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Details

Stereochemistry RACEMIC
Molecular Formula C18H22N2S.C3H6O3
Molecular Weight 388.524
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VORTIOXETINE DL-LACTATE

SMILES

CC(O)C(O)=O.CC1=CC=C(SC2=CC=CC=C2N3CCNCC3)C(C)=C1

InChI

InChIKey=KJXWEKCEAVJWHZ-UHFFFAOYSA-N
InChI=1S/C18H22N2S.C3H6O3/c1-14-7-8-17(15(2)13-14)21-18-6-4-3-5-16(18)20-11-9-19-10-12-20;1-2(4)3(5)6/h3-8,13,19H,9-12H2,1-2H3;2,4H,1H3,(H,5,6)

HIDE SMILES / InChI

Molecular Formula C3H6O3
Molecular Weight 90.0779
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula C18H22N2S
Molecular Weight 298.446
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Vortioxetine DL-lactate is a lactate salt of vortioxetine and its chemical name is 1-[2-(2,4-dimethylphenylsulfanyl)-phenyl]-piperazine (RS)-2-hydroxypropanoate. Vortioxetine DL-lactate is manufactured from the milled Vortioxetine hydrobromide via the nonisolated free base. One site is involved in the manufacture of the lactate salt of Vortioxetine. Vortioxetine is an antidepressant for the treatment of major depressive disorder. Unlike the film-coated tablets where a hydrobromide salt of the active substance is used, the oral drops formulation contains vortioxetine DL-lactate as the active substance which shows higher solubility in polar solvents. Vortioxetine is a novel multimodal antidepressant that acts as a serotonin (5-HT)3, 5-HT7, and 5-HT1D receptor antagonist; 5-HT1B receptor partial agonist; 5-HT1A receptor agonist; and 5-HT transporter inhibitor in vitro.

CNS Activity

Curator's Comment: Vortioxetine binds to the presynaptic serotonin reuptake site, increasing the level of serotonin (5-HT) in the neuronal synapse, as well as selectively binding to a variety of other serotonin receptors, thus enhancing CNS serotonergic activity.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Brintellix

Approved Use

BRINTELLIX is indicated for the treatment of major depressive disorder (MDD)

Launch Date

2013
PubMed

PubMed

TitleDatePubMed
Discovery of 1-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine (Lu AA21004): a novel multimodal compound for the treatment of major depressive disorder.
2011 May 12
Differentiated effects of the multimodal antidepressant vortioxetine on sleep architecture: Part 2, pharmacological interactions in rodents suggest a role of serotonin-3 receptor antagonism.
2015 Oct
Patents

Sample Use Guides

Each ml of solution contains vortioxetine (D,L)-lactate equivalent to 20 mg vortioxetine. Each drop contains 1 mg vortioxetine. The starting and recommended dose of Brintellix is 10 mg vortioxetine once daily in adults less than 65 years of age. Depending on individual patient response, the dose may be increased to a maximum of 20 mg vortioxetine once daily or decreased to a minimum of 5 mg vortioxetine once daily. 5 mg corresponding to 5 drops. 10 mg corresponding to 10 drops. 15 mg corresponding to 15 drops. 20 mg corresponding to 20 drops. After the depressive symptoms resolve, treatment for at least 6 months is recommended for consolidation of the antidepressive response.
Route of Administration: Oral
In vitro characterization showed that Vortioxetine was a potent rSERT inhibitor (IC50 = 5.3 nM) when assessed in rat brain synaptosomes, and a similar potency was found on hSERT when expressed in Chinese hamster ovary (CHO) cells (IC50 = 5.4 nM).
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:01:13 GMT 2023
Edited
by admin
on Sat Dec 16 10:01:13 GMT 2023
Record UNII
V39BK25ME9
Record Status Validated (UNII)
Record Version
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Name Type Language
VORTIOXETINE DL-LACTATE
Common Name English
VORTIOXETINE-DL-LACTATE
Common Name English
PROPANOIC ACID, 2-HYDROXY-, COMPD. WITH 1-(2-((2,4-DIMETHYLPHENYL)THIO)PHENYL)PIPERAZINE (1:1)
Systematic Name English
Vortioxetine lactate [WHO-DD]
Common Name English
Code System Code Type Description
PUBCHEM
75293775
Created by admin on Sat Dec 16 10:01:13 GMT 2023 , Edited by admin on Sat Dec 16 10:01:13 GMT 2023
PRIMARY
EVMPD
SUB130400
Created by admin on Sat Dec 16 10:01:13 GMT 2023 , Edited by admin on Sat Dec 16 10:01:13 GMT 2023
PRIMARY
SMS_ID
100000156466
Created by admin on Sat Dec 16 10:01:13 GMT 2023 , Edited by admin on Sat Dec 16 10:01:13 GMT 2023
PRIMARY
CAS
1253056-29-9
Created by admin on Sat Dec 16 10:01:13 GMT 2023 , Edited by admin on Sat Dec 16 10:01:13 GMT 2023
PRIMARY
FDA UNII
V39BK25ME9
Created by admin on Sat Dec 16 10:01:13 GMT 2023 , Edited by admin on Sat Dec 16 10:01:13 GMT 2023
PRIMARY