Almotriptan

Almotriptan
Ball-and-stick model of the almotriptan molecule
Names
Trade namesAxert
Other namesAlmotriptan hydrogen malate[1]
IUPAC name
  • N,N-dimethyl-2- [5-(pyrrolidin-1-ylsulfonylmethyl)- 1H-indol-3-yl]-ethanamine
Clinical data
Drug classTriptan[1]
Main usesMigraine headaches[1]
Side effectsNausea, dry mouth, sleepiness, numbness[2]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Routes of
use		By mouth
Typical dose12.5 mg[1]
External links
AHFS/Drugs.comMonograph
MedlinePlusa603028
Legal
License data
Legal status
  • UK: POM (Prescription only)
  • US: ℞-only [3][4]
  • EU: Rx-only [5]
  • In general: ℞ (Prescription only)
Pharmacokinetics
Bioavailability70%
Protein binding35%
MetabolismLiver
Elimination half-life3–4 hours
Chemical and physical data
FormulaC17H25N3O2S
Molar mass335.47 g·mol−1
3D model (JSmol)
SMILES
  • CN(C)CCc2c[nH]c3ccc(CS(=O)(=O)N1CCCC1)cc23
InChI
  • InChI=1S/C17H25N3O2S/c1-19(2)10-7-15-12-18-17-6-5-14(11-16(15)17)13-23(21,22)20-8-3-4-9-20/h5-6,11-12,18H,3-4,7-10,13H2,1-2H3 checkY
  • Key:WKEMJKQOLOHJLZ-UHFFFAOYSA-N checkY

Almotriptan, sold under the brand name Axert among others, is a medication used to treat migraine headaches.[1] It may be used in people over the age of 11.[6] There is a lack of evidence for cluster headaches.[6] It is taken by mouth.[1]

Common side effects include nausea, dry mouth, sleepiness, and numbness.[2] Other side effects may include heart problems, stroke, Raynaud syndrome, serotonin syndrome, and medication overuse headaches.[2] Use in pregnancy may harm the baby.[2] It is a triptan.[1]

Almotriptan was patented in 1992 and approved for medical use in 2000.[7] It is available as a generic medication.[1] In the United Kingdom it costs the NHS about £2.80 a dose as of 2021.[1] This amount in the United States is about 9 USD.[8]

Medical uses

Almotriptan is prescribed to treat the acute headache phase of migraine attacks with or without aura.[9]

Efficacy

The efficacy and tolerability of almotriptan has been studied in trials totaling more than 4800 adults with either moderate or severe attacks of migraine. Its efficacy is more than placebo and alleviates nausea, photophobia and phonophobia linked to migraine attacks. Almotriptan has similar efficacy as a standard dose of sumatriptan, another triptan drug, and fewer adverse effects.[10]

Dosage

It is generally taken at a dose of 12.5 mg, with a second dose of 12.5 mg after two hours if needed.[1] More than 25 mg in a 24 hour period should not be used.[1] Low doses should be used in people with liver or kidney problems.[2]

Contraindications

As with other triptans, almotriptan should not be used in patients with a history, symptoms or signs of ischaemic heart disease (myocardial infarction, angina pectoris, documented silent ischaemia, Prinzmetal’s angina) or severe hypertension and uncontrolled mild or moderate hypertension. Other contraindications are previous cerebrovascular accident (CVA) or transient ischaemic attack (TIA), peripheral vascular disease, severe hepatic impairment, concomitant administration of ergotamine, ergotamine derivatives (including methysergide) and other 5-HT1B/D agonists.

Side effects

Almotriptan has proved to have an adverse effects profile similar to placebo when used following the Summary of Product Characteristics instructions (see references).

Interactions

Almotriptan is metabolized mainly by MAO-A and to lesser extent by CYP3A4 and CYP2D6. Studies of drugs used as preventive against migraine (propranolol and verapamil), anti-depressants (moclobemide and fluoxetine) yielded results that showed significant altering of the pharmacokinetics of almotriptan though they were deemed not clinically relevant.[10]

Pharmacology

Mechanism of action

Further information: Serotonin receptor agonist and Triptan § Mechanism_of_action

Like all triptans, almotriptan has a high and specific affinity for serotonin 5-HT1B/1D receptors. Binding of the drug to the receptor leads to vasoconstriction of the cranial (brain) blood vessels and thus affects the redistribution of blood flow. Almotriptan significantly increases cerebral blood flow and reduces blood flow through extracerebral cranial vessels. Even though it affects cranial blood vessels a single standard dose of almotriptan has no clinically significant effect on blood pressure or heart rate in both young and elderly healthy volunteers. Larger doses seem to slightly increase blood pressure but not beyond clinical relevance.[10]

Pharmacokinetics

Almotriptan has linear pharmacokinetics up to the 16-fold standard dose. Its biological half-life is 3 hours, and its bioavailability 70%. Cmax is observed 1.5–4 hours after oral administration, and approximately 50% of the drug is excreted unchanged in the urine. Metabolism is mediated through the enzymes MAO-A and CYP3A4 and CYP2D6 oxidation. Almotriptan clearance is moderately reduced in the elderly but does not require dose adjustment. Sex does not alter the pharmacokinetics of the drug. People with moderate-to-severe renal dysfunction are recommended to use only half the dose.[11]

Society and culture

Brand names

Brand names include Axert (US, Canada), Almogran (Belgium, Denmark, Finland, France, Germany, Italy, Ireland Portugal, Spain, the United Kingdom, the Netherlands, Sweden, Switzerland, South Korea…), Almotrex (Italy), Almozen (Bulgaria and Poland) and Amignul (Spain).

References

  1. 1 2 3 4 5 6 7 8 9 10 11 BNF 81: March-September 2021. BMJ Group and the Pharmaceutical Press. 2021. p. 500. ISBN 978-0857114105.
  2. 1 2 3 4 5 "DailyMed - ALMOTRIPTAN MALATE- almotriptan tablet, film coated". dailymed.nlm.nih.gov. Archived from the original on 22 March 2021. Retrieved 14 January 2022.
  3. ↑ "Almotriptan tablet, film coated". DailyMed. Archived from the original on 24 March 2021. Retrieved 17 February 2021.
  4. ↑ "Axert- almotriptan malate tablet, coated". DailyMed. Archived from the original on 23 March 2021. Retrieved 17 February 2021.
  5. ↑ "Archive copy" (PDF). Archived (PDF) from the original on 2021-11-05. Retrieved 2021-02-18.{{cite web}}: CS1 maint: archived copy as title (link)
  6. 1 2 "Almotriptan Monograph for Professionals". Drugs.com. Archived from the original on 23 January 2021. Retrieved 14 January 2022.
  7. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 531. ISBN 9783527607495. Archived from the original on 2020-10-23. Retrieved 2021-02-18.
  8. ↑ "Almotriptan Prices, Coupons & Savings Tips - GoodRx". GoodRx. Archived from the original on 14 June 2016. Retrieved 14 January 2022.
  9. ↑ "Almotriptan Facts and Comparisons". Drugs.com. Archived from the original on 7 November 2012. Retrieved 7 October 2012.
  10. 1 2 3 Keam SJ, Goa KL, Figgitt DP (2002). "Almotriptan: a review of its use in migraine". Drugs. 62 (2): 387–414. doi:10.2165/00003495-200262020-00010. PMID 11817980.
  11. ↑ McEnroe JD, Fleishaker JC (2005). "Clinical pharmacokinetics of almotriptan, a serotonin 5-HT(1B/1D) receptor agonist for the treatment of migraine". Clinical Pharmacokinetics. 44 (3): 237–46. doi:10.2165/00003088-200544030-00002. PMID 15762767. S2CID 23136754.
Identifiers:
  • "Almotriptan". Drug Information Portal. U.S. National Library of Medicine. Archived from the original on 2020-09-27. Retrieved 2021-02-18.
  • "Almotriptan malate". Drug Information Portal. U.S. National Library of Medicine. Archived from the original on 2021-03-18. Retrieved 2021-02-18.
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