Sumatriptan Succinate

Sumatriptan Succinate

Cat Number
API103628484
CAS Number
103628-48-4

For research use only. We do not supply to patients.

For pharmaceutical-grade products or other inquiries, please contact our experts.

CAS Number
103628-48-4
EINECS
600-463-4
Storage
Store at room temperature
Synonyms
Sumavel DosePro; Alsuma; Onzetra Xsail; Imitrex Statdose; GR 43175C; Zembrace SymTouch; Sumatriptan Galpharm
Molecular Formula
C18H27N3O6S
Molecular Weight
413.5
Smiles
CNS(=O)(=O)CC1=CC2=C(C=C1)NC=C2CCN(C)C.C(CC(=O)O)C(=O)O
Appearance
White to off-white powder
Melting Point
165-166°C
Boiling Point
497.7±55.0°C at 760 mmHg
Relative Density
1.2±0.1
General Description
Sumatriptan succinate is the succinate salt of the first-generation triptan, a sulfonamide-containing tryptamine derivative with a dimethylaminoethyl side chain. The parent molecule is 3-(2-(dimethylamino)ethyl)-N-methyl-1H-indole-5-methanesulfonamide. The succinate salt enhances water solubility and chemical stability.
Mechanism of Action
Sumatriptan activates 5-HT1B receptors on intracranial blood vessels, causing vasoconstriction of dilated cerebral arteries, and 5-HT1D receptors on presynaptic trigeminal nerve terminals, inhibiting the release of calcitonin gene-related peptide (CGRP) and other pro-inflammatory neuropeptides. This dual action relieves the vascular and neurogenic components of migraine. The drug does not cross the blood-brain barrier well, so its central effects are minimal.
Application
Sumatriptan is indicated for the acute treatment of migraine attacks with or without aura and for cluster headaches. It is not intended for prophylaxis. The drug is effective in relieving headache pain, photophobia, phonophobia, and nausea. Due to its vasoconstrictor activity, it is contraindicated in patients with coronary artery disease, uncontrolled hypertension, or hemiplegic/basilar migraine.

Sumatriptan is effective for acute migraine across all four routes of administration (oral, subcutaneous, intranasal, rectal), but efficacy varies by route. Subcutaneous 6 mg provides the highest pain‑free rate at 2 hours (59% vs. 15% placebo; NNT 2.3), while oral 50 mg achieves complete relief in about 28% (NNT 6.1). Adverse events are generally mild and short‑lived, most common with subcutaneous and higher oral/intranasal doses. The authors conclude that route selection should balance efficacy, tolerability, cost, and patient preference, with subcutaneous being most potent but also most expensive and associated with more adverse effects.

Fig. 1 Calculated NNTs for a pain‐free response after a specified time, in participants treating moderate or severe migraine pain. (Derry CJ, <i>et al</i>., 2014) Fig. 1 Calculated NNTs for a pain‐free response after a specified time, in participants treating moderate or severe migraine pain. (Derry CJ, et al., 2014)

References

  1. Derry CJ, et al. Sumatriptan (all routes of administration) for acute migraine attacks in adults - overview of Cochrane reviews. Cochrane Database Syst Rev. 2014;2014(5):CD009108.

This review summarizes AVP‑825 (ONZETRA® Xsail®), an intranasal sumatriptan powder delivery system for acute migraine. By exploiting nasal anatomy for efficient absorption, it achieves rapid uptake and lower systemic exposure than oral sumatriptan. Clinical studies demonstrate earlier onset of efficacy and a lower rate of atypical sensations than oral triptans, with mostly mild dysgeusia. The design aligns pharmacokinetics, anatomy, and device features to optimize acute migraine treatment, offering a fast‑acting, non‑oral alternative.

Fig. 2 AVP-825 for intranasal delivery of sumatriptan powder. (Tepper SJ, <i>et al</i>., 2018) Fig. 2 AVP-825 for intranasal delivery of sumatriptan powder. (Tepper SJ, et al., 2018)

References

  1. Tepper SJ, Johnstone MR. Breath-powered sumatriptan dry nasal powder: an intranasal medication delivery system for acute treatment of migraine. Med Devices (Auckl). 2018;11:147-156.

Does Sumatriptan Succinate require protection from light during long-term storage?

Yes, it is photosensitive. UV light can cause photodegradation and discoloration. Store in light-resistant containers, preferably original opaque packaging.

What is the recommended storage temperature for Sumatriptan Succinate?

Store at controlled room temperature (15-25°C). Avoid temperatures above 30°C, which can accelerate oxidative degradation of the indole ring.

Is Sumatriptan Succinate stable in solution for injection or nasal spray?

Aqueous solutions are stable when protected from light and stored at room temperature for up to 24 hours.

How is the impurity sumatriptan N-oxide (an oxidative degradation product) monitored?

This degradation product is quantified using a stability-indicating HPLC method with UV or electrochemical detection, ensuring it remains within ICH limits.
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