Mirogabalin besylate
[CAS# 1138245-21-2]

Identification

• Classification: API >> Other chemicals
• Name: Mirogabalin besylate
• Synonyms: (1R,5S,6S)-6-(Aminomethyl)-3-ethyl-bicyclo[3.2.0]hept-3-ene-6-acetic acid benzenesulfonate (1:1); DS 5565 besylate
• Molecular Formula: C₁₂H₁₉NO₂.C₆H₆O₃S
• Molecular Weight: 367.46
• CAS Registry Number: 1138245-21-2
• EC Number: 983-325-9
• SMILES: CCC1=C[C@@H]2[C@H](C1)C[C@@]2(CC(=O)O)CN.C1=CC=C(C=C1)S(=O)(=O)O

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS08 Danger
• Risk Statements: H315-H317-H318-H334-H335-H361-H373-H413
• Safety Statements: P203-P233-P260-P261-P264-P264+P265-P271-P272-P273-P280-P284-P302+P352-P304+P340-P305+P354+P338-P317-P318-P319-P321-P332+P317-P333+P317-P342+P316-P362+P364-P403-P403+P233-P405-P501

Discovery and Applications

Mirogabalin besylate is a pharmaceutical compound that is primarily used for the treatment of neuropathic pain. It is a selective ligand for the α2δ subunit of voltage-gated calcium channels, which plays a significant role in modulating excitatory neurotransmission in the central nervous system.

The discovery of mirogabalin was part of a broader effort to develop drugs that target the α2δ subunit, a component of the calcium channel involved in the transmission of pain signals. Mirogabalin is an analog of pregabalin and gabapentin, two other well-known α2δ ligands. It was developed by the pharmaceutical company Daiichi Sankyo, and its clinical development aimed at improving the efficacy and safety profile of similar compounds.

Mirogabalin has been shown to be effective in treating neuropathic pain, particularly in conditions such as diabetic peripheral neuropathy and postherpetic neuralgia. These conditions are characterized by chronic pain resulting from nerve damage or dysfunction, and mirogabalin’s ability to modulate calcium channel activity is thought to alleviate this pain by reducing the release of excitatory neurotransmitters. Its mechanism of action is similar to that of pregabalin and gabapentin, which also act on the α2δ subunit of voltage-gated calcium channels.

Clinical studies have demonstrated that mirogabalin can provide significant pain relief with a lower incidence of side effects compared to other drugs in its class. This is particularly important, as traditional treatments for neuropathic pain often come with adverse effects such as dizziness, sedation, and weight gain. Mirogabalin's more favorable side effect profile has made it a promising option for the treatment of chronic neuropathic pain, offering an alternative for patients who do not respond well to other medications.

Mirogabalin is marketed in the form of its besylate salt, which is used to improve the solubility and stability of the drug. The besylate salt form of mirogabalin has been shown to enhance its bioavailability and improve its pharmacokinetic properties, making it suitable for oral administration.

In conclusion, mirogabalin besylate is a selective α2δ ligand used in the treatment of neuropathic pain. Its discovery and development have provided a new therapeutic option for patients suffering from chronic pain conditions. Mirogabalin's clinical efficacy and safety profile, alongside its favorable side effect profile, make it a valuable addition to the available treatments for neuropathic pain.

References

2024. Usefulness of Mirogabalin in Central Neuropathic Pain After Stroke: Post Hoc Analysis of a Phase 3 Study by Stroke Type and Location. Pain and Therapy.
DOI: 10.1007/s40122-024-00616-3

2024. Efficacy and safety of add-on mirogabalin to conventional therapy for the treatment of peripheral neuropathic pain after thoracic surgery: the multicenter, randomized, open-label ADMIT-NeP study. BMC Cancer.
DOI: 10.1186/s12885-023-11708-2

2019. Mirogabalin: First Global Approval. Drugs.
DOI: 10.1007/s40265-019-01070-8