Review Artikel: Sintesis dan Isomerisasi Senyawa Kimia pada Obat

Authors

  • Alhara Yuwanda Author

DOI:

https://doi.org/10.70608/p8yxr427

Keywords:

Isomer, Obat, Sintesis, Rasemat, Stereokimia

Abstract

Isomerisme pada senyawa obat merupakan salah satu parameter yang mempengaruhi farmakologi klinis dan farmakoterapi. Diperlukan tinjauan literatur dilakukan untuk beberapa obat kiral yang melibatkan parameter farmakokinetik dan farmakodinamik dari perbedaan senyawa isomer serta penggunaannya dalam kondisi penyakit tertentu. Saat ini, pengetahuan tentang isomerisme telah membantu kita dalam memperkenalkan alternatif obat yang lebih aman dan lebih efektif baik untuk obat-obatan baru maupun yang sudah ada. Banyak obat yang sudah dilakukan modifikasi, seperti dalam bentuk kiral seperti beralih dari campuran rasematik menjadi salah satu isomernya. Resolusi berkaitan dengan pemisahan senyawa rasematik yang menunjukkan keandalan untuk memperoleh sifat-sifat enantiomer yang diinginkan. Dalam artikel ini, kami telah mencoba untuk mengulas konsep dasar dari stereokimia dan kiralitas serta signifikansinya dalam farmakoterapi.

Downloads

Download data is not yet available.

References

[1] M. Abu Rasheed, A. Alshaghel, and A. A. Sakur, “A new bonded silica based on an amino acid derivative as a TLC stationary phase to solve nitrophenol structural isomerism and ibuprofen stereoisomerism,” Future J. Pharm. Sci., vol. 6, no. 1, 2020, doi: 10.1186/s43094-020-00064-8. DOI: https://doi.org/10.1186/s43094-020-00064-8

[2] T. Nakagita, C. Taketani, M. Narukawa, T. Hirokawa, T. Kobayashi, and T. Misaka, “Ibuprofen, a nonsteroidal anti-inflammatory drug, is a potent inhibitor of the human sweet taste receptor,” Chem. Senses, vol. 45, no. 8, pp. 667–673, 2020, doi: 10.1093/chemse/bjaa057. DOI: https://doi.org/10.1093/chemse/bjaa057

[3] C. M. Clemente, M. I. Freiberger, S. Ravetti, D. M. Beltramo, and A. G. Garro, “An in silico analysis of ibuprofen enantiomers in high concentrations of sodium chloride with SARS-CoV-2 main protease,” J. Biomol. Struct. Dyn., vol. 40, no. 12, pp. 5653–5664, 2022, doi: 10.1080/07391102.2021.1872420. DOI: https://doi.org/10.1080/07391102.2021.1872420

[4] V. O. Doroschuk, V. Y. Sabko, O. V. Ivashko, L. O. Popova, and A. S. Shalamay, “Enantioselective determination of S- and R-isomers of ibuprofen in plasma by ultra-performance liquid chromatography–tandem mass spectrometry,” Methods Objects Chem. Anal., vol. 15, no. 1, pp. 40–46, 2020, doi: 10.17721/moca.2020.40-46. DOI: https://doi.org/10.17721/moca.2020.40-46

[5] M. W. Ha and S. M. Paek, “Recent advances in the synthesis of ibuprofen and naproxen,” Molecules, vol. 26, no. 16, 2021, doi: 10.3390/molecules26164792. DOI: https://doi.org/10.3390/molecules26164792

[6] M. Rasoolidanesh and M. Darvish Ganji, “Separation of ibuprofen drugs enantiomers by using chiral carbon nanotube with molecular dynamics simulation,” Med. Sci. J., vol. 30, no. 3, pp. 227–236, 2020, doi: 10.29252/iau.30.3.227. DOI: https://doi.org/10.29252/iau.30.3.227

[7] S. Bouabdallah, M. T. Ben Dhia, and M. R. Driss, “Study of a conformational equilibrium of lisinopril by HPLC, NMR, and DFT,” Int. J. Anal. Chem., vol. 2014, Art. no. 494719, 2014, doi: 10.1155/2014/494719. DOI: https://doi.org/10.1155/2014/494719

[8] U. J. Undiandeye et al., “Spectroscopic, conformational analysis, structural benchmarking, excited state dynamics, and the photovoltaic properties of enalapril and lisinopril,” J. Indian Chem. Soc., vol. 99, no. 7, Art. no. 100500, 2022, doi: 10.1016/j.jics.2022.100500. DOI: https://doi.org/10.1016/j.jics.2022.100500

[9] M. M. Abdou, D. Dong, P. M. O’Neill, E. Amigues, and M. Matziari, “Diastereoselective synthesis of a novel phosphinic peptide as ACE inhibitor: Fragment-based design approach,” Arab. J. Chem., vol. 16, no. 2, Art. no. 104499, 2023, doi: 10.1016/j.arabjc.2022.104499. DOI: https://doi.org/10.1016/j.arabjc.2022.104499

[10] S. Manoharan, “Is it still relevant to discover new ACE inhibitors from natural products? YES, but only with comprehensive approaches to address the patients’ real problems: Chronic dry cough and angioedema,” Molecules, vol. 28, no. 11, 2023, doi: 10.3390/molecules28114532. DOI: https://doi.org/10.3390/molecules28114532

[11] V. Shinde, A. Trivedi, P. R. Upadhayay, N. L. Gupta, D. G. Kanase, and R. Chikate, “Identification of a new impurity in lisinopril,” J. Pharm. Biomed. Anal., vol. 43, no. 1, pp. 381–386, 2007, doi: 10.1016/j.jpba.2006.06.046. DOI: https://doi.org/10.1016/j.jpba.2006.06.046

[12] S. Bouabdallah, H. Trabelsi, K. Bouzouita, and S. Sabbah, “Reversed-phase liquid chromatography of lisinopril conformers,” J. Biochem. Biophys. Methods, vol. 54, no. 1–3, pp. 391–405, 2002, doi: 10.1016/S0165-022X(02)00140-9. DOI: https://doi.org/10.1016/S0165-022X(02)00140-9

[13] T. N. Calvey, “Isomerism and anaesthetic drugs,” Acta Anaesthesiol. Scand., vol. 39, no. Table I, pp. 83–90, 1995, doi: 10.1111/j.1399-6576.1995.tb04316.x. DOI: https://doi.org/10.1111/j.1399-6576.1995.tb04316.x

[14] J. C. Duque M., C. A. A. Valadão, A. Farias, R. M. De Almeida, and N. Oleskovicz, “Pre-emptive epidural ketamine or S(+)-ketamine in post-incisional pain in dogs: A comparative study,” Vet. Surg., vol. 33, no. 4, pp. 361–367, 2004, doi: 10.1111/j.1532-950X.2004.04052.x. DOI: https://doi.org/10.1111/j.1532-950X.2004.04052.x

[15] L. Arendt-Nielsen, J. Nielsen, S. Petersen-Felix, T. W. Schnider, and A. M. Zbinden, “Effect of racemic mixture and the (S+)-isomer of ketamine on temporal and spatial summation of pain,” Br. J. Anaesth., vol. 77, no. 5, pp. 625–631, 1996, doi: 10.1093/bja/77.5.625. DOI: https://doi.org/10.1093/bja/77.5.625

[16] J. C. Duque, N. Oleskovicz, E. C. B. P. Guirro, C. A. A. Valadão, and V. E. Soares, “Relative potency of ketamine and S(+)-ketamine in dogs,” J. Vet. Pharmacol. Ther., vol. 31, no. 4, pp. 344–348, 2008, doi: 10.1111/j.1365-2885.2008.00965.x. DOI: https://doi.org/10.1111/j.1365-2885.2008.00965.x

[17] M. Wiryana et al., “Low dose ketamin,” Bali J. Anesthesiol., vol. 1, no. 1, pp. 13–19, 2017, doi: 10.15562/bjoa.v1i1.4. DOI: https://doi.org/10.15562/bjoa.v1i1.4

[18] T. Passie, H. A. Adams, F. Logemann, S. D. Brandt, B. Wiese, and M. Karst, “Comparative effects of (S)-ketamine and racemic (R/S)-ketamine on psychopathology, state of consciousness and neurocognitive performance in healthy volunteers,” Eur. Neuropsychopharmacol., vol. 44, pp. 92–104, 2021, doi: 10.1016/j.euroneuro.2021.01.005. DOI: https://doi.org/10.1016/j.euroneuro.2021.01.005

[19] F. A. Sandbaumhüter, J. T. Aerts, R. Theurillat, P. E. Andrén, W. Thormann, and E. T. Jansson, “Enantioselective CE–MS analysis of ketamine metabolites in urine,” Electrophoresis, vol. 44, no. 1–2, pp. 125–134, 2023, doi: 10.1002/elps.202200175. DOI: https://doi.org/10.1002/elps.202200175

[20] S. Schmidt and U. Holzgrabe, “Method development, optimization, and validation of the separation of ketamine enantiomers by capillary electrophoresis using design of experiments,” Chromatographia, vol. 86, no. 1, pp. 87–95, 2023, doi: 10.1007/s10337-022-04229-w. DOI: https://doi.org/10.1007/s10337-022-04229-w

[21] H. Toki, J. ichi Yamaguchi, A. Mizuno-Yasuhira, and H. Endo, “Chiral LC-MS/MS method for the simultaneous determination of (R,S)-ketamine, (R,S)-norketamine, and (2R,6R;2S,6S)-hydroxynorketamine in mouse plasma and brain,” J. Pharm. Biomed. Anal., vol. 224, p. 115168, 2023, doi: 10.1016/j.jpba.2022.115168. DOI: https://doi.org/10.1016/j.jpba.2022.115168

[22] L. Kurzweil, L. Danyeli, Z. D. Şen, A. Fejtova, M. Walter, and S. Gensberger-Reigl, “Targeted mass spectrometry of ketamine and its metabolites cis-6-hydroxynorketamine and norketamine in human blood serum,” J. Chromatogr. B, vol. 1152, p. 122214, 2020, doi: 10.1016/j.jchromb.2020.122214. DOI: https://doi.org/10.1016/j.jchromb.2020.122214

[23] M. Reyes-Parada, P. Iturriaga-Vasquez, and B. K. Cassels, “Amphetamine derivatives as monoamine oxidase inhibitors,” Front. Pharmacol., vol. 10, pp. 1–17, 2020, doi: 10.3389/fphar.2019.01590. DOI: https://doi.org/10.3389/fphar.2019.01590

[24] J. Mendelson et al., “Human pharmacology of the methamphetamine stereoisomers,” Clin. Pharmacol. Ther., vol. 80, no. 4, pp. 403–420, 2006, doi: 10.1016/j.clpt.2006.06.013. DOI: https://doi.org/10.1016/j.clpt.2006.06.013

[25] D. J. Heal, N. W. Buckley, J. Gosden, N. Slater, C. P. France, and D. Hackett, “A preclinical evaluation of the discriminative and reinforcing properties of lisdexamfetamine in comparison to D-amfetamine, methylphenidate and modafinil,” Neuropharmacology, vol. 73, pp. 348–358, 2013, doi: 10.1016/j.neuropharm.2013.05.021. DOI: https://doi.org/10.1016/j.neuropharm.2013.05.021

[26] H. L. Rowley, R. Kulkarni, J. Gosden, R. Brammer, D. Hackett, and D. J. Heal, “Lisdexamfetamine and immediate release d-amfetamine—Differences in pharmacokinetic/pharmacodynamic relationships revealed by striatal microdialysis in freely-moving rats with simultaneous determination of plasma drug concentrations and locomotor activity,” Neuropharmacology, vol. 63, no. 6, pp. 1064–1074, 2012, doi: 10.1016/j.neuropharm.2012.07.008. DOI: https://doi.org/10.1016/j.neuropharm.2012.07.008

[27] A. Thomas and M. Thevis, “Stereoisomers in sports drug testing: Analytical strategies and applications,” J. Chromatogr. A, vol. 1674, Art. no. 463154, 2022, doi: 10.1016/j.chroma.2022.463154. DOI: https://doi.org/10.1016/j.chroma.2022.463154

[28] M. Hassan-Alin, T. Andersson, M. Niazi, and K. Röhss, “A pharmacokinetic study comparing single and repeated oral doses of 20 mg and 40 mg omeprazole and its two optical isomers, S-omeprazole (esomeprazole) and R-omeprazole, in healthy subjects,” Eur. J. Clin. Pharmacol., vol. 60, no. 11, pp. 779–784, 2005, doi: 10.1007/s00228-004-0841-1. DOI: https://doi.org/10.1007/s00228-004-0841-1

[29] X. Q. Li, L. Weidolf, R. Simonsson, and T. B. Andersson, “Enantiomer/enantiomer interactions between the S- and R-isomers of omeprazole in human cytochrome P450 enzymes: Major role of CYP2C19 and CYP3A4,” J. Pharmacol. Exp. Ther., vol. 315, no. 2, pp. 777–787, 2005, doi: 10.1124/jpet.105.090928. DOI: https://doi.org/10.1124/jpet.105.090928

[30] R. I. Neuman et al., “Omeprazole administration in preterm preeclampsia: A randomized controlled trial to study its effect on sFlt-1, PlGF, and ET-1,” Hypertension, vol. 79, no. 6, pp. 1297–1307, 2022, doi: 10.1161/HYPERTENSIONAHA.122.19070. DOI: https://doi.org/10.1161/HYPERTENSIONAHA.122.19070

[31] S. Hiromoto et al., “Use of omeprazole, the proton pump inhibitor, as a potential therapy for the capecitabine-induced hand-foot syndrome,” Sci. Rep., vol. 11, no. 1, Art. no. 8964, 2021, doi: 10.1038/s41598-021-88460-9. DOI: https://doi.org/10.1038/s41598-021-88460-9

[32] S. Agatonovic-Kustrin, N. Markovic, M. Ginic-Markovic, M. Mangan, and B. D. Glass, “Compatibility studies between mannitol and omeprazole sodium isomers,” J. Pharm. Biomed. Anal., vol. 48, no. 2, pp. 356–360, 2008, doi: 10.1016/j.jpba.2008.02.009. DOI: https://doi.org/10.1016/j.jpba.2008.02.009

[33] T. Andersson, M. Hassan-Alin, G. Hasselgren, K. Röhss, and L. Weidolf, “Pharmacokinetic studies with esomeprazole, the (S)-isomer of omeprazole,” Clin. Pharmacokinet., vol. 40, no. 6, pp. 411–426, 2001, doi: 10.2165/00003088-200140060-00003. DOI: https://doi.org/10.2165/00003088-200140060-00003

[34] T. Andersson, K. Röhss, E. Bredberg, and M. Hassan-Alin, “Pharmacokinetics and pharmacodynamics of esomeprazole, the S-isomer of omeprazole,” Aliment. Pharmacol. Ther., vol. 15, no. 10, pp. 1563–1569, 2001, doi: 10.1046/j.1365-2036.2001.01087.x. DOI: https://doi.org/10.1046/j.1365-2036.2001.01087.x

[35] J. Saito et al., “Esomeprazole during pregnancy and lactation: Esomeprazole levels in maternal serum, cord blood, breast milk, and the infant’s serum,” Breastfeed. Med., vol. 15, no. 9, pp. 598–601, 2020, doi: 10.1089/bfm.2020.0175. DOI: https://doi.org/10.1089/bfm.2020.0175

[36] T. Andersson, M. Hassan-Alin, G. Hasselgren, and K. Röhss, “Drug interaction studies with esomeprazole, the (S)-isomer of omeprazole,” Clin. Pharmacokinet., vol. 40, no. 7, pp. 523–537, 2001, doi: 10.2165/00003088-200140070-00004. DOI: https://doi.org/10.2165/00003088-200140070-00004

[37] E. I. El-Kimary and M. A. A. Ragab, “Recent analytical methodologies for the determination of omeprazole and/or its active isomer esomeprazole in different matrices: A critical review,” Crit. Rev. Anal. Chem., pp. 1–25, 2020, doi: 10.1080/10408347.2020.1791042. DOI: https://doi.org/10.1080/10408347.2020.1791042

[38] M. R. C. C. Pharmacology, “Pharmacokinetics of dextro-, laevo- and racemic propranolol in man,” vol. 76, pp. 74–76, 1972. DOI: https://doi.org/10.1007/BF00562500

[39] V. A. Tran et al., “Facile synthesis of propranolol and novel derivatives,” J. Chem., vol. 2020, Art. no. 9597426, 2020, doi: 10.1155/2020/9597426. DOI: https://doi.org/10.1155/2020/9597426

[40] A. M. Barrett and V. A. Cullum, “The biological properties of the optical isomers of propranolol and their effects on cardiac arrhythmias,” Br. J. Pharmacol., vol. 34, no. 1, pp. 43–55, 1968, doi: 10.1111/j.1476-5381.1968.tb07949.x. DOI: https://doi.org/10.1111/j.1476-5381.1968.tb07949.x

[41] K. H. Rahn, A. Hawlina, F. Kersting, and G. Planz, “Studies on the antihypertensive action of the optical isomers of propranolol in man,” Naunyn Schmiedebergs Arch. Pharmacol., vol. 286, no. 3, pp. 319–323, 1974, doi: 10.1007/BF00498314. DOI: https://doi.org/10.1007/BF00498314

[42] E. M. V. Williams, E. E. Bagwell, and B. N. Singh, “Cardiospecificity of β-receptor blockade: A comparison of the relative potencies on cardiac and peripheral vascular β-adrenoceptors of propranolol, of practolol and its ortho-substituted isomer, and of oxprenolol and its para-substituted isomer,” Cardiovasc. Res., vol. 7, no. 2, pp. 226–240, 1973, doi: 10.1093/cvr/7.2.226. DOI: https://doi.org/10.1093/cvr/7.2.226

[43] J. Yamamoto, K. Hiroshi, and M. Atsushi, “Cardiovascular isomers,” vol. imm, no. 4.

[44] N. Turković, J. Savić, B. Ivković, and A. Ivković, “Separation of propranolol enantiomers using chiral HPLC,” Kragujevac J. Sci., vol. 45, no. 45, pp. 41–49, 2023, doi: 10.5937/kgjsci2345041t. DOI: https://doi.org/10.5937/KgJSci2345041T

[45] T. Sedghamizand and M. Bahrami, “Chiral ionic liquid interface as a chiral selector for recognition of propranolol enantiomers: A molecular dynamics simulations study,” J. Mol. Liq., vol. 292, Art. no. 111441, 2019, doi: 10.1016/j.molliq.2019.111441. DOI: https://doi.org/10.1016/j.molliq.2019.111441

[46] S. Keller and J. Womersley, “Measurement of the,” Eur. Phys. J. C, vol. 5, no. 2, p. 249, 1998, doi: 10.1007/s100520050266. DOI: https://doi.org/10.1007/s100529800925

[47] E. J. Valente, E. C. Lingafelter, W. R. Porter, and W. F. Trager, “Structure of warfarin in solution,” J. Med. Chem., vol. 20, no. 11, pp. 1489–1493, 1977, doi: 10.1021/jm00221a025. DOI: https://doi.org/10.1021/jm00221a025

[48] R. J. Lewis, W. F. Trager, and K. K. Chan, “Warfarin: Stereochemical aspects of its metabolism and the interaction with phenylbutazone,” J. Clin. Invest., vol. 53, no. 6, pp. 1607–1617, 1974, doi: 10.1172/JCI107711. DOI: https://doi.org/10.1172/JCI107711

[49] S. S. Sakpal, D. Ghosh, M. A. Manae, A. Hazra, and S. Bagchi, “The curious case of aqueous warfarin: Structural isomers or distinct excited states?,” J. Phys. Chem. B, vol. 125, no. 11, pp. 2871–2878, 2021, doi: 10.1021/acs.jpcb.0c10824. DOI: https://doi.org/10.1021/acs.jpcb.0c10824

[50] B. K. Park, “Warfarin: Metabolism and mode of action,” Biochem. Pharmacol., vol. 37, no. 1, pp. 19–27, 1988, doi: 10.1016/0006-2952(88)90750-2. DOI: https://doi.org/10.1016/0006-2952(88)90750-2

[51] A. D. Krystal, “Sleep therapeutics and neuropsychiatric illness,” Neuropsychopharmacology, vol. 45, no. 1, pp. 166–175, 2020, doi: 10.1038/s41386-019-0474-9. DOI: https://doi.org/10.1038/s41386-019-0474-9

[52] S. Fanali, Z. Aturki, V. Kašicka, M. A. Raggi, and G. D’Orazio, “Enantiomeric separation of mirtazapine and its metabolites by nano-liquid chromatography with UV-absorption and mass spectrometric detection,” J. Sep. Sci., vol. 28, no. 14, pp. 1719–1728, 2005, doi: 10.1002/jssc.200500142. DOI: https://doi.org/10.1002/jssc.200500142

[53] J. Wen et al., “Enantioselective separation of mirtazapine and its metabolites by capillary electrophoresis with acetonitrile field-amplified sample stacking and its application,” Molecules, vol. 19, no. 4, pp. 4907–4923, 2014, doi: 10.3390/molecules19044907. DOI: https://doi.org/10.3390/molecules19044907

[54] C. McGrath, G. D. Burrows, and T. R. Norman, “Neurochemical effects of the enantiomers of mirtazapine in normal rats,” Eur. J. Pharmacol., vol. 356, no. 2–3, pp. 121–126, 1998, doi: 10.1016/S0014-2999(98)00509-3. DOI: https://doi.org/10.1016/S0014-2999(98)00509-3

[55] N. S. Zefirov and L. G. Gurvich, “Stereochemical studies,” J. Organomet. Chem., vol. 81, no. 3, pp. 309–320, 1974, doi: 10.1016/S0022-328X(00)88197-8. DOI: https://doi.org/10.1016/S0022-328X(00)88197-8

[56] K. Goyal, N. Tomar, A. P. Singh, R. K. Sarin, and S. K. Shukla, “Validation of an analytical method for the detection of ephedrine and its analogues in forensic samples using HPTLC–MS,” J. Planar Chromatogr.—Mod. TLC, vol. 33, no. 4, pp. 397–404, 2020, doi: 10.1007/s00764-020-00049-6. DOI: https://doi.org/10.1007/s00764-020-00049-6

[57] E. N. Obukhova and A. K. Buryak, “Determination of isomers in doping control by chromatography–mass spectrometry,” J. Anal. Chem., vol. 74, no. 9, pp. 847–860, 2019, doi: 10.1134/S1061934819090077. DOI: https://doi.org/10.1134/S1061934819090077

[58] M. Protti, R. Mandrioli, J. Gonzalez-Rodriguez, and L. Mercolini, “Enantioselective analysis of the methamphetamine precursors ephedrine and pseudoephedrine by capillary electrokinetic chromatography using cyclodextrins as chiral selectors,” J. Chromatogr. Open, vol. 2, 2022, doi: 10.1016/j.jcoa.2022.100032. DOI: https://doi.org/10.1016/j.jcoa.2022.100032

[59] P. Dehydrogenases, “crossm Biodegradation of ephedrine isomers by Arthrobacter sp.,” vol. 86, no. 6, pp. 1–12, 2020.

[60] Q. Wang et al., “Development of sampling, pretreatment and detection methods for ephedrine and related substances in complex samples,” Microchem. J., vol. 189, p. 108538, 2023, doi: 10.1016/j.microc.2023.108538. DOI: https://doi.org/10.1016/j.microc.2023.108538

[61] R. Young, M. Bondarev, and R. A. Glennon, “An examination of isomeric phenylpropanolamines in (−)-ephedrine-trained rats,” Drug Alcohol Depend., vol. 57, no. 1, pp. 1–6, 1999, doi: 10.1016/S0376-8716(99)00052-6. DOI: https://doi.org/10.1016/S0376-8716(99)00052-6

[62] H. Segawa et al., “Stereoselective analysis of ephedrine and its stereoisomers as impurities and/or by-products in seized methamphetamine by supercritical fluid chromatography/tandem mass spectrometry,” Forensic Sci. Int., vol. 318, p. 110591, 2021, doi: 10.1016/j.forsciint.2020.110591. DOI: https://doi.org/10.1016/j.forsciint.2020.110591

[63] S. S. Vansal and D. R. Feller, “Direct effects of ephedrine isomers on human β-adrenergic receptor subtypes,” Biochem. Pharmacol., vol. 58, no. 5, pp. 807–810, 1999, doi: 10.1016/S0006-2952(99)00152-5. DOI: https://doi.org/10.1016/S0006-2952(99)00152-5

[64] J. Rice, K. Proctor, L. Lopardo, S. Evans, and B. Kasprzyk-Hordern, “Stereochemistry of ephedrine and its environmental significance: Exposure and effects directed approach,” J. Hazard. Mater., vol. 348, pp. 39–46, 2018, doi: 10.1016/j.jhazmat.2018.01.020. DOI: https://doi.org/10.1016/j.jhazmat.2018.01.020

[65] K. Lertratanangkoon, “OF,” 1982.

[66] J. Roberts, “Separation of isomeric metabolites of carbamazepine by liquid chromatography and high resolution accurate mass,” 2023.

[67] T. A. Simon, J. H. Simon, E. G. Heaning, A. Gomez-Caminero, and J. P. Marcu, “Delta-8, a cannabis-derived tetrahydrocannabinol isomer: Evaluating case report data in the Food and Drug Administration Adverse Event Reporting System (FAERS) database,” Drug Healthc. Patient Saf., vol. 15, pp. 25–38, 2023, doi: 10.2147/DHPS.S391857. DOI: https://doi.org/10.2147/DHPS.S391857

[68] F. Pisani et al., “Impairment of carbamazepine-10,11-epoxide elimination by valnoctamide, a valpromide isomer, in healthy subjects,” Br. J. Clin. Pharmacol., vol. 34, no. 1, pp. 85–87, 1992, doi: 10.1111/j.1365-2125.1992.tb04114.x. DOI: https://doi.org/10.1111/j.1365-2125.1992.tb04114.x

[69] A. O. Surov, A. G. Ramazanova, A. P. Voronin, K. V. Drozd, A. V. Churakov, and G. L. Perlovich, “Virtual screening, structural analysis, and formation thermodynamics of carbamazepine cocrystals,” Pharmaceutics, vol. 15, no. 3, pp. 1–23, 2023, doi: 10.3390/pharmaceutics15030836. DOI: https://doi.org/10.3390/pharmaceutics15030836

[70] M. Hill et al., “Effects of valproate and carbamazepine monotherapy on neuroactive steroids, their precursors and metabolites in adult men with epilepsy,” J. Steroid Biochem. Mol. Biol., vol. 122, no. 4, pp. 239–252, 2010, doi: 10.1016/j.jsbmb.2010.06.003. DOI: https://doi.org/10.1016/j.jsbmb.2010.06.003

[71] G. Palareti et al., “Comparison between different D-dimer cutoff values to assess the individual risk of recurrent venous thromboembolism: Analysis of results obtained in the DULCIS study,” Int. J. Lab. Hematol., vol. 38, no. 1, pp. 42–49, 2016, doi: 10.1111/ijlh.12426. DOI: https://doi.org/10.1111/ijlh.12426

[72] A. Bahlmann, W. Brack, R. J. Schneider, and M. Krauss, “Carbamazepine and its metabolites in wastewater: Analytical pitfalls and occurrence in Germany and Portugal,” Water Res., vol. 57, pp. 104–114, 2014, doi: 10.1016/j.watres.2014.03.022. DOI: https://doi.org/10.1016/j.watres.2014.03.022

[73] P. M. Nowak, M. Mitoraj, F. Sagan, and R. Wietecha-Posłuszny, “Differentiation of isomeric metabolites of carbamazepine based on acid-base properties: Experimental vs theoretical approach,” J. Chromatogr. A, vol. 1651, 2021, doi: 10.1016/j.chroma.2021.462275. DOI: https://doi.org/10.1016/j.chroma.2021.462275

Downloads

Published

2023-11-11

How to Cite

Review Artikel: Sintesis dan Isomerisasi Senyawa Kimia pada Obat. (2023). Journal of Pharmacy and Halal Studies, 1(1), 23-33. https://doi.org/10.70608/p8yxr427