Sumatriptan
Identification
- Summary
Sumatriptan is a serotonin receptor agonist used to treat migraines and cluster headaches.
- Brand Names
- Imitrex, Onzetra, Sumavel, Tosymra, Treximet, Zembrace
- Generic Name
- Sumatriptan
- DrugBank Accession Number
- DB00669
- Background
Sumatriptan is a serotonin receptor agonist commonly used to treat migraines and sometimes cluster headaches.5,6,7,8,9,10 Sumatriptan is the first of the triptans and was made available in Europe in 1991 to treat migraines.4 Sumatriptan was granted FDA approval on 28 December 1992.8
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
- Weight
- Average: 295.4
Monoisotopic: 295.135447621 - Chemical Formula
- C14H21N3O2S
- Synonyms
- (3-[2-(dimethylamino)ethyl]-1H-indol-5-yl)-N-methylmethanesulfonamide
- 1-[3-(2-dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide
- 3-(2-(dimethylamino)ethyl)-N-methyl-1H-indole-5-methanesulfonamide
- 3-[2-(dimethylamino)ethyl]-N-methylindole-5-methanesulfonamide
- Sumatriptan
- Sumatriptán
- Sumatriptanum
- External IDs
- GR 43175 A
- GR 43175 C
- GR 43175 X
- NP101
- SN 308
Pharmacology
- Indication
A combination sumatriptan and naproxen tablet is indicated for the treatment of migraines with or without auras in patients 12 years of age and older.5 Sumatriptan nasal powder, nasal spray, subcutaneous injection, and tablets are indicated to treat migraines with or without auras in adults.6,7,8,9,10 One of the subcutaneous formulations of sumatriptan is also indicated to treat cluster headaches in adults8, while the other subcutaneous formulation is not.9
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Acute migraine •••••••••••• ••••• Treatment of Acute migraine ••• ••••• ••••••••• Treatment of Acute migraine ••• ••••• •••••••••• Used in combination to treat Acute migraine Combination Product in combination with: Naproxen (DB00788) •••••••••••• ••••• Treatment of Acute cluster headache •••••••••••• ••••• - Contraindications & Blackbox Warnings
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- Pharmacodynamics
Sumatriptan constricts cranial blood vessels and prevents the release of vasoactive peptides.2 The dose of sumatriptan varies widely by route of administration and in most cases, no more than 2 doses should be given daily.5,6,7,8,9,10 Medication overuse headaches may occur in patients who use sumatriptan frequently.5,6,7,8,9,10
- Mechanism of action
Sumatriptan is an agonist of 5-HT1B and 5-HT1D.5,6,7,8,9,10 This agonism leads to constriction of cranial blood vessels and inhibits the release of pro-inflammatory neuropeptides.5,6,7,8,9,10 Sumatriptan decreases carotid arterial blood flow, but increases blood flow velocity in the internal carotid artery and middle cerebral artery.2,2,2
Target Actions Organism A5-hydroxytryptamine receptor 1A agonistHumans A5-hydroxytryptamine receptor 1D agonistHumans A5-hydroxytryptamine receptor 1B agonistHumans A5-hydroxytryptamine receptor 1F agonistHumans - Absorption
A 6mg subcutaneous injection of sumatriptan reaches a Cmax of 69.5ng/mL (95% CI of 62.8-76.9ng/mL) with a Tmax of 0.17h (95% CI of 0.08-0.33h), an AUC of 9.0h*ng/mL (95% CI of 7.5-10.9h*ng/mL), and a bioavailability of 100%.3
A 25mg oral dose of sumatriptan reaches a Cmax of 16.5ng/mL (95% CI of 13.5-20.1ng/mL) with a Tmax of 1.50h (95% CI of 0.50-2.00h), an AUC of 8.7h*ng/mL (95% CI of 6.1-12.5h*ng/mL), and a bioavailability of 14.3% (95% CI of 11.4-17.9%).3
A 20mg intranasal dose of sumatriptan reaches a Cmax of 12.9ng/mL (95% CI of 10.5-15.9ng/mL) with a Tmax of 1.50h (95% CI of 0.25-3.00h), an AUC of 7.4h*ng/mL (95% CI of 5.0-10.8h*ng/mL), and a bioavailability of 15.8% (95% CI of 12.6-19.8%).3
A 25mg rectal dose of sumatriptan reaches a Cmax of 22.9ng/mL (95% CI of 18.4-28.6ng/mL) with a Tmax of 1.00h (95% CI of 0.75-3.00h), an AUC of 14.6h*ng/mL (95% CI of 11.3-18.8h*ng/mL), and a bioavailability of 19.2% (95% CI of 15.3-24.1%).3
- Volume of distribution
Sumatriptan has a volume of distribution of 50±8L for a 6mg subcutaneous dose7, or 2.7L/kg.10
- Protein binding
Sumatriptan is 14%-21% bound to protein in circulation.5,6,7,8,9,10
- Metabolism
Sumatriptan is predominantly metabolized by monoamine oxidase A7,10,8,10,5,9. The main metabolites are the inactive indole acetic acid and indole acetic acid glucuronide.7,10,8,10,5,9
Hover over products below to view reaction partners
- Route of elimination
22±4% is excreted in the urine as unchanged sumatriptan and 38±7% in urine as indole acetic acid7,8 approximately 40% is excreted in the feces10,5.
- Half-life
Subcutaneous sumatriptan has a half life of 1.9h (95% CI of 1.7-2.0h).3 Oral sumatriptan has a half life of 1.7h (95% CI of 1.4-1.9h).3 Rectal sumatriptan has a half life of 1.8h (95% CI of 1.6-2.2h).3 Intrsnasal sumatriptan has a half life of 1.8h (95% CI of 1.7-2.0h).3
- Clearance
Subcutaneous sumatriptan has a clearance of 0.22L/min (95% CI of 0.19-0.25L/min).3 Oral sumatriptan has a clearance of 0.17L/min (95% CI of 0.14-0.21L/min).3 Rectal sumatriptan has a clearance of 0.17L/min (95% CI of 0.14-0.21L/min).3 Intrsnasal sumatriptan has a clearance of 0.21L/min (95% CI of 0.18-0.25L/min).3 Total plasma clearance of sumatriptan is approximately 1200mL/min.6
- Adverse Effects
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- Toxicity
Symptoms of overdose include convulsions, tremor, paralysis, inactivity, ptosis, erythema of the extremities, abnormal respiration, cyanosis, ataxia, mydriasis, salivation, and lacrimation.5,6,7,8,9,10 Overdoses may be fatal and patients should be monitored for 3-5 half lives or while symptoms persist.5,6,7,8,9,10
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Guanine nucleotide-binding protein G(I)/G(S)/G(T) subunit beta-3 --- (T;T) / (C;T) T Allele Effect Directly Studied Patients with this genotype have an increased likelihood of responding to sumatriptan when treating (condition: cluster headache). Details
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Sumatriptan is combined with 1,2-Benzodiazepine. Abacavir Sumatriptan may decrease the excretion rate of Abacavir which could result in a higher serum level. Abemaciclib Abemaciclib may decrease the excretion rate of Sumatriptan which could result in a higher serum level. Acarbose The therapeutic efficacy of Acarbose can be increased when used in combination with Sumatriptan. Acebutolol Sumatriptan may decrease the antihypertensive activities of Acebutolol. - Food Interactions
- Avoid excessive or chronic alcohol consumption. Alcohol increased the risk of GI bleeding, ulcer, and perforation when taken with sumatriptan.
- Take with or without food.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Sumatriptan hemisulfate 7T9PTJ824O 143675-45-0 ZPBKNEYMSRHSSI-UHFFFAOYSA-N Sumatriptan succinate J8BDZ68989 103628-48-4 PORMUFZNYQJOEI-UHFFFAOYSA-N - Product Images
- International/Other Brands
- Adracon (Inti) / Altaxa (Alapis Pharma) / Apigrane (Advanced Pharmaceutical) / Boots Pharmacy Migraine Relief (Boots) / Cinie (Zentiva) / Frimig (Orion) / Illument (Pliva) / Imigen (Mylan) / Imigran (GlaxoSmithKline) / Imigran mite (GlaxoSmithKline) / Imigran Radis (GlaxoSmithKline) / Imigrane (GlaxoSmithKline) / Imitrex Oral (GlaxoSmithKline) / Migralgin (GMP) / Migraneitor (Driburg) / Nazdav (Dr. Reddy's) / Sapphirex (Hemofarm) / Sumatran (Rowex) / Sumax (Libbs) / Suminat (Sun) / Youshu (Simcere)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Act Sumatriptan Tablet 50 mg Oral Actavis Pharma Company 2005-08-24 2018-06-19 Canada Act Sumatriptan Tablet 25 mg Oral Actavis Pharma Company 2005-08-24 2018-06-19 Canada Act Sumatriptan Tablet 100 mg Oral TEVA Canada Limited 2005-08-24 2021-07-30 Canada Alsuma Injection, solution 6 mg/0.5mL Subcutaneous Us World Meds, Llc 2010-10-15 2013-08-31 US Alsuma Injection, solution 6 mg/0.5mL Subcutaneous Pfizer Laboratories Div Pfizer Inc. 2009-08-31 2015-08-31 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-sumatriptan Tablet 25 mg Oral Apotex Corporation Not applicable Not applicable Canada Apo-sumatriptan Spray 20 mg / dose Nasal Apotex Corporation Not applicable Not applicable Canada Apo-sumatriptan Tablet 100 mg Oral Apotex Corporation 2005-08-24 Not applicable Canada Apo-sumatriptan Spray 5 mg / dose Nasal Apotex Corporation Not applicable Not applicable Canada Apo-sumatriptan Tablet 50 mg Oral Apotex Corporation 2005-08-24 Not applicable Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Sumatriptan and Naproxen Sodium Sumatriptan succinate (85 mg/1) + Naproxen sodium (500 mg/1) Tablet, film coated Oral Northstar RxLLC 2018-11-27 Not applicable US Sumatriptan and Naproxen Sodium Sumatriptan succinate (85 mg/1) + Naproxen sodium (500 mg/1) Tablet, film coated Oral Aurobindo Pharma Limited 2018-02-15 Not applicable US Sumatriptan and Naproxen Sodium Sumatriptan succinate (85 mg/1) + Naproxen sodium (500 mg/1) Tablet, film coated Oral Innovida Phamaceutique Corporation 2020-12-09 Not applicable US Sumatriptan and Naproxen Sodium Sumatriptan succinate (85 mg/1) + Naproxen sodium (500 mg/1) Tablet, film coated Oral Sun Pharmaceutical Industries, Inc. 2018-07-20 Not applicable US Sumatriptan and Naproxen Sodium Sumatriptan succinate (85 mg/1) + Naproxen sodium (500 mg/1) Tablet, film coated Oral Mylan Pharmaceuticals Inc. 2018-09-04 2021-12-31 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Migranow Sumatriptan succinate (50 mg/1) + Menthol (10 g/100g) + Synthetic camphor (4 g/100g) Gel; Kit; Tablet Oral; Topical PureTek Corporation 2016-04-18 Not applicable US SumaChip Sumatriptan succinate (100 mg/1) + Capsaicin (0.0375 g/100g) + Menthol (5 g/100g) Kit Oral; Topical Basiem 2015-11-29 2016-03-04 US Sumansetron Sumatriptan succinate (50 mg/1) + Ondansetron hydrochloride dihydrate (4 mg/1) Kit; Tablet; Tablet, film coated Oral PureTek Corporation 2021-01-01 Not applicable US
Categories
- ATC Codes
- N02CC01 — Sumatriptan
- N02CC — Selective serotonin (5HT1) agonists
- N02C — ANTIMIGRAINE PREPARATIONS
- N02 — ANALGESICS
- N — NERVOUS SYSTEM
- Drug Categories
- Agents that produce hypertension
- Amides
- Amines
- Analgesics
- Antidepressive Agents
- Antimigraine Preparations
- BCRP/ABCG2 Substrates
- Biogenic Amines
- Biogenic Monoamines
- Cardiovascular Agents
- Central Nervous System Depressants
- Drugs that are Mainly Renally Excreted
- Genito Urinary System and Sex Hormones
- Heterocyclic Compounds, Fused-Ring
- Indoles
- Monoamine Oxidase A Substrates
- Nervous System
- Neurotransmitter Agents
- OATP1B1/SLCO1B1 Substrates
- P-glycoprotein substrates
- Selective Serotonin 5-HT1 Receptor Agonists
- Selective Serotonin Agonists
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Serotonin 1b Receptor Agonists
- Serotonin 1d Receptor Agonists
- Serotonin 5-HT1 Receptor Agonists
- Serotonin Agents
- Serotonin Modulators
- Serotonin Receptor Agonists
- Serotonin-1b and Serotonin-1d Receptor Agonist
- Sulfonamides
- Sulfones
- Sulfur Compounds
- Triptans
- Tryptamines
- Vasoconstrictor Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as tryptamines and derivatives. These are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Indoles and derivatives
- Sub Class
- Tryptamines and derivatives
- Direct Parent
- Tryptamines and derivatives
- Alternative Parents
- 3-alkylindoles / Aralkylamines / Substituted pyrroles / Organosulfonamides / Organic sulfonamides / Benzenoids / Heteroaromatic compounds / Aminosulfonyl compounds / Trialkylamines / Azacyclic compounds show 3 more
- Substituents
- 3-alkylindole / Amine / Aminosulfonyl compound / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Heteroaromatic compound / Hydrocarbon derivative / Indole show 16 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- sulfonamide, tryptamines (CHEBI:10650)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 8R78F6L9VO
- CAS number
- 103628-46-2
- InChI Key
- KQKPFRSPSRPDEB-UHFFFAOYSA-N
- InChI
- InChI=1S/C14H21N3O2S/c1-15-20(18,19)10-11-4-5-14-13(8-11)12(9-16-14)6-7-17(2)3/h4-5,8-9,15-16H,6-7,10H2,1-3H3
- IUPAC Name
- 1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide
- SMILES
- CNS(=O)(=O)CC1=CC=C2NC=C(CCN(C)C)C2=C1
References
- Synthesis Reference
Rajeev Mathur, T. Kumar, Sunilendu Roy, Rajiv Malik, "Taste masked sumatriptan tablets and processes for their preparation." U.S. Patent US20060233875, issued October 19, 2006.
US20060233875- General References
- Nikai T, Basbaum AI, Ahn AH: Profound reduction of somatic and visceral pain in mice by intrathecal administration of the anti-migraine drug, sumatriptan. Pain. 2008 Oct 31;139(3):533-40. doi: 10.1016/j.pain.2008.06.002. Epub 2008 Aug 23. [Article]
- Ferrari MD, Saxena PR: Clinical effects and mechanism of action of sumatriptan in migraine. Clin Neurol Neurosurg. 1992;94 Suppl:S73-7. [Article]
- Duquesnoy C, Mamet JP, Sumner D, Fuseau E: Comparative clinical pharmacokinetics of single doses of sumatriptan following subcutaneous, oral, rectal and intranasal administration. Eur J Pharm Sci. 1998 Apr;6(2):99-104. [Article]
- Humphrey PP: The discovery and development of the triptans, a major therapeutic breakthrough. Headache. 2008 May;48(5):685-7. doi: 10.1111/j.1526-4610.2008.01097.x. [Article]
- FDA Approved Drug Products: Sumatriptan and Naproxen Oral Tablets [Link]
- FDA Approved Drug Products: Sumatriptan Nasal Powder [Link]
- FDA Approved Drug Products: Sumatriptan Nasal Spray [Link]
- FDA Approved Drug Products: Sumatriptan Subcutaneous Injection [Link]
- FDA Approved Drug Products: Sumatriptan Subcutaneous Solution [Link]
- FDA Approved Drug Products: Sumatriptan Oral Tablets [Link]
- Sumatriptan Tablets, USP monograph [Link]
- External Links
- Human Metabolome Database
- HMDB0005037
- KEGG Drug
- D00451
- KEGG Compound
- C07319
- PubChem Compound
- 5358
- PubChem Substance
- 46506520
- ChemSpider
- 5165
- BindingDB
- 50005835
- 37418
- ChEBI
- 10650
- ChEMBL
- CHEMBL128
- ZINC
- ZINC000000014360
- Therapeutic Targets Database
- DNC001649
- PharmGKB
- PA451566
- Guide to Pharmacology
- GtP Drug Page
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Sumatriptan
- MSDS
- Download (49.9 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Not Available Migraine 1 4 Completed Other Workplace Migraine Treatment 1 4 Completed Prevention Migraine 2 4 Completed Treatment Chronic Migraine 1 4 Completed Treatment Headache 1
Pharmacoeconomics
- Manufacturers
- Glaxosmithkline
- King pharmaceuticals inc
- App pharmaceuticals llc
- Bedford laboratories div ben venue laboratories inc
- Bedford laboratories
- Jhp pharmaceuticals llc
- Par pharmaceutical inc
- Sagent strides llc
- Sandoz canada inc
- Teva parenteral medicines inc
- Wockhardt ltd
- Zogenix inc
- Aurobindo pharma ltd
- Dr reddys laboratories inc
- Mylan pharmaceuticals inc
- Orchid healthcare
- Ranbaxy laboratories ltd
- Roxane laboratories inc
- Sandoz inc
- Sun pharmaceutical industries ltd
- Teva pharmaceuticals usa inc
- Watson laboratories inc
- Packagers
- 3M Health Care
- Advanced Pharmaceutical Services Inc.
- Amerisource Health Services Corp.
- Apotheca Inc.
- APP Pharmaceuticals
- A-S Medication Solutions LLC
- Ascend Therapeutics
- Aurobindo Pharma Ltd.
- AzurPharma Inc.
- Barr Pharmaceuticals
- Bayer Healthcare
- Bedford Labs
- Ben Venue Laboratories Inc.
- Bradley Pharmaceuticals Inc.
- Bristol-Myers Squibb Co.
- Cardinal Health
- Caremark LLC
- Cobalt Pharmaceuticals Inc.
- Contract Pharm
- Cura Pharmaceutical Co. Inc.
- Direct Dispensing Inc.
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- Doctor Reddys Laboratories Ltd.
- DPT Laboratories Ltd.
- Duramed
- Esprit Pharma Inc.
- Fielding Pharmaceutical Co.
- GlaxoSmithKline Inc.
- Greenstone LLC
- Innovative Manufacturing and Distribution Services Inc.
- JHP Pharmaceuticals LLC
- Kaiser Foundation Hospital
- Laboratoires Besins International
- Lake Erie Medical and Surgical Supply
- Major Pharmaceuticals
- Murfreesboro Pharmaceutical Nursing Supply
- Mylan
- Novartis AG
- Novavax Inc.
- Noven Pharmaceuticals Inc.
- Novo Nordisk Inc.
- Nucare Pharmaceuticals Inc.
- Ohm Laboratories Inc.
- Orion Corporation
- Palmetto Pharmaceuticals Inc.
- Par Pharmaceuticals
- PD-Rx Pharmaceuticals Inc.
- Penn Labs
- Pharmaceutical Utilization Management Program VA Inc.
- Pharmaceutics International Inc.
- Pharmacia Inc.
- Pharmpak Inc.
- Physicians Total Care Inc.
- Preferred Pharmaceuticals Inc.
- Prepackage Specialists
- QPharm Inc.
- Qualitest
- Ranbaxy Laboratories
- Rebel Distributors Corp.
- Redpharm Drug
- Resource Optimization and Innovation LLC
- Sandoz
- Southwood Pharmaceuticals
- Stat Rx Usa
- Sun Pharmaceutical Industries Ltd.
- Teva Pharmaceutical Industries Ltd.
- Unimed Pharmaceuticals Inc.
- Upsher Smith Laboratories
- Warner Chilcott Co. Inc.
- Watson Pharmaceuticals
- Wockhardt Ltd.
- Zogenix Inc.
- Dosage Forms
Form Route Strength Spray Nasal 20 mg / dose Spray Nasal 5 mg / dose Injection, solution Subcutaneous 6 mg Solution Nasal 20.000 mg Spray Nasal 10 MG Spray Nasal 20 MG Suppository 25 MG Tablet Oral 100.000 mg Spray Nasal Tablet, film coated Oral 100 MG Tablet, film coated Oral Injection Parenteral 6 mg/0.5ml Tablet Oral 50.000 mg Tablet, orally disintegrating Oral Aerosol Respiratory (inhalation) 10 mg Aerosol Respiratory (inhalation) 20 mg Injection, solution 6 mg/0.5ml Spray Nasal 20 mg/1 Spray Nasal 20 mg / act Spray Nasal 5 mg/1 Spray Nasal 5 mg / act Tablet Oral 50 mg Liquid Subcutaneous 12 mg / mL Gel; kit; tablet Oral; Topical Kit Nasal 11 mg/1 Capsule Nasal 11 mg/1 Tablet Oral 25 mg Solution Parenteral 6 mg Solution Subcutaneous 6 mg Tablet Oral 100 mg Solution Nasal; Respiratory (inhalation) 10 mg Kit Oral; Topical Injection, solution Subcutaneous Kit; tablet; tablet, film coated Oral Spray Nasal 20 mg/100uL Spray Nasal 20 mg/0.1mL Spray Nasal 5 mg/100uL Spray Nasal 5 mg/0.1mL Tablet, coated Oral 100 mg/1 Tablet, coated Oral 50 mg/1 Tablet, delayed release Oral 50 mg Tablet Oral Solution Subcutaneous 12 mg / mL Injection Subcutaneous 4 mg/0.5mL Injection Subcutaneous 6 mg/0.5mL Injection, solution Subcutaneous 4 mg/0.5mL Injection, solution Subcutaneous 6 mg/0.5mL Tablet Oral 100 mg/1 Tablet Oral 25 mg/1 Tablet Oral 50 mg/1 Tablet, coated Oral 25 mg/1 Tablet, film coated Oral 100 mg/1 Tablet, film coated Oral 25 mg/1 Tablet, film coated Oral 50 mg/1 Tablet Oral Injection, solution Parenteral 6 MG/0.5ML Injection, solution 3 MG/0.5ML Tablet, coated Oral 100 mg Solution Subcutaneous 6 mg / 0.5 mL Spray Nasal 10 mg/1 Spray Nasal 10 mg/0.1mL Tablet, coated Oral Tablet, film coated Oral Patch, extended release, electrically controlled Transdermal 6.5 mg/4h Injection, solution Subcutaneous 3 mg/1 Tablet, film coated Oral 50 mg Tablet, coated Oral 50 mg - Prices
Unit description Cost Unit Imitrex 4 mg/0.5 ml syringe kit 229.02USD kit Imitrex 6 mg/0.5 ml syringe kit 229.02USD kit Imitrex STATdose Refill 1 Ea = 2 unit Refill Box 217.16USD box Imitrex 4 mg/0.5 ml kit refill 216.92USD kit Imitrex 6 mg/0.5 ml kit refill 216.92USD kit SUMAtriptan Succinate Refill 6 mg/0.5ml Kit Box 191.84USD box Sumatriptan 6 mg/0.5 ml refill 184.46USD each Sumatriptan 4 mg/0.5 ml refill 184.44USD each Imitrex 6 mg/0.5 ml vial 106.84USD vial Imitrex 6 mg/0.5ml Solution 0.5ml Vial 98.93USD vial Imitrex 5 mg/act Solution Nasal Inhaler 55.49USD inhaler Imitrex 20 mg nasal spray 45.73USD each Imitrex 5 mg nasal spray 45.73USD each Imitrex 20 mg/act Solution Nasal Inhaler 43.44USD inhaler Sumatriptan 20 mg nasal spray 38.89USD each Sumatriptan 5 mg nasal spray 38.89USD each Imitrex 25 mg tablet 32.45USD tablet Imitrex 100 mg tablet 30.16USD tablet Imitrex 50 mg tablet 30.16USD tablet Sumatriptan Succinate 25 mg tablet 28.14USD tablet Sumatriptan succ 25 mg tablet 27.06USD tablet Sumatriptan Succinate 100 mg tablet 26.15USD tablet Sumatriptan Succinate 50 mg tablet 26.15USD tablet Sumatriptan succ 100 mg tablet 25.14USD tablet Sumatriptan succ 50 mg tablet 25.14USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5705520 No 1998-01-06 2011-12-10 US CA2469019 No 2005-09-13 2022-12-04 Canada CA2098302 No 2001-10-16 2011-12-10 Canada US6060499 Yes 2000-05-09 2018-02-14 US US7332183 Yes 2008-02-19 2026-04-02 US US6586458 Yes 2003-07-01 2018-02-14 US US5872145 Yes 1999-02-16 2018-02-14 US US8022095 Yes 2011-09-20 2018-02-14 US US8491524 No 2013-07-23 2022-11-21 US US6681810 No 2004-01-27 2015-12-13 US US8287489 No 2012-10-16 2024-12-06 US US6135979 No 2000-10-24 2017-03-21 US US6280410 No 2001-08-28 2017-03-27 US US6174304 No 2001-01-16 2015-12-13 US US8343130 No 2013-01-01 2022-10-18 US US8241243 No 2012-08-14 2023-08-10 US US8241244 No 2012-08-14 2022-11-21 US US5957886 No 1999-09-28 2016-03-08 US US8267903 No 2012-09-18 2023-03-18 US US7901385 No 2011-03-08 2026-07-31 US US6251091 No 2001-06-26 2016-12-09 US US8118771 No 2012-02-21 2023-08-10 US US7776007 No 2010-08-17 2026-11-22 US US7811254 No 2010-10-12 2027-08-26 US US7973058 No 2011-07-05 2027-04-12 US US8155737 No 2012-04-10 2027-04-12 US US8366600 No 2013-02-05 2029-04-21 US US8470853 No 2013-06-25 2027-04-12 US US8983594 No 2015-03-17 2030-11-19 US US6745071 No 2004-06-01 2023-02-21 US US8597272 No 2013-12-03 2027-04-12 US US9272137 No 2016-03-01 2027-09-07 US US8875704 No 2014-11-04 2028-04-07 US US8590530 No 2013-11-26 2025-09-15 US US8327844 No 2012-12-11 2023-10-03 US US7975690 No 2011-07-12 2025-08-18 US US8899229 No 2014-12-02 2030-08-18 US US9108015 No 2015-08-18 2025-09-15 US US6715485 No 2004-04-06 2020-03-03 US US8555877 No 2013-10-15 2020-03-03 US US8550073 No 2013-10-08 2029-10-22 US US8978647 No 2015-03-17 2030-12-06 US US8047202 No 2011-11-01 2023-07-02 US US9119932 No 2015-09-01 2024-04-23 US US9327114 No 2016-05-03 2032-10-08 US US9427578 No 2016-08-30 2027-04-12 US US9649456 No 2017-05-16 2030-10-21 US US10076615 No 2018-09-18 2029-07-30 US US10076614 No 2018-09-18 2034-10-20 US US10124132 No 2018-11-13 2027-03-06 US US9211282 No 2015-12-15 2031-07-19 US US9974770 No 2018-05-22 2030-06-16 US US8440631 No 2013-05-14 2026-05-09 US US9610280 No 2017-04-04 2030-06-16 US US9283280 No 2016-03-15 2025-07-01 US US8268791 No 2012-09-18 2026-05-09 US US10478574 No 2019-11-19 2033-11-04 US US10398859 No 2019-09-03 2027-12-19 US US10537554 No 2020-01-21 2036-01-29 US US10603305 No 2020-03-31 2030-06-16 US US10722667 No 2020-07-28 2028-12-30 US US11337962 No 2010-06-16 2030-06-16 US US11364224 No 2016-01-29 2036-01-29 US US11571531 No 2006-02-23 2026-02-23 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 169-170 http://www.chemspider.com/Chemical-Structure.5165.html water solubility 54mg/mL Sumatriptan Tablets, USP monograph logP 0.93 ADLARD,M ET AL. (1995) pKa 4.9 Sumatriptan Tablets, USP monograph - Predicted Properties
Property Value Source Water Solubility 0.127 mg/mL ALOGPS logP 1.17 ALOGPS logP 0.74 Chemaxon logS -3.4 ALOGPS pKa (Strongest Acidic) 11.24 Chemaxon pKa (Strongest Basic) 9.54 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 65.2 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 82.08 m3·mol-1 Chemaxon Polarizability 32.31 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9626 Caco-2 permeable - 0.8957 P-glycoprotein substrate Substrate 0.5914 P-glycoprotein inhibitor I Non-inhibitor 0.8782 P-glycoprotein inhibitor II Non-inhibitor 0.9081 Renal organic cation transporter Non-inhibitor 0.7344 CYP450 2C9 substrate Non-substrate 0.8014 CYP450 2D6 substrate Non-substrate 0.5913 CYP450 3A4 substrate Substrate 0.6029 CYP450 1A2 substrate Non-inhibitor 0.5603 CYP450 2C9 inhibitor Non-inhibitor 0.7898 CYP450 2D6 inhibitor Non-inhibitor 0.7422 CYP450 2C19 inhibitor Non-inhibitor 0.7428 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6974 Ames test Non AMES toxic 0.649 Carcinogenicity Non-carcinogens 0.8134 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.5404 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.5668 hERG inhibition (predictor II) Non-inhibitor 0.7046
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 183.9224126 predictedDarkChem Lite v0.1.0 [M-H]- 184.4840126 predictedDarkChem Lite v0.1.0 [M-H]- 161.67427 predictedDeepCCS 1.0 (2019) [M+H]+ 183.7482126 predictedDarkChem Lite v0.1.0 [M+H]+ 184.7080126 predictedDarkChem Lite v0.1.0 [M+H]+ 164.06984 predictedDeepCCS 1.0 (2019) [M+Na]+ 183.0707126 predictedDarkChem Lite v0.1.0 [M+Na]+ 184.3173126 predictedDarkChem Lite v0.1.0 [M+Na]+ 170.11028 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Serotonin receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
- Gene Name
- HTR1A
- Uniprot ID
- P08908
- Uniprot Name
- 5-hydroxytryptamine receptor 1A
- Molecular Weight
- 46106.335 Da
References
- Johnson DE, Rollema H, Schmidt AW, McHarg AD: Serotonergic effects and extracellular brain levels of eletriptan, zolmitriptan and sumatriptan in rat brain. Eur J Pharmacol. 2001 Aug 17;425(3):203-10. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Serotonin receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive subst...
- Gene Name
- HTR1D
- Uniprot ID
- P28221
- Uniprot Name
- 5-hydroxytryptamine receptor 1D
- Molecular Weight
- 41906.38 Da
References
- Koran LM, Pallanti S, Quercioli L: Sumatriptan, 5-HT(1D) receptors and obsessive-compulsive disorder. Eur Neuropsychopharmacol. 2001 Apr;11(2):169-72. [Article]
- Baxter LR Jr: Brain mediation of Anolis social dominance displays. III. Differential forebrain 3H-sumatriptan binding in dominant vs. submissive males. Brain Behav Evol. 2001 Apr;57(4):202-13. [Article]
- Razzaque Z, Pickard JD, Ma QP, Shaw D, Morrison K, Wang T, Longmore J: 5-HT1B-receptors and vascular reactivity in human isolated blood vessels: assessment of the potential craniovascular selectivity of sumatriptan. Br J Clin Pharmacol. 2002 Mar;53(3):266-74. [Article]
- Akin D, Gurdal H: Involvement of 5-HT1B and 5-HT1D receptors in sumatriptan mediated vasocontractile response in rabbit common carotid artery. Br J Pharmacol. 2002 May;136(2):177-82. [Article]
- Zohar J, Kennedy JL, Hollander E, Koran LM: Serotonin-1D hypothesis of obsessive-compulsive disorder: an update. J Clin Psychiatry. 2004;65 Suppl 14:18-21. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Mitsikostas DD, Sanchez del Rio M, Moskowitz MA, Waeber C: Both 5-HT1B and 5-HT1F receptors modulate c-fos expression within rat trigeminal nucleus caudalis. Eur J Pharmacol. 1999 Mar 26;369(3):271-7. [Article]
- Cohen ML, Schenck KW, Hemrick-Luecke SH: 5-Hydroxytryptamine(1A) receptor activation enhances norepinephrine release from nerves in the rabbit saphenous vein. J Pharmacol Exp Ther. 1999 Sep;290(3):1195-201. [Article]
- Roy A, Brand NJ, Yacoub MH: Expression of 5-hydroxytryptamine receptor subtype messenger RNA in interstitial cells from human heart valves. J Heart Valve Dis. 2000 Mar;9(2):256-60; discussion 260-1. [Article]
- Nikai T, Basbaum AI, Ahn AH: Profound reduction of somatic and visceral pain in mice by intrathecal administration of the anti-migraine drug, sumatriptan. Pain. 2008 Oct 31;139(3):533-40. doi: 10.1016/j.pain.2008.06.002. Epub 2008 Aug 23. [Article]
- Mitsikostas DD, Sanchez del Rio M, Waeber C: 5-Hydroxytryptamine(1B/1D) and 5-hydroxytryptamine1F receptors inhibit capsaicin-induced c-fos immunoreactivity within mouse trigeminal nucleus caudalis. Cephalalgia. 2002 Jun;22(5):384-94. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Serotonin receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive subst...
- Gene Name
- HTR1B
- Uniprot ID
- P28222
- Uniprot Name
- 5-hydroxytryptamine receptor 1B
- Molecular Weight
- 43567.535 Da
References
- Dupuis DS, Perez M, Halazy S, Colpaert FC, Pauwels PJ: Magnitude of 5-HT1B and 5-HT1A receptor activation in guinea-pig and rat brain: evidence from sumatriptan dimer-mediated [35S]GTPgammaS binding responses. Brain Res Mol Brain Res. 1999 Apr 6;67(1):107-23. [Article]
- Mitsikostas DD, Sanchez del Rio M, Moskowitz MA, Waeber C: Both 5-HT1B and 5-HT1F receptors modulate c-fos expression within rat trigeminal nucleus caudalis. Eur J Pharmacol. 1999 Mar 26;369(3):271-7. [Article]
- Cohen ML, Schenck KW, Hemrick-Luecke SH: 5-Hydroxytryptamine(1A) receptor activation enhances norepinephrine release from nerves in the rabbit saphenous vein. J Pharmacol Exp Ther. 1999 Sep;290(3):1195-201. [Article]
- Cohen Z, Bouchelet I, Olivier A, Villemure JG, Ball R, Stanimirovic DB, Hamel E: Multiple microvascular and astroglial 5-hydroxytryptamine receptor subtypes in human brain: molecular and pharmacologic characterization. J Cereb Blood Flow Metab. 1999 Aug;19(8):908-17. [Article]
- Granas C, Larhammar D: Identification of an amino acid residue important for binding of methiothepin and sumatriptan to the human 5-HT(1B) receptor. Eur J Pharmacol. 1999 Sep 10;380(2-3):171-81. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Razzaque Z, Pickard JD, Ma QP, Shaw D, Morrison K, Wang T, Longmore J: 5-HT1B-receptors and vascular reactivity in human isolated blood vessels: assessment of the potential craniovascular selectivity of sumatriptan. Br J Clin Pharmacol. 2002 Mar;53(3):266-74. [Article]
- Akin D, Gurdal H: Involvement of 5-HT1B and 5-HT1D receptors in sumatriptan mediated vasocontractile response in rabbit common carotid artery. Br J Pharmacol. 2002 May;136(2):177-82. [Article]
- Roy A, Brand NJ, Yacoub MH: Expression of 5-hydroxytryptamine receptor subtype messenger RNA in interstitial cells from human heart valves. J Heart Valve Dis. 2000 Mar;9(2):256-60; discussion 260-1. [Article]
- Nikai T, Basbaum AI, Ahn AH: Profound reduction of somatic and visceral pain in mice by intrathecal administration of the anti-migraine drug, sumatriptan. Pain. 2008 Oct 31;139(3):533-40. doi: 10.1016/j.pain.2008.06.002. Epub 2008 Aug 23. [Article]
- Mitsikostas DD, Sanchez del Rio M, Waeber C: 5-Hydroxytryptamine(1B/1D) and 5-hydroxytryptamine1F receptors inhibit capsaicin-induced c-fos immunoreactivity within mouse trigeminal nucleus caudalis. Cephalalgia. 2002 Jun;22(5):384-94. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Serotonin receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various alkaloids and psychoactive substances. Ligand binding causes a conformation change that trig...
- Gene Name
- HTR1F
- Uniprot ID
- P30939
- Uniprot Name
- 5-hydroxytryptamine receptor 1F
- Molecular Weight
- 41708.505 Da
References
- Razzaque Z, Heald MA, Pickard JD, Maskell L, Beer MS, Hill RG, Longmore J: Vasoconstriction in human isolated middle meningeal arteries: determining the contribution of 5-HT1B- and 5-HT1F-receptor activation. Br J Clin Pharmacol. 1999 Jan;47(1):75-82. [Article]
- Pauwels PJ, John GW: Present and future of 5-HT receptor agonists as antimigraine drugs. Clin Neuropharmacol. 1999 May-Jun;22(3):123-36. [Article]
- Cohen ML, Schenck K: Contractile responses to sumatriptan and ergotamine in the rabbit saphenous vein: effect of selective 5-HT(1F) receptor agonists and PGF(2alpha). Br J Pharmacol. 2000 Oct;131(3):562-8. [Article]
- Janssen P, Tack J, Sifrim D, Meulemans AL, Lefebvre RA: Influence of 5-HT1 receptor agonists on feline stomach relaxation. Eur J Pharmacol. 2004 May 25;492(2-3):259-67. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Mitsikostas DD, Sanchez del Rio M, Moskowitz MA, Waeber C: Both 5-HT1B and 5-HT1F receptors modulate c-fos expression within rat trigeminal nucleus caudalis. Eur J Pharmacol. 1999 Mar 26;369(3):271-7. [Article]
- Nikai T, Basbaum AI, Ahn AH: Profound reduction of somatic and visceral pain in mice by intrathecal administration of the anti-migraine drug, sumatriptan. Pain. 2008 Oct 31;139(3):533-40. doi: 10.1016/j.pain.2008.06.002. Epub 2008 Aug 23. [Article]
- Mitsikostas DD, Sanchez del Rio M, Waeber C: 5-Hydroxytryptamine(1B/1D) and 5-hydroxytryptamine1F receptors inhibit capsaicin-induced c-fos immunoreactivity within mouse trigeminal nucleus caudalis. Cephalalgia. 2002 Jun;22(5):384-94. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Serotonin binding
- Specific Function
- Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
- Gene Name
- MAOA
- Uniprot ID
- P21397
- Uniprot Name
- Amine oxidase [flavin-containing] A
- Molecular Weight
- 59681.27 Da
References
- Fox AW: Subcutaneous sumatriptan pharmacokinetics: delimiting the monoamine oxidase inhibitor effect. Headache. 2010 Feb;50(2):249-55. doi: 10.1111/j.1526-4610.2009.01568.x. Epub 2009 Nov 17. [Article]
- Fuseau E, Petricoul O, Moore KH, Barrow A, Ibbotson T: Clinical pharmacokinetics of intranasal sumatriptan. Clin Pharmacokinet. 2002;41(11):801-11. [Article]
- Med-Psych Drug-Drug Interactions Update: Triptans [File]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
- Gene Name
- SLCO1A2
- Uniprot ID
- P46721
- Uniprot Name
- Solute carrier organic anion transporter family member 1A2
- Molecular Weight
- 74144.105 Da
References
- Lu R, Kanai N, Bao Y, Wolkoff AW, Schuster VL: Regulation of renal oatp mRNA expression by testosterone. Am J Physiol. 1996 Feb;270(2 Pt 2):F332-7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Mahar Doan KM, Humphreys JE, Webster LO, Wring SA, Shampine LJ, Serabjit-Singh CJ, Adkison KK, Polli JW: Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther. 2002 Dec;303(3):1029-37. [Article]
- Pontier C, Pachot J, Botham R, Lenfant B, Arnaud P: HT29-MTX and Caco-2/TC7 monolayers as predictive models for human intestinal absorption: role of the mucus layer. J Pharm Sci. 2001 Oct;90(10):1608-19. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
- Gene Name
- ABCG2
- Uniprot ID
- Q9UNQ0
- Uniprot Name
- ATP-binding cassette sub-family G member 2
- Molecular Weight
- 72313.47 Da
References
- Janvilisri T, Venter H, Shahi S, Reuter G, Balakrishnan L, van Veen HW: Sterol transport by the human breast cancer resistance protein (ABCG2) expressed in Lactococcus lactis. J Biol Chem. 2003 Jun 6;278(23):20645-51. Epub 2003 Mar 28. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
- Gene Name
- SLCO1B1
- Uniprot ID
- Q9Y6L6
- Uniprot Name
- Solute carrier organic anion transporter family member 1B1
- Molecular Weight
- 76447.99 Da
References
- Suzuki H, Sugiyama Y: Transport of drugs across the hepatic sinusoidal membrane: sinusoidal drug influx and efflux in the liver. Semin Liver Dis. 2000;20(3):251-63. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55