Naratriptan

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Structural formula
Structure of naratriptan
General
Non-proprietary name Naratriptan
other names

N -Methyl-3- (1-methyl-4-piperidyl) indole-5-ethanesulfonamide

Molecular formula
  • C 17 H 25 N 3 O 2 S (naratriptan)
  • C 17 H 25 N 3 O 2 S HCl (naratriptan hydrochloride)
External identifiers / databases
CAS number
  • 121679-13-8 (naratriptan)
  • 143388-64-1 (naratriptan hydrochloride )
EC number 601-800-8
ECHA InfoCard 100.121.501
PubChem 4440
DrugBank DB00952
Wikidata Q421315
Drug information
ATC code

N02 CC02

Drug class

Triptans

Mechanism of action

Selective 5-HT 1 receptor agonist

properties
Molar mass
  • 335.46 g · mol -1 (naratriptan)
  • 371.93 g · mol -1 (· naratriptan hydrochloride)
Melting point
  • 170-171 ° C (naratriptan)
  • 237–239 ° C (naratriptan hydrochloride)
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Naratriptan is a selective serotonin agonist from the triptan group . It is used as a medicinal substance in the acute therapy of migraines and in the prevention of cluster headaches . Naratriptan was developed by GlaxoSmithKline and is effective in a lower dose compared to other triptans ( DDD = 2.5 mg).

Naratriptan was the first ever prescription- free triptan in the world. In Germany, it was available from April 2016 in pack sizes of up to 2 tablets of 2.5 mg for the acute treatment of the headache phases of migraine attacks in self-medication.

pharmacology

Mechanism of action

Naratriptan is a selective agonist at the serotonin receptors 5-HT 1B and 5-HT 1D , which occur on cerebral blood vessels and presynaptically on neurons . Activation of these receptors by naratriptan thus leads, on the one hand, to a constriction of the dilated cerebral blood vessels during a migraine attack and, on the other hand, to a reduction in the release of inflammatory mediators .

Pharmacokinetics

Maximum plasma levels are reached within 2 to 3 hours.

Side effects

One of the most characteristic, albeit rare, side effects of naratriptan use is angina- like pressure and tightness in the chest, which are attributed to a constriction of the coronary arteries . An increase in blood pressure can also be observed in some patients. In studies, these side effects were no more common with the currently commercially available dose of 2.5 mg than with placebo , which is why the prescription requirement for packs of up to 2 tablets of 2.5 mg has been lifted.

Interactions

Naratriptan should not be used in combination with ergotamine as there is an increased risk of coronary spasms.

The American health authority warns of the potentially life-threatening interaction of the serotonin syndrome (the body accumulates too much serotonin in the nervous system) when a triptan and an antidepressant from the group of SSRIs (selective serotonin reuptake inhibitors) or SNRI (selective serotonin and noradrenaline) are taken at the same time. Reuptake inhibitors) when triptans are taken with an SSRI or an SNRI. Symptoms of serotonin syndrome can include restlessness, hallucinations, loss of coordination, rapid heartbeat, fluctuations in blood pressure, increased body temperature, increased reflexes, nausea, vomiting, and diarrhea. In extreme cases, death is even possible if serotonin syndrome is not recognized and / or treated incorrectly.

Studies

A meta-analysis compared the efficacy and safety profile of various triptans in the acute therapy of migraine.

Trade names

Monopreparations

Antimigrin (A), Formigran (D), Naramig (D, A, CH), several generics

Individual evidence

  1. a b The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition, 2006, p. 1110, ISBN 978-0-911910-00-1 .
  2. This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  3. Elke Wolf: Naratriptan without a prescription , Pharmazeutische Zeitung, April 28, 2006.
  4. Limmroth V: mechanism of action of triptans . In: Pharmacy in our time . 31, No. 5, 2002, pp. 458-461. doi : 10.1002 / 1615-1003 (200209) 31: 5 <458 :: AID-PAUZ458> 3.0.CO; 2-G . PMID 12369163 .
  5. GlaxoSmithKline Consumer Healthcare: Product Information Formigran 2.5 mg film-coated tablets . As of June 2016.
  6. Ferrari MD, Roon KI, Lipton RB, Goadsby PJ: Oral triptans (serotonin 5-HT (1B / 1D) agonists) in acute migraine treatment: a meta-analysis of 53 trials . In: The Lancet . 358, No. 9294, November 2001, pp. 1668-75. doi : 10.1016 / S0140-6736 (01) 06711-3 . PMID 11728541 .