Vortioxetine

Base Information

• Chemical Name: Vortioxetine
• CAS No.: 508233-74-7
• Molecular Formula: C18H22N2S
• Molecular Weight: 298.452
• Hs Code.: 2933599090
• European Community (EC) Number: 823-919-6
• UNII: 3O2K1S3WQV
• DSSTox Substance ID: DTXSID80965062
• Nikkaji Number: J3.095.728H
• Wikipedia: Vortioxetine
• Wikidata: Q3563148
• NCI Thesaurus Code: C152917
• RXCUI: 1455099
• Pharos Ligand ID: 61XVHP11WT9M
• Metabolomics Workbench ID: 152123
• ChEMBL ID: CHEMBL2104993
• Mol file: 508233-74-7.mol

Synonyms:1-(2-(2,4-dimethylphenylsulfanyl)phenyl)piperazine;brintellix;Lu AA21004;Lu-AA21004;LuAA21004;vortioxetine;vortioxetine hydrobromide

Chemical Property of Vortioxetine

Chemical Property:

• Boiling Point: 424.833 °C at 760 mmHg
• PKA: 8.85±0.10(Predicted)
• Flash Point: 210.732 °C
• PSA: 40.57000
• Density: 1.164 g/cm³
• LogP: 4.25800
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 298.15036988
• Heavy Atom Count: 21
• Complexity: 316

Purity/Quality:

HPLC>99% ^*data from raw suppliers

Vortioxetine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Drug Classes: Antidepressant Agents
• Canonical SMILES: CC1=CC(=C(C=C1)SC2=CC=CC=C2N3CCNCC3)C
• Recent ClinicalTrials: Sequenced Treatment Alternatives to Relieve Adolescent Depression (STAR-AD)
• Recent EU Clinical Trials: Cognitive effects of adjuntive Vortioxetine in early Schizophrenia
• Recent NIPH Clinical Trials: A Bioequivalence Study of the Lu AA21004 20 mg and 2x10 mg Tablets
• Description: In September 2013, vortioxetine (also known as Lu AA21004) was approved in the United States for the treatment of major depressive disorder (MDD). Vortioxetine was discovered from a designed multiple ligand approach to identifying an antidepressant agent that combined SERT inhibition with 5-HT1A agonism to more rapidly desensitize 5-HT1A receptors and 5-HT3A antagonism to improve mood and cognitive function. Vortioxetine has a human SERT IC50=5.4 nM, an EC50=200 nM as a human 5-HT1A receptor agonist (efficacy=96%; Ki=39 nM), and an IC50=12 nM as a human 5-HT3A receptor antagonist (Ki=3.7 nM). It has weak inhibition of the dopamine and norepinephrine transporters, but high affinity for the human β1-noradrenergic receptor (Ki=46 nM), human 5-HT1B receptor (Ki=33 nM, partial agonist), and the human 5-HT-7 receptor (Ki=19 nM, antagonist).
• Uses: Vortioxetine can be used in biological study of effectiveness of long term vortioxetine treatment of patients with major depressive disorder.
• Drug interactions: Potentially hazardous interactions with other drugs Antibacterials: avoid with linezolid; concentration reduced by rifampicin - consider increasing vortioxetine dose. Antidepressants: possible increased risk of convulsions with SSRIs and, tricyclics; avoid with moclobemide; increased risk of hypertension and CNS excitation with MAOIs - avoid. Antiepileptics: concentration possibly reduced by carbamazepine, fosphenytoin and phenytoin - consider increasing vortioxetine dose. Antimalarials: possible increased risk of convulsions with mefloquine; avoid with artemether with lumefantrine and artenimol with piperaquine. Antipsychotics: possible increased risk of convulsions with butyrophenones, phenothiazines and thioxanthenes. Dopaminergics: risk of CNS excitation and hypertension with rasagiline and selegiline.

Technology Process of Vortioxetine

There total 112 articles about Vortioxetine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

1-[2-(2,4-dimethyl-phenylsulfanyl)-phenyl]-piperazine L-(+)mandelic acid salt → vortioxetine (508233-74-7)

Guidance literature:

With sodium hydroxide; In dichloromethane;

Reference yield: 98.0%

Vortioxetine hydrobromide (960203-27-4) → vortioxetine (508233-74-7)

Guidance literature:

With sodium hydroxide; water; In ethyl acetate; for 0.166667h;

Reference yield: 98.0%

1-{2-[(2,4-dimethylphenyl)sulfanyl]phenyl}piperazine hydrobromide → vortioxetine (508233-74-7)

Guidance literature:

With sodium hydroxide; In ethyl acetate; for 0.166667h;

upstream raw materials:

Vortioxetine hydrobromide

4-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine-1-carboxylic acid tert-butyl ester

piperazine

1-Bromo-2-iodobenzene

Downstream raw materials:

Vortioxetine hydrobromide

Vortioxetine hydrochloride

Vortioxetine mesylate

1-[2-(2,4-dimethylphenylsulfanyl)-phenyl]piperazine sulfate

Refernces

• 1、 Dodds, Amy C.,Sutherland, Andrew. "Regioselective C-H Thioarylation of Electron-Rich Arenes by Iron(III) Triflimide Catalysis". . p. 5922 - 5932. Retrieved 2021/05/04.
• 2、 -. "Preparation method of novel severe depression treatment drug". Paragraph 0025; 0027; 0029-0031; 0036. . Retrieved 2021/10/30.