Thermodynamic Parameters of Fluoxetine Estimated by Group Contribution Method

Zhao Mingrui; Peng Peng

doi:doi:10.11648/j.ijpc.20230904.11

| Peer-Reviewed

Thermodynamic Parameters of Fluoxetine Estimated by Group Contribution Method

Zhao Mingrui, Peng Peng

Published in International Journal of Pharmacy and Chemistry (Volume 9, Issue 4)

Received: 21 July 2023 Accepted: 23 August 2023 Published: 13 September 2023

Views: Downloads:

Download PDF

Share This Article

Twitter
Linked In
Facebook

Abstract

Background: fluoxetine is a commonly used antidepressant in clinic. There are many synthetic methods, but the total yield is not very high. 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 order to provide data support for industrial production of Fluoxetine, the thermodynamic parameters of fluoxetinewere estimated by Joback group contribution method which always used to estimated the thermodynamic parameters of industry product. 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. Since the melting boiling point is generally related to the structure of the substance, it is found that the measured value is basically consistent with the estimated value by group contribution method. Based on the group contribution method, other thermodynamic properties such as molar melting, standard enthalpy of formation and residual entropy are also estimated to provide data support for the calculation in industrial production. Subjects and Methods: The structure of fluoxetine 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 Fluoxetine. Results: the standard formation enthalpy of fluoxetineis202.09 kJ•mol^-1, standard molar isobaric heat capacity of fluoxetineis 54590 J•mol^-1•K^-1, and residual entropy of fluoxetineis 261.5 J•mol^-1•K^-1. The melting temperature of fluoxetinewas also estimated by Joback group contribution method at 825.94 K, which measured by experiment is 158°C, or 456 K, with average relative error ARD = 8.11%. The boiling point temperature of fluoxetine was estimated by Joback method is 733.87 K, which was 569.2°C (867.35K) by measured. The average relative error ARD is 15.38%. Conclusions: The results show that the thermodynamic parameters of fluoxetine can be estimated by Joback group contribution method. Joback method has a high accuracy in estimating the boiling point of Fluoxetine, and it quite fit with the melting point after revised.

Published in	International Journal of Pharmacy and Chemistry (Volume 9, Issue 4)
DOI	10.11648/j.ijpc.20230904.11
Page(s)	38-42
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

Fluoxetine, Antidepressant Drug, Group Contribution, Standard Enthalpy of Formation, Joback Method

References

[1]	You Qidong, medicinal chemistry, Beijing: Chemical Industry Press, 2003. 10.
[2]	Xu Feng, medicinal chemistry, Beijing: Chemical Industry Press, 2016. 03.
[3]	Du Y, Gao XR, Peng L, et al. Crosstalk between the microbiotagut-brain axis and depression. Heliyon, 2020, 6 (6): e04097. DOI: 10.1016/j.heliyon.2020.e04097.
[4]	Gabriel Hancu, Monica Budău, Daniela Lucia Muntean etal. Capillary electrophoresis in the enantioseparation of modern antidepressants: An overview, Biomedical Chromatography. 2018; 32: e4335. https://doi.org/10.1002/bmc.4335
[5]	Tu hong-wei, Liu peng-hong, Zhang ke-rang. Research progress on the effect of selective Serotonin reuptake inhibitor antidepressants on intestinal microflora. Neurology and mental health 2022, 22 (3): 194-197.
[6]	Peiyu Xu, Sijie Huang, Huibing Zhang, etal. Structural insights into the lipid and ligand regulation of serotonin receptors. Nature, 2021, 592: 469-486.
[7]	Wong DT, Bymaster FP, Horng JS, Molloy BB. A new selective inhibitor for uptake of serotonin into synaptosomes of rat brain: 3-(p-trifluoromethylphenoxy). N-methyl-3-phenylpropylamine. Pharmacol Exp Ther 1975; 193 (3): 804-11.
[8]	Duan Yu, Xuan Yining. Organic catalytic asymmetric synthesis of fluoxetine (English). Chinese journal of medicinal chemistry, 2022 (7): 1-5.
[9]	TongLingFei, luo, Lu Jun. Study on the asymmetric synthesis of (S)-(-) -3-chloro-1-phenyl-1-propanol and (S) -fluoxetine hydrochloride. Fine and special chemicals, 2013, 21 (05): 45-48. DOI: 10.19482/j.cn11-3237.2013.05.020.
[10]	sun wenqian, li aijun, liu dongzhi, cao he, zhou xueqin. Synthesis of fluoxetinehydrochloride. Chinese Journal of Synthetic Chemistry, 2008 (03): 354-355 361.
[11]	Chengyu Liu, Lei Zhang, Liming Cao, etal. Iridium-catalyzed enantioselective synthesis of chiral γ-amino alcohols and intermediates of (S)-duloxetine, (R)-flfluoxetine, and(R)-atomoxetine.
[12]	Communication chemistry, 2022, 63 (5): 1-11 https://doi.org/10.1038/s42004-022-00678-4
[13]	Fu Xiancai, Shen Wenxia, Yao Tianyang. Physical Chemistry. Beijing: Higher Education Press. 2000, 6.
[14]	Li Huiping. Synthesis and engineering of 2-methyl-1, 3-Propandiol. Zhengzhou: Zhengzhou University, 2007.
[15]	Zhang Weitao. Group contribution artificial neural network ensemble method for estimating melting point of organic compounds. Taiyuan: North University of China, 2015.
[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]	Barin, I., Thermochemical Data of Pure Substances, 3rd Edition. WILEY-VCH Verlag GmbH, 1995, Translated by Cheng Nai-liang, Niu si-tong, Xu gui-ying. Handbook of Thermochemistry of Pure Substances (Vol. 1 and vol. 2), Beijing: Science Press, 2003.
[18]	Holmes, J. L.; Lossing, F. P.; Mayer, P. M. Heats of formation of oxygen-containing organic free radicals from appearance energy measurements, J. Am. Chem. Soc. 1991, 113, 9723.
[19]	Wang Fuan, Jiang Denggao. Chemical data guide, Beijing: Chemical Industry Press, 1995.
[20]	Li J, Liu R, Wang L, Liu X, Gao H. Enantioseparation of chiral pharmaceuticals by vancomycin-bonded stationary phase and analysis of chiral recognition mechanism. Chirality. 2019; 31: 236–247.
[21]	Paulo S. Carvalho, Jr., Javier Ellena, Dmitry S. Yufifit, etal. Rare Case of Polymorphism in a Racemic fluoxetineNitrate Salt: Phase Behavior and Relative Stability [J]. Crystal Growth Design. 2016, 16, 3875−3883. DOI: 10.1021/acs.cgd.6b00442.

Cite This Article

Plain Text BibTeX RIS

APA Style

Zhao Mingrui, Peng Peng. (2023). Thermodynamic Parameters of Fluoxetine Estimated by Group Contribution Method. International Journal of Pharmacy and Chemistry, 9(4), 38-42. https://doi.org/10.11648/j.ijpc.20230904.11

Copy | Download

ACS Style

Zhao Mingrui; Peng Peng. Thermodynamic Parameters of Fluoxetine Estimated by Group Contribution Method. Int. J. Pharm. Chem. 2023, 9(4), 38-42. doi: 10.11648/j.ijpc.20230904.11

Copy | Download

AMA Style

Zhao Mingrui, Peng Peng. Thermodynamic Parameters of Fluoxetine Estimated by Group Contribution Method. Int J Pharm Chem. 2023;9(4):38-42. doi: 10.11648/j.ijpc.20230904.11

Copy | Download

@article{10.11648/j.ijpc.20230904.11,
  author = {Zhao Mingrui and Peng Peng},
  title = {Thermodynamic Parameters of Fluoxetine Estimated by Group Contribution Method},
  journal = {International Journal of Pharmacy and Chemistry},
  volume = {9},
  number = {4},
  pages = {38-42},
  doi = {10.11648/j.ijpc.20230904.11},
  url = {https://doi.org/10.11648/j.ijpc.20230904.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ijpc.20230904.11},
  abstract = {Background: fluoxetine is a commonly used antidepressant in clinic. There are many synthetic methods, but the total yield is not very high. 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 order to provide data support for industrial production of Fluoxetine, the thermodynamic parameters of fluoxetinewere estimated by Joback group contribution method which always used to estimated the thermodynamic parameters of industry product. 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. Since the melting boiling point is generally related to the structure of the substance, it is found that the measured value is basically consistent with the estimated value by group contribution method. Based on the group contribution method, other thermodynamic properties such as molar melting, standard enthalpy of formation and residual entropy are also estimated to provide data support for the calculation in industrial production. Subjects and Methods: The structure of fluoxetine 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 Fluoxetine. Results: the standard formation enthalpy of fluoxetineis202.09 kJ•mol-1, standard molar isobaric heat capacity of fluoxetineis 54590 J•mol-1•K-1, and residual entropy of fluoxetineis 261.5 J•mol-1•K-1. The melting temperature of fluoxetinewas also estimated by Joback group contribution method at 825.94 K, which measured by experiment is 158°C, or 456 K, with average relative error ARD = 8.11%. The boiling point temperature of fluoxetine was estimated by Joback method is 733.87 K, which was 569.2°C (867.35K) by measured. The average relative error ARD is 15.38%. Conclusions: The results show that the thermodynamic parameters of fluoxetine can be estimated by Joback group contribution method. Joback method has a high accuracy in estimating the boiling point of Fluoxetine, and it quite fit with the melting point after revised.},
 year = {2023}
}

Copy | Download

TY  - JOUR
T1  - Thermodynamic Parameters of Fluoxetine Estimated by Group Contribution Method
AU  - Zhao Mingrui
AU  - Peng Peng
Y1  - 2023/09/13
PY  - 2023
N1  - https://doi.org/10.11648/j.ijpc.20230904.11
DO  - 10.11648/j.ijpc.20230904.11
T2  - International Journal of Pharmacy and Chemistry
JF  - International Journal of Pharmacy and Chemistry
JO  - International Journal of Pharmacy and Chemistry
SP  - 38
EP  - 42
PB  - Science Publishing Group
SN  - 2575-5749
UR  - https://doi.org/10.11648/j.ijpc.20230904.11
AB  - Background: fluoxetine is a commonly used antidepressant in clinic. There are many synthetic methods, but the total yield is not very high. 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 order to provide data support for industrial production of Fluoxetine, the thermodynamic parameters of fluoxetinewere estimated by Joback group contribution method which always used to estimated the thermodynamic parameters of industry product. 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. Since the melting boiling point is generally related to the structure of the substance, it is found that the measured value is basically consistent with the estimated value by group contribution method. Based on the group contribution method, other thermodynamic properties such as molar melting, standard enthalpy of formation and residual entropy are also estimated to provide data support for the calculation in industrial production. Subjects and Methods: The structure of fluoxetine 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 Fluoxetine. Results: the standard formation enthalpy of fluoxetineis202.09 kJ•mol-1, standard molar isobaric heat capacity of fluoxetineis 54590 J•mol-1•K-1, and residual entropy of fluoxetineis 261.5 J•mol-1•K-1. The melting temperature of fluoxetinewas also estimated by Joback group contribution method at 825.94 K, which measured by experiment is 158°C, or 456 K, with average relative error ARD = 8.11%. The boiling point temperature of fluoxetine was estimated by Joback method is 733.87 K, which was 569.2°C (867.35K) by measured. The average relative error ARD is 15.38%. Conclusions: The results show that the thermodynamic parameters of fluoxetine can be estimated by Joback group contribution method. Joback method has a high accuracy in estimating the boiling point of Fluoxetine, and it quite fit with the melting point after revised.
VL  - 9
IS  - 4
ER  -

Copy | Download

Author Information

Zhao Mingrui

College of Pharmacy, Henan Medical College, Zhengzhou, China
Peng Peng

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

Download PDF

Sections

Plain Text BibTeX RIS

APA Style

Zhao Mingrui, Peng Peng. (2023). Thermodynamic Parameters of Fluoxetine Estimated by Group Contribution Method. International Journal of Pharmacy and Chemistry, 9(4), 38-42. https://doi.org/10.11648/j.ijpc.20230904.11

Copy | Download

ACS Style

Zhao Mingrui; Peng Peng. Thermodynamic Parameters of Fluoxetine Estimated by Group Contribution Method. Int. J. Pharm. Chem. 2023, 9(4), 38-42. doi: 10.11648/j.ijpc.20230904.11

Copy | Download

AMA Style

Zhao Mingrui, Peng Peng. Thermodynamic Parameters of Fluoxetine Estimated by Group Contribution Method. Int J Pharm Chem. 2023;9(4):38-42. doi: 10.11648/j.ijpc.20230904.11

Copy | Download

@article{10.11648/j.ijpc.20230904.11,
  author = {Zhao Mingrui and Peng Peng},
  title = {Thermodynamic Parameters of Fluoxetine Estimated by Group Contribution Method},
  journal = {International Journal of Pharmacy and Chemistry},
  volume = {9},
  number = {4},
  pages = {38-42},
  doi = {10.11648/j.ijpc.20230904.11},
  url = {https://doi.org/10.11648/j.ijpc.20230904.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ijpc.20230904.11},
  abstract = {Background: fluoxetine is a commonly used antidepressant in clinic. There are many synthetic methods, but the total yield is not very high. 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 order to provide data support for industrial production of Fluoxetine, the thermodynamic parameters of fluoxetinewere estimated by Joback group contribution method which always used to estimated the thermodynamic parameters of industry product. 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. Since the melting boiling point is generally related to the structure of the substance, it is found that the measured value is basically consistent with the estimated value by group contribution method. Based on the group contribution method, other thermodynamic properties such as molar melting, standard enthalpy of formation and residual entropy are also estimated to provide data support for the calculation in industrial production. Subjects and Methods: The structure of fluoxetine 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 Fluoxetine. Results: the standard formation enthalpy of fluoxetineis202.09 kJ•mol-1, standard molar isobaric heat capacity of fluoxetineis 54590 J•mol-1•K-1, and residual entropy of fluoxetineis 261.5 J•mol-1•K-1. The melting temperature of fluoxetinewas also estimated by Joback group contribution method at 825.94 K, which measured by experiment is 158°C, or 456 K, with average relative error ARD = 8.11%. The boiling point temperature of fluoxetine was estimated by Joback method is 733.87 K, which was 569.2°C (867.35K) by measured. The average relative error ARD is 15.38%. Conclusions: The results show that the thermodynamic parameters of fluoxetine can be estimated by Joback group contribution method. Joback method has a high accuracy in estimating the boiling point of Fluoxetine, and it quite fit with the melting point after revised.},
 year = {2023}
}

Copy | Download

TY  - JOUR
T1  - Thermodynamic Parameters of Fluoxetine Estimated by Group Contribution Method
AU  - Zhao Mingrui
AU  - Peng Peng
Y1  - 2023/09/13
PY  - 2023
N1  - https://doi.org/10.11648/j.ijpc.20230904.11
DO  - 10.11648/j.ijpc.20230904.11
T2  - International Journal of Pharmacy and Chemistry
JF  - International Journal of Pharmacy and Chemistry
JO  - International Journal of Pharmacy and Chemistry
SP  - 38
EP  - 42
PB  - Science Publishing Group
SN  - 2575-5749
UR  - https://doi.org/10.11648/j.ijpc.20230904.11
AB  - Background: fluoxetine is a commonly used antidepressant in clinic. There are many synthetic methods, but the total yield is not very high. 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 order to provide data support for industrial production of Fluoxetine, the thermodynamic parameters of fluoxetinewere estimated by Joback group contribution method which always used to estimated the thermodynamic parameters of industry product. 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. Since the melting boiling point is generally related to the structure of the substance, it is found that the measured value is basically consistent with the estimated value by group contribution method. Based on the group contribution method, other thermodynamic properties such as molar melting, standard enthalpy of formation and residual entropy are also estimated to provide data support for the calculation in industrial production. Subjects and Methods: The structure of fluoxetine 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 Fluoxetine. Results: the standard formation enthalpy of fluoxetineis202.09 kJ•mol-1, standard molar isobaric heat capacity of fluoxetineis 54590 J•mol-1•K-1, and residual entropy of fluoxetineis 261.5 J•mol-1•K-1. The melting temperature of fluoxetinewas also estimated by Joback group contribution method at 825.94 K, which measured by experiment is 158°C, or 456 K, with average relative error ARD = 8.11%. The boiling point temperature of fluoxetine was estimated by Joback method is 733.87 K, which was 569.2°C (867.35K) by measured. The average relative error ARD is 15.38%. Conclusions: The results show that the thermodynamic parameters of fluoxetine can be estimated by Joback group contribution method. Joback method has a high accuracy in estimating the boiling point of Fluoxetine, and it quite fit with the melting point after revised.
VL  - 9
IS  - 4
ER  -

Copy | Download