|Molecular formula||C 14 H 21 N 3 O 2 S|
|External identifiers / databases|
|Mechanism of action||
selective serotonin agonist
|Molar mass||295.40 g · mol -1|
169-171 ° C
|As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .|
Application areas (indications)
Sumatriptan must not be used in patients with a heart attack , suspected ischemic heart disease, coronary vasospasm ( Prinzmetal's angina ), peripheral blood vessel disorders , moderate to severe or uncontrolled high blood pressure . Sumatriptan should also not be used in the case of known severe liver dysfunction and a history of transient ischemic attacks.
Sumatriptan must not be used at the same time as ergot alkaloids and their derivatives (e.g. ergotamine , dihydroergotamine ), as there is an increased risk of vasospasm. Sumatriptan should also be used no earlier than two weeks after the end of treatment with monoamine oxidase inhibitors , as these inhibit the breakdown of sumatriptan.
Sumatriptan must not be used in the case of known hypersensitivity to the active substance. Particular caution is also required in the case of a known allergy to sulfonamides .
Use during pregnancy and breastfeeding
There is currently insufficient experience with its use in pregnancy . Previous experience does not indicate an increased risk of malformations during pregnancy. However, animal studies in rabbits have shown an embryotoxic effect of sumatriptan.
Sumatriptan is excreted in breast milk . Any potential risk to the child can be avoided by expressing and discarding breast milk up to 12 hours after taking sumatriptan.
One of the most frequently discussed, albeit rare, side effects of the use of sumatriptan is angina pectoris- like pressure and tightness in the chest, which are attributed to a constriction of the coronary arteries . In animal experiments, however, it was only possible to produce a narrowing of the coronary arteries with much higher concentrations of the substance in the blood . An increase in blood pressure can also be observed in some patients.
Taken in high doses, the color of the blood can change green-black. This is called sulfhemoglobinemia and is caused by the fact that the sulfur contained in the substance in the form of a sulfonamide group is incorporated into hemoglobin. In an average-sized adult male, 200 mg a day can cause this color change.
Although the data are limited, there is a risk of aggravating the side effects of ergot alkaloids when used concomitantly with sumatriptan. Sumatriptan should therefore not be used in combination with ergotamine (see contraindications). After using ergotamine, a safety interval of at least 24 hours before sumatriptan therapy should be observed; in the opposite case, the minimum interval should be 6 hours.
MAOIs can increase the effects and side effects of these substances by inhibiting the breakdown of sumatriptan and the body's own serotonin. Therefore, the simultaneous use of sumatriptan and MAOIs is contraindicated.
In rare cases, when a triptan and an antidepressant from the group of SSRIs (selective serotonin reuptake inhibitors) or SNRI (selective serotonin and noradrenaline reuptake inhibitors) are taken at the same time, potentially life-threatening interactions of the serotonin syndrome occur. Too much serotonin accumulates in the nervous system and its effect is intensified by sumatriptan. Symptoms of serotonin syndrome can include restlessness, hallucinations, loss of coordination, rapid heartbeat, fluctuations in blood pressure, increased body temperature, increased reflexes, nausea, vomiting, diarrhea, and death.
Mechanism of action
Sumatriptan is a selective agonist at the serotonin receptors 5-HT 1B , 5-HT 1D and 5-HT 1F , which occur on cerebral blood vessels and presynaptically on neurons . Activation of these receptors by sumatriptan leads to a narrowing of the enlarged (dilated) cerebral blood vessels during a migraine attack. On the other hand, sumatriptan leads to a reduction in the release of inflammatory mediators such as serotonin, calcitonin gene-related peptides (CGRP) and substance P, which dilate blood vessels and cause pain .
Since sumatriptan has poor oral bioavailability and can only insufficiently cross the blood-brain barrier , numerous so-called "2nd generation triptans" with improved pharmacokinetic properties have been developed.
Sumatriptan was the first triptan to be approved for medicinal purposes and came onto the market in 1991 under the brand name Imitrex (USA) and a little later as Imigran (D, CH, A). Since the drug's patent protection expired in May 2006, numerous generics are now available. Various forms of application are available for sumatriptan . In addition to oral dosage forms (tablets with 50 or 100 mg), non-oral sumatriptan preparations such as suppositories, nasal sprays, pre-filled syringes or pens for subcutaneous administration are also approved. Non-oral dosage forms can be advantageous, particularly in the case of pronounced migraine nausea with vomiting. Nasal and subcutaneous dosage forms should enable a faster onset of action. The low oral bioavailability can be circumvented by subcutaneous administration of the active ingredient.
- A. Schuurmans, C. van Weel: Pharmacologic treatment of migraine. Comparison of guidelines. In: Can Fam Physician. 51, June 2005, pp. 838-843. PMID 15986940
- The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition. 2006, ISBN 0-911910-00-X , p. 1544.
- harmonized classification for this substance . A labeling of 1- [3- (2-dimethylaminoethyl) -1H-indol-5-yl] -N-methylmethanesulfonamide in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on 12. July 2020. There is not yet a
- Specialist information Imigran ® Injekt, Imigran ® 50/100 mg film- coated tablets. GlaxoSmithKline GmbH & Co. KG. As of May 2008.
- When sulfhemoglobin turns the blood dark green. ( Memento from March 4, 2016 in the Internet Archive ) on: aerzteblatt.de
- FDA Public Health Advisory: Combined Use of 5-Hydroxytryptamine Receptor Agonists (Triptans), Selective Serotonin Reuptake Inhibitors (SSRIs) or Selective Serotonin / Norepinephrine Reuptake Inhibitors (SNRIs) May Result in Life-threatening Serotonin Syndrome. July 19, 2006.
- V. Limmroth: mechanism of action of triptans . In: Pharmacy in our time . tape 31 , no. 5 , 2002, p. 458-461 , doi : 10.1002 / 1615-1003 (200209) 31: 5 <458 :: AID-PAUZ458> 3.0.CO; 2-G , PMID 12369163 .
- NuPathe's Zecuity Approved by the FDA for the Acute Treatment of Migraine .
Imigran (D, A, CH), numerous generics (D, CH)