<abstract xmlns="http://www.w3.org/1999/xhtml">

<p>Stereochemistry plays an important role in drug design because the enantiomers of a drug frequently vary in their biological action and pharmacokinetic profiles. Racemates of a drug with either an inactive or an unsafe enantiomer can lead to detrimental effects. The manufacturing industry may still produce racemates, but such decisions must pass through rigorous analyses of the pharmacological and pharmacokinetic characteristics of the particular enantiomer related to the racemates. The pharmacokinetics of antidepressants or antidepressive agents is stereoselective and predominantly favors one enantiomer. The use of pure enantiomers offers (i) better specificity than the racemates in terms of certain pharmacological actions, (ii) enhanced clinical indications, and (iii) optimized pharmacokinetics. Therefore, controlling the stereoselectivity in the pharmacokinetics of antidepressive drugs is of critical importance in dealing with depression and psychiatric conditions. The objective of this review is to highlight the importance of the stereochemistry of antidepressants in the context of the design and development of new chirally pure pharmaceuticals, the potential complications caused by using racemates, and the benefits of using pure enantiomers.</p>
</abstract>

Stereochemistry plays an important role in drug design because the enantiomers of a drug frequently vary in their biological action and pharmacokinetic profiles. Racemates of a drug with either an inactive or an unsafe enantiomer can lead to detrimental effects. The manufacturing industry may still produce racemates, but such decisions must pass through rigorous analyses of the pharmacological and pharmacokinetic characteristics of the particular enantiomer related to the racemates. The pharmacokinetics of antidepressants or antidepressive agents is stereoselective and predominantly favors one enantiomer. The use of pure enantiomers offers (i) better specificity than the racemates in terms of certain pharmacological actions, (ii) enhanced clinical indications, and (iii) optimized pharmacokinetics. Therefore, controlling the stereoselectivity in the pharmacokinetics of antidepressive drugs is of critical importance in dealing with depression and psychiatric conditions. The objective of this review is to highlight the importance of the stereochemistry of antidepressants in the context of the design and development of new chirally pure pharmaceuticals, the potential complications caused by using racemates, and the benefits of using pure enantiomers.

Chirality of antidepressive drugs: an overview of stereoselectivity

Asian Biomedicine

This work is licensed under the Creative Commons Attribution 4.0 International License.

{"article-title":"Chirality of antidepressive drugs: an overview of stereoselectivity"}

Stereochemistry plays an important role in drug design because the enantiomers of a drug frequently vary in their biological action and pharmacokinetic...

Class	Generic name	Brand name	Available as	More active form
SSRI	citalopram	Celexa, Cipramil, Zetalo, Lexapro	Racemate and (S)-citalopram	(S)-citalopram
	fluoxetine	Prozac, Sarafem, Rapiflux	Racemate and (S)-fluoxetine	(S)-fluoxetine
	sertraline	Zoloft, Actiser, Bioserene, Episod, Mentolift	Racemate and (+)-cis-(1S,4S)-sertraline	(+)-cis-(1S,4S)-sertraline
SNRI	paroxetine	Paxil, Brisdelle, Paxil CR, Pexeva	(−)-trans-(3S,4R)-paroxetine	(−)-trans-(3S,4R)-paroxetine
	venlafaxine	Effexor, Effexor XR	Racemate	(R)-venlafaxine
	duloxetine	Cymbalta, Drizalma Sprinkle, Irenka	(S)-duloxetine	(S)-duloxetine
	milnacipran	Ixel, Savella, Dalcipran, Toledomin	Mixture of d-milnacipran (1S,2R) and l-milnacipran (1R,2S)	d-milnacipran (1S,2R)
NRI	reboxetine	Edronax, Pfizer	Mixture of (S,R)-reboxetine, (R,R)-, (R,S)-reboxetine (S,S)-reboxetine	(S,S)-reboxetine
NDRI	bupropion	Wellbutrin, Zyban	Racemate	(R)-bupropion
MAOI	selegiline	Eldepryl, Zelapar	Racemate	(+)-selegiline
TeCA	mianserin	Bonserin, Tolvon, Athimil, Depnon, Deprexolet, Lantanon, Lerivon, Demisone, and others	Racemate	(S)-mianserin
NASSA	mirtazapine	Remeron, Mirataz, and others	Racemate	(S)-mirtazapine

Chirality of antidepressive drugs: an overview of stereoselectivity

Article Category: Review

Data publikacji: 29 kwi 2022

Zakres stron: 55 - 69

DOI: https://doi.org/10.2478/abm-2022-0008

Słowa kluczowe
antidepressive agents, chiral, depression, pharmacokinetics, stereoselective

© 2022 Vinod Kumar Vashistha et al., published by Sciendo

This work is licensed under the Creative Commons Attribution 4.0 International License.

Figure 1

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Classification of chiral antidepressant drugs

Chirality of antidepressive drugs: an overview of stereoselectivity

Article Category: Review

Data publikacji: 29 kwi 2022

Zakres stron: 55 - 69

DOI: https://doi.org/10.2478/abm-2022-0008

Słowa kluczoweantidepressive agents, chiral, depression, pharmacokinetics, stereoselective

© 2022 Vinod Kumar Vashistha et al., published by Sciendo

This work is licensed under the Creative Commons Attribution 4.0 International License.

Figure 1

Figure 2

Figure 3

Figure 4

Figure 5

Figure 6

Figure 7

Figure 8

Figure 9

Figure 10

Figure 11

Figure 12

Classification of chiral antidepressant drugs

Słowa kluczowe
antidepressive agents, chiral, depression, pharmacokinetics, stereoselective