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	143413-68-7 ;
PubChem CID	178132;
ChemSpider	8002134 ;
UNII	34E28BM822;
ChEMBL	CHEMBL2104091;
Chemical and physical data
Formula	C26H38N2O4
Molar mass	442.589 g/mol
3D model (Jmol)	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 ;
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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[edit]

^ ^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 (Berl). 108 (1-2): 47–50. doi:10.1007/BF02245284. PMID 1357709.
^ 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 (Berl). 108 (1-2): 47–50. doi:10.1007/BF02245284. PMID 1357709.

[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.

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[2]

[3]

v t e Anxiolytics (N05B)

5-HT_1AR agonists	Buspirone 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 Etifoxine; Herbs: Kava Skullcap Valerian

α₂δ VDCC blockers	Gabapentin Gabapentin enacarbil Phenibut Pregabalin

Antidepressants	SSRIs (e.g., escitalopram) SNRIs (e.g., duloxetine) NaSSAs (e.g., mirtazapine) SARIs (e.g., trazodone) TCAs (e.g., imipramine) TeCAs (e.g., amoxapine) MAOIs (e.g., phenelzine); Others: Agomelatine Bupropion Tianeptine Vilazodone Vortioxetine

Sympatholytics	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

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 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)	Almitrine Amperozide BRL-15,572 Buclizine BW373U86 Cetirizine Chlorbenzoxamine Chlorcyclizine Cinnarizine Clocinizine Cyclizine DBL-583 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 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 Zipeprol

Alnespirone

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References[edit]

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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	143413-68-7^Y
PubChem CID	178132
ChemSpider	8002134^Y
UNII	34E28BM822
ChEMBL	CHEMBL2104091
Chemical and physical data
Formula	C₂₆H₃₈N₂O₄
Molar mass	442.589 g/mol
3D model (Jmol)	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^Y Key:QYFHCFNBYQZGKW-BDQAORGHSA-N^Y
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