Sumatriptan

Sumatriptan, sold under the brand name Imitrex among others, is a medication used to treat migraine headaches and cluster headaches.[4][1] It is taken orally, intranasally, or by subcutaneous injection.[5] Therapeutic effects generally occur within three hours.[5] Sumatriptan is a serotonin (5-HT1B/1D) receptor agonist (triptan).[1]

The drug acts as a serotonin 5-HT1B, 5-HT1D, and 5-HT1F receptor agonist[6] and its common side effects include chest pressure, fatigue, vomiting, tingling, and vertigo. Serious side effects may include serotonin syndrome, heart attack, stroke, and seizures. With excessive use, medication overuse headaches may occur.[5] It is unclear if use during pregnancy or breastfeeding is safe.[7] The mechanism of action is not entirely clear. It is in the triptan class of medications.[5]

Sumatriptan was patented in 1982 and approved for medical use in 1992.[1][8] It is on the World Health Organization's List of Essential Medicines.[9] It is available as a generic medication.[4] In 2023, it was the 107th most commonly prescribed medication in the United States, with more than 6million prescriptions.[10][11] It is also available as the combination product sumatriptan/naproxen.[12]

Medical uses

Sumatriptan is indicated for the acute treatment of migraine with or without aura in adults; or the acute treatment of cluster headache in adults.[1]

Sumatriptan is effective for ending or relieving the intensity of migraine and cluster headaches.[13] Injected sumatriptan is more effective than other formulations.[14]

Oral sumatriptan can be used also in the treatment of post-dural puncture headache.[15]

Contraindications

Contraindications of sumatriptan include history of coronary artery disease (atherosclerosis) or coronary artery vasospasm, Wolff–Parkinson–White syndrome or other cardiac accessory conduction pathway disorders, history of stroke, transient ischemic attack, or hemiplegic or basilar migraine, peripheral vascular disease, ischemic bowel disease, uncontrolled hypertension, use of another triptan or ergot-related medication within the last 24hours, concomitant or recent use of a monoamine oxidase inhibitor (MAOI), hypersensitivity to sumatriptan, and severe hepatic impairment.[1]

Adverse effects

Serious cardiac events, including some that have been fatal, have occurred following the use of sumatriptan injection or tablets. Events reported have included coronary artery vasospasm, transient myocardial ischemia, myocardial infarction, ventricular tachycardia, and ventricular fibrillation.[16] There are reports of Takotsubo cardiomyopathy and transient amnesia after sumatriptan use.[17]

The most common side effects[1] reported by at least 2% of patients in controlled trials of sumatriptan (25-, 50-, and 100-mg tablets) for migraine are atypical sensations (paresthesia and warm/cold sensations) reported by 4% in the placebo group and 5–6% in the sumatriptan groups, pain and other pressure sensations (including chest pain) reported by 4% in the placebo group and 6–8% in the sumatriptan groups, neurological events (vertigo) reported by less than 1% in the placebo group and less than 1% to 2% in the sumatriptan groups. Malaise/fatigue occurred in less than 1% of the placebo group and 2–3% of the sumatriptan groups. Sleep disturbance occurred in less than 1% in the placebo group to 2% in the sumatriptan group.

Overdose

Overdose in animals produced effects including convulsions, tremor, paralysis, inactivity, extremity erythema, abnormal breathing, cyanosis, ataxia, mydriasis, and injection site reactions.[1] The elimination half-life of sumatriptan in humans is 2.5hours.[1] The effect of dialysis on sumatriptan levels is unknown.[1]

Overdose of sumatriptan can cause sulfhemoglobinemia, a rare condition in which the blood changes from red to green, due to the integration of sulfur into the hemoglobin molecule. If sumatriptan is discontinued, the condition reverses within a few weeks.[21]

Interactions

Concurrent use with other triptans or ergot-containing medications (e.g., ergotamine, dihydroergotamine) within 24 hours can result in additive vasoconstriction.[22][23] Increased systemic exposure to sumatriptan can occur if used within 2 weeks after a monoamine oxidase inhibitor (MAOI).[23] Cases of serotonin syndrome have been reported with co-administration of triptans and serotonin reuptake inhibitors.[22]

Pharmacology

Chemistry

Sumatriptan, also known as 5-(methylsulfamoylmethyl)-N,N-dimethyltryptamine, is a tryptamine derivative and a 5-substituted derivative of the psychedelic drug dimethyltryptamine (DMT).[56]

The experimental log P of sumatriptan is 0.8 to 0.93 and its predicted log P is 0.46 to 1.17.[57]

History

In 1991, Glaxo received approval for sumatriptan, which was the first available triptan.[58]

In July 2009, the US Food and Drug Administration (FDA) approved a single-use jet injector formulation of sumatriptan. The device delivers a subcutaneous injection of sumatriptan, without the use of a needle. Autoinjectors with needles have been previously available in Europe and North America.[59]

Phase III studies with an iontophoretic transdermal patch (Zelrix/Zecuity) started in July 2008.[60] This patch uses low voltage controlled by a pre-programmed microchip to deliver a single dose of sumatriptan through the skin within 30 minutes.[61][62]

Society and culture

External links