Sumatriptan

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Cat Number

API0232222

CAS Number

103628-46-2

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Product Detail Description Scientific Support Customer Q&A

CAS Number

103628-46-2

EINECS

600-462-9

Storage

Store at room temperature

Synonyms

Imitrex; Sumatran; Sumax; Imigran; Sumatriptanum; 1-(3-(2-(dimethylamino)ethyl)-1H-indol-5-yl)-N-methylmethanesulfonamide

Molecular Formula

C14H21N3O2S

Molecular Weight

295.4

Smiles

CNS(=O)(=O)CC1=CC2=C(C=C1)NC=C2CCN(C)C

Appearance

White to off-white solid powder

Melting Point

169-171°C

Boiling Point

497.7±55.0°C at 760 mmHg

Relative Density

1.2±0.1

General Description

Sumatriptan is a synthetic tryptamine derivative with a sulfonamide group, belonging to the first-generation triptans. Its chemical structure is 3-[2-(dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide. Sumatriptan is a white to off-white powder with a molecular weight of 295.4 Da (as the base), and is formulated as the succinate salt for stability.

Mechanism of Action

Sumatriptan acts as a selective agonist at the 5-HT1B and 5-HT1D receptors, causing vasoconstriction of the intracranial arteries and inhibiting the release of pro-inflammatory neuropeptides from the trigeminal nerve terminals. This reduces the neurogenic inflammation and vascular components of migraine. The drug also has a weak effect on the 5-HT1F receptor, but this is not the primary target.

Application

Sumatriptan is indicated for the acute treatment of migraine attacks with or without aura and for the treatment of cluster headaches. It is effective in reducing headache pain, photophobia, phonophobia, and nausea.

This is a protocol for a phase III double-blinded placebo-controlled trial comparing subcutaneous sumatriptan to placebo for acute postcraniotomy pain. The primary outcome is pain difference on VAS 60 min after study drug administration (n=136). The trial will assess whether sumatriptan adds to usual opioid analgesia.

Fig. 1 Participant timeline. NRS,Numerical Rating Score; VAS, Visual Analogue Scale. (Licina A, et al., 2019)

References

Licina A, et al. Subcutaneous sumatriptan for the treatment of postcraniotomy pain (SUPS trial): protocol for a randomised double-blinded placebo controlled trial. BMJ Open. 2019;9(8):e032388.

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

Yes, it is photosensitive. UV exposure can cause photodegradation and discoloration of the indole ring. Store in light-resistant containers, preferably amber glass or original packaging.

What is the recommended storage temperature for Sumatriptan?

Store at controlled room temperature (15-25°C). Avoid excessive heat above 30°C, which can accelerate oxidative degradation and sulfoxide formation.

Is Sumatriptan stable in solution for injection and nasal spray formulations?

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 electrochemical detection, ensuring it remains within pharmacopoeial limits.