VORTIOXETINE DL-LACTATE

Possibly Marketed Outside US

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 Search

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

Description
Sources: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/002717/WC500159447.pdf | https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/204447s011lbl.pdf | http://www.ema.europa.eu/docs/en_GB/document_library/Report/2013/08/WC500147012.pdf | https://www.ncbi.nlm.nih.gov/pubmed/26945513

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Serotonin 1a (5-HT1a) receptor 172 Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21486038 \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204447s000lbl.pdf	Agonist 2678	15.0 nM [Ki]
Serotonin 3a (5-HT3a) receptor 46 Target ID: CHEMBL1899 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21486038 \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204447s000lbl.pdf	Antagonist 2778	3.7 nM [Ki]
Serotonin transporter 178 Target ID: CHEMBL228 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21486038 \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204447s000lbl.pdf	Inhibitor 8297	1.6 nM [Ki]
Serotonin 7 (5-HT7) receptor 31 Target ID: CHEMBL3155 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21486038 \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204447s000lbl.pdf	Antagonist 2778	19.0 nM [Ki]
Serotonin 1b (5-HT1b) receptor 46 Target ID: CHEMBL1898 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21486038 \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204447s000lbl.pdf	Partial Agonist 290	33.0 nM [Ki]
Serotonin 1d (5-HT1d) receptor 52 Target ID: CHEMBL1983 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21486038 \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204447s000lbl.pdf	Antagonist 2778	54.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Major depressive disorder 173 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/002717/WC500159447.pdf	Primary		Approved 8429	Brintellix Approved Use BRINTELLIX is indicated for the treatment of major depressive disorder (MDD) Launch Date 2013

PubMed

Title	Date	PubMed
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	21486038
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	26174134

Patents

Sample Use Guides

In Vivo Use Guide

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 Use Guide

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).

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