Chemistry:Sumatriptan

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Sumatriptan, sold under the brand name Imitrex among others, is a medication used to treat migraine headaches and cluster headaches.[1][2] It is taken orally, intranasally, or by subcutaneous injection.[3] Therapeutic effects generally occur within three hours.[3] Sumatriptan is a serotonin (5-HT1B/1D) receptor agonist (triptan).[2]

The drug acts as a serotonin 5-HT1B, 5-HT1D, and 5-HT1F receptor agonism[4][5] 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.[3] It is unclear if use during pregnancy or breastfeeding is safe.[6] The mechanism of action is not entirely clear. It is in the triptan class of medications.[3]

Sumatriptan was patented in 1982 and approved for medical use in 1992.[2][7] It is on the World Health Organization's List of Essential Medicines.[8] It is available as a generic medication.[1] In 2023, it was the 107th most commonly prescribed medication in the United States, with more than 6 million prescriptions.[9][10] It is also available as the combination product sumatriptan/naproxen.[11]

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.[2]

Sumatriptan is effective for ending or relieving the intensity of migraine and cluster headaches.[12] Injected sumatriptan is more effective than other formulations.[13]

Oral sumatriptan can be used also in the treatment of post-dural puncture headache.[14]

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 24 hours, concomitant or recent use of a monoamine oxidase inhibitor (MAOI), hypersensitivity to sumatriptan, and severe hepatic impairment.[2]

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.[15] There are reports of Takotsubo cardiomyopathy and transient amnesia after sumatriptan use.[16]

The most common side effects[2] 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.

Sumatriptan has a low abuse potential;[17] however overuse is associated with medication overuse headache.[18] Moreover, prolonged sumatriptan use is associated with pronociceptive effects, resulting in allodynia. This effect's association with medication overuse headache, however, is controversial, due to the fact that animal-model studies are not consistent with typical presentation of this disorder.[19]

Overdose

Overdose in animals produced effects including convulsions, tremor, paralysis, inactivity, ptosis[disambiguation needed], extremity erythema, abnormal breathing, cyanosis, ataxia, mydriasis, salivation, lacrimation, and death.[2] The elimination half-life of sumatriptan in humans is 2.5 hours.[2] The effect of dialysis on sumatriptan levels is unknown.[2]

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.[20]

Interactions

Concurrent use with other triptans or ergot-containing medications (e.g., ergotamine, dihydroergotamine) within 24 hours can result in additive vasoconstriction.[21][22] Increased systemic exposure to sumatriptan can occur if used within 2 weeks after a monoamine oxidase inhibitor (MAOI).[22] Cases of serotonin syndrome have been reported with co-administration of triptans and serotonin reuptake inhibitors.[21]

Pharmacology

Mechanism of action

Sumatriptan activities
Target Affinity (Ki, nM)
5-HT1A 72–1,100 (Ki)
>10,000 (EC50)
35–93% (Emax)
5-HT1B 0.5–62 (Ki)
12–234 (EC50)
96–102% (Emax)
5-HT1D 0.5–30 (Ki)
2.0–220 (EC50)
86–103% (Emax)
5-HT1E 646–2,520 (Ki)
1,020–10,000 (EC50)
56% (Emax)
5-HT1F 11–501 (Ki)
9.3–250 (EC50)
98% (Emax)
5-HT2A 376–>10,000 (Ki)
>10,000 (EC50)
5-HT2B 126–>10,000 (Ki)
>10,000 (EC50)
5-HT2C >10,000 (Ki)
>10,000 (EC50) (pig)
5-HT3 >10,000 (Ki) (rat)
>10,000 (EC50) (mouse)
5-HT4 1,000 (Ki) (rat)
>10,000 (EC50) (guinea pig)
5-HT5A 3,200–5,000
5-HT5B 807–7,943 (rat/mouse)
5-HT6 2,600–>10,000
5-HT7 25–1,380 (Ki)
6,030 (EC50)
α1A–α1D ND
α2A–α2C ND
β1–β3 ND
D1, D2 >10,000
D3–D5 ND
H1–H4 ND
M1–M5 ND
I1, I2 ND
σ1, σ2 ND
TAAR1 ND
SERT ND
NET ND
DAT ND
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [23][24][25][26][27][28][29][30][31][32][33]
[34][35][36][37][38][39][40][41][42]

Sumatriptan is structurally similar to the neurotransmitter serotonin (5-HT) and acts as an agonist of the serotonin 5-HT1B, 5-HT1D, and 5-HT1F receptors.[4] Sumatriptan's primary therapeutic effect is related in its inhibition of the release of calcitonin gene-related peptide (CGRP), likely through its 5-HT1D/1B receptor agonist action.[43] This has been substantiated by the efficacy of more recently developed CGRP targeting drugs and antibodies developed for the preventive treatment of migraine.[44] How agonism of the 5-HT1D/1B receptors inhibits CGRP release is not fully understood. CGRP is believed to cause sensitization of trigeminal nociceptive neurons, contributing to the pain experienced in migraine.[45]

Sumatriptan is also shown to decrease the activity of the trigeminal nerve, which presumably accounts for sumatriptan's efficacy in treating cluster headaches. The injectable form of the drug has been shown to abort a cluster headache within 30 minutes in 77% of cases.[46]

Pharmacokinetics

Absorption

Sumatriptan is administered in several forms: tablets, subcutaneous injection, and nasal spray. Oral administration (as succinate salt) has low bioavailability, partly due to presystemic metabolism—some of it gets broken down in the stomach and bloodstream before it reaches the target arteries. There is no simple, direct relationship between sumatriptan concentration (pharmacokinetics) per se in the blood and its anti-migraine effect (pharmacodynamics). This paradox has, to some extent, been resolved by comparing the rates of absorption of the various sumatriptan formulations, rather than the absolute amounts of drug that they deliver.[47][48]

Distribution

Sumatriptan is a relatively hydrophilic molecule, which may limit its ability to cross the blood–brain barrier and enter the central nervous system.[49] In accordance, early animal studies found lack of indication of central penetration by sumatriptan.[49] This was in contrast to more lipophilic triptans like zolmitriptan, naratriptan, rizatriptan, and eletriptan.[49] For these reasons, it was thought for many years that sumatriptan could not cross the blood–brain barrier in significant amounts to exert central effects.[49]

However, in subsequent animal studies, sumatriptan was found to enter the brain and produce centrally mediated effects.[49] Besides animal research, clinical studies have found sumatriptan to produce centrally mediated side effects such as sleepiness, tiredness, thinking difficulty, and dizziness, among others.[49] In addition, sumatriptan has been found to be discernibly psychoactive in human drug discrimination tests, with effects like apathy, sedation, and mild dysphoria.[49] Certain other clinical findings also support centrally mediated effects of sumatriptan.[49]

A 2010 literature review concluded that sumatriptan can enter the brain to some minor extent in both animals and humans but that this minor penetration is nonetheless sufficient to cause pharmacological effects.[49] Subsequent research has found sumatriptan given during migraine attacks decreases brain serotonin 5-HT1B receptor binding in humans, with a corresponding receptor occupancy of 16%.[50][51] However, this apparent occupancy could alternatively be due to increased serotonin release during migraine attacks.[50] In contrast to receptor antagonists, it is notable that agonists like sumatriptan require only a low fractional receptor occupancy to produce central effects.[49] It is notable in this regard that the possible occupancy with sumatriptan was comparable to that with centrally acting opioids.[51] Besides the clinical findings, further animal studies have found that sumatriptan rapidly enters the brain in spite of its poor lipophilicity and was able to do so more quickly than the benzodiazepine oxazepam.[51][52]

Metabolism

Sumatriptan metabolic pathways (MAO-A – monoamine oxidase A, CYP - cytochrome P450 isoenzymes).[53]

Sumatriptan is metabolized primarily by monoamine oxidase A into indol-3-yl-acetaldehyde and then into corresponding carboxylic acid. It is further modified by UDP-glucuronosyltransferase into a conjugate with glucuronic acid. Other pathways are mediated by cytochrome P450 isoenzymes, which give an N-oxide derivative, and N-desmethyl and N,N-didesmethyl forms (the latter can be converted into the aldehyde by monoamine oxidase A). The N-desmethyl derivative can also undergo a reaction with D-cysteine.[53]

Elimination

The metabolites of sumatriptan are excreted in the urine and bile. Only about 3% of the active drug may be recovered unchanged.[3]

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).[54]

The experimental log P of sumatriptan is 0.8 to 0.93 and its predicted log P is 0.46 to 1.17.[55]

History

Sumatriptan vials


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.[56]

Phase III studies with an iontophoretic transdermal patch (Zelrix/Zecuity) started in July 2008.[57] This patch uses low voltage controlled by a pre-programmed microchip to deliver a single dose of sumatriptan through the skin within 30 minutes.[58][59] Zecuity was approved by the FDA in January 2013.[60] Sales of Zecuity have been stopped following reports of skin burns and irritation.[61]

Society and culture

In the United States, it is available only by medical prescription. It is available over the counter in many states in Australia. The product requires labelling by a pharmacist and is only available in packs of two without a medical prescription.[62] However, it can be bought over the counter in the UK[63] and Sweden.[64]

In Russia, versions of sumatriptan which are not registered in the State Register of Medicines may be regarded as narcotic drugs (derivatives of dimethyltryptamine).[65]

Generics

Glaxo patents for sumatriptan expired in February 2009. At that time, Imitrex sold for about $25 a pill.[66] Par Pharmaceutical then introduced generic versions of sumatriptan injection (sumatriptan succinate injection) 4- and 6-mg starter kits and 4- and 6-mg filled syringe cartridges, and 6-mg vials soon after.[67]

Mylan Laboratories Inc., Sun Pharma, Sandoz (a subsidiary of Novartis), Dr. Reddy's Laboratories, and other companies have been producing generic versions of sumatriptan tablets in 25-, 50-, and 100-mg doses. Generic forms of the drug are available in US and European markets after Glaxo's patent protections expired in the respective countries. A nasal spray form of sumatriptan known as AVP-825 has been developed by Avanir and is generically available in some countries.[68]

Controversy

According to the American Headache Society, "Patients frequently state that they have difficulty accessing triptans prescribed to them."[69] In the US, triptans cost from $12 to $120 each, and more than 80% of US health insurance plans place a limit on the amount of pills available to a patient per month, which has been called "arbitrary and unfair."[70]

References

  1. ↑ 1.0 1.1 British National Formulary: BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 474. ISBN 978-0-85711-338-2. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 2.6 2.7 2.8 Cite error: Invalid <ref> tag; no text was provided for refs named Imitrex FDA label
  3. ↑ 3.0 3.1 3.2 3.3 3.4 "Sumatriptan Monograph for Professionals". American Society of Health-System Pharmacists. https://www.drugs.com/monograph/sumatriptan.html. 
  4. ↑ 4.0 4.1 "Is selective 5-HT1F receptor agonism an entity apart from that of the triptans in antimigraine therapy?". Pharmacol Ther 186: 88–97. June 2018. doi:10.1016/j.pharmthera.2018.01.005. PMID 29352859. 
  5. ↑ "Sumatriptan/Naproxen Sodium: A Review in Migraine". Drugs 76 (1): 111–121. January 2016. doi:10.1007/s40265-015-0521-8. PMID 26628293. 
  6. ↑ "Sumatriptan Use During Pregnancy". https://www.drugs.com/pregnancy/sumatriptan.html. 
  7. ↑ Analogue-based Drug Discovery. John Wiley & Sons. 2006. p. 531. ISBN 978-3-527-60749-5. https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA531. 
  8. ↑ World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. 2021. WHO/MHP/HPS/EML/2021.02. 
  9. ↑ "Top 300 of 2023". https://clincalc.com/DrugStats/Top300Drugs.aspx. 
  10. ↑ "Sumatriptan Drug Usage Statistics, United States, 2013 - 2023". https://clincalc.com/DrugStats/Drugs/Sumatriptan. 
  11. ↑ "Treximet- sumatriptan succinate and naproxen sodium tablet, film coated". 23 December 2024. https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=42ddf376-8dc0-4236-be2a-0c6ae92ece04. 
  12. ↑ "Sumatriptan (all routes of administration) for acute migraine attacks in adults - overview of Cochrane reviews". The Cochrane Database of Systematic Reviews 2014 (5). May 2014. doi:10.1002/14651858.CD009108.pub2. PMID 24865446. 
  13. ↑ "Sumatriptan: pharmacological basis and clinical results". Current Medical Research and Opinion 17 (Suppl 1): s35–s45. 2001. doi:10.1185/0300799039117010. PMID 12463276. http://www.medscape.com/viewarticle/429671_4. Retrieved 16 July 2016. 
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  22. ↑ 22.0 22.1 "Drugs for Migraine" (in en). The Medical Letter on Drugs and Therapeutics (The Medical Letter Inc.) 65 (678): 89–96. June 2023. doi:10.58347/tml.2023.1678a. PMID 37266987. https://secure.medicalletter.org/TML-article-1678a#:~:text=Subcutaneous%20sumatriptan%20is%20the%20most,in%20patients%20with%20vascular%20disease.. Retrieved 3 May 2024. 
  23. ↑ "Kᵢ Database". 5 July 2025. https://pdspdb.unc.edu/kidb2/kidb/web/kis-results/index?KisResultsSearch%5Binput_receptors%5D=&KisResultsSearch%5Binput_sources%5D=&KisResultsSearch%5Binput_species%5D=&KisResultsSearch%5Binput_hot_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D%5B%5D=1788&KisResultsSearch%5Binput_citations%5D=&KisResultsSearch%5BsearchType%5D=&KisResultsSearch%5Bki_val_from%5D=&KisResultsSearch%5Bki_val_to%5D=&KisResultsSearch%5Bcustom_ki_val%5D=. 
  24. ↑ Liu, Tiqing. "BindingDB BDBM50005835 (3-[2-(dimethylamino)ethyl-1H-indol-5-yl)-N-methylmethanesulfonamide::1-[3-(2-dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide::1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide::3-(2-(dimethylamino)ethyl)-N-methyl-1H-indole-5-methanesulfonamide::3-[2-(dimethylamino)ethyl]-N-methylindole-5-methanesulfonamide::CHEMBL128::SUMATRIPTAN::Sumatran::Sumax"]. https://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50005835. 
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  36. ↑ Perez, M.; Halazy, S.; Pauwels, P.J.; Colpaert, F.C.; John, G.W. (1999). "F-11356". Drugs of the Future 24 (6): 0605. doi:10.1358/dof.1999.024.06.537284. http://access.portico.org/stable?au=pjbf78x6c9d. Retrieved 23 June 2025. 
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  49. ↑ 49.00 49.01 49.02 49.03 49.04 49.05 49.06 49.07 49.08 49.09 "Does sumatriptan cross the blood-brain barrier in animals and man?". J Headache Pain 11 (1): 5–12. February 2010. doi:10.1007/s10194-009-0170-y. PMID 20012125. 
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  57. ↑ Clinical trial number NCT00724815 for "The Efficacy and Tolerability of NP101 Patch in the Treatment of Acute Migraine (NP101-007)" at ClinicalTrials.gov
  58. ↑ "SmartRelief -electronically assisted drug delivery (iontophoresis)". http://www.nupathe.com/description.php?secid=3&subsecid=7#_ELECTRONIC_DRUG. 
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  60. ↑ "Zecuity Approved by the FDA for the Acute Treatment of Migraine". http://ir.nupathe.com/press-releases/nupathe-s-zecuity-approved-by-the-fda-for-the-acut-nasdaq-path-975802NuPathe's. 
  61. ↑ "Teva pulls migraine patch Zecuity on reports of burning, scarring". 13 June 2016. http://www.fiercepharma.com/pharma/teva-pulls-migraine-patch-zecuity-reports-burning-scarring. 
  62. ↑ "Poisons Standard June 2017". 18 May 2017. https://www.legislation.gov.au/Details/F2017L00605/Html/Text#_Toc471222305. 
  63. ↑ "Press release: First Over The Counter (OTC) migraine pill made available". Medicines and Healthcare Products Regulatory Agency. http://www.mhra.gov.uk/NewsCentre/Pressreleases/CON2023768. 
  64. ↑ "Assessment Report: Sumatriptan Galpharm 50 mg Tablets". European Medicines Agency. 23 November 2011. p. 20. http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/002140/WC500122862.pdf. 
  65. ↑ "Постановление Правительства РФ от 30 июня 1998 г. N 681 "Об утверждении перечня наркотических средств, психотропных веществ и их прекурсоров, подлежащих контролю в Российской Федерации" (с изменениями и дополнениями)" (in ru). Гарант. http://base.garant.ru/12112176/. "ДМТ (диметилтриптамин) и его производные, за исключением производных, включенных в качестве самостоятельных позиций в перечень" 
  66. ↑ "GlaxoSmithKline sets out to dupe migraine sufferers with Treximet smoke and mirrors". Community Catalyst. 24 April 2008. https://www.communitycatalyst.org/blog/glaxosmithkline-sets-out-to-dupe-migraine-sufferers-with-treximet-smoke-and-mirrors-pal. 
  67. ↑ "Par Pharmaceutical begins shipment of sumatriptan injection". Par Pharmaceutical. 6 November 2008. http://www.parpharm.com/media/NR_20081106.jsp. 
  68. ↑ "If You 'Want To Make A Good Drug Great' Cost Must Be Factored In". Forbes. 2 March 2015. https://www.forbes.com/sites/johnlamattina/2015/03/03/if-you-want-to-make-a-good-drug-great-cost-must-be-factored-in/. 
  69. ↑ "Variation in Prescription Drug Coverage for Triptans: Analysis of Insurance Formularies", Headache: The Journal of Head and Face Pain (Wiley) 57 (8): 1243–1251, 2017, doi:10.1111/head.13134, PMID 28691382 
  70. ↑ "Practice Matters Wide Variation in Triptan Coverage Across Commercial and Government Health Plans", Neurology Today (American Academy of Neurology) 17 (17): 7, 7 September 2017, doi:10.1097/01.NT.0000524839.20893.03 



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