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Elzasonan

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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^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)

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[edit]

^ Vela JM, Buschmann H, Holenz J, Párraga A, Torrens A (2007). Antidepressants, Antipsychotics, Anxiolytics: From Chemistry and Pharmacology to Clinical Application. Weinheim: Wiley-VCH. ISBN 978-3-527-31058-6.

^ Stahl SM (2008). Stahl's essential psychopharmacology: neuroscientific basis and practical applications. Cambridge, UK: Cambridge University Press. ISBN 978-0-521-85702-4.

^ ^a ^b Dawson LA, Bromidge SM (August 2008). "5-HT1 receptor augmentation strategies as enhanced efficacy: therapeutics for psychiatric disorders". Current Topics in Medicinal Chemistry. 8 (12): 1008–1023. doi:10.2174/156802608785161439. PMID 18691129.

^ Norman P (2002). "Pfizer, Inc.: analysis of patenting 1998 – 2001". Expert Opinion on Therapeutic Patents. 12 (5): 725–732. doi:10.1517/13543776.12.5.725. S2CID 84645020.

^ Kirchhoff VD, Nguyen HT, Soczynska JK, Woldeyohannes H, McIntyre RS (October 2009). "Discontinued psychiatric drugs in 2008". Expert Opinion on Investigational Drugs. 18 (10): 1431–1443. doi:10.1517/13543780903184591. PMID 19715445. S2CID 34201544.

Antidepressants (N06A)

Specific reuptake inhibitors and/or receptor modulators

SSRIsTooltip Selective serotonin reuptake inhibitors	Citalopram Escitalopram Fluoxetine^# Fluvoxamine Indalpine^‡ Paroxetine Sertraline Zimelidine^‡
SNRIsTooltip Serotonin–norepinephrine reuptake inhibitors	Desvenlafaxine Duloxetine Levomilnacipran Milnacipran Tofenacin Venlafaxine
NRIsTooltip Norepinephrine reuptake inhibitors	Atomoxetine Reboxetine Viloxazine
NDRIsTooltip Norepinephrine–dopamine reuptake inhibitors	Amineptine^‡ Bupropion Nomifensine^‡
NaSSAsTooltip Noradrenergic and specific serotonergic antidepressants	Mianserin Mirtazapine Setiptiline
SARIsTooltip Serotonin antagonist and reuptake inhibitors	Etoperidone Nefazodone Trazodone
SMSTooltip Serotonin modulator and stimulators	Vilazodone Vortioxetine
Others	Agomelatine Amisulpride Dextromethorphan/bupropion Esketamine Etryptamine^‡ Gepirone Indeloxazine Flupentixol Ketamine^§ Medifoxamine^‡ Metryptamine^‡ Oxaflozane^‡ Pivagabine^‡ Tandospirone Teniloxazine Tianeptine

Tricyclic and tetracyclic antidepressants

TCAs

TeCAs

Others

Tiazesim

Monoamine oxidase inhibitors

Non-selective

Reversible: Caroxazone^‡

Mixed: Bifemelane

MAO_A-selective

MAO_B-selective

Irreversible: Selegiline

Adjunctive therapies

Atypical antipsychotics (aripiprazole, brexpiprazole, lurasidone, olanzapine, quetiapine, risperidone)
Buspirone
Lithium (lithium carbonate, lithium citrate)
Thyroid hormones (triiodothyronine (T₃), levothyroxine (T₄))

Miscellaneous

^#WHO-EM

^‡Withdrawn from market

Clinical trials:

^†Phase III
^§Never to phase III

v t e Anxiolytics (N05B)
5-HT_1ARTooltip 5-HT1A receptor agonists	Buspirone Gepirone Tandospirone
GABA_ARTooltip GABAA receptor PAMsTooltip positive allosteric modulators	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) Carisoprodol Chlormezanone^‡ Ethanol (alcohol) Etifoxine
Hypnotics	Zopiclone
Gabapentinoids (α₂δ VDCC blockers)	Gabapentin Gabapentin enacarbil Phenibut Pregabalin
Antidepressants	SSRIsTooltip Selective serotonin reuptake inhibitors (e.g., escitalopram) SNRIsTooltip Serotonin-norepinephrine reuptake inhibitors (e.g., duloxetine) SARIsTooltip Serotonin antagonist and reuptake inhibitors (e.g., trazodone) TCAsTooltip Tricyclic antidepressants (e.g., clomipramine^#) TeCAsTooltip Tetracyclic antidepressants (e.g., mirtazapine) MAOIsTooltip Monoamine oxidase inhibitors (e.g., phenelzine); Others: Agomelatine Bupropion Tianeptine Vilazodone Vortioxetine
Antipsychotics	Quetiapine Flupentixol
Sympatholytics (Antiadrenergics)	Alpha-1 blockers (e.g., prazosin) Alpha-2 agonists (e.g., clonidine, dexmedetomidine, guanfacine) Beta blockers (e.g., propranolol)
Others	Benzoctamine Cycloserine Fabomotizole Hydroxyzine 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