Chemistry:Zalospirone

Zalospirone
Clinical data
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	In general: uncontrolled;
Pharmacokinetic data
Elimination half-life	1-4 hours
Identifiers
	IUPAC name (3aα,4α,4aβ,6aβ,7α,7aα)-Hexahydro-2-(4-(4-(2-pyrimidinyl)-1-piperazinyl)butyl)-4,7-etheno-1H-cyclobut[f]isoindole-1,3(2H)-dione;
CAS Number	114298-18-9;
PubChem CID	163925;
IUPHAR/BPS	58;
ChemSpider	143768;
UNII	0449O95Z1J;
Chemical and physical data
Formula	C24H29N5O2
Molar mass	419.529 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C1N(C(=O)[C@@H]4[C@H]1[C@@H]2\C=C/[C@H]4[C@H]3\C=C/[C@@H]23)CCCCN6CCN(c5ncccn5)CC6;
	InChI InChI=1S/C24H29N5O2/c30-22-20-18-6-7-19(17-5-4-16(17)18)21(20)23(31)29(22)11-2-1-10-27-12-14-28(15-13-27)24-25-8-3-9-26-24/h3-9,16-21H,1-2,10-15H2/t16-,17+,18-,19+,20-,21+; Key:AERLHOTUXIJQFV-RCPZPFRWSA-N;
	(verify)

Short description: Chemical compound

Zalospirone (WY-47,846) is a selective 5-HT_1A partial agonist of the azapirone chemical class.^[1]^[2] It was found to be effective in the treatment of anxiety and depression in clinical trials, but a high proportion of subjects dropped out due to side effects and development was subsequently never completed.^[3]

References

↑ "5-HT1A agonist effects on punished responding of squirrel monkeys". Pharmacology, Biochemistry, and Behavior 37 (2): 335–7. October 1990. doi:10.1016/0091-3057(90)90344-H. PMID 1981937.
↑ "Antidepressant-like activity of compounds with varying efficacy at 5-HT1A receptors". Neuropharmacology 32 (4): 331–40. April 1993. doi:10.1016/0028-3908(93)90153-T. PMID 8497336.
↑ "Zalospirone in major depression: a placebo-controlled multicenter study". Journal of Clinical Psychopharmacology 16 (3): 212–7. June 1996. doi:10.1097/00004714-199606000-00004. PMID 8784652.

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[1] "5-HT1A agonist effects on punished responding of squirrel monkeys". Pharmacology, Biochemistry, and Behavior 37 (2): 335–7. October 1990. doi:10.1016/0091-3057(90)90344-H. PMID 1981937.

[2] "Antidepressant-like activity of compounds with varying efficacy at 5-HT1A receptors". Neuropharmacology 32 (4): 331–40. April 1993. doi:10.1016/0028-3908(93)90153-T. PMID 8497336.

[3] "Zalospirone in major depression: a placebo-controlled multicenter study". Journal of Clinical Psychopharmacology 16 (3): 212–7. June 1996. doi:10.1097/00004714-199606000-00004. PMID 8784652.

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[2]

[3]

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

v t e Piperazines
Simple piperazines (no additional rings)	1-Cyclohexylpiperazine Aminoethylpiperazine Diethylcarbamazine HEPPS Midafotel Piperazine PIPES
Phenylpiperazines	Acaprazine Antrafenine Aripiprazole Batoprazine Bifeprunox BRL-15,572 Ciprofloxacin CSP-2503 Dapiprazole DCPP DMPP Diphenylpiperazine Dropropizine EGIS-12,233 Elopiprazole Eltoprazine Enpiprazole Ensaculin Etoperidone Flesinoxan Fluanisone Flibanserin Fluprazine Itraconazole Ketoconazole Levodropropizine Lorpiprazole mCPP Mefway MeOPP Mepiprazole Naftopidil Naluzotan Naphthylpiperazine Nefazodone Niaprazine Oxypertine Pardoprunox pCPP pFPP Posaconazole S-14,506 S-14,671 S-15,535 SB-258,585 SB-271,046 SB-357,134 SB-399,885 Sonepiprazole TFMPP Tolpiprazole Trazodone Urapidil Vesnarinone Vilazodone Vortioxetine WAY-100,135 WAY-100,635
Benzylpiperazines	2C-B-BZP Befuraline Bifeprunox Buclizine BZP Chlorbenzoxamine DBZP Fipexide Imatinib MBZP MDBZP Meclozine Methoxypiperamide Piberaline Piribedil Sunifiram Trimetazidine Vesnarinone
Diphenylalkylpiperazines (benzhydrylalkylpiperazines)	AD-1211 Almitrine Amperozide BRL-15,572 Buclizine BW373U86 Cetirizine Chlorbenzoxamine Chlorcyclizine Cinnarizine Clocinizine Cyclizine DBL-583 Diphenpipenol Diphenylmethylpiperazine Dotarizine DPI-221 DPI-287 DPI-3290 GBR-12,783 GBR-12,935 GBR-13,069 GBR-13,098 GBR-13,119 Hydroxyzine Lidoflazine Manidipine Meclozine MT-45 Oxatomide SNC-80 Vanoxerine
Pyrimidinylpiperazines	Buspirone Dasatinib Eptapirone Gepirone Ipsapirone Piribedil Prazitone Pyrimidinylpiperazine Revospirone Tandospirone Tirilazad Trimazosin Umespirone Zalospirone
Pyridinylpiperazines	Atevirdine Azaperone Delavirdine Mirtazapine Pyridinylpiperazine
Benzo(iso)thiazolyl piperazines	Lurasidone Perospirone Revospirone Tiospirone Ziprasidone
Tricyclics (piperazine attached via side chain)	Amoxapine Clopenthixol Clorotepine Clozapine Cyanothepin Doclothepin Docloxythepin Flupentixol Fluphenazine Isofloxythepin Loxapine Meperathiepin Metitepine Octomethothepin Olanzapine Opipramol Oxyclothepin Oxyprothepin Peradithiepin Perathiepin Perazine Perphenazine Pirenzepine Prochlorperazine Thiethylperazine Thiothixene Trifluoperazine Trifluthepin Zuclopenthixol
Others/Uncategorized	6-Nitroquipazine Azimilide Cinepazet Cinepazic acid Cinepazide Cyclohexylpiperazine EGIS-7625 Hexocyclium Indinavir JNJ-7777120 Lodenafil Mirodenafil PB-28 Quipazine Ranolazine SA-4503 Sildenafil Tadalafil Vardenafil VUF-6002 WY-46824 Zipeprol

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Clinical data

Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: uncontrolled
Pharmacokinetic data
Elimination half-life	1-4 hours
Identifiers
IUPAC name (3aα,4α,4aβ,6aβ,7α,7aα)-Hexahydro-2-(4-(4-(2-pyrimidinyl)-1-piperazinyl)butyl)-4,7-etheno-1H-cyclobut[f]isoindole-1,3(2H)-dione
CAS Number	114298-18-9
PubChem CID	163925
IUPHAR/BPS	58
ChemSpider	143768
UNII	0449O95Z1J
Chemical and physical data
Formula	C₂₄H₂₉N₅O₂
Molar mass	419.529 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C1N(C(=O)[C@@H]4[C@H]1[C@@H]2\C=C/[C@H]4[C@H]3\C=C/[C@@H]23)CCCCN6CCN(c5ncccn5)CC6
InChI InChI=1S/C24H29N5O2/c30-22-20-18-6-7-19(17-5-4-16(17)18)21(20)23(31)29(22)11-2-1-10-27-12-14-28(15-13-27)24-25-8-3-9-26-24/h3-9,16-21H,1-2,10-15H2/t16-,17+,18-,19+,20-,21+ Key:AERLHOTUXIJQFV-RCPZPFRWSA-N
(verify)

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Chemistry:Zalospirone

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