| Revision as of 02:04, 8 September 2011 editBoghog (talk | contribs)Autopatrolled, Extended confirmed users, IP block exemptions, New page reviewers, Pending changes reviewers, Rollbackers, Template editors137,912 edits not in the current Sunovion pipeline so apparently no longer being developed← Previous edit |
Latest revision as of 02:41, 12 January 2025 edit undoArthurfragoso (talk | contribs)Extended confirmed users, Template editors4,591 edits dark mode fix |
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{{Short description|Chemical compound}} |
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{{cs1 config|name-list-style=vanc}} |
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{{Drugbox |
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{{Drugbox |
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| verifiedrevid = 408461107 |
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| IUPAC_name = (1R)-1--3-methylbutan-1-amine |
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| verifiedrevid = 449042592 |
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| image = SEP-225289 structure.png |
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| image = Dasotraline.svg |
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| image_class = skin-invert-image |
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| width = 200 |
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| IUPAC_name = (1''R'',4''S'')-4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| pregnancy_category = |
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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| PubChem = 9900576 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=15 | H=22 | Cl=1 | N=1 |
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| C=16 | H=15 | Cl=2 | N=1 |
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| CAS_number = 675126-05-3 |
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| molecular_weight = 251.794 g/mol |
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| CAS_number_Ref = {{cascite|correct|CAS}} |
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| smiles = c1cc(Cl)ccc1C2(CCC2)C(N)CC(C)C |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 4D28EY0L5T |
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| PubChem = 9947999 |
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| DrugBank = |
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| ChEMBL = 3301595 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 8123611 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D10700 |
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| smiles = C1C(C2=CC=CC=C21C3=CC(=C(C=C3)Cl)Cl)N |
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| 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 |
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| StdInChIKey = SRPXSILJHWNFMK-MEDUHNTESA-N |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category = |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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'''SEP-225,289''' is an ] ] derived from the active ] of ], which was being developed by ]. It is a so-called ] (TRI).<ref name="pmid17714023">{{cite journal | author = Chen Z, Skolnick P | title = Triple uptake inhibitors: therapeutic potential in depression and beyond | journal = Expert Opin Investig Drugs | volume = 16 | issue = 9 | pages = 1365–77 | year = 2007 | month = September | pmid = 17714023 | doi = 10.1517/13543784.16.9.1365 }}</ref><ref name="pmid21680689">{{cite journal | author = DeLorenzo C, Lichenstein S, Schaefer K, Dunn J, Marshall R, Organisak L, Kharidia J, Robertson B, Mann JJ, Parsey RV | title = SEP-225289 serotonin and dopamine transporter occupancy: a PET study | journal = J. Nucl. Med. | volume = 52 | issue = 7 | pages = 1150–5 | year = 2011 | month = July | pmid = 21680689 | doi = 10.2967/jnumed.110.084525 }}</ref> |
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'''Dasotraline''' (];<ref>{{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}}</ref> former developmental code name '''SEP-225,289''') is a ] (SNDRI) that was under development by ] for the treatment of ] (ADHD) and ] (BED).<ref name="pmid17714023">{{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 }}</ref><ref name="pmid21680689">{{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 }}</ref><ref>{{cite journal | vauthors = Ziegler L, Küffer G, Euler E, Wilhelm K | title = | 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 }}</ref><ref>{{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 }}</ref> Structurally, dasotraline is a ] of ] (DMS), which is an ] of the marketed ] (SSRI) ] ] (Zoloft). |
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== References == |
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==Adverse Effects== |
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In phase I clinical trials for ], test subjects reported the following side effects:<ref>{{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 }}</ref> |
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{{Reflist}} |
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==Further reading== |
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== History == |
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In 2017, the U.S. ] accepted Sunovion's ] (NDA) for review for the treatment of ADHD;<ref>{{cite press release |author=<!--Staff writer(s); no by-line.--> |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 }}</ref> however, the NDA was ultimately rejected citing the need for additional studies to determine efficacy and tolerability.<ref>{{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 }}</ref><ref>{{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}}</ref><ref>{{ClinicalTrialsGov|NCT02276209|Dasotraline Adult ADHD Study}}</ref> In July 2019, Sunovion’s NDA for the treatment of BED was accepted with an expected action date of May 2020.<ref>{{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 }}</ref> In May 2020, Sunovion halted its drug development program for dasotraline, withdrawing both NDAs for ADHD and BED.<ref name="Sunovion dc 2020">{{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}}</ref> |
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;Original Sibutramine patents |
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* {{US Patent|4746680}} |
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* {{US Patent|4806570}} |
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== Law == |
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=== Finland === |
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Dasotraline is completely unscheduled. |
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== See also == |
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* ] |
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== References == |
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{{Reflist|2}} |
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== Further reading == |
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;Liming Shao Patent |
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;Liming Shao Patent |
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* {{ 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 = }} |
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* {{ 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 = }} |
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* {{ 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 = }} |
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* {{ 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 = }} |
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{{Monoamine reuptake inhibitors}} |
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{{Antidepressants}} |
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{{Anxiolytics}} |
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{{Adrenergics}} |
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{{Dopaminergics}} |
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{{Serotonergics}} |
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{{nervous-system-drug-stub}} |
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