Chemistry:Elzasonan

Elzasonan
Clinical data
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	In general: uncontrolled;
Identifiers
	IUPAC name 4-(3,4-dichlorophenyl)-2-[2-(4-methylpiperazin-1-yl)-benzylidene]-thiomorpholin-3-one;
CAS Number	361343-19-3 ; HCl: 220322-05-4 ;
PubChem CID	19544192; HCl: 6914152;
ChemSpider	5290108;
UNII	933PJL964R; HCl: X38F62RR8L ;
Chemical and physical data
Formula	C22H23Cl2N3OS
Molar mass	448.41 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc4c(Cl)cc(N1C(=O)C(\SCC1)=C\c3ccccc3N2CCN(C)CC2)cc4;
	InChI InChI=1S/C22H23Cl2N3OS/c1-25-8-10-26(11-9-25)20-5-3-2-4-16(20)14-21-22(28)27(12-13-29-21)17-6-7-18(23)19(24)15-17/h2-7,14-15H,8-13H2,1H3/b21-14-; Key:LHYMPSWMHXUWSK-STZFKDTASA-N;
	(verify)

Short description: Chemical compound

Elzasonan (CP-448,187) is a selective 5-HT_1B and 5-HT_1D receptor antagonist that was under development by Pfizer for the treatment of depression but was discontinued, possibly due to poor efficacy.^[1]^[2]^[3]^[4]^[5] By preferentially blocking 5-HT_1B and 5-HT_1D autoreceptors, elzasonan is thought to enhance serotonergic innervations originating from the raphe nucleus, thereby improving signaling to limbic regions like the hippocampus and prefrontal cortex and ultimately resulting in antidepressant effects.^[3]

References

↑ Antidepressants, Antipsychotics, Anxiolytics: From Chemistry and Pharmacology to Clinical Application. Weinheim: Wiley-VCH. 2007. ISBN 978-3-527-31058-6. https://books.google.com/books?id=yXD4QA-Y_Z0C&pg=PA255.
↑ Stahl's essential psychopharmacology: neuroscientific basis and practical applications. Cambridge, UK: Cambridge University Press. 2008. ISBN 978-0-521-85702-4. https://books.google.com/books?id=cWbYxSfKN3cC&q=Elzasonan&pg=PA659.
↑ ^3.0 ^3.1 "5-HT1 receptor augmentation strategies as enhanced efficacy: therapeutics for psychiatric disorders". Current Topics in Medicinal Chemistry 8 (12): 1008–1023. August 2008. doi:10.2174/156802608785161439. PMID 18691129.
↑ "Pfizer, Inc.: analysis of patenting 1998 – 2001". Expert Opinion on Therapeutic Patents 12 (5): 725–732. 2002. doi:10.1517/13543776.12.5.725.
↑ "Discontinued psychiatric drugs in 2008". Expert Opinion on Investigational Drugs 18 (10): 1431–1443. October 2009. doi:10.1517/13543780903184591. PMID 19715445.

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v t e Anxiolytics (N05B)
5-HT_1AR agonists	Buspirone Gepirone^† Tandospirone
GABA_AR PAMs	Benzodiazepines: Adinazolam Alprazolam Bromazepam Camazepam Chlordiazepoxide Clobazam Clonazepam Clorazepate Clotiazepam Cloxazolam Diazepam^# Ethyl loflazepate Etizolam Fludiazepam Halazepam Ketazolam Lorazepam^# Medazepam Nordazepam Oxazepam Pinazepam Prazepam; Others: Alpidem^‡ Barbiturates (e.g., phenobarbital) Carbamates (e.g., meprobamate) Chlormezanone^‡ Ethanol (alcohol) Etifoxine Imepitoin; Herbs: Kava Skullcap Valerian
Gabapentinoids (α₂δ VDCC blockers)	Gabapentin Gabapentin enacarbil Phenibut Pregabalin
Antidepressants	SSRIs (e.g., escitalopram) SNRIs (e.g., duloxetine) SARIs (e.g., trazodone) TCAs (e.g., clomipramine^#) TeCAs (e.g., mirtazapine) MAOIs (e.g., phenelzine); Others: Agomelatine Bupropion Tianeptine Vilazodone Vortioxetine
Sympatholytics (Antiadrenergics)	Alpha-1 blockers (e.g., prazosin) Alpha-2 agonists (e.g., clonidine, dexmedetomidine, guanfacine) Beta blockers (e.g., propranolol)
Others	Benzoctamine Cannabidiol Cycloserine Fabomotizole Hydroxyzine Kanna Lavender Lorpiprazole Mebicar Mepiprazole Nicotine Opipramol Oxaflozane^‡ Phenaglycodol Phenibut Picamilon Selank Tiagabine Tofisopam Validolum
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

Clinical data

Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name 4-(3,4-dichlorophenyl)-2-[2-(4-methylpiperazin-1-yl)-benzylidene]-thiomorpholin-3-one
CAS Number	361343-19-3^Y HCl: 220322-05-4^Y
PubChem CID	19544192 HCl: 6914152
ChemSpider	5290108
UNII	933PJL964R HCl: X38F62RR8L^Y
Chemical and physical data
Formula	C₂₂H₂₃Cl₂N₃OS
Molar mass	448.41 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES Clc4c(Cl)cc(N1C(=O)C(\SCC1)=C\c3ccccc3N2CCN(C)CC2)cc4
InChI InChI=1S/C22H23Cl2N3OS/c1-25-8-10-26(11-9-25)20-5-3-2-4-16(20)14-21-22(28)27(12-13-29-21)17-6-7-18(23)19(24)15-17/h2-7,14-15H,8-13H2,1H3/b21-14- Key:LHYMPSWMHXUWSK-STZFKDTASA-N
(verify)