Chemistry:Tedatioxetine

Tedatioxetine
Clinical data
Other names	Lu AA24530; Lu-AA-24530
ATC code	none;
Legal status
Legal status	Investigational;
Identifiers
	IUPAC name 4-{2-[(4-methylphenyl)sulfanyl]phenyl}piperidine;
CAS Number	508233-95-2 ;
PubChem CID	9878913;
ChemSpider	8054590 ;
UNII	5H681S8O3S;
KEGG	D10170 ;
Chemical and physical data
Formula	C18H21NS
Molar mass	283.43 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C=C1)=CC=C1SC2=C(C3CCNCC3)C=CC=C2;
	InChI InChI=1S/C18H21NS/c1-14-6-8-16(9-7-14)20-18-5-3-2-4-17(18)15-10-12-19-13-11-15/h2-9,15,19H,10-13H2,1H3 ; Key:CVASBKDYSQKLSO-UHFFFAOYSA-N ;
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Short description: Chemical compound

Tedatioxetine (developmental code name Lu AA24530) is an experimental antidepressant that was discovered by scientists at Lundbeck; in 2007 Lundbeck and Takeda entered into a partnership that included tedatioxetine but was focused on another, more advanced Lundbeck drug candidate, vortioxetine.^[1]

Tedatioxetine is reported to act as a triple reuptake inhibitor (serotonin > norepinephrine > dopamine) and 5-HT_2A, 5-HT_2C, 5-HT₃, and α_1A-adrenergic receptor antagonist.^[2]^[3]^[4]^[5]

As of 2009, it was in phase II clinical trials for major depressive disorder,^[5] but there have been no updates since then, and as of August 2013 it was no longer displayed on Lundbeck's product pipeline.^[6]^[7]

On May 10, 2016, all work on tedatioxetine stopped.^[8]

A Chinese patent shows that there has been interest in this compound outside of Lundbeck.^[9]

References

↑ "Lundbeck, Takeda enter strategic alliance for mood disorder, anxiety drugs"]. First Word Pharma. 5 September 2007. http://www.firstwordpharma.com/node/88051?tsid=17#axzz3xkIEA5eH.
↑ Stensbol TB, Miller S, "4-[2-(4-methylphenylsulfanyd-phenyl] piperidine with combined serotonin and norepinephrine reuptake inhibition for the treatment of adhd, melancholia, treatment resistant depression or residual symptoms in depression", US patent 2010144788, published 10 June 2010, assigned to H Lundbeck AS
↑ Depression and bipolar disorder: Stahl's essential psychopharmacology. Cambridge University Press. 19 May 2008. pp. 206. ISBN 978-0-521-88663-5. https://books.google.com/books?id=zqvVZOea2JAC&pg=PA206. Retrieved 22 November 2011.
↑ Encyclopedia of Psychopharmacology. Springer. 30 August 2010. pp. 105. ISBN 978-3-540-68698-9. https://books.google.com/books?id=qoyYobgX0uwC&pg=PA105. Retrieved 22 November 2011.
↑ ^5.0 ^5.1 "Lu AA24530 shows positive results in major depressive disorder phase II study". FierceBiotech. 2 July 2009. http://www.fiercebiotech.com/press-releases/lu-aa24530-shows-positive-results-major-depressive-disorder-phase-ii-study.
↑ "Pipeline of Lundbeck". http://investor.lundbeck.com/pipeline.cfm.
↑ "Tedatioxetine". UK Medicines Information. http://www.ukmi.nhs.uk/applications/ndo/record_view_open.asp?newDrugID=4990.
↑ "Tedatioxetine". AdisInsight. Springer Nature Switzerland AG. http://adisinsight.springer.com/drugs/800023694.
↑ Cao, Longji; Jianchuang Xin & Xiangping Yang, "Compound for preparing 4-(2-(4-methylphenylthio))phenylpiperidine, and preparation method and use thereof", WO patent 2015090160, published 2015-06-25

External links

Lu AA24530 shows positive results in major depressive disorder phase II study

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

[1] "Lundbeck, Takeda enter strategic alliance for mood disorder, anxiety drugs"]. First Word Pharma. 5 September 2007. http://www.firstwordpharma.com/node/88051?tsid=17#axzz3xkIEA5eH.

[urlUSPTO20100144788-2] Stensbol TB, Miller S, "4-[2-(4-methylphenylsulfanyd-phenyl] piperidine with combined serotonin and norepinephrine reuptake inhibition for the treatment of adhd, melancholia, treatment resistant depression or residual symptoms in depression", US patent 2010144788, published 10 June 2010, assigned to H Lundbeck AS

[Stahl2008-3] Depression and bipolar disorder: Stahl's essential psychopharmacology. Cambridge University Press. 19 May 2008. pp. 206. ISBN 978-0-521-88663-5. https://books.google.com/books?id=zqvVZOea2JAC&pg=PA206. Retrieved 22 November 2011.

[Stolerman2010-4] Encyclopedia of Psychopharmacology. Springer. 30 August 2010. pp. 105. ISBN 978-3-540-68698-9. https://books.google.com/books?id=qoyYobgX0uwC&pg=PA105. Retrieved 22 November 2011.

[Fierce-5] 5.0 ^5.1 "Lu AA24530 shows positive results in major depressive disorder phase II study". FierceBiotech. 2 July 2009. http://www.fiercebiotech.com/press-releases/lu-aa24530-shows-positive-results-major-depressive-disorder-phase-ii-study.

[urlPipeline_of_Lundbeck-6] "Pipeline of Lundbeck". http://investor.lundbeck.com/pipeline.cfm.

[7] "Tedatioxetine". UK Medicines Information. http://www.ukmi.nhs.uk/applications/ndo/record_view_open.asp?newDrugID=4990.

[8] "Tedatioxetine". AdisInsight. Springer Nature Switzerland AG. http://adisinsight.springer.com/drugs/800023694.

[9] Cao, Longji; Jianchuang Xin & Xiangping Yang, "Compound for preparing 4-(2-(4-methylphenylthio))phenylpiperidine, and preparation method and use thereof", WO patent 2015090160, published 2015-06-25

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v t e Adrenergic receptor modulators
α₁	Agonists: 6-FNE Amidephrine Anisodine Buspirone Cirazoline Corbadrine Desglymidodrine Dexisometheptene Dipivefrine Dopamine Droxidopa (L-DOPS) Ephedrine Epinephrine Etilefrine Etilevodopa Ethylnorepinephrine Indanidine Isometheptene L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Melevodopa Metaraminol Methoxamine Methyldopa Midodrine Naphazoline Norepinephrine Octopamine (drug) Oxymetazoline Phenylephrine Phenylpropanolamine Pseudoephedrine Synephrine Tetryzoline Tiamenidine XP21279 Xylometazoline Antagonists: Abanoquil Adimolol Ajmalicine Alfuzosin Amosulalol Anisodamine Arotinolol Atiprosin Atypical antipsychotics (e.g., brexpiprazole, clozapine,Chemistry:Olanzapine
α₂	Agonists: (R)-3-Nitrobiphenyline 4-NEMD 6-FNE Amitraz Apraclonidine Brimonidine Cannabivarin Clonidine Corbadrine Detomidine Dexmedetomidine Dihydroergotamine Dipivefrine Dopamine Droxidopa (L-DOPS) Etilevodopa Ephedrine Ergotamine Epinephrine Etilefrine Ethylnorepinephrine Guanabenz Guanfacine Guanoxabenz L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Lofexidine Medetomidine Melevodopa Methyldopa Mivazerol Naphazoline Norepinephrine Oxymetazoline Phenylpropanolamine Piperoxan Pseudoephedrine Rezatomidine Rilmenidine Romifidine Talipexole Tasipimidine Tetrahydrozoline Tiamenidine Tizanidine Tolonidine Urapidil Vatinoxan XP21279 Xylazine Xylometazoline Antagonists: 1-PP Adimolol Amesergide Aptazapine Atipamezole Atypical antipsychotics (e.g., asenapine, Chemistry:Brexpiprazole
β	Agonists: Abediterol Alifedrine Amibegron Arbutamine Arformoterol Arotinolol BAAM Bambuterol Befunolol Bitolterol Broxaterol Buphenine Carbuterol Carmoterol Cimaterol Clenbuterol Colterol Corbadrine Denopamine Dipivefrine Dobutamine Dopamine Dopexamine Droxidopa (L-DOPS) Ephedrine Epinephrine Etafedrine Etilefrine Etilevodopa Ethylnorepinephrine Fenoterol Formoterol Hexoprenaline Higenamine Indacaterol Isoetarine Isoprenaline Isoxsuprine L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Levosalbutamol Mabuterol Melevodopa Methoxyphenamine Methyldopa Mirabegron Norepinephrine Orciprenaline Oxyfedrine PF-610355 Phenylpropanolamine Pirbuterol Prenalterol Ractopamine Procaterol Pseudoephedrine Reproterol Rimiterol Ritodrine Salbutamol Salmeterol Solabegron Terbutaline Tretoquinol Tulobuterol Vilanterol Xamoterol XP21279 Zilpaterol Zinterol Antagonists: Acebutolol Adaprolol Adimolol Afurolol Alprenolol Alprenoxime Amosulalol Ancarolol Arnolol Arotinolol Atenolol Befunolol Betaxolol Bevantolol Bisoprolol Bopindolol Bornaprolol Brefonalol Bucindolol Bucumolol Bufetolol Bufuralol Bunitrolol Bunolol Bupranolol Butaxamine Butidrine Butofilolol Capsinolol Carazolol Carpindolol Carteolol Carvedilol Celiprolol Cetamolol Cicloprolol Cinamolol Cloranolol Cyanopindolol Dalbraminol Dexpropranolol Diacetolol Dichloroisoprenaline Dihydroalprenolol Dilevalol Diprafenone Draquinolol Ecastolol Epanolol Ericolol Ersentilide Esatenolol Esprolol Eugenodilol Exaprolol Falintolol Flestolol Flusoxolol Hydroxycarteolol Hydroxytertatolol ICI-118,551 Idropranolol Indenolol Indopanolol Iodocyanopindolol Iprocrolol Isoxaprolol Isamoltane Labetalol Landiolol Levobetaxolol Levobunolol Levomoprolol Medroxalol Mepindolol Metipranolol Metoprolol Moprolol Nadolol Nadoxolol Nebivolol Nifenalol Nipradilol Oxprenolol Pacrinolol Pafenolol Pamatolol Pargolol Penbutolol Pindolol Practolol Primidolol Procinolol Pronethalol Propafenone Propranolol Ridazolol Ronactolol Soquinolol Sotalol Spirendolol SR 59230A Sulfinalol Talinolol Tazolol Tertatolol Tienoxolol Tilisolol Timolol Tiprenolol Tolamolol Toliprolol Xibenolol Xipranolol

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