NMR Spectral Analyses of Meropenem and Protected Meropenem

Abstract

Abstract:

Meropenem is a second-generation carbapenems antibiotics with an exceptionally broad spectrum of activity, which is currently used in the treatment of a variety of infections. In this paper, the ¹H and ¹³C NMR chemical shifts of the compound in CDCl₃ and CD₃OD (solvents) were assigned. The assignment errors for C-6 and C-7 in the literature were corrected. The C-N bond rotational barrier of protected Meropenem was investigated.

Key words: nuclear magnetic resonance (NMR), rotational barrier, Meropenem, protected Meropenem

CLC Number:

O482. 53

SU Feng，LIANG Xian-rui*. NMR Spectral Analyses of Meropenem and Protected Meropenem[J]. Chinese Journal of Magnetic Resonance.

References

[1] Zhang Li-juan(张丽娟), Shi Jin-ying(史金英), Liang Gui-qin(梁桂琴), et al. Clinical observation of thymosin and meropenem in treatment of severe lower respiratory tract infection of gram-negative bacilli(胸肽腺联合美罗培南治疗革兰阴性杆菌重症下呼吸道感染临床疗效观察)[J]. Clinical Focus(临床荟萃), 2011, 26(8): 678-680.

[2] Zhao Yun-feng(赵云峰), Zhang Wei-guo(张卫国). Ealuation of meropenem in 36 patients with severe pneumonia(美罗培南治疗重症肺炎36例)[J]. Chinese J Infect Chemother(中国感染与化疗杂志), 2010, 10(4): 273-276.

[3] Liu Zhao-e(刘兆娥), Yang Bo(杨波). Clinical evaluation of meropenem in preterm neonates for Severe Infections(美罗培南治疗早产儿重症细菌感染的临床疗效及安全性评价)[J]. J Pedi Pharm(儿科药学杂志), 2011, 17(5): 22-24.

[4] Cui Hong-quan(崔洪泉), Zhao Yun-li(赵运立), Wang Ji-mei(王继美), et al. Clinical study on meropenem in the treatment of bacterial infection(美罗培南治疗细菌性感染的临床研究)[J]. Chinese J Exp Clin Infect Dis(中华实验和临床感染病杂志), 2012, 6(4): 337-340.

[5] Mendez A, Chagastelles P, Palma E, et al. Thermal and alkaline stability of meropenem: Degradation products and cytotoxicity[J]. Int J Pharm, 2008, 35: 95-102.

[6] Michael J, John D, Mark A, et al. Meropenem exists in equilibrium with a carbon dioxide adduct in bicarbonate solution[J]. J Pharm Sci, 1998, 35: 663-664.

[7] Tamiki N, Akira S, Makoto S, et al. Conformational analysis of meropenem and desmethyl meropenem; the effect of 1β-methyl group on carbapenem antibiotics[J]. Bioorg Med Chem Lett, 1996, 6: 1 881-1 886.

[8] Jedrzejczyk D, Ziora Z, Kafarski P. ¹H NMR studies of rotational isomerism in phosphonic analogues of aspartic acid[J]. Magn Reson Chem, 2000, 38: 370-374.

[9] Basso E A, Oliveira P R, Wiectzycoski F, et al. NMR and theoretical study of the (C=O)-N rotational barrier in the isomers cis- and trans- 2-N, N-dimethylaminecyclohexyl 1-N′, N′-dimethylcarbamate[J]. J Mol Struct, 2005,753: 139-146.

[10] Zhu Chuan-jun(朱传钧), Jin Xiao-feng(金晓锋), Jiang Biao(姜标), et al. NMR characteristics and conformational analysis of oxiracetam(奥拉西坦的核磁共振波谱特征与构象研究)[J]. Chinese J Magn Reson(波谱学杂志), 2010, 27(4): 609-616.

[11] Zhu Chuan-jun(朱传钧), Zhu Mei-ling(朱美玲), Cui Yu-xin(崔育新), et al. NMR characteristics and conformational analysis of (E)-3-(4-hydroxyphenyl)-1-(piperidin-1-yl) prop-2-en-1-one derivatives((E)-3-(4-羟基苯)-1-(哌啶-1-基) 丙-2-烯-1-酮衍生物核磁共振特征与构象分析)[J]. Chinese J Magn Reson(波谱学杂志), 2011, 28(3): 390-398.

[12] Qiao Rui-rui (乔瑞瑞), Sun Jing(孙静), Yang Chun-hui(杨春晖), et al. Isomerization of the amide bond in piperidin amides studied by variable-temperature NMR spectroscopy(吡啶酰胺类化合物中酰胺键异构化的变温核磁共振研究)[J]. Chinese J Magn Reson(波谱学杂志), 2008, 25(3): 307-314.

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