Chemistry:Flesinoxan

Flesinoxan
Clinical data
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	In general: uncontrolled;
Identifiers
	IUPAC name 4-fluoro-N-(2-{4-[(2S)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-5-yl]piperazin-1-yl}ethyl)benzamide;
CAS Number	98206-10-1;
PubChem CID	57347;
IUPHAR/BPS	1;
ChemSpider	51700;
UNII	3V574S89E1;
KEGG	D02568;
ChEMBL	ChEMBL1742477;
Chemical and physical data
Formula	C22H26FN3O4
Molar mass	415.465 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CN(CCN1CCNC(=O)C2=CC=C(C=C2)F)C3=C4C(=CC=C3)O[C@H](CO4)CO;
	InChI InChI=1S/C22H26FN3O4/c23-17-6-4-16(5-7-17)22(28)24-8-9-25-10-12-26(13-11-25)19-2-1-3-20-21(19)29-15-18(14-27)30-20/h1-7,18,27H,8-15H2,(H,24,28)/t18-/m0/s1; Key:NYSDRDDQELAVKP-SFHVURJKSA-N;

Short description: Chemical compound

Flesinoxan (DU-29,373) is a potent and selective 5-HT_1A receptor partial/near-full agonist of the phenylpiperazine class.^[1]^[2]^[3] Originally developed as a potential antihypertensive drug,^[1]^[2]^[4] flesinoxan was later found to possess antidepressant and anxiolytic effects in animal tests.^[5]^[6] As a result, it was investigated in several small human pilot studies for the treatment of major depressive disorder, and was found to have robust effectiveness and very good tolerability.^[7]^[8] However, due to "management decisions", the development of flesinoxan was stopped and it was not pursued any further.^[9]

In patients, flesinoxan enhances REM sleep latency, decreases body temperature, and increases ACTH, cortisol, prolactin, and growth hormone secretion.^[2]^[8]

References

↑ ^1.0 ^1.1 "Centrally acting hypotensive agents with affinity for 5-HT1A binding sites inhibit forskolin-stimulated adenylate cyclase activity in calf hippocampus". British Journal of Pharmacology 95 (3): 975–85. November 1988. doi:10.1111/j.1476-5381.1988.tb11728.x. PMID 3207999.
↑ ^2.0 ^2.1 ^2.2 "Hormonal and temperature responses to flesinoxan in normal volunteers: an antagonist study". European Neuropsychopharmacology 14 (2): 151–5. March 2004. doi:10.1016/S0924-977X(03)00108-1. PMID 15013031.
↑ "Characterization of 5-hydroxytryptamine1A properties of flesinoxan: in vivo electrophysiology and hypothermia study". Neuropharmacology 34 (10): 1311–26. October 1995. doi:10.1016/0028-3908(95)00098-Q. PMID 8570029.
↑ "Flesinoxan lowers blood pressure and heart rate in cats via 5-HT1A receptors". European Journal of Pharmacology 149 (3): 213–23. May 1988. doi:10.1016/0014-2999(88)90651-6. PMID 2842163.
↑ "Flesinoxan shows antidepressant activity in a DRL 72-s screen". Psychopharmacology 107 (4): 474–9. 1992. doi:10.1007/BF02245258. PMID 1351303.
↑ "Antianxiety and behavioral suppressant actions of the novel 5-HT1A receptor agonist, flesinoxan". Pharmacology, Biochemistry, and Behavior 48 (4): 959–63. August 1994. doi:10.1016/0091-3057(94)90205-4. PMID 7972301.
↑ "An open study of oral flesinoxan, a 5-HT1A receptor agonist, in treatment-resistant depression". International Clinical Psychopharmacology 8 (3): 167–72. 1993. doi:10.1097/00004850-199300830-00005. PMID 8263314.
↑ ^8.0 ^8.1 "Pilot study of flesinoxan, a 5-HT1A agonist, in major depression: Effects on sleep REM latency and body temperature.". Human Psychopharmacology: Clinical and Experimental 8 (4): 279–283. 2004. doi:10.1002/hup.470080407. https://orbi.uliege.be/bitstream/2268/87817/1/Pilot%20study%20of%20flesinoxan%20in%20major%20depression.%20Effect%20on%20REM%20latency%20and%20body%20temperature.pdf.
↑ "Serotonin 5-HT1A receptors as targets for agents to treat psychiatric disorders: rationale and current status of research". CNS Drugs 27 (9): 703–16. September 2013. doi:10.1007/s40263-013-0071-0. PMID 23757185.

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Original source: https://en.wikipedia.org/wiki/Flesinoxan. Read more

[pmid3207999-1] 1.0 ^1.1 "Centrally acting hypotensive agents with affinity for 5-HT1A binding sites inhibit forskolin-stimulated adenylate cyclase activity in calf hippocampus". British Journal of Pharmacology 95 (3): 975–85. November 1988. doi:10.1111/j.1476-5381.1988.tb11728.x. PMID 3207999.

[pmid15013031-2] 2.0 ^2.1 ^2.2 "Hormonal and temperature responses to flesinoxan in normal volunteers: an antagonist study". European Neuropsychopharmacology 14 (2): 151–5. March 2004. doi:10.1016/S0924-977X(03)00108-1. PMID 15013031.

[pmid8570029-3] "Characterization of 5-hydroxytryptamine1A properties of flesinoxan: in vivo electrophysiology and hypothermia study". Neuropharmacology 34 (10): 1311–26. October 1995. doi:10.1016/0028-3908(95)00098-Q. PMID 8570029.

[pmid2842163-4] "Flesinoxan lowers blood pressure and heart rate in cats via 5-HT1A receptors". European Journal of Pharmacology 149 (3): 213–23. May 1988. doi:10.1016/0014-2999(88)90651-6. PMID 2842163.

[pmid1351303-5] "Flesinoxan shows antidepressant activity in a DRL 72-s screen". Psychopharmacology 107 (4): 474–9. 1992. doi:10.1007/BF02245258. PMID 1351303.

[pmid7972301-6] "Antianxiety and behavioral suppressant actions of the novel 5-HT1A receptor agonist, flesinoxan". Pharmacology, Biochemistry, and Behavior 48 (4): 959–63. August 1994. doi:10.1016/0091-3057(94)90205-4. PMID 7972301.

[pmid8263314-7] "An open study of oral flesinoxan, a 5-HT1A receptor agonist, in treatment-resistant depression". International Clinical Psychopharmacology 8 (3): 167–72. 1993. doi:10.1097/00004850-199300830-00005. PMID 8263314.

[Marc_Ansseau,_William_Pitchot,_Antonio_Gonzalez_Moreno,_Jacques_Wauthy,_Patrick_Papart_2004_279–283-8] 8.0 ^8.1 "Pilot study of flesinoxan, a 5-HT1A agonist, in major depression: Effects on sleep REM latency and body temperature.". Human Psychopharmacology: Clinical and Experimental 8 (4): 279–283. 2004. doi:10.1002/hup.470080407. https://orbi.uliege.be/bitstream/2268/87817/1/Pilot%20study%20of%20flesinoxan%20in%20major%20depression.%20Effect%20on%20REM%20latency%20and%20body%20temperature.pdf.

[pmid23757185-9] "Serotonin 5-HT1A receptors as targets for agents to treat psychiatric disorders: rationale and current status of research". CNS Drugs 27 (9): 703–16. September 2013. doi:10.1007/s40263-013-0071-0. PMID 23757185.

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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

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
Identifiers
IUPAC name 4-fluoro-N-(2-{4-[(2S)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-5-yl]piperazin-1-yl}ethyl)benzamide
CAS Number	98206-10-1
PubChem CID	57347
IUPHAR/BPS	1
ChemSpider	51700
UNII	3V574S89E1
KEGG	D02568
ChEMBL	ChEMBL1742477
Chemical and physical data
Formula	C₂₂H₂₆FN₃O₄
Molar mass	415.465 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1CN(CCN1CCNC(=O)C2=CC=C(C=C2)F)C3=C4C(=CC=C3)O[C@H](CO4)CO
InChI InChI=1S/C22H26FN3O4/c23-17-6-4-16(5-7-17)22(28)24-8-9-25-10-12-26(13-11-25)19-2-1-3-20-21(19)29-15-18(14-27)30-20/h1-7,18,27H,8-15H2,(H,24,28)/t18-/m0/s1 Key:NYSDRDDQELAVKP-SFHVURJKSA-N

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Chemistry:Flesinoxan

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