Rizatriptan Benzoate (MK-462 Benzoate)

Alias: MK-462 Benzoate; izatriptan Benzoate; MK-0462; MK 462; rizatriptan benzoate; Maxalt; MK 0462; MK 462
Cat No.:V0979 Purity: ≥98%
Rizatriptan Benzoate (Maxalt; formerly MK 0462; MK 462)is a potent and selective agonist at serotonin 5-HT1B and 5-HT1D receptors with anti-migraine activity.
Rizatriptan Benzoate (MK-462 Benzoate) Chemical Structure CAS No.: 145202-66-0
Product category: 5-HT Receptor
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
10mg
25mg
50mg
100mg
250mg
500mg
1g
Other Sizes

Other Forms of Rizatriptan Benzoate (MK-462 Benzoate):

  • Rizatriptan-d6 benzoate (rizatriptan benzoate d6 (benzoate))
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Rizatriptan Benzoate (Maxalt; formerly MK 0462; MK 462) is a potent and selective agonist at serotonin 5-HT1B and 5-HT1D receptors with anti-migraine activity. It might be applied to the management of severe migraines.

Biological Activity I Assay Protocols (From Reference)
Targets
5-HT1
ln Vitro

In vitro activity: Rizatriptan Benzoate (also known as MK-462 Benzoate) is a brand-new, highly effective, and selective agonist at serotonin 5-HT1B and 5-HT1D receptors; it may be utilized to treat acute attacks of migraines.

ln Vivo
Rizatriptan blocks the release of CGRP in anesthetized guinea pigs by acting on 5-HT(1D) receptors on perivascular trigeminal nerves, thereby inhibiting neurogenic vasodilation. In anesthetized guinea pigs, rizatriptan causes a brief decrease in dural blood vessel diameter, which returns to baseline levels in 10 minutes.[1] The dural plasma protein extravasation that results from intense electrical stimulation of the trigeminal ganglion is markedly inhibited by rizatriptan. In rats under anesthesia, ritariptan dramatically lowers electrically induced dural vasodilation.[2] It has been observed that Rizatriptan Benzoate can downregulate SP gene expression in the rat midbrain by significantly reducing SP mRNA levels in the midbrains of both normal and model group rats. In rat models of migraine, rizatriptan benzoate diminishes the analgesic effects of the endogenous pain modulatory system by significantly lowering midbrain PENK mRNA expression, which in turn lowers midbrain met-enkephalin and leu-enkephalin levels.[3] The number of Fos-like immunoreactive neurons in the caudal part and raphe magnus nucleus of the spinal trigeminal nucleus decreased in conscious rats, while the number increased in the periaqueductal gray and remained unchanged in the ventromedial hypothalamic and mediodorsal thalamus nuclei. These findings were observed in rats administered Riztriptan Benzoate.[4] Rizatriptan Benzoate significantly lowers the rats' head-flicking frequency. Additionally, compared to when treatment is not received, rizatriptan benzoate significantly shortens the duration of grooming behavior by almost two times. [5]
Animal Protocol
N/A
Rats
References

[1]. Br J Pharmacol . 2001 Aug;133(7):1029-34.

[2]. Eur J Pharmacol . 1997 Jun 5;328(1):61-4.

[3]. Neural Regen Res . 2012 Jan 15;7(2):131-5.

[4]. Brain Res . 2011 Jan 7:1367:340-6.

[5]. Brain Res . 2011 Jan 12:1368:151-8.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C22H25N5O2
Molecular Weight
391.47
Exact Mass
391.2
Elemental Analysis
C, 67.50; H, 6.44; N, 17.89; O, 8.17
CAS #
145202-66-0
Related CAS #
Rizatriptan-d6 benzoate; 1216984-85-8
Appearance
Solid powder
SMILES
CN(C)CCC1=CNC2=C1C=C(C=C2)CN3C=NC=N3.C1=CC=C(C=C1)C(=O)O
InChi Key
JPRXYLQNJJVCMZ-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H19N5.C7H6O2/c1-19(2)6-5-13-8-17-15-4-3-12(7-14(13)15)9-20-11-16-10-18-20;8-7(9)6-4-2-1-3-5-6/h3-4,7-8,10-11,17H,5-6,9H2,1-2H3;1-5H,(H,8,9)
Chemical Name
benzoic acid;N,N-dimethyl-2-[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethanamine
Synonyms
MK-462 Benzoate; izatriptan Benzoate; MK-0462; MK 462; rizatriptan benzoate; Maxalt; MK 0462; MK 462
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: 20~50 mg/mL (51.1~127.7 mM)
Water: ~46 mg/mL (~117.5 mM)
Ethanol: <1 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.39 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 (6.39 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 (6.39 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: 50 mg/mL (127.72 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.5545 mL 12.7724 mL 25.5447 mL
5 mM 0.5109 mL 2.5545 mL 5.1089 mL
10 mM 0.2554 mL 1.2772 mL 2.5545 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

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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?
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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:
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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.)
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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.

(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
NCT04384367 Recruiting Drug: Maxalt 10Mg Tablet
Drug: Flanax 550mg
Migraine Eurofarma Laboratorios S.A. December 30, 2022 Phase 3
NCT00897949 Completed Drug: rizatriptan benzoate
(MK0462)
Drug: Comparator: placebo
Migraine Headache Organon and Co March 1995 Phase 3
NCT00899379 Completed Drug: rizatriptan benzoate
Drug: Comparator: Placebo
Migraine Headache Organon and Co April 1995 Phase 3
NCT01286207 Completed Drug: Rizatriptan 5 mg
Drug: Rizatriptan 10 mg
Migraine Disorders Organon and Co March 1995 Phase 3
NCT00812006 Completed Drug: rizatriptan benzoate
Drug: Comparator: placebo
Migraine Organon and Co March 24, 2009 Phase 3
Biological Data
  • Rizatriptan Benzoate
    Effects of (a) 0.3 mg kg−1 i.v. human-αCGRP(8-37) on neurogenic dural vasodilation and (b) rizatriptan on neurogenic or rat-αCGRP-evoked dural vasodilation in anaesthetized guinea-pigs.Br J Pharmacol.2001 Aug;133(7):1029-34.
  • Rizatriptan Benzoate
    Effects of (a) PNU-142633 and (b) LY334370 on neurogenic dural vasodilation in anaesthetized guinea-pigs.Br J Pharmacol.2001 Aug;133(7):1029-34.
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