Synonym
GR-43175; GR43175; GR 43175; Sumatriptan; Sumatran; Sumax
IUPAC/Chemical Name
1-(3-(2-(dimethylamino)ethyl)-1H-indol-5-yl)-N-methylmethanesulfonamide succinate
InChi Key
PORMUFZNYQJOEI-UHFFFAOYSA-N
InChi Code
InChI=1S/C14H21N3O2S.C4H6O4/c1-15-20(18,19)10-11-4-5-14-13(8-11)12(9-16-14)6-7-17(2)3;5-3(6)1-2-4(7)8/h4-5,8-9,15-16H,6-7,10H2,1-3H3;1-2H2,(H,5,6)(H,7,8)
SMILES Code
O=S(CC1=CC2=C(NC=C2CCN(C)C)C=C1)(NC)=O.O=C(O)CCC(O)=O
Appearance
White to off-white solid powder.
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Sumatriptan is used to treat migraine headaches and cluster headaches. It is taken orally, intranasally, or by subcutaneous injection. Therapeutic effects generally occur within three hours.
Biological target:
Sumatriptan succinate targets the serotonin 5-HT1B/1D receptors. Sumatriptan acts as an agonist at these receptors, leading to
vasoconstriction of cranial blood vessels and inhibition of pro-inflammatory neuropeptide release, ultimately resulting in the
alleviation of migraine symptoms.
In vitro activity:
This study aimed to develop solid lipid nanoparticles (SLNPs) of sumatriptan succinate for brain targeting via nasal delivery due to its
poor oral bioavailability and side effects. The in vitro experiments demonstrated that the optimized SLNP formulation achieved small
particle size, favorable zeta potential, high drug entrapment efficiency, exhibited sustained drug release, quick permeation across nasal
mucosa, and maintained the integrity of the nasal mucosa.
Reference: Yadav RK, Shah K, Dewangan HK. Intranasal drug delivery of sumatriptan succinate-loaded polymeric solid lipid
nanoparticles for brain targeting. Drug Dev Ind Pharm. 2022 Jan;48(1):21-28.
In vivo activity:
Sumatriptan succinate, in combination with naproxen sodium (Treximet®), has demonstrated efficacy in treating migraine in
adolescents and adults, with higher rates of pain relief compared to placebo at 2 hours post-administration.
Reference: Syed YY. Sumatriptan/Naproxen Sodium: A Review in Migraine. Drugs. 2016 Jan;76(1):111-21.
|
Solvent |
mg/mL |
mM |
| Solubility |
| Water |
41.4 |
100.00 |
| DMSO |
31.0 |
75.00 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
413.49
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
Hansraj GP, Singh SK, Kumar P. Sumatriptan succinate loaded chitosan solid lipid nanoparticles for enhanced anti-migraine potential. Int J Biol Macromol. 2015 Nov;81:467-76. doi: 10.1016/j.ijbiomac.2015.08.035. Epub 2015 Aug 21. PMID: 26299709.
Syed YY. Sumatriptan/Naproxen Sodium: A Review in Migraine. Drugs. 2016 Jan;76(1):111-21. doi: 10.1007/s40265-015-0521-8. PMID: 26628293.
Ronnander JP, Simon L, Koch A. Transdermal Delivery of Sumatriptan Succinate Using Iontophoresis and Dissolving Microneedles. J Pharm Sci. 2019 Nov;108(11):3649-3656. doi: 10.1016/j.xphs.2019.07.020. Epub 2019 Jul 30. PMID: 31374318.
Yadav RK, Shah K, Dewangan HK. Intranasal drug delivery of sumatriptan succinate-loaded polymeric solid lipid nanoparticles for brain targeting. Drug Dev Ind Pharm. 2022 Jan;48(1):21-28. doi: 10.1080/03639045.2022.2090575. Epub 2022 Jun 21. PMID: 35703403.
In vitro protocol:
Ronnander JP, Simon L, Koch A. Transdermal Delivery of Sumatriptan Succinate Using Iontophoresis and Dissolving Microneedles. J Pharm Sci. 2019 Nov;108(11):3649-3656. doi: 10.1016/j.xphs.2019.07.020. Epub 2019 Jul 30. PMID: 31374318.
Yadav RK, Shah K, Dewangan HK. Intranasal drug delivery of sumatriptan succinate-loaded polymeric solid lipid nanoparticles for brain targeting. Drug Dev Ind Pharm. 2022 Jan;48(1):21-28. doi: 10.1080/03639045.2022.2090575. Epub 2022 Jun 21. PMID: 35703403.
In vivo protocol:
Hansraj GP, Singh SK, Kumar P. Sumatriptan succinate loaded chitosan solid lipid nanoparticles for enhanced anti-migraine potential. Int J Biol Macromol. 2015 Nov;81:467-76. doi: 10.1016/j.ijbiomac.2015.08.035. Epub 2015 Aug 21. PMID: 26299709.
Syed YY. Sumatriptan/Naproxen Sodium: A Review in Migraine. Drugs. 2016 Jan;76(1):111-21. doi: 10.1007/s40265-015-0521-8. PMID: 26628293.
1: Tajti J, Csáti A, Szok D. Szumatriptán–naproxén-nátrium fix dózisú kombinációja a migrén akut kezelésében – irodalmi áttekintés [Sumatriptan- naproxen sodium fix-dose combination for acute migraine treatment, a review]. Ideggyogy Sz. 2023 Sep 30;76(9-10):293-296. Hungarian. doi: 10.18071/isz.76.0293. PMID: 37782065.
2: Hauser Chatterjee J, Hartford EA, Law E, Barry D, Blume H. Sumatriptan as a First-Line Treatment for Headache in the Pediatric Emergency Department. Pediatr Neurol. 2023 May;142:68-75. doi: 10.1016/j.pediatrneurol.2023.01.016. Epub 2023 Feb 4. PMID: 36958085.
3: Amini N, Modir H, Omidvar S, Kia MK, Pazoki S, Harorani M, Moradzadeh R, Derakhshani M. The Effect of Sumatriptan, Theophylline, Pregabalin and Caffeine on Prevention of Headache Caused By Spinal Anaesthesia (PDPH): A Systematic Review. J West Afr Coll Surg. 2022 Oct-Dec;12(4):102-116. doi: 10.4103/jwas.jwas_183_22. Epub 2022 Nov 23. PMID: 36590776; PMCID: PMC9802600.
4: Assadpour S, Shiran MR, Asadi P, Akhtari J, Sahebkar A. Harnessing Intranasal Delivery Systems of Sumatriptan for the Treatment of Migraine. Biomed Res Int. 2022 Jan 15;2022:3692065. doi: 10.1155/2022/3692065. PMID: 35075426; PMCID: PMC8783720.
5: Mother To Baby | Fact Sheets [Internet]. Brentwood (TN): Organization of Teratology Information Specialists (OTIS); 1994–. Sumatriptán. 2021 Nov. PMID: 35952242.
6: Mother To Baby | Fact Sheets [Internet]. Brentwood (TN): Organization of Teratology Information Specialists (OTIS); 1994–. Sumatriptan. 2021 Nov 1. PMID: 35952241.
7: Gaul C, Förderreuther S. Sumatriptan 3 mg subkutan : Klinische Relevanz in der Akuttherapie der Migräne trotz Dosisreduktion [Sumatriptan 3 mg subcutaneous : Clinical relevance of acute treatment of migraine despite dose reduction]. Nervenarzt. 2022 Jun;93(6):612-617. German. doi: 10.1007/s00115-021-01189-8. Epub 2021 Sep 23. PMID: 34557933.
8: Tfelt-Hansen P. Naratriptan is as effective as sumatriptan for the treatment of migraine attacks when used properly. A mini-review. Cephalalgia. 2021 Dec;41(14):1499-1505. doi: 10.1177/03331024211028959. Epub 2021 Jul 18. PMID: 34275352.
9: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Sumatriptan. 2021 May 17. PMID: 30000314.
10: Ala M, Ghasemi M, Mohammad Jafari R, Dehpour AR. Beyond its anti-migraine properties, sumatriptan is an anti-inflammatory agent: A systematic review. Drug Dev Res. 2021 Nov;82(7):896-906. doi: 10.1002/ddr.21819. Epub 2021 Apr 1. PMID: 33792938.
11: Tepper SJ, Johnstone MR. Breath-powered sumatriptan dry nasal powder: an intranasal medication delivery system for acute treatment of migraine. Med Devices (Auckl). 2018 May 3;11:147-156. doi: 10.2147/MDER.S130900. PMID: 29760572; PMCID: PMC5937501.
12: Silberstein SD. A review of clinical safety data for sumatriptan nasal powder administered by a breath powered exhalation delivery system in the acute treatment of migraine. Expert Opin Drug Saf. 2018 Jan;17(1):89-97. doi: 10.1080/14740338.2018.1390563. Epub 2017 Oct 20. PMID: 28994319.
13: Menshawy A, Ahmed H, Ismail A, Abushouk AI, Ghanem E, Pallanti R, Negida A. Intranasal sumatriptan for acute migraine attacks: a systematic review and meta- analysis. Neurol Sci. 2018 Jan;39(1):31-44. doi: 10.1007/s10072-017-3119-y. Epub 2017 Sep 23. PMID: 28942578.
14: Silberstein S. AVP-825: a novel intranasal delivery system for low-dose sumatriptan powder in the treatment of acute migraine. Expert Rev Clin Pharmacol. 2017 Aug;10(8):821-832. doi: 10.1080/17512433.2017.1339600. Epub 2017 Jul 3. PMID: 28605258.
15: Al-Salama ZT, Scott LJ. Sumatriptan Nasal Powder: A Review in Acute Treatment of Migraine. Drugs. 2016 Oct;76(15):1477-1484. doi: 10.1007/s40265-016-0641-9. PMID: 27681528.
16: Tfelt-Hansen PC. Delayed absorption of many (paracetamol, aspirin, other NSAIDs and zolmitriptan) but not all (sumatriptan, rizatriptan) drugs during migraine attacks and most likely normal gastric emptying outside attacks. A review. Cephalalgia. 2017 Aug;37(9):892-901. doi: 10.1177/0333102416644745. Epub 2016 Jun 20. PMID: 27330004.
17: Freitag FG, Shumate DA. The efficacy and safety of sumatriptan intranasal powder in adults with acute migraine. Expert Rev Neurother. 2016 Jul;16(7):743-7. doi: 10.1080/14737175.2016.1195687. PMID: 27260875.
18: Law S, Derry S, Moore RA. Sumatriptan plus naproxen for the treatment of acute migraine attacks in adults. Cochrane Database Syst Rev. 2016 Apr 20;4(4):CD008541. doi: 10.1002/14651858.CD008541.pub3. PMID: 27096438; PMCID: PMC6485397.
19: Barleycorn D. Systematic review: Is Metoclopramide more effective than Sumatriptan in relieving pain from migraine in adults in the Emergency Department (ED) setting? Int Emerg Nurs. 2016 Jul;27:51-5. doi: 10.1016/j.ienj.2016.02.004. Epub 2016 Mar 11. PMID: 26975891.
20: Syed YY. Sumatriptan/Naproxen Sodium: A Review in Migraine. Drugs. 2016 Jan;76(1):111-21. doi: 10.1007/s40265-015-0521-8. PMID: 26628293.
