drug delivery by MgO nanocage, Appl. Surf. Sci., 469 (2019) 103–112.
  • [14] Lu T., Chen F., Multiwfn: a multifunctional wavefunction analyzer, J. Comput. Chem., 33 (2012) 580–592.
  • [15] Bader R.F.W., Atoms in Molecules: A Quantum Theory, Clarendon, New York, 1990.
  • [16] Reed A.E., Weinstock R.B., Weinhold F., Natural population analysis, J. Chem. Phys., 83 (1985) 735–746.
  • [17] Reed A.E., Curtiss L.A., Weinhold F., Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint, Chem. Rev., 88 (1988) 899–926.
  • [18] Alver Ö., FT-IR, Raman and DFT Studies on the vibrational spectra of 2,2-bis(aminoethoxy)propane, Bull. Chem. Soc. Ethiop., 30(1) (2016) 147-151.
  • [19] Hadad A., Azevedo D.L., Caetano E.W.S., Freire V.N., Mendonça G.L.F., Neto P.L., Albuquerque E.L., Margis R., Gottfried C., Two-level adsorption of ibuprofen on C60 fullerene for transdermal delivery: classical molecular dynamics and density functional theory computations, J. Phys. Chem. C., 115(50) (2011) 24501-24511.
  • [20]Saikia U., Saikia N., Waters K., Pandey R., Sahariah M.B., Electronic properties of acetaminophen adsorbed on 2D clusters: A first principles density functional study, Chemistry Select., 2(13) (2017) 3613-3621.
  • [21] Dennington R.D., Keith T.A., Millam J.M., GaussView 5.0.8, Gaussian Inc., 2008.
  • [22] Parlak C., Alver Ö., A density functional theory investigation on amantadine drug interaction with pristine and B, Al, Si, Ga, Ge doped C60 fullerenes, Chem. Phys. Lett., 678 (2017) 85-90.
  • [23]Boys S.F., Bernardi F., The calculation of small molecular interactions by the differences of separate total energies. Some procedures with reduced errors, Mol. Phys., 19(4) (1970) 553-566.
  • [24]Gutowski M., Chalasinski G., Critical evaluation of some computational approaches to the problem of basis set superposition error, J. Chem. Phys., 98 (1993) 5540-5554.
  • [25]Beheshtian J., Peyghan A.A., Bagheri Z., Carbon nanotube functionalization with carboxylic derivatives: a DFT study, J. Mol. Model., 19(1) (2013) 391–396.
  • [26]Peyghan A.A., Soltani A., Pahlevani A.A., Kanani Y., Khajeh S., A first-principles study of the adsorption behavior of CO on Al- and Ga-doped single-walled BN nanotubes, Appl. Surf. Sci., 270 (2013) 25–32.
  • [27] Frisch M.J., Trucks G.W., Schlegel H.B., Gaussian 09, Revision A.1, Gaussian Inc., Wallingford, CT, 2009.
  • [28]Daina A., Michielin O., Zoete V., SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Sci Rep., 42717(7) (2017).
  • [29]Rozas I., Alkorta I., Elguero J., Behavior of ylides containing N, O and C atoms as hydrogen bond acceptors, J. Am. Chem. Soc., 122(45) (2000) 11154-11161.
  • [30]Bhattacharjee A.K., Skanchy D.J., Jennings B., Hudson T.H., Brendle J.J., Werbovetz K.A., Analysis of stereoelectronic properties, mechanism of action and pharmacophore of synthetic indolo[2,1-b]quinazoline-6,12-dione derivatives in relation to antileishmanial activity using quantum chemical, cyclic voltammetry and 3-D-QSAR Catalyst procedures, Bioorg. Med. Chem., 10 (6) (2002) 1979-1989.
  • [31] Al Wasidi A.S., Hassan A.S., Naglah A.M., In vitro cytotoxicity and druglikeness of pyrazolines and pyridines bearing benzofuran moiety, J. Appl. Pharm. Sci., 10(4) (2020) 142–148.
  • [32]Lipinski C.A., Lombardo F., Dominy B.W., Feeney P.J., Experimental and computational approaches to estimate solubility in drug discovery and development settings, Adv. Drug. Deliv. Rev., 46(1-3) (2001) 3-26
  • [33]Ghose A.K., Viswanadhan V.N., Wendoloski J.J., A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. A qualitative and quantitative characterization of known drug databases, J. Comb. Chem., 1(1) (1999) 55-68.
  • [34]Veber D.F., Johnson S.R., Cheng H.-Y., Smith B.R., Ward K.W., Kopple K.D., Molecular properties that influence the oral bioavailability of drug candidates, J. Med. Chem., 45(12) (2002) 2615-2623.
  • [35]Egan W.J., Merz K.M., Baldwin J.J., Prediction of drug absorption using multivariate statistics, J. Med. Chem., 43(21) (2000) 3867-3877.
  • [36]Muegge I., Heald S.L., Brittelli D., Simple selection criteria for drug-like chemical matter, J. Med. Chem., 44(12) (2001) 1841-1846.

Year 2023, , 188 - 196, 26.03.2023

Cemal Parlak , Özgür Alver , Özge Bağlayan , Onur Demirel

https://doi.org/10.17776/csj.1112531
Cited By: 1

Abstract

Project Number

20ADP133

References

  • [1] Roushani M., Shahdost-Fard F., Applicability of AuNPs@N-GQDs nanocomposite in the modeling of the amplified electrochemical Ibuprofen aptasensing assay by monitoring of riboflavin, Bioelectrochemistry, 126 (2019) 38-47.
  • [2] Lazarević J.J., Uskoković–Marković S., Jelikić–Stankov M., Radonjić M., Tanasković D., Lazarević N., Popović Z.V., Intermolecular and low-frequency intramolecular Raman scattering study of racemic ibuprofen, Spectrochim. Acta A., 126 (2014) 301-305.
  • [3] Fanali G., di Masi A., Trezza V., Marino M., Fasano M., Ascenzi P., Human serum albumin: From bench to bedside, Mol Aspects Med., 33(3) (2012) 209-290.
  • [4] Anderson B.J., Paracetamol (acetaminophen): mechanisms of action, Paediatr Anaesth., 18(10) (2008) 915-921.
  • [5] Langhendries J.P., Allegaert K., Van Den Anker J.N., Veyckemans F., Smets F., Possible effects of repeated exposure to ibuprofen and acetaminophen on the intestinal immune response in young infants, Med. Hypotheses, 87 (2016) 90-96.
  • [6] Derry C.J., Derry S., Moore R.A., Single dose oral ibuprofen plus paracetamol (acetaminophen) for acute postoperative pain, Cochrane Database Syst. Rev., (6) CD010210 (2013).
  • [7] Doherty M., Hawkey C., Goulder M., Gibb I., Hill N., Aspley S., Reader S., A randomised controlled trial of ibuprofen, paracetamol or a combination tablet of ibuprofen/paracetamol in community-derived people with knee pain, Ann. Rheum. Dis., 70(9) (2011) 1534-1541.
  • [8] Eccles R., Holbrook A., Jawad M., A double-blind, randomised, crossover study of two doses of a single-tablet combination of ibuprofen/paracetamol and placebo for primary dysmenorrhoea, Curr. Med. Res. Opin., 26 (11) (2010) 2689-2699.
  • [9] Mehlisch D.R., Aspley S., Daniels S.E., Bandy D. P., Comparison of the analgesic efficacy of concurrent ibuprofen and paracetamol with ibuprofen or paracetamol alone in the management of moderate to severe acute postoperative dental pain in adolescents and adults: a randomized, double-blind, placebo-controlled, parallel-group, single-dose, two-center, modified factorial study, Clin. Ther., 32(5) (2010) 882-895.
  • [10] Merry A.F., Gibbs R.D., Edwards J., Ting G.S., Frampton C., Davies E., Anderson B.J., Combined acetaminophen and ibuprofen for pain relief after oral surgery in adults: a randomized controlled trial, Br. J. Anaesth., 104(1) (2010) 80-88.
  • [11] Kawakami J., Kakinami H., Matsushima N., Nakane A., Kitahara H., Nagaki M., Ito S., Structure-activity relationship analysis for antimicrobial activities of tryptanthrin derivatives using quantum chemical calculations, J. Comput. Chem. Jpn., 12(2) (2013) 109-112.
  • [12] Venkataramanan N.S., Suvitha A., Kawazoe Y., Intermolecular interaction in nucleobases and dimethylsulfoxide/water molecules: A DFT, NBO, AIM and NCI analysis, J. Mol. Graph. Model., 78 (2017) 48–60.
  • [13] Ravaei I., Haghighat M., Azami S.M., A DFT, AIM and NBO study of isoniazid drug delivery by MgO nanocage, Appl. Surf. Sci., 469 (2019) 103–112.
  • [14] Lu T., Chen F., Multiwfn: a multifunctional wavefunction analyzer, J. Comput. Chem., 33 (2012) 580–592.
  • [15] Bader R.F.W., Atoms in Molecules: A Quantum Theory, Clarendon, New York, 1990.
  • [16] Reed A.E., Weinstock R.B., Weinhold F., Natural population analysis, J. Chem. Phys., 83 (1985) 735–746.
  • [17] Reed A.E., Curtiss L.A., Weinhold F., Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint, Chem. Rev., 88 (1988) 899–926.
  • [18] Alver Ö., FT-IR, Raman and DFT Studies on the vibrational spectra of 2,2-bis(aminoethoxy)propane, Bull. Chem. Soc. Ethiop., 30(1) (2016) 147-151.
  • [19] Hadad A., Azevedo D.L., Caetano E.W.S., Freire V.N., Mendonça G.L.F., Neto P.L., Albuquerque E.L., Margis R., Gottfried C., Two-level adsorption of ibuprofen on C60 fullerene for transdermal delivery: classical molecular dynamics and density functional theory computations, J. Phys. Chem. C., 115(50) (2011) 24501-24511.
  • [20]Saikia U., Saikia N., Waters K., Pandey R., Sahariah M.B., Electronic properties of acetaminophen adsorbed on 2D clusters: A first principles density functional study, Chemistry Select., 2(13) (2017) 3613-3621.
  • [21] Dennington R.D., Keith T.A., Millam J.M., GaussView 5.0.8, Gaussian Inc., 2008.
  • [22] Parlak C., Alver Ö., A density functional theory investigation on amantadine drug interaction with pristine and B, Al, Si, Ga, Ge doped C60 fullerenes, Chem. Phys. Lett., 678 (2017) 85-90.
  • [23]Boys S.F., Bernardi F., The calculation of small molecular interactions by the differences of separate total energies. Some procedures with reduced errors, Mol. Phys., 19(4) (1970) 553-566.
  • [24]Gutowski M., Chalasinski G., Critical evaluation of some computational approaches to the problem of basis set superposition error, J. Chem. Phys., 98 (1993) 5540-5554.
  • [25]Beheshtian J., Peyghan A.A., Bagheri Z., Carbon nanotube functionalization with carboxylic derivatives: a DFT study, J. Mol. Model., 19(1) (2013) 391–396.
  • [26]Peyghan A.A., Soltani A., Pahlevani A.A., Kanani Y., Khajeh S., A first-principles study of the adsorption behavior of CO on Al- and Ga-doped single-walled BN nanotubes, Appl. Surf. Sci., 270 (2013) 25–32.
  • [27] Frisch M.J., Trucks G.W., Schlegel H.B., Gaussian 09, Revision A.1, Gaussian Inc., Wallingford, CT, 2009.
  • [28]Daina A., Michielin O., Zoete V., SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Sci Rep., 42717(7) (2017).
  • [29]Rozas I., Alkorta I., Elguero J., Behavior of ylides containing N, O and C atoms as hydrogen bond acceptors, J. Am. Chem. Soc., 122(45) (2000) 11154-11161.
  • [30]Bhattacharjee A.K., Skanchy D.J., Jennings B., Hudson T.H., Brendle J.J., Werbovetz K.A., Analysis of stereoelectronic properties, mechanism of action and pharmacophore of synthetic indolo[2,1-b]quinazoline-6,12-dione derivatives in relation to antileishmanial activity using quantum chemical, cyclic voltammetry and 3-D-QSAR Catalyst procedures, Bioorg. Med. Chem., 10 (6) (2002) 1979-1989.
  • [31] Al Wasidi A.S., Hassan A.S., Naglah A.M., In vitro cytotoxicity and druglikeness of pyrazolines and pyridines bearing benzofuran moiety, J. Appl. Pharm. Sci., 10(4) (2020) 142–148.
  • [32]Lipinski C.A., Lombardo F., Dominy B.W., Feeney P.J., Experimental and computational approaches to estimate solubility in drug discovery and development settings, Adv. Drug. Deliv. Rev., 46(1-3) (2001) 3-26
  • [33]Ghose A.K., Viswanadhan V.N., Wendoloski J.J., A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. A qualitative and quantitative characterization of known drug databases, J. Comb. Chem., 1(1) (1999) 55-68.
  • [34]Veber D.F., Johnson S.R., Cheng H.-Y., Smith B.R., Ward K.W., Kopple K.D., Molecular properties that influence the oral bioavailability of drug candidates, J. Med. Chem., 45(12) (2002) 2615-2623.
  • [35]Egan W.J., Merz K.M., Baldwin J.J., Prediction of drug absorption using multivariate statistics, J. Med. Chem., 43(21) (2000) 3867-3877.
  • [36]Muegge I., Heald S.L., Brittelli D., Simple selection criteria for drug-like chemical matter, J. Med. Chem., 44(12) (2001) 1841-1846.
There are 36 citations in total.

Details

Primary Language English
Subjects Classical Physics (Other)
Journal Section Natural Sciences
Authors

Cemal Parlak 0000-0002-6115-6098

Özgür Alver 0000-0003-0647-4242

Özge Bağlayan 0000-0002-0753-0325

Onur Demirel 0000-0001-9695-9141

Project Number 20ADP133
Publication Date March 26, 2023
Submission Date May 5, 2022
Acceptance Date November 16, 2022
Published in Issue Year 2023

Cite

APA Parlak, C., Alver, Ö., Bağlayan, Ö., Demirel, O. (2023). Ibuprofen and Paracetamol when They Meet: Quantum Theory of Atoms in Molecules Perspective. Cumhuriyet Science Journal, 44(1), 188-196. https://doi.org/10.17776/csj.1112531

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