Dasotraline
{{Short description|Chemical compound}}
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{{Drugbox
| Verifiedfields = changed
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| verifiedrevid = 449042592
| image = Dasotraline.svg
| image_class = skin-invert-image
| width = 200
| IUPAC_name = (1R,4S)-4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine
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| C=16 | H=15 | Cl=2 | N=1
| CAS_number = 675126-05-3
| CAS_number_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 4D28EY0L5T
| PubChem = 9947999
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| ChEMBL = 3301595
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 8123611
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D10700
| smiles = C1C[C@H](C2=CC=CC=C2[C@@H]1C3=CC(=C(C=C3)Cl)Cl)N
| StdInChI = 1S/C16H15Cl2N/c17-14-7-5-10(9-15(14)18)11-6-8-16(19)13-4-2-1-3-12(11)13/h1-5,7,9,11,16H,6,8,19H2/t11-,16+/m0/s1
| StdInChIKey = SRPXSILJHWNFMK-MEDUHNTESA-N
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Dasotraline (INN;{{cite journal |title=International Nonproprietary Names for Pharmaceutical Substances (INN) |journal=WHO Drug Information |volume=27 |issue=4 |year=2013 |url=https://www.who.int/medicines/publications/druginformation/PL_110.pdf |publisher=WHO |access-date=4 November 2014}} former developmental code name SEP-225,289) is a serotonin-norepinephrine-dopamine reuptake inhibitor (SNDRI) that was under development by Sunovion for the treatment of attention-deficit hyperactivity disorder (ADHD) and binge eating disorder (BED).{{cite journal | vauthors = Chen Z, Skolnick P | title = Triple uptake inhibitors: therapeutic potential in depression and beyond | journal = Expert Opinion on Investigational Drugs | volume = 16 | issue = 9 | pages = 1365–77 | date = September 2007 | pmid = 17714023 | doi = 10.1517/13543784.16.9.1365 | s2cid = 20271918 }}{{cite journal | vauthors = DeLorenzo C, Lichenstein S, Schaefer K, Dunn J, Marshall R, Organisak L, Kharidia J, Robertson B, Mann JJ, Parsey RV | display-authors = 6 | title = SEP-225289 serotonin and dopamine transporter occupancy: a PET study | journal = Journal of Nuclear Medicine | volume = 52 | issue = 7 | pages = 1150–5 | date = July 2011 | pmid = 21680689 | pmc = 3856248 | doi = 10.2967/jnumed.110.084525 }}{{cite journal | vauthors = Ziegler L, Küffer G, Euler E, Wilhelm K | title = [Arthrographic imaging of ganglions of the hand] | language = de | journal = RöFo | volume = 153 | issue = 2 | pages = 143–6 | date = August 1990 | pmid = 2168068 | doi = 10.1055/s-2008-1033352 | s2cid = 260312446 | trans-title = Arthrographic imaging of ganglions of the hand }}{{cite journal | vauthors = Guiard B, Chenu F, El Mansari M, Blier P |title=P.1.c.059 Electrophysiological properties of the triple reuptake inhibitor SEP 225289 on monoaminergic neurons |journal=European Neuropsychopharmacology |volume=19 |year=2009 |pages=S285 |doi=10.1016/S0924-977X(09)70419-5 |s2cid=54263757 }} Structurally, dasotraline is a stereoisomer of desmethylsertraline (DMS), which is an active metabolite of the marketed selective serotonin reuptake inhibitor (SSRI) antidepressant sertraline (Zoloft).
Adverse Effects
In phase I clinical trials for attention deficit hyperactivity disorder, test subjects reported the following side effects:{{cite journal | vauthors = Koblan KS, Hopkins SC, Sarma K, Jin F, Goldman R, Kollins SH, Loebel A | title = Dasotraline for the Treatment of Attention-Deficit/Hyperactivity Disorder: A Randomized, Double-Blind, Placebo-Controlled, Proof-of-Concept Trial in Adults | journal = Neuropsychopharmacology | volume = 40 | issue = 12 | pages = 2745–52 | date = November 2015 | pmid = 25948101 | pmc = 4864650 | doi = 10.1038/npp.2015.124 }}
History
In 2017, the U.S. Food and Drug Administration accepted Sunovion's New Drug Application (NDA) for review for the treatment of ADHD;{{cite press release |author= |title=Sunovion Announces FDA Acceptance for Review of New Drug Application for Dasotraline for the Treatment of ADHD |url=http://news.sunovion.com/press-release/sunovion-announces-fda-acceptance-review-new-drug-application-dasotraline-treatment |location=Marlborough, Massachusetts |publisher=Sunovion |agency=Business Wire |date=November 10, 2017 |access-date=2018-05-01 |archive-date=2018-05-01 |archive-url=https://web.archive.org/web/20180501160846/http://news.sunovion.com/press-release/sunovion-announces-fda-acceptance-review-new-drug-application-dasotraline-treatment |url-status=dead }} however, the NDA was ultimately rejected citing the need for additional studies to determine efficacy and tolerability.{{cite web | title = FDA Issues a Complete Response Letter for New Drug Application for Dasotraline for the Treatment of Adhd | url = https://news.sunovion.com/press-release/fda-issues-complete-response-letter-new-drug-application-dasotraline-treatment-adhd | publisher = Sumitomo Dainippon Pharma Co., Ltd. | date = August 31, 2018 | access-date = October 13, 2019 | archive-date = October 13, 2019 | archive-url = https://web.archive.org/web/20191013171910/https://news.sunovion.com/press-release/fda-issues-complete-response-letter-new-drug-application-dasotraline-treatment-adhd | url-status = dead }}{{cite web|title=Pipeline Report: Brand Drugs|url=https://www.welldynerx.com/content/uploads/2018/02/PipelineReport-Brand-Drugs.pdf|publisher=Welldyne|access-date=1 May 2018|pages=1, 4|date=February 2018}}{{ClinicalTrialsGov|NCT02276209|Dasotraline Adult ADHD Study}} In July 2019, Sunovion’s NDA for the treatment of BED was accepted with an expected action date of May 2020.{{cite web | title = Sunovion Announces Acceptance by the US FDA of the New Drug Application for Dasotraline for the Treatment of Adults with Moderate-to-Severe Binge Eating Disorder | url = https://news.sunovion.com/press-release/sunovion-announces-acceptance-us-fda-new-drug-application-dasotraline-treatment | publisher = Sumitomo Dainippon Pharma Co., Ltd. | date = July 30, 2019 | access-date = October 13, 2019 | archive-date = October 13, 2019 | archive-url = https://web.archive.org/web/20191013171930/https://news.sunovion.com/press-release/sunovion-announces-acceptance-us-fda-new-drug-application-dasotraline-treatment | url-status = dead }} In May 2020, Sunovion halted its drug development program for dasotraline, withdrawing both NDAs for ADHD and BED.{{cite web |title=Sunovion Discontinues Dasotraline Program |url=https://www.businesswire.com/news/home/20200513005363/en/Sunovion-Discontinues-Dasotraline-Program |website=www.businesswire.com |access-date=27 June 2020 |language=en |date=13 May 2020}}
Law
= Finland =
Dasotraline is completely unscheduled.
See also
References
{{Reflist|2}}
Further reading
;Liming Shao Patent
- {{ cite patent | country = US | number = 2007203111 | status = application | title = Cycloalkylamines as monoamine reuptake inhibitors | pubdate = 2007-08-30 | inventor =Shao L, Wang F, Malcolm SC, Hewitt MC, Bush LR, Ma J, Varney MA, Campbell U, Engel SR, Hardy LW, Koch P, Campbell JE | assign1 = Sepracor Inc. | class = }}
;Asymmetry Patent
- {{ cite patent | country = US | number = 7129378 | status = patent | title = Method of preparing amine stereoisomers | pubdate = 2005-07-28 | inventor = Han X, Krishnamurthy D, Senanayake CH, Lu Z-H | assign1 = Apsinterm LLC | class = }}
{{Monoamine reuptake inhibitors}}
Category:Chlorobenzene derivatives
Category:Serotonin–norepinephrine–dopamine reuptake inhibitors