Vortioxetine hydrobromide
- CAS No.
- 960203-27-4
- Chemical Name:
- Vortioxetine hydrobromide
- Synonyms
- Vortioxetine HBr;1-[2-[(2,4-Dimethylphenyl)thio]phenyl]piperazine hydrobromide;Vortioxetin hydrobromide;CS-1537;AA21004;AA 21004;AA-21004;Lu AA21004 (HBr);Vortioxetine impurity L;Fluoxetine Hydrobromide
- CBNumber:
- CB72614372
- Molecular Formula:
- C18H23BrN2S
- Molecular Weight:
- 379.36
- MOL File:
- 960203-27-4.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/5/15 13:17:26
| Melting point | >223°C (dec.) |
|---|---|
| storage temp. | Refrigerator |
| solubility | DMSO (Slightly), Methanol (Slightly) |
| form | Solid |
| color | Pale Beige to Light Beige |
| InChI | InChI=1S/C18H22N2S.BrH/c1-14-7-8-17(15(2)13-14)21-18-6-4-3-5-16(18)20-11-9-19-10-12-20;/h3-8,13,19H,9-12H2,1-2H3;1H |
| InChIKey | VNGRUFUIHGGOOM-UHFFFAOYSA-N |
| SMILES | S(C1C=CC(C)=CC=1C)C1C=CC=CC=1N1CCNCC1.Br |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   GHS07,GHS09 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H410-H317-H302 | |||||||||
| Precautionary statements | P261-P272-P280-P302+P352-P333+P313-P321-P363-P501-P273-P391-P501-P264-P270-P301+P312-P330-P501 | |||||||||
| HS Code | 29339900 | |||||||||
| NFPA 704 |
|
Vortioxetine hydrobromide Chemical Properties,Uses,Production
Uses
Vortioxetine Hydrobromide is a multimodal serotonergic agent that inhibits 5-HT1A, 5-HT1B, 5-HT3A, 5-HT7 receptor and SERT (1,2,3).
Definition
ChEBI: Vortioxetine hydrobromide is a hydrobromide obtained by combining vortioxetine with one molar equivalent of hydrobromic acid. Used for treatment of major depressive disorder. It has a role as an antidepressant, an anxiolytic drug, a serotonergic antagonist and a serotonergic agonist. It contains a vortioxetine(1+).
Synthesis
As the picture 2 showed, we have developed a new and practical synthetic route to vortioxetine hydrobromide on a hectogram scale. Adopting commercially available materials, through simple and traditional steps, including nucleophilic substitution, catalytic hydrogenation, and cyclization of the piperazine ring, gave the final product in 63.2% yield over three steps and with 99.3% purity (HPLC). Purification methods for the intermediates involved in the route are also given.
Pic.3 A new synthetic route to vortioxetine hydrobromide
Solubility in water
Vortioxetine hydrobromide is slightly soluble in water; at ambient temperature solubility is equivalent to approximately 1.3 mg base/mL, pH being 5.5 in the saturated solution.
Mode of action
Vortioxetine Hydrobromide is a hydrobromide salt form of vortioxetine, a serotonin (5-HT) modulator and stimulator (SMS), with antidepressant activity. Vortioxetine inhibits the reuptake of serotonin and norepinephrine from the synaptic cleft and acts variably as a serotonin receptor agonist (5-HT1A), partial agonist (5-HT1B) or antagonist (5-HT3, 5-HT1D and 5-HT7). It is not clear how this agent's purported multimodal mechanism of action contributes to its antidepressant effect; however, it is presumed to increase the synaptic availability of serotonin and norepinephrine.
Precautions
Vortioxetine is a serotonergic drug that has a risk of causing serotonin syndrome, especially when combined with other serotonergic drugs such as SSRIs, SNRIs, TCAs, or MAOIs.
Vortioxetine has been known to cause an increase in the risk of bleeding because of interference with serotonin reuptake. The concomitant use of NSAIDs, aspirin, warfarin, and anticoagulants may increase the risk of abnormal bleeding.
Among patients using vortioxetine, reports of symptoms of mania/hypo-mania were less than 0.1%. However, this drug should be used with caution in patients with a personal or family history of bipolar disorder, mania, or hypomania.
Hyponatremia was reported in one patient taking vortioxetine. Hyponatremia is related to the syndrome of inappropriate antidiuretic hormone secretion (SIADH). Elderly patients are at higher risk for hyponatremia, as well as patients taking diuretics. Vortioxetine should be discontinued if signs and symptoms of hyponatremia are present and if there is a decrease in sodium levels[6].
References
[1]. connie sanchez, karen e. asin, francesc artigas, et al. vortioxetine, a novel antidepressant with multimodal activity: review of preclinical and clinical data. pharmacology & therapeutics, 2015, 145:43-57.
[2]. er-min gu, chengke huang, bingqing liang, et al. an uplc–ms/ms method for the quantitation of vortioxetine in rat plasma: application to a pharmacokinetic study. j. chromatogr. b, 2015, 997:70-74.
[3]. a. mørk, a. pehrson, l.t. brennum, s. møller nielsen, et al. pharmacological effects of lu aa21004: a novel multimodal compound for the treatment of major depressive disorder. j. pharmacol. exp. ther., 2012, 340:666-675.
[4]. david m. lovinger. serotonin’s role in alcohol’s effects on the brain. alcohol health & research world, 1997, 21(2):114-120.
[5]. arne mørk, liliana p. montezinho, silke miller, et al. vortioxetine (lu aa21004), a novel multimodal antidepressant, enhances memory in rats. pharmacology, biochemistry and behavior, 2013, 105:41-50.
[6] Andrew, et al. "Vortioxetine (brintellix): a new serotonergic antidepressant. "P & T : a peer-reviewed journal for formulary management(2015).
Vortioxetine hydrobromide Preparation Products And Raw materials
Raw materials
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