(S)-3-Amino-3-(4-chlorophenyl)propionic acid
[CAS# 131690-60-3]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Other amino acid derivatives
• Name: (S)-3-Amino-3-(4-chlorophenyl)propionic acid
• Synonyms: (3S)-3-amino-3-(4-chlorophenyl)propanoic acid
• Molecular Formula: C₉H₁₀ClNO₂
• Molecular Weight: 199.63
• Protein Sequence: X
• CAS Registry Number: 131690-60-3
• EC Number: 635-379-7
• SMILES: C1=CC(=CC=C1[C@H](CC(=O)O)N)Cl

Properties

• Density: 1.333±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.588, Calc.^*
• Boiling Point: 345.8±32.0 °C (760 mmHg), Calc.^*
• Flash Point: 162.9±25.1 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

(S)-3-Amino-3-(4-chlorophenyl)propionic acid, also known as Zavegepant, is a chemical compound that has garnered significant attention in recent years due to its therapeutic potential, particularly in the treatment of migraines. The compound is a selective CGRP receptor antagonist, which makes it a promising candidate for the acute treatment of migraines, a debilitating neurological disorder that affects millions of people worldwide. Zavegepant's development highlights the growing interest in targeting the calcitonin gene-related peptide (CGRP) pathway, a key player in the pathophysiology of migraines.

The discovery of Zavegepant can be traced back to the increasing understanding of the role of CGRP in migraine mechanisms. CGRP is a neuropeptide that plays a significant role in vasodilation and inflammation, both of which are involved in migraine attacks. Researchers have focused on developing CGRP receptor antagonists as a means of preventing or treating migraines by blocking the action of CGRP. Zavegepant was developed as part of these efforts and has been shown to effectively block CGRP receptors, preventing the cascade of events that lead to a migraine attack.

Zavegepant is typically administered as a nasal spray, which allows for rapid absorption and quick onset of action, making it an attractive option for acute migraine relief. Clinical trials have demonstrated that Zavegepant is highly effective in reducing migraine symptoms when compared to placebo treatments. Its ability to rapidly alleviate pain and other symptoms associated with migraines has made it a valuable addition to the arsenal of treatments available to patients suffering from this condition. Furthermore, Zavegepant has shown a favorable safety profile, with minimal side effects reported during clinical trials, making it a promising option for long-term use in migraine management.

In addition to its use in treating migraines, there is ongoing research into the broader applications of CGRP receptor antagonists like Zavegepant. Scientists are exploring their potential for treating other conditions associated with CGRP dysregulation, such as cluster headaches and certain types of pain syndromes. The continued development and refinement of Zavegepant and other CGRP receptor antagonists may lead to new therapeutic options for patients suffering from a range of neurovascular disorders.

Zavegepant's success exemplifies the advances in targeted drug development, particularly in the context of neurological disorders. By specifically targeting the CGRP receptor, Zavegepant offers a more direct and effective approach to treating migraines compared to traditional treatments, which often have broader effects on the body and come with more significant side effects. As research continues, it is likely that Zavegepant will play a significant role in the evolving landscape of migraine treatment.

References

2019. Synthesis of β-Amino Acids. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-232-00203

2015. Synthesis of β-Amino Acids. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-215-00164