Tasimelteon

Alias: VEC162; BMS-214778; VEC-162; BMS214778; VEC 162; BMS 214778; Tasimelteon; Hetlioz

Cat No.:V3725 Purity: ≥98%

COA Product Data Instructions for use SDS

Tasimelteon Chemical Structure CAS No.: 609799-22-6
Product category: Melatonin Receptor

This product is for research use only, not for human use. We do not sell to patients.

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ADD TO CART CHECKOUT BULK INQUIRY

1-708-310-1919 sales@invivochem.com

Other Forms of Tasimelteon:

Tasimelteon-d5 (BMS-214778-d5; VEC-162-d5)

Official Supplier of:

Top Publications Citing lnvivochem Products

Nature 2021, 597(7874):119-125.

Cell 2020,183:1202-1218.e25.

Science Adv 2022: 8, eabm9427.

Nature 597, 119–125 (2021)

Cell Stem Cell 2020,26(6):845-861.e12.

Science Trans Med 2023,15(701):eadd7872.

STTT 2023,8(1):91.

Cell Reports 2023,42(4):112313

Science Trans Med 2023, 15: eadd7872.

Cancer Cell 2021,39(4):529-547.e7.

Cancer Discov 2022,12(4):1106-1127.

Immunity 2023,56(3):620-634.e11.

J Am Chem Soc 2022,144:21831-21836.

Cell 2020,183:1202-1218.e25.

Science Adv 2022:8,eabm9427.

Nature 2021,597(7874):119-125.

Cell 2020,183:1202-1218.e25.

PNAS Nexus 2022,1(3):pgac063.

ACS Nano 2023,17(10):9110-9125.

Biomaterial 2023 Sep16:302:122333.

Purity & Quality Control Documentation

Current batch：

Purity: ≥98%

COA

MSDS

Instructions

Product Description
Bioactivity & Protocols
Physicochemical Properties
Solubility Data
Calculators
Clinical Trial Information
Biological Data

Product Description

Tasimelteon (formerly BMS-214778; VEC-162; trade name: Hetlioz), a novel circadian regulator, is the first medication approved by both FDA and European Medicines Agency (EMA) for the treatment of Non-24-hour Sleep-Wake Disorder (Non-24), or sleep-wake disorder in blind individuals. Tasimelteon is a strong and selective agonist of the melatonin (MT1 and MT2) receptor that has a 2- to 4-fold higher affinity for the MT2 receptor. Tasimelteon therapy over the long term was risk-free and well-tolerated. Placebo-controlled data in patients with insomnia and those who are not 24 support this.

Biological Activity I Assay Protocols (From Reference)

Targets

MT2 receptor ( pKi = 9.8 ); MT1 receptor ( pKi = 9.45 )

ln Vitro

In vitro activity: Tasimelteon is a dual melatonin receptor agonist, a circadian regulator that resets the master clock in the suprachiasmatic nuclei of the hypothalamus by binding to both melatonin MT1 and MT2 receptors[3]. Tasimelteon's affinity for the MT2 receptor is four times greater than that of the MT1 receptor[2].

ln Vivo

Tasimelteon has a half-life of roughly two hours in rats and monkeys, which is longer than that of melatonin[1]. The mean absolute bioavailability of tasimelteon is about 38.3%. Tasimelteon's metabolites have higher oral-to-IV exposure ratios and lower metabolite-to-parent ratios following IV administration. These data suggest that while tasimelteon undergoes first-pass metabolism, a significant portion of its metabolism happens post- rather than presystemically. Tasimelteon administered intravenously orally was well tolerated[2].

Animal Protocol

Rats and monkeys

References

[1]. Expert Opin Investig Drugs . 2011 Jul;20(7):987-93.

[2]. Am J Ther . 2015 Sep-Oct;22(5):355-60.

[3]. J Clin Pharmacol. 2015 May; 55(5): 525–533.

These protocols are for reference only. InvivoChem does not independently validate these methods.

Physicochemical Properties

Molecular Formula

C15H19NO2

Molecular Weight

245.32

Exact Mass

245.14

Elemental Analysis

C, 73.44; H, 7.81; N, 5.71; O, 13.04

CAS #

609799-22-6

Related CAS #

Tasimelteon-d5; 1962124-51-1

Appearance

Solid powder

SMILES

N-[[(1R,2R)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methyl]propanamide

InChi Key

PTOIAAWZLUQTIO-GXFFZTMASA-N

InChi Code

InChI=1S/C15H19NO2/c1-2-15(17)16-9-10-8-13(10)11-4-3-5-14-12(11)6-7-18-14/h3-5,10,13H,2,6-9H2,1H3,(H,16,17)/t10-,13+/m0/s1

Chemical Name

N-[[(1R,2R)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methyl]propanamide

Synonyms

VEC162; BMS-214778; VEC-162; BMS214778; VEC 162; BMS 214778; Tasimelteon; Hetlioz

HS Tariff Code

2934.99.9001

Storage

Powder -20°C 3 years

4°C 2 years

In solvent -80°C 6 months

-20°C 1 month

Shipping Condition

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Solubility Data

Solubility (In Vitro)

DMSO: 49 mg/mL (~199.7 mM)

Water: N/A

Ethanol: N/A

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (10.19 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (10.19 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (10.19 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

Solubility in Formulation 4: 5%DMSO + Corn oil: 2.0mg/ml (8.15mM)

(Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	4.0763 mL	20.3815 mL	40.7631 mL
	5 mM	0.8153 mL	4.0763 mL	8.1526 mL
	10 mM	0.4076 mL	2.0382 mL	4.0763 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Mass

Concentration

Volume

Molecular Weight*

Calculate Reset

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

Calculate the Mass of a compound required to prepare a solution of known volume and concentration
Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume

See Example

An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?

Enter 350.26 in the Molecular Weight (MW) box
Enter 10 in the Concentration box and choose the correct unit (mM)
Enter 5 in the Volume box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Concentration (Start)

Volume (Start)

Concentration (End)

Volume (End)

Calculate Reset

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:

Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
Enter 25 into the Concentration (End) box and select the correct unit (mM)
Enter 25 into the Volume (End) box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box

Molecular formula

Total molecular weight

g/mol

Calculate Reset

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4 c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:

To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.

Definitions of molecular mass, molecular weight, molar mass and molar weight:

Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.

Volume (to add to vial)

Mass (in vial)

Desired Reconstitution Concentration

Calculate Reset

Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
Click the “Calculate” button
The answer appears in the Volume (to add to vial) box

In vivo Formulation Calculator (Clear solution)

Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)

Dosage mg/kg

Average weight of animals g

Dosing volume per animal μL

Number of animals

Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)

% DMSO

% Tween 80

% ddH₂O

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Calculation results

Working concentration： mg/mL；

Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH₂O，mix and clarify.

Note： (1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.

Clinical Trial Information

NCT Number	Recruitment	interventions	Conditions	Sponsor/Collaborators	Start Date	Phases
NCT05572281	Active Recruiting	Drug: Tasimelteon Oral Capsule Drug: Tasimelteon Oral Suspension	Healthy	Vanda Pharmaceuticals	May 18, 2022	Phase 1
NCT05361707	Recruiting	Drug: Tasimelteon Oral Capsule, Tasimelteon Liquid Suspension	Sleep Disorder Sleep Disturbance	Vanda Pharmaceuticals	July 28, 2021	Phase 3
NCT05922995	Not yet recruiting	Drug: Tasimelteon	REM Behavior Disorder	Brigham and Women's Hospital	September 30, 2023	Early Phase 1
NCT01477619	Completed	Drug: Tasimelteon	Healthy Volunteers	Vanda Pharmaceuticals	November 2011	Phase 1
NCT01540500	Completed	Drug: Tasimelteon Drug: Fluvoxamine	Healthy Volunteers	Vanda Pharmaceuticals	February 2012	Phase 1

Biological Data

Mean plasma concentrations of tasimelteon (plotted on a semilogarithmic scale) after oral administration of 20 mg of tasimelteon to subjects with (A) mild (N = 8) or (B) moderate (N = 8) hepatic impairment and healthy matched controls (N = 8 for both groups). J Clin Pharmacol. 2015 May; 55(5): 525–533.

Summary of AUC for tasimelteon and its metabolites after oral administration of 20 mg of tasimelteon to (A) subjects with mild or moderate hepatic impairment and healthy matched controls and (B) subjects with severe renal impairment or ESRD and healthy matched controls. J Clin Pharmacol. 2015 May; 55(5): 525–533.

Mean plasma concentrations of tasimelteon after oral administration of single 20 mg doses of tasimelteon to subjects with ESRD (N = 8), subjects with severe impairment (N = 8), and matched controls (N = 8 for both groups)—linear (A) and semilogarithmic axes (B). Expert Opin Investig Drugs . 2011 Jul;20(7):987-93.