Rizatriptan benzoate
[CAS# 145202-66-0]

Identification

• Classification: Biochemical >> Inhibitor >> Neuronal signaling >> 5-HT receptor agonist
• Name: Rizatriptan benzoate
• Synonyms: N,N-Dimethyl-2-[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethylamine benzoate
• Molecular Formula: C₁₅H₁₉N₅.C₇H₆O₂
• Molecular Weight: 391.47
• CAS Registry Number: 145202-66-0
• EC Number: 604-465-6
• SMILES: CN(C)CCC1=CNC2=C1C=C(C=C2)CN3C=NC=N3.C1=CC=C(C=C1)C(=O)O

Properties

• Solubility: 20 mg/mL (DMSO), 46 mg/mL (water)
• Melting point: 178-180 °C

Safety Data

• Hazard Symbols: GHS07;GHS08 Danger
• Risk Statements: H302-H319-H336-H360-H361-H372
• Safety Statements: P203-P260-P261-P264-P264+P265-P270-P271-P280-P301+P317-P304+P340-P305+P351+P338-P318-P319-P330-P337+P317-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Reproductive toxicity	Repr.	1B	H360
Specific target organ toxicity - single exposure	STOT SE	3	H336
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Acute toxicity	Acute Tox.	4	H302
Reproductive toxicity	Repr.	2	H361
Reproductive toxicity	Lact.	-	H362
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Serious eye damage	Eye Dam.	1	H318

Discovery and Applications

Rizatriptan benzoate, a pharmaceutical compound used in the treatment of migraines, was discovered through the systematic exploration of serotonin receptor agonists for migraine therapy. Developed by Merck & Co., Rizatriptan benzoate emerged as a result of targeted drug design efforts aimed at identifying selective serotonin 5-HT1B/1D receptor agonists. This compound was synthesized with the intention of specifically targeting serotonin receptors involved in the pathophysiology of migraines, particularly those associated with vasoconstriction and pain modulation. After extensive preclinical studies, Rizatriptan benzoate entered clinical trials, demonstrating efficacy in relieving migraine symptoms and achieving FDA approval in 1998 as an acute treatment for migraines.

References

2024-06. Neurophysiological and Vascular Mechanisms of Action of Serotoninergic Drugs for Abortive Migraine Treatment
DOI: 10.1007/s11055-024-01652-4

2016-04-28. Multivariate Optimization of Rizatriptan Benzoate-Loaded Solid Lipid Nanoparticles for Brain Targeting and Migraine Management
DOI: 10.1208/s12249-016-0532-0

2005-05. Anti-migraine action of triptans is preceded by transient aggravation of headache caused by activation of meningeal nociceptors
DOI: 10.1016/j.pain.2005.01.027