U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H15Cl2N.ClH
Molecular Weight 328.664
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DASOTRALINE HYDROCHLORIDE

SMILES

Cl.N[C@@H]1CC[C@@H](C2=CC(Cl)=C(Cl)C=C2)C3=CC=CC=C13

InChI

InChIKey=YKXHIERZIRLOLD-DFIJPDEKSA-N
InChI=1S/C16H15Cl2N.ClH/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;1H/t11-,16+;/m0./s1

HIDE SMILES / InChI
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C16H15Cl2N
Molecular Weight 292.203
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Dasotraline, also known as SEP-225,289, is a serotonin-norepinephrine-dopamine reuptake inhibitor (SNDRI). It has an extended half-life (47-77 hours) that supports the potential for plasma concentrations yielding a continuous therapeutic effect over the 24-hour dosing interval at steady state. Dasotraline has shown a lower potential for abuse than methylphenidate in clinical testing. Dasotraline was discovered by Sunovion Pharmaceuticals Inc. and is currently in development to evaluate its use in treating ADHD in adults and children, and BED in adults in the United States. It has not been approved by the U.S. Food and Drug Administration (FDA) for the treatment of ADHD, BED or any other disorder.

CNS Activity

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Inhibitor
8297
 11.0 nM [IC50]
Inhibitor
8297
 6.0 nM [IC50]
Inhibitor
8297
 4.0 nM [IC50]
Sodium-dependent serotonin transporter
40
Target ID: P31645
Gene ID: 6532.0
Gene Symbol: SLC6A4
Target Organism: Homo sapiens (Human)
Inhibitor
8297
Sodium-dependent dopamine transporter
42
Target ID: Q01959
Gene ID: 6531.0
Gene Symbol: SLC6A3
Target Organism: Homo sapiens (Human)
Inhibitor
8297
Sodium-dependent noradrenaline transporter
38
Target ID: P23975
Gene ID: 6530.0
Gene Symbol: SLC6A2
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
656
Unknown

Approved Use

Unknown
Primary
Phase III
656
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
14 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26794682
36 mg single, oral
dose: 36 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DASOTRALINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
740 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26794682
36 mg single, oral
dose: 36 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DASOTRALINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
36 mg single, oral
Highest studied dose
Dose: 36 mg
Route: oral
Route: single
Dose: 36 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/26794682
Page: p.32
healthy, ADULT
n = 39
Health Status: healthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 39
Sources:
https://pubmed.ncbi.nlm.nih.gov/26794682
Page: p.32
Disc. AE: Ventricular tachycardia...
AEs leading to
discontinuation/dose reduction:
Ventricular tachycardia (2.6%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/26794682
Page: p.32
5.5 mg 1 times / day multiple, oral (mean)
Studied dose
Dose: 5.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5.5 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/32926604
Page: e5, sup. table 2
unhealthy, ADULT
n = 155
Health Status: unhealthy
Condition: eating disorder
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 155
Sources:
https://pubmed.ncbi.nlm.nih.gov/32926604
Page: e5, sup. table 2
Disc. AE: Insomnia, Paranoia...
AEs leading to
discontinuation/dose reduction:
Insomnia (grade 3, 1.3%)
Paranoia (grade 3, 0.65%)
Visual hallucinations (grade 3, 0.65%)
Anxiety (grade 3, 0.65%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/32926604
Page: e5, sup. table 2
4 mg 1 times / day multiple, oral
Studied dose
Dose: 4 mg, 1 times / day
Route: oral
Route: multiple
Dose: 4 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30694697
Page: p.6
unhealthy, CHILD
n = 115
Health Status: unhealthy
Condition: attention deficit hyperactivity disorder
Age Group: CHILD
Sex: M+F
Food Status: UNKNOWN
Population Size: 115
Sources:
https://pubmed.ncbi.nlm.nih.gov/30694697
Page: p.6
Disc. AE: Abnormal behavior, Attention deficit hyperactivity disorder...
AEs leading to
discontinuation/dose reduction:
Abnormal behavior (0.9%)
Attention deficit hyperactivity disorder (0.9%)
Visual hallucinations (0.9%)
Visual hallucinations (0.9%)
Hypnopompic hallucination (0.9%)
Insomnia (3.5%)
Hallucinations, mixed (0.9%)
Chest pain (0.9%)
Irritability (0.9%)
Costochondritis (0.9%)
Pruritus (0.9%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/30694697
Page: p.6
AEs

AEs

AESignificanceDosePopulation
Ventricular tachycardia 2.6%
Disc. AE
36 mg single, oral
Highest studied dose
Dose: 36 mg
Route: oral
Route: single
Dose: 36 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/26794682
Page: p.32
healthy, ADULT
n = 39
Health Status: healthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 39
Sources:
https://pubmed.ncbi.nlm.nih.gov/26794682
Page: p.32
Anxiety grade 3, 0.65%
Disc. AE
5.5 mg 1 times / day multiple, oral (mean)
Studied dose
Dose: 5.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5.5 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/32926604
Page: e5, sup. table 2
unhealthy, ADULT
n = 155
Health Status: unhealthy
Condition: eating disorder
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 155
Sources:
https://pubmed.ncbi.nlm.nih.gov/32926604
Page: e5, sup. table 2
Paranoia grade 3, 0.65%
Disc. AE
5.5 mg 1 times / day multiple, oral (mean)
Studied dose
Dose: 5.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5.5 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/32926604
Page: e5, sup. table 2
unhealthy, ADULT
n = 155
Health Status: unhealthy
Condition: eating disorder
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 155
Sources:
https://pubmed.ncbi.nlm.nih.gov/32926604
Page: e5, sup. table 2
Visual hallucinations grade 3, 0.65%
Disc. AE
5.5 mg 1 times / day multiple, oral (mean)
Studied dose
Dose: 5.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5.5 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/32926604
Page: e5, sup. table 2
unhealthy, ADULT
n = 155
Health Status: unhealthy
Condition: eating disorder
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 155
Sources:
https://pubmed.ncbi.nlm.nih.gov/32926604
Page: e5, sup. table 2
Insomnia grade 3, 1.3%
Disc. AE
5.5 mg 1 times / day multiple, oral (mean)
Studied dose
Dose: 5.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5.5 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/32926604
Page: e5, sup. table 2
unhealthy, ADULT
n = 155
Health Status: unhealthy
Condition: eating disorder
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 155
Sources:
https://pubmed.ncbi.nlm.nih.gov/32926604
Page: e5, sup. table 2
Abnormal behavior 0.9%
Disc. AE
4 mg 1 times / day multiple, oral
Studied dose
Dose: 4 mg, 1 times / day
Route: oral
Route: multiple
Dose: 4 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30694697
Page: p.6
unhealthy, CHILD
n = 115
Health Status: unhealthy
Condition: attention deficit hyperactivity disorder
Age Group: CHILD
Sex: M+F
Food Status: UNKNOWN
Population Size: 115
Sources:
https://pubmed.ncbi.nlm.nih.gov/30694697
Page: p.6
Attention deficit hyperactivity disorder 0.9%
Disc. AE
4 mg 1 times / day multiple, oral
Studied dose
Dose: 4 mg, 1 times / day
Route: oral
Route: multiple
Dose: 4 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30694697
Page: p.6
unhealthy, CHILD
n = 115
Health Status: unhealthy
Condition: attention deficit hyperactivity disorder
Age Group: CHILD
Sex: M+F
Food Status: UNKNOWN
Population Size: 115
Sources:
https://pubmed.ncbi.nlm.nih.gov/30694697
Page: p.6
Chest pain 0.9%
Disc. AE
4 mg 1 times / day multiple, oral
Studied dose
Dose: 4 mg, 1 times / day
Route: oral
Route: multiple
Dose: 4 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30694697
Page: p.6
unhealthy, CHILD
n = 115
Health Status: unhealthy
Condition: attention deficit hyperactivity disorder
Age Group: CHILD
Sex: M+F
Food Status: UNKNOWN
Population Size: 115
Sources:
https://pubmed.ncbi.nlm.nih.gov/30694697
Page: p.6
Costochondritis 0.9%
Disc. AE
4 mg 1 times / day multiple, oral
Studied dose
Dose: 4 mg, 1 times / day
Route: oral
Route: multiple
Dose: 4 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30694697
Page: p.6
unhealthy, CHILD
n = 115
Health Status: unhealthy
Condition: attention deficit hyperactivity disorder
Age Group: CHILD
Sex: M+F
Food Status: UNKNOWN
Population Size: 115
Sources:
https://pubmed.ncbi.nlm.nih.gov/30694697
Page: p.6
Hallucinations, mixed 0.9%
Disc. AE
4 mg 1 times / day multiple, oral
Studied dose
Dose: 4 mg, 1 times / day
Route: oral
Route: multiple
Dose: 4 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30694697
Page: p.6
unhealthy, CHILD
n = 115
Health Status: unhealthy
Condition: attention deficit hyperactivity disorder
Age Group: CHILD
Sex: M+F
Food Status: UNKNOWN
Population Size: 115
Sources:
https://pubmed.ncbi.nlm.nih.gov/30694697
Page: p.6
Hypnopompic hallucination 0.9%
Disc. AE
4 mg 1 times / day multiple, oral
Studied dose
Dose: 4 mg, 1 times / day
Route: oral
Route: multiple
Dose: 4 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30694697
Page: p.6
unhealthy, CHILD
n = 115
Health Status: unhealthy
Condition: attention deficit hyperactivity disorder
Age Group: CHILD
Sex: M+F
Food Status: UNKNOWN
Population Size: 115
Sources:
https://pubmed.ncbi.nlm.nih.gov/30694697
Page: p.6
Irritability 0.9%
Disc. AE
4 mg 1 times / day multiple, oral
Studied dose
Dose: 4 mg, 1 times / day
Route: oral
Route: multiple
Dose: 4 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30694697
Page: p.6
unhealthy, CHILD
n = 115
Health Status: unhealthy
Condition: attention deficit hyperactivity disorder
Age Group: CHILD
Sex: M+F
Food Status: UNKNOWN
Population Size: 115
Sources:
https://pubmed.ncbi.nlm.nih.gov/30694697
Page: p.6
Pruritus 0.9%
Disc. AE
4 mg 1 times / day multiple, oral
Studied dose
Dose: 4 mg, 1 times / day
Route: oral
Route: multiple
Dose: 4 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30694697
Page: p.6
unhealthy, CHILD
n = 115
Health Status: unhealthy
Condition: attention deficit hyperactivity disorder
Age Group: CHILD
Sex: M+F
Food Status: UNKNOWN
Population Size: 115
Sources:
https://pubmed.ncbi.nlm.nih.gov/30694697
Page: p.6
Visual hallucinations 0.9%
Disc. AE
4 mg 1 times / day multiple, oral
Studied dose
Dose: 4 mg, 1 times / day
Route: oral
Route: multiple
Dose: 4 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30694697
Page: p.6
unhealthy, CHILD
n = 115
Health Status: unhealthy
Condition: attention deficit hyperactivity disorder
Age Group: CHILD
Sex: M+F
Food Status: UNKNOWN
Population Size: 115
Sources:
https://pubmed.ncbi.nlm.nih.gov/30694697
Page: p.6
Visual hallucinations 0.9%
Disc. AE
4 mg 1 times / day multiple, oral
Studied dose
Dose: 4 mg, 1 times / day
Route: oral
Route: multiple
Dose: 4 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30694697
Page: p.6
unhealthy, CHILD
n = 115
Health Status: unhealthy
Condition: attention deficit hyperactivity disorder
Age Group: CHILD
Sex: M+F
Food Status: UNKNOWN
Population Size: 115
Sources:
https://pubmed.ncbi.nlm.nih.gov/30694697
Page: p.6
Insomnia 3.5%
Disc. AE
4 mg 1 times / day multiple, oral
Studied dose
Dose: 4 mg, 1 times / day
Route: oral
Route: multiple
Dose: 4 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30694697
Page: p.6
unhealthy, CHILD
n = 115
Health Status: unhealthy
Condition: attention deficit hyperactivity disorder
Age Group: CHILD
Sex: M+F
Food Status: UNKNOWN
Population Size: 115
Sources:
https://pubmed.ncbi.nlm.nih.gov/30694697
Page: p.6
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1587
inhibitor
1767
inhibitor
1852

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
1524

CYP2C8
911

CYP3A
214

CYP2C19
1478

CYP2B6
810
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
1692
 no
CYP2C8
965
 no
CYP2C9
1819
 no
CYP3A4
1925
 no
CYP2C19
1553
 weak [Inhibition 0.1 uM]
CYP2B6
1001
 yes [IC50 0.33 uM]
CYP2D6
1891
 yes [IC50 1 uM]
CYP3A
298
 yes [IC50 4.7 uM]
PubMed

PubMed

TitleDatePubMed
Triple uptake inhibitors: therapeutic potential in depression and beyond.
2007 Sep
Characterization of the electrophysiological properties of triple reuptake inhibitors on monoaminergic neurons.
2011 Mar
Patents

Patents

08097760
2
08524950
2
20040092605
2
20060014982
3

Sample Use Guides

In Vivo Use Guide
Adult Attention Deficit Hyperactivity Disorder: Dasotraline 4 mg, 6 mg, 8 mg, flexibly dosed, once daily
Route of Administration: Oral
In Vitro Use Guide
Average in vitro potencies for transporter function inhibition by SEP-225289 have been measured (8, 17, and 10 nM, for the dopamine, norepinephrine, and serotonin transporters, respectively).
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:49:42 GMT 2023
Edited
by admin
on Fri Dec 15 15:49:42 GMT 2023
Record UNII
1VIY7J4C0I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DASOTRALINE HYDROCHLORIDE
USAN   WHO-DD  
USAN  
Official Name English
1-NAPHTHALENAMINE, 4-(3,4-DICHLOROPHENYL)-1,2,3,4-TETRAHYDRO-, (1R,4S)-, HYDROCHLORIDE
Systematic Name English
NORSERTRALINE HYDROCHLORIDE, (1R,4S)-TRANS-
Common Name English
SEP-225289 HYDROCHLORIDE
Code English
DASOTRALINE HYDROCHLORIDE [USAN]
Common Name English
Dasotraline hydrochloride [WHO-DD]
Common Name English
(1R,4S)-4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-amine hydrochloride
Systematic Name English
(1R,4S)-TRANS-NORSERTRALINE HYDROCHLORIDE
Common Name English
Code System Code Type Description
NCI_THESAURUS
C166517
Created by admin on Fri Dec 15 15:49:42 GMT 2023 , Edited by admin on Fri Dec 15 15:49:42 GMT 2023
PRIMARY
CAS
675126-08-6
Created by admin on Fri Dec 15 15:49:42 GMT 2023 , Edited by admin on Fri Dec 15 15:49:42 GMT 2023
PRIMARY
PUBCHEM
25192248
Created by admin on Fri Dec 15 15:49:42 GMT 2023 , Edited by admin on Fri Dec 15 15:49:42 GMT 2023
PRIMARY
DRUG BANK
DBSALT002174
Created by admin on Fri Dec 15 15:49:42 GMT 2023 , Edited by admin on Fri Dec 15 15:49:42 GMT 2023
PRIMARY
FDA UNII
1VIY7J4C0I
Created by admin on Fri Dec 15 15:49:42 GMT 2023 , Edited by admin on Fri Dec 15 15:49:42 GMT 2023
PRIMARY
USAN
BC-41
Created by admin on Fri Dec 15 15:49:42 GMT 2023 , Edited by admin on Fri Dec 15 15:49:42 GMT 2023
PRIMARY
SMS_ID
300000044618
Created by admin on Fri Dec 15 15:49:42 GMT 2023 , Edited by admin on Fri Dec 15 15:49:42 GMT 2023
PRIMARY
ChEMBL
CHEMBL3301595
Created by admin on Fri Dec 15 15:49:42 GMT 2023 , Edited by admin on Fri Dec 15 15:49:42 GMT 2023
PRIMARY
Related Record Type Details
Structure of DASOTRALINE
PARENT -> SALT/SOLVATE
NIH
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