Journal of Drug Design and Medicinal Chemistry

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Estimated Thermodynamic Parameters of Amlodipine by Group Contribution Method

Received: Jun. 27, 2023    Accepted: Jul. 13, 2023    Published: Aug. 31, 2023
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Abstract

Objective: Amlodipine is the third-generation Calcium channel antagonist of dihydropyridine. which belongs to the first-line antihypertensive drug in clinic and used as racemate and levoisomer. The antihypertensive effection of levo-Amlodipine is twice as much as that of racemate. Physical property data of compounds are often used in scientific research, pharmaceutical process design, chemical and pharmaceutical production, synthesis and resolution of chiral drugs, etc., distinct and accurate estimation of physical property data will greatly save time and effort. In particular, thermodynamic parameters such as enthalpy, entropy and heat capacity are state functions, so in practical applications, a state of matter can be arbitrarily chosen as a reference state, and then calculated. In order to provide data support for the separation and industrial production of Amlodipine, the thermodynamic parameters of Amlodipine were estimated by Joback group contribution method which always used to estimated the thermodynamic parameters of industry product. The physical properties of Amlodipine, such as the melting boiling point, are generally related to the structure of matter. In this paper, by comparing the measurement of melting boiling point with the estimated value of group contribution method, it is shown that the group contribution method is reasonable to split the group, and the values of other thermodynamic properties estimated by the group contribution method have a certain degree of credibility, it can be used to calculate physical properties in industrial production. Method: The structure of Amlodipine was divided by Joback group contribution method, and the group contribution value was calculated to get the standard enthalpy of formation, Standard molar isobaric heat capacity, and residual entropy of Amlodipine. Result: the standard formation enthalpy of Amlodipine is -143.4KJ•mol-1, standard molar isobaric heat capacity of Amlodipine is108500J•K-1•mol-1, and residual entropy of Amlodipine is349.86J•K-1•mol-1. The melting temperature of Amlodipine was also estimated by Joback group contribution method at 1188.74 K, which was 230°C (503.15 K) measured by experiment and average relative error nearly4.05%. The boiling point temperature of Amlodipine was estimated by Joback method is 1005.97 K, which was 527.2°C (800.35 K) by measured. The average relative error ARD is 2.57%. Conclusion: The results show that the thermodynamic parameters of Amlodipine can be estimated by Joback group contribution method. Joback method has a high accuracy in estimating the boiling point of Amlodipine, and it quite fit with the melting point after revised.

DOI 10.11648/j.jddmc.20230902.12
Published in Journal of Drug Design and Medicinal Chemistry ( Volume 9, Issue 2, June 2023 )
Page(s) 23-28
Creative Commons

This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2024. Published by Science Publishing Group

Keywords

Antihypertensive Drug, Amlodipine, Group Contribution Method, Standard Enthalpy of Formation Method, Group Contribution Method, Joback Method

References
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[2] Lai Shenzhi, preparation of surface imprinted materials and chiral separation of Amlodipine drugs, University of Xiangtan, China, 2017.
[3] Zhang Hui, past and present life of Nimodipine, university chemistry, 2018, 33 (7): 43 -55.
[4] Dorottya Fruzsina Banhegyi, Dora Szolcs anyi, Janos Madar asz, etal. Enantiomeric separation of racemic Amlodipine by sequential fractional crystallization through formation of diastereomeric salt solvates and co-crystals of solvate-like compounds with specific structure — A tandem resolution.. Chirality. 2022; 34: 374–395.
[5] Guo Dong, Preliminary study on the integrated chiral spectrometric method of chiral compounds, Xiamen University, 2016: 1-2.
[6] Junli Pu, Hongwei Wang, Chao Huang, etal. Progress of molecular imprinting technique for enantioseparation of chiral drugs in recent ten years. Journal of Chromatography A 1668 (2022) 462914.
[7] Liu Min, Studies on the enantiomeric separation of Amlodipine by immobilized ionic liquids, Zhejiang University, 2020.
[8] Fu Xiancai, Shen Wenxia, Yao Tianyang. Physical Chemistry. Beijing: Higher Education Press. 2000, 6.
[9] Gao Guanghua, chemical thermodynamics, Beijing: Tsinghua University Press. 2022, 2.
[10] Zhu Ziqiang, edited by Wu youting, chemical thermodynamics, Beijing: Chemical Industry Press, 2021, 3.
[11] Wang Fu 'an, Jiang Denggao. Chemical Industry Data Guidance, Beijing: Chemical Industry Press, 1995.
[12] Xie Wei, Wang Jing, Huang Zengwei, Wei Dongping, Yuan Aiqun, Ma Shao-mei. Thermodynamic analysis of aspirin synthesis catalyzed by aluminum tripolyphosphates. Chinese journal of biochemical drugs, 2015, 35 (03): 169-171 175. (in Chinese).
[13] Yang Lixin, Wang Dahui, Chen Huaijing, Zhang Xiaodong, Yu Yue Shan, Xu Li. ΔH (f, 298) ~ θ and ΔG (f, 298) ~ θ of Lini cathode materials for li-ion power battery were estimated by group contribution method. Rare metals materials and engineering, 2020, 49 (01): 161-168.
[14] Wu Hongmei, Li Huiting, Li Yongcheng, Wang Hongqing, Wang Meng. Prediction of glass transition temperature of poly (m-phthaloyl-p-phenylenediamine) based on group contribution method and Molecular dynamics method. Journal of college chemistry, 2019, 40 (01): 180-186.
[15] Che Chunwen, Yin Yonggao. A group-contribution model for gas-liquid equilibria of non-azeotropic refrigerants. Journal of Engineering Thermophysics, 2021, 42 (12): 3113-3118.
[16] Ming-rui Zhao, Hongjie Wang, Shuyu Wang, et al. Thermodynamic properties of diosgenin determined by oxygen-bomb calorimetry and DSC, Russian Journal of Physical Chemistry A, 2014, 12 (88): 1081-1084.
[17] Dong Yajuan, Hui Zhiqian, Rong Zongming. The HLB value of Poly (ethylene glycol) monomethyl ether-poly (lactic acid) amphiphilic block copolymer was estimated by group contribution method. Journal of East China University of Science and Technology Science, 2017, 43 (05): 640-646.
[18] Li Xiaobing, Cui Xibao, Feng Tianyang, Jiehui Min, Xu Li, Lin Ruirong. Group contribution method for predicting the refractive index of ionic liquids. Chemical Industry and engineering, 2017, 34 (03): 37-42. DOI: 10.13353/J. ISSN. 1004.9533.20151115.
[19] Dong Shengming, Wang Huoda, Wang Bo, Hu Xiaowei, Sun Zhili, Tian Shen. Study on the reliability of group contribution method for predicting thermodynamic properties of R1234YF and R290. Refrigeration technology, 2022, 45 (02): 37-42.
[20] Shi Wentao, Zang Tingting, Wang Zhichao, Liu Chang. Chemical thermodynamics: from group contribution to computer-aided molecular design. Times of chemical engineering, 2017, 31 (06): 3-6 + 40. DOI: 10.16597/J. CNKI. ISSN. 1002-154x. 2017.06.002.
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  • APA Style

    Zhao Mingrui, Peng Peng. (2023). Estimated Thermodynamic Parameters of Amlodipine by Group Contribution Method. Journal of Drug Design and Medicinal Chemistry, 9(2), 23-28. https://doi.org/10.11648/j.jddmc.20230902.12

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    ACS Style

    Zhao Mingrui; Peng Peng. Estimated Thermodynamic Parameters of Amlodipine by Group Contribution Method. J. Drug Des. Med. Chem. 2023, 9(2), 23-28. doi: 10.11648/j.jddmc.20230902.12

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    AMA Style

    Zhao Mingrui, Peng Peng. Estimated Thermodynamic Parameters of Amlodipine by Group Contribution Method. J Drug Des Med Chem. 2023;9(2):23-28. doi: 10.11648/j.jddmc.20230902.12

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  • @article{10.11648/j.jddmc.20230902.12,
      author = {Zhao Mingrui and Peng Peng},
      title = {Estimated Thermodynamic Parameters of Amlodipine by Group Contribution Method},
      journal = {Journal of Drug Design and Medicinal Chemistry},
      volume = {9},
      number = {2},
      pages = {23-28},
      doi = {10.11648/j.jddmc.20230902.12},
      url = {https://doi.org/10.11648/j.jddmc.20230902.12},
      eprint = {https://download.sciencepg.com/pdf/10.11648.j.jddmc.20230902.12},
      abstract = {Objective: Amlodipine is the third-generation Calcium channel antagonist of dihydropyridine. which belongs to the first-line antihypertensive drug in clinic and used as racemate and levoisomer. The antihypertensive effection of levo-Amlodipine is twice as much as that of racemate. Physical property data of compounds are often used in scientific research, pharmaceutical process design, chemical and pharmaceutical production, synthesis and resolution of chiral drugs, etc., distinct and accurate estimation of physical property data will greatly save time and effort. In particular, thermodynamic parameters such as enthalpy, entropy and heat capacity are state functions, so in practical applications, a state of matter can be arbitrarily chosen as a reference state, and then calculated. In order to provide data support for the separation and industrial production of Amlodipine, the thermodynamic parameters of Amlodipine were estimated by Joback group contribution method which always used to estimated the thermodynamic parameters of industry product. The physical properties of Amlodipine, such as the melting boiling point, are generally related to the structure of matter. In this paper, by comparing the measurement of melting boiling point with the estimated value of group contribution method, it is shown that the group contribution method is reasonable to split the group, and the values of other thermodynamic properties estimated by the group contribution method have a certain degree of credibility, it can be used to calculate physical properties in industrial production. Method: The structure of Amlodipine was divided by Joback group contribution method, and the group contribution value was calculated to get the standard enthalpy of formation, Standard molar isobaric heat capacity, and residual entropy of Amlodipine. Result: the standard formation enthalpy of Amlodipine is -143.4KJ•mol-1, standard molar isobaric heat capacity of Amlodipine is108500J•K-1•mol-1, and residual entropy of Amlodipine is349.86J•K-1•mol-1. The melting temperature of Amlodipine was also estimated by Joback group contribution method at 1188.74 K, which was 230°C (503.15 K) measured by experiment and average relative error nearly4.05%. The boiling point temperature of Amlodipine was estimated by Joback method is 1005.97 K, which was 527.2°C (800.35 K) by measured. The average relative error ARD is 2.57%. Conclusion: The results show that the thermodynamic parameters of Amlodipine can be estimated by Joback group contribution method. Joback method has a high accuracy in estimating the boiling point of Amlodipine, and it quite fit with the melting point after revised.},
     year = {2023}
    }
    

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  • TY  - JOUR
    T1  - Estimated Thermodynamic Parameters of Amlodipine by Group Contribution Method
    AU  - Zhao Mingrui
    AU  - Peng Peng
    Y1  - 2023/08/31
    PY  - 2023
    N1  - https://doi.org/10.11648/j.jddmc.20230902.12
    DO  - 10.11648/j.jddmc.20230902.12
    T2  - Journal of Drug Design and Medicinal Chemistry
    JF  - Journal of Drug Design and Medicinal Chemistry
    JO  - Journal of Drug Design and Medicinal Chemistry
    SP  - 23
    EP  - 28
    PB  - Science Publishing Group
    SN  - 2472-3576
    UR  - https://doi.org/10.11648/j.jddmc.20230902.12
    AB  - Objective: Amlodipine is the third-generation Calcium channel antagonist of dihydropyridine. which belongs to the first-line antihypertensive drug in clinic and used as racemate and levoisomer. The antihypertensive effection of levo-Amlodipine is twice as much as that of racemate. Physical property data of compounds are often used in scientific research, pharmaceutical process design, chemical and pharmaceutical production, synthesis and resolution of chiral drugs, etc., distinct and accurate estimation of physical property data will greatly save time and effort. In particular, thermodynamic parameters such as enthalpy, entropy and heat capacity are state functions, so in practical applications, a state of matter can be arbitrarily chosen as a reference state, and then calculated. In order to provide data support for the separation and industrial production of Amlodipine, the thermodynamic parameters of Amlodipine were estimated by Joback group contribution method which always used to estimated the thermodynamic parameters of industry product. The physical properties of Amlodipine, such as the melting boiling point, are generally related to the structure of matter. In this paper, by comparing the measurement of melting boiling point with the estimated value of group contribution method, it is shown that the group contribution method is reasonable to split the group, and the values of other thermodynamic properties estimated by the group contribution method have a certain degree of credibility, it can be used to calculate physical properties in industrial production. Method: The structure of Amlodipine was divided by Joback group contribution method, and the group contribution value was calculated to get the standard enthalpy of formation, Standard molar isobaric heat capacity, and residual entropy of Amlodipine. Result: the standard formation enthalpy of Amlodipine is -143.4KJ•mol-1, standard molar isobaric heat capacity of Amlodipine is108500J•K-1•mol-1, and residual entropy of Amlodipine is349.86J•K-1•mol-1. The melting temperature of Amlodipine was also estimated by Joback group contribution method at 1188.74 K, which was 230°C (503.15 K) measured by experiment and average relative error nearly4.05%. The boiling point temperature of Amlodipine was estimated by Joback method is 1005.97 K, which was 527.2°C (800.35 K) by measured. The average relative error ARD is 2.57%. Conclusion: The results show that the thermodynamic parameters of Amlodipine can be estimated by Joback group contribution method. Joback method has a high accuracy in estimating the boiling point of Amlodipine, and it quite fit with the melting point after revised.
    VL  - 9
    IS  - 2
    ER  - 

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Author Information
  • College of Pharmacy, Henan Medical College, Zhengzhou, China

  • School of Art and Design, Zhengzhou University of Light Industry, Zhengzhou, China

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