Alnespirone

Alnespirone
Clinical data
ATC code	none;
Identifiers
	IUPAC name (+)-4-dihydro-2H-chromen-3-yl]-propylamino]butyl]-8-azaspiro[4.5]decane-7,9-dione;
CAS Number	138298-79-0 ;
PubChem CID	178132;
ChemSpider	8002134 ;
UNII	34E28BM822;
ChEMBL	ChEMBL2104091;
CompTox Dashboard (EPA)	DTXSID30160560 ;
Chemical and physical data
Formula	C26H38N2O4
Molar mass	442.600 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Cl.O=C1N(C(=O)CC2(C1)CCCC2)CCCCN([C@H]3Cc4c(OC)cccc4OC3)CCC;
	InChI InChI=1S/C26H38N2O4.ClH/c1-3-13-27(20-16-21-22(31-2)9-8-10-23(21)32-19-20)14-6-7-15-28-24(29)17-26(18-25(28)30)11-4-5-12-26;/h8-10,20H,3-7,11-19H2,1-2H3;1H/t20-;/m0./s1 ; Key:QYFHCFNBYQZGKW-BDQAORGHSA-N ;
	(verify)

Alnespirone (S-20,499) is a selective 5-HT_1A receptor full agonist of the azapirone chemical class.^[1]^[2]^[3] It has antidepressant and anxiolytic effects.^[1]

References

^ ^a ^b Griebel G, Misslin R, Pawlowski M, Guardiola Lemaître B, Guillaumet G, Bizot-Espiard J (1992). "Anxiolytic-like effects of a selective 5-HT1A agonist, S20244, and its enantiomers in mice". NeuroReport. 3 (1): 84–86. doi:10.1097/00001756-199201000-00022. PMID 1351756.
^ Simon P, Guardiola B, Bizot-Espiard J, Schiavi P, Costentin J (1992). "5-HT1A receptor agonists prevent in rats the yawning and penile erections induced by direct dopamine agonists". Psychopharmacology. 108 (1–2): 47–50. doi:10.1007/BF02245284. PMID 1357709. S2CID 22385029.
^ Astier B, Lambás Señas L, Soulière F, Schmitt P, Urbain N, Rentero N, Bert L, Denoroy L, Renaud B, Lesourd M, Muñoz C, Chouvet G (2003). "In vivo comparison of two 5-HT1A receptors agonists alnespirone (S-20499) and buspirone on locus coeruleus neuronal activity". Eur J Pharmacol. 459 (1): 17–26. doi:10.1016/S0014-2999(02)02814-5. PMID 12505530.

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[pmid1351756-1] Griebel G, Misslin R, Pawlowski M, Guardiola Lemaître B, Guillaumet G, Bizot-Espiard J (1992). "Anxiolytic-like effects of a selective 5-HT1A agonist, S20244, and its enantiomers in mice". NeuroReport. 3 (1): 84–86. doi:10.1097/00001756-199201000-00022. PMID 1351756.

[pmid1357709-2] Simon P, Guardiola B, Bizot-Espiard J, Schiavi P, Costentin J (1992). "5-HT1A receptor agonists prevent in rats the yawning and penile erections induced by direct dopamine agonists". Psychopharmacology. 108 (1–2): 47–50. doi:10.1007/BF02245284. PMID 1357709. S2CID 22385029.

[pmid12505530-3] Astier B, Lambás Señas L, Soulière F, Schmitt P, Urbain N, Rentero N, Bert L, Denoroy L, Renaud B, Lesourd M, Muñoz C, Chouvet G (2003). "In vivo comparison of two 5-HT1A receptors agonists alnespirone (S-20499) and buspirone on locus coeruleus neuronal activity". Eur J Pharmacol. 459 (1): 17–26. doi:10.1016/S0014-2999(02)02814-5. PMID 12505530.

[1]

[2]

[3]

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

v t e Piperazines
Simple piperazines (no additional rings)	Aminoethylpiperazine Diethylcarbamazine HEPPS Midafotel Piperazine PIPES
Phenylpiperazines	2C-B-PP 3,4-CFP 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 3-Methylbenzylpiperazine Befuraline Bifeprunox Buclizine BZP Chlorbenzoxamine DBZP Fipexide Imatinib MBZP MDBZP Meclozine Methoxypiperamide NSI-189 Piberaline Piribedil RN-1747 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 JJC8-088 Lidoflazine Manidipine Meclozine MT-45 Oxatomide SNC-80 Vanoxerine
Pyrimidinylpiperazines	Buspirone Dasatinib Eptapirone Gepirone Ipsapirone Piribedil Pyrimidinylpiperazine Revospirone Tandospirone Tirilazad Trimazosin Umespirone Zalospirone
Pyridinylpiperazines	Atevirdine Azaperone Delavirdine Mirtazapine ORG-12962 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 AP-238 Azimilide Bucinnazine Cinepazet Cinepazic acid Cinepazide CPD-1 Cyclohexylpiperazine EGIS-7625 Hexocyclium Indinavir JNJ-7777120 Lodenafil MK-212 Mirodenafil PB-28 Quipazine Ranolazine SA-4503 Sildenafil Tadalafil Vardenafil VUF-6002 WY-46824 Zipeprol

See also

References