Identification

Name
Sumatriptan
Accession Number
DB00669  (APRD00379)
Type
Small Molecule
Groups
Approved, Investigational
Description

A serotonin agonist that acts selectively at 5HT1 receptors. It is used in the treatment of migraine disorders. A transdermal patch version of sumatriptan is currently in phase I trials in the U.S. under the code name NP101 (NuPathe).

Structure
Thumb
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
  • NP101
  • Sumatran
  • Sumatriptan
  • Sumatriptán
  • Sumatriptanum
  • Sumax
  • triptan
External IDs
GR 43175 A / GR 43175 C / GR 43175 X / N02CC01 / SN 308
Product Ingredients
IngredientUNIICASInChI Key
Sumatriptan SuccinateJ8BDZ68989Not AvailableNot applicable
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act SumatriptanTablet50 mgOralActavis Pharma Company2005-08-24Not applicableCanada
Act SumatriptanTablet25 mgOralActavis Pharma Company2005-08-24Not applicableCanada
Act SumatriptanTablet100 mgOralActavis Pharma Company2005-08-24Not applicableCanada
AlsumaInjection, solution6 mg/0.5mLSubcutaneousUs World Meds, Llc2010-10-152013-08-31Us
AlsumaInjection, solution6 mg/0.5mLSubcutaneousPfizer Laboratories Div Pfizer Inc.2009-08-312015-08-31Us
ImitrexInjection4 mg/0.5mLSubcutaneousGlaxo Operations UK Ltd2006-04-062017-12-21Us
ImitrexInjection4 mg/0.5mLSubcutaneousGlaxosmithkline Inc2006-04-06Not applicableUs
ImitrexSpray20 mg/1NasalGlaxoSmithKline LLC1997-09-18Not applicableUs
ImitrexSpray20 mg/1NasalPhysicians Total Care, Inc.1997-09-182011-06-30Us
ImitrexLiquid6 mgSubcutaneousGlaxosmithkline Inc1999-08-30Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-sumatriptanSpray5 mgNasalApotex CorporationNot applicableNot applicableCanada
Apo-sumatriptanTablet100 mgOralApotex Corporation2005-08-24Not applicableCanada
Apo-sumatriptanTablet25 mgOralApotex CorporationNot applicableNot applicableCanada
Apo-sumatriptanTablet50 mgOralApotex Corporation2005-08-24Not applicableCanada
Apo-sumatriptanSpray20 mgNasalApotex CorporationNot applicableNot applicableCanada
Ava-sumatriptanTablet50 mgOralAvanstra Inc2011-09-192014-08-21Canada
Ava-sumatriptanTablet100 mgOralAvanstra Inc2011-09-192014-08-21Canada
Dom-sumatriptanTablet50 mgOralDominion Pharmacal2005-09-29Not applicableCanada
Dom-sumatriptanTablet25 mgOralDominion Pharmacal2005-09-29Not applicableCanada
Dom-sumatriptanTablet100 mgOralDominion Pharmacal2005-09-29Not applicableCanada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Sumatriptan and Naproxen SodiumSumatriptan Succinate (85 mg/1) + Naproxen sodium (500 mg/1)Tablet, film coatedOralSun Pharmaceutical Industries, Inc.2018-07-20Not applicableUs
Sumatriptan and Naproxen SodiumSumatriptan Succinate (85 mg/1) + Naproxen sodium (500 mg/1)Tablet, film coatedOralMylan Pharmaceuticals Inc.2018-09-04Not applicableUs
Sumatriptan and Naproxen SodiumSumatriptan Succinate (85 mg/1) + Naproxen sodium (500 mg/1)Tablet, film coatedOralAurobindo Pharma2018-02-15Not applicableUs
Sumatriptan Succinate and Naproxen SodiumSumatriptan Succinate (85 mg/1) + Naproxen sodium (500 mg/1)TabletOralMacoven2015-05-14Not applicableUs
TreximetSumatriptan Succinate (10 mg/1) + Naproxen sodium (60 mg/1)Tablet, film coatedOralPernix Therapeutics2015-05-14Not applicableUs
TreximetSumatriptan Succinate (85 mg/1) + Naproxen sodium (500 mg/1)Tablet, film coatedOralRebel Distributors2008-04-25Not applicableUs
TreximetSumatriptan Succinate (85 mg/1) + Naproxen sodium (500 mg/1)Tablet, film coatedOralGlaxo Operations UK Ltd2008-04-252018-02-14Us
TreximetSumatriptan Succinate (85 mg/1) + Naproxen sodium (500 mg/1)Tablet, film coatedOralPernix Therapeutics2015-05-14Not applicableUs
TreximetSumatriptan Succinate (85 mg/1) + Naproxen sodium (500 mg/1)Tablet, film coatedOralGlaxosmithkline Inc2008-04-252018-07-31Us
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
MigranowSumatriptan Succinate (50 mg/1) + Menthol (10 g/100g) + Synthetic Camphor (4 g/100g)KitPure Tek Corporation2016-04-18Not applicableUs
SumaChipSumatriptan Succinate (100 mg/1) + Capsaicin (0.0375 g/100g) + Menthol (5 g/100g)KitBasiem2015-11-292016-03-04Us
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 / Imitrex Oral (GlaxoSmithKline) / Migralgin (GMP) / Migraneitor (Driburg) / Nazdav (Dr. Reddy's) / Sapphirex (Hemofarm) / Sumatran (Rowex) / Sumax (Libbs) / Suminat (Sun) / Youshu (Simcere)
Categories
UNII
8R78F6L9VO
CAS number
103628-46-2
Weight
Average: 295.4
Monoisotopic: 295.135447621
Chemical Formula
C14H21N3O2S
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=CC2=C(NC=C2CCN(C)C)C=C1

Pharmacology

Indication

For the treatment of migraine attacks with or without aura.

Associated Conditions
Pharmacodynamics

Sumatriptan, an antimigraine drug, is a selective agonist of vascular serotonin ((5-hydroxytryptamine; 5-HT) type 1-like receptors, likely the 5-HT1D and 5-HT1B subtypes. It has no significant affinity (as measured using standard radioligand binding assays) or pharmacological activity at 5-HT2, 5-HT3 receptor subtypes or at alpha1-, alpha2-, or beta-adrenergic; dopamine1; dopamine2; muscarinic; or benzodiazepine receptors.

Mechanism of action

The 5-HT1B and 5-HT1D receptors function as autoreceptors, which inhibit the firing of serotonin neurons and a reduction in the synthesis and release of serotonin upon activation. After sumatriptan binds to these receptors, adenylate cyclase activity is inhibited via regulatory G proteins, incrases intracellular calcium, and affects other intracellular events. This results in vasoconstriction and inhibtion of sensory nociceptive (trigeminal) nerve firing and vasoactive neuropeptide release.

TargetActionsOrganism
A5-hydroxytryptamine receptor 1D
agonist
Human
A5-hydroxytryptamine receptor 1B
agonist
Human
A5-hydroxytryptamine receptor 1F
agonist
Human
A5-hydroxytryptamine receptor 1A
agonist
Human
Absorption

Approximately 15%

Volume of distribution
  • 2.7 L/kg [subcutaneous dosing]
Protein binding

14%-21%

Metabolism

Hepatic. In vitro studies with human microsomes suggest that sumatriptan is metabolized by monoamine oxidase (MAO), predominantly the A isoenzyme.

Route of elimination

Only 3% of the dose is excreted in the urine as unchanged sumatriptan; 42% of the dose is excreted as the major metabolite, the indole acetic acid analogue of sumatriptan.

Half life

2.5 hours

Clearance
  • 1200 mL/min [Following a 6-mg SC injection]
Toxicity

Symptoms of overdose include convulsions, tremor, paralysis, inactivity, ptosis, erythema of the extremities, abnormal respiration, cyanosis, ataxia, mydriasis, salivation, and lacrimation.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Guanine nucleotide-binding protein G(I)/G(S)/G(T) subunit beta-3---(C;T) / (T;T)T AlleleEffect Directly StudiedPatients with this genotype have an increased likelihood of responding to sumatriptan when treating (condition: cluster headache).Details

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of adverse effects can be increased when Sumatriptan is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of adverse effects can be increased when Sumatriptan is combined with (S)-Warfarin.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be increased when used in combination with Sumatriptan.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when Sumatriptan is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of serotonin syndrome can be increased when Sumatriptan is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of serotonin syndrome can be increased when Sumatriptan is combined with 3,4-Methylenedioxyamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of serotonin syndrome can be increased when Sumatriptan is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-hydroxycoumarinThe risk or severity of adverse effects can be increased when Sumatriptan is combined with 4-hydroxycoumarin.
4-MethoxyamphetamineThe metabolism of Sumatriptan can be decreased when combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of serotonin syndrome can be increased when Sumatriptan is combined with 5-methoxy-N,N-dimethyltryptamine.
Food Interactions
Not Available

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
  1. 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. [PubMed:18723285]
External Links
Human Metabolome Database
HMDB0005037
KEGG Drug
D00451
KEGG Compound
C07319
PubChem Compound
5358
PubChem Substance
46506520
ChemSpider
5165
BindingDB
50005835
ChEBI
10650
ChEMBL
CHEMBL128
Therapeutic Targets Database
DNC001649
PharmGKB
PA451566
IUPHAR
119
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Sumatriptan
ATC Codes
N02CC01 — SumatriptanG01AE10 — Combinations of sulfonamides
AHFS Codes
  • 28:32.28 — Selective Serotonin Agonists
FDA label
Download (142 KB)
MSDS
Download (49.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingBasic ScienceHealthy Volunteers1
1Active Not RecruitingTreatmentMigraine Disorders1
1Active Not RecruitingTreatmentMigraines1
1CompletedNot AvailableHealthy Volunteers4
1CompletedNot AvailableMigraine Disorders / Migraines1
1CompletedBasic ScienceAcute Treatment of Migraine / Migraines1
1CompletedBasic ScienceCompare Bioequivalence Patches Previously Used in the NP101-007 Study / Compare the Bioequivalence Between NP101 Patches Previously Used in the NP101-007 Study and NP101 Patches With Minor Modifications, in Healthy Adult Volunteers1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedBasic ScienceMigraine Disorders1
1CompletedTreatmentCluster Headache / Migraine Disorders / Migraine With or Without Aura / Migraines1
1CompletedTreatmentHealthy Volunteers4
1CompletedTreatmentMigraine Disorders2
1CompletedTreatmentMigraine, Acute1
1CompletedTreatmentMigraines1
2CompletedTreatmentMigraine - Acute1
2CompletedTreatmentMigraine Disorders1
2CompletedTreatmentMigraine With Aura1
2CompletedTreatmentMigraines1
2CompletedTreatmentRapidly Escalating Migraine1
2RecruitingTreatmentPost-Traumatic Headaches1
2TerminatedTreatmentMigrainous Headache1
2, 3CompletedTreatmentAdolescent Migraine / Migraines1
2, 3CompletedTreatmentMigraine Disorders / Migraine With and Without Aura / Migraine With Aura / Migraine Without Aura / Migraine, Acute / Migraine, Classic / Migraine;Premenstrual1
3CompletedTreatmentCluster Headache / Migraine Disorders / Migraines1
3CompletedTreatmentHeadaches / Migraines1
3CompletedTreatmentMigraine Disorders4
3CompletedTreatmentMigraine Disorders / Migraine, Acute1
3CompletedTreatmentMigraine Disorders / Migraines1
3CompletedTreatmentMigraine With Aura / Migraine Without Aura1
3CompletedTreatmentMigraine With or Without Aura2
3CompletedTreatmentMigraine, Acute1
3CompletedTreatmentMigraine, Without Aura1
3CompletedTreatmentMigraines1
3CompletedTreatmentMigrainous Headache6
4CompletedNot AvailableMigraines1
4CompletedOtherWorkplace Migraine Treatment1
4CompletedPreventionMigraines2
4CompletedTreatmentChronic Migraine1
4CompletedTreatmentHeadache Disorders, Primary / Headache, Tension-Type / Migraines1
4CompletedTreatmentMenstrual Migraines1
4CompletedTreatmentMigraine Disorders / Migraine With or Without Aura / Migraine, Acute / Migrainous Headache1
4CompletedTreatmentMigraines4
4CompletedTreatmentMigrainous Headache1
4CompletedTreatmentPain, Migraine1
4TerminatedPreventionPost-Traumatic Headaches1
Not AvailableCompletedNot AvailableAcute Gouty Arthritis / Arthritis / Headaches / Migraines / Muscle Spasms / Radicular syndrome / Synovitis / Tendonitis1
Not AvailableCompletedNot AvailableHealthy Volunteers2
Not AvailableCompletedNot AvailableHealthy Volunteers / Migraines1
Not AvailableCompletedNot AvailableMigraine Disorders5
Not AvailableCompletedNot AvailableMigraines1
Not AvailableCompletedTreatmentMigraines3
Not AvailableRecruitingTreatmentMigraines1
Not AvailableRecruitingTreatmentPostoperative Migrainous Headache / Postoperative Quality of Recovery1
Not AvailableUnknown StatusNot AvailableCognitive Impairments / Migrainous Headache1
Not AvailableUnknown StatusTreatmentMigraine With Aura1
Not AvailableWithdrawnTreatmentHeadache Disorders, Primary / Migraine Disorders / Migraine With Aura / Migraine Without Aura / Migraines / Migrainous Headache1
Not AvailableWithdrawnTreatmentMigraines1

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
FormRouteStrength
SprayNasal20 mg
SprayNasal5 mg
LiquidSubcutaneous6 mg
SprayNasal20 mg/1
SprayNasal5 mg/1
TabletOral100 mg
TabletOral50 mg
LiquidSubcutaneous12 mg
KitNasal11 mg/1
TabletOral25 mg
Kit
SprayNasal20 mg/100uL
SprayNasal20 mg/0.1mL
SprayNasal5 mg/100uL
SprayNasal5 mg/0.1mL
Tablet, coatedOral100 mg/1
Tablet, coatedOral50 mg/1
SolutionSubcutaneous12 mg
InjectionSubcutaneous4 mg/0.5mL
InjectionSubcutaneous6 mg/0.5mL
Injection, solutionSubcutaneous4 mg/0.5mL
Injection, solutionSubcutaneous6 mg/0.5mL
TabletOral100 mg/1
TabletOral25 mg/1
TabletOral50 mg/1
Tablet, coatedOral25 mg/1
Tablet, film coatedOral100 mg/1
Tablet, film coatedOral25 mg/1
Tablet, film coatedOral50 mg/1
TabletOral
SolutionSubcutaneous6 mg
Tablet, film coatedOral
Patch, extended release, electrically controlledTransdermal6.5 mg/4h
Injection, solutionSubcutaneous3 mg/1
Prices
Unit descriptionCostUnit
Imitrex 4 mg/0.5 ml syringe kit229.02USD kit
Imitrex 6 mg/0.5 ml syringe kit229.02USD kit
Imitrex STATdose Refill 1 Ea = 2 unit Refill Box217.16USD box
Imitrex 4 mg/0.5 ml kit refill216.92USD kit
Imitrex 6 mg/0.5 ml kit refill216.92USD kit
SUMAtriptan Succinate Refill 6 mg/0.5ml Kit Box191.84USD box
Sumatriptan 6 mg/0.5 ml refill184.46USD each
Sumatriptan 4 mg/0.5 ml refill184.44USD each
Imitrex 6 mg/0.5 ml vial106.84USD vial
Imitrex 6 mg/0.5ml Solution 0.5ml Vial98.93USD vial
Imitrex 5 mg/act Solution Nasal Inhaler55.49USD inhaler
Imitrex 20 mg nasal spray45.73USD each
Imitrex 5 mg nasal spray45.73USD each
Imitrex 20 mg/act Solution Nasal Inhaler43.44USD inhaler
Sumatriptan 20 mg nasal spray38.89USD each
Sumatriptan 5 mg nasal spray38.89USD each
Imitrex 25 mg tablet32.45USD tablet
Imitrex 100 mg tablet30.16USD tablet
Imitrex 50 mg tablet30.16USD tablet
Sumatriptan Succinate 25 mg tablet28.14USD tablet
Sumatriptan succ 25 mg tablet27.06USD tablet
Sumatriptan Succinate 100 mg tablet26.15USD tablet
Sumatriptan Succinate 50 mg tablet26.15USD tablet
Sumatriptan succ 100 mg tablet25.14USD tablet
Sumatriptan succ 50 mg tablet25.14USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5705520No1998-01-062011-12-10Us
CA2469019No2005-09-132022-12-04Canada
CA2098302No2001-10-162011-12-10Canada
US6060499Yes2000-05-092018-02-14Us
US7332183Yes2008-02-192026-04-02Us
US6586458Yes2003-07-012018-02-14Us
US5872145Yes1999-02-162018-02-14Us
US8022095Yes2011-09-202018-02-14Us
US8491524No2013-07-232022-11-21Us
US6681810No2004-01-272015-12-13Us
US8287489No2012-10-162024-12-06Us
US6135979No2000-10-242017-03-21Us
US6280410No2001-08-282017-03-27Us
US6174304No2001-01-162015-12-13Us
US8343130No2013-01-012022-10-18Us
US8241243No2012-08-142023-08-10Us
US8241244No2012-08-142022-11-21Us
US5957886No1999-09-282016-03-08Us
US8267903No2012-09-182023-03-18Us
US7901385No2011-03-082026-07-31Us
US6251091No2001-06-262016-12-09Us
US8118771No2012-02-212023-08-10Us
US7776007No2010-08-172026-11-22Us
US7811254No2010-10-122027-08-26Us
US7973058No2011-07-052027-04-12Us
US8155737No2012-04-102027-04-12Us
US8366600No2013-02-052029-04-21Us
US8470853No2013-06-252027-04-12Us
US8983594No2015-03-172030-11-19Us
US6745071No2004-06-012023-02-21Us
US8597272No2013-12-032027-04-12Us
US9272137No2016-03-012027-09-07Us
US8875704No2014-11-042028-04-07Us
US8590530No2013-11-262025-09-15Us
US8327844No2012-12-112023-10-03Us
US7975690No2011-07-122025-08-18Us
US8899229No2014-12-022030-08-18Us
US9108015No2015-08-182025-09-15Us
US6715485No2004-04-062020-03-03Us
US8555877No2013-10-152020-03-03Us
US8550073No2013-10-082029-10-22Us
US8978647No2015-03-172030-12-06Us
US8047202No2011-11-012023-07-02Us
US9119932No2015-09-012024-04-23Us
US9327114No2016-05-032032-10-08Us
US9427578No2016-08-302027-04-12Us
US9649456No2017-05-162030-10-21Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)169-171 °CNot Available
water solubility21.4 mg/mlNot Available
logP0.93ADLARD,M ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.127 mg/mLALOGPS
logP1.17ALOGPS
logP0.74ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)11.24ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area65.2 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity82.08 m3·mol-1ChemAxon
Polarizability32.31 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9626
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.5914
P-glycoprotein inhibitor INon-inhibitor0.8782
P-glycoprotein inhibitor IINon-inhibitor0.9081
Renal organic cation transporterNon-inhibitor0.7344
CYP450 2C9 substrateNon-substrate0.8014
CYP450 2D6 substrateNon-substrate0.5913
CYP450 3A4 substrateSubstrate0.6029
CYP450 1A2 substrateNon-inhibitor0.5603
CYP450 2C9 inhibitorNon-inhibitor0.7898
CYP450 2D6 inhibitorNon-inhibitor0.7422
CYP450 2C19 inhibitorNon-inhibitor0.7428
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6974
Ames testNon AMES toxic0.649
CarcinogenicityNon-carcinogens0.8134
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5404 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5668
hERG inhibition (predictor II)Non-inhibitor0.7046
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0a4i-9400000000-93cc7dc7e521f98aa292
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-0390000000-cdddf05865e6d570c337
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-2910000000-8769dc29dcac8fede7d1

Taxonomy

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
Tryptamine / 3-alkylindole / Indole / Aralkylamine / Substituted pyrrole / Organic sulfonic acid amide / Benzenoid / Organosulfonic acid amide / Pyrrole / Organic sulfonic acid or derivatives
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
sulfonamide, tryptamines (CHEBI:10650)

Targets

Kind
Protein
Organism
Human
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
  1. Koran LM, Pallanti S, Quercioli L: Sumatriptan, 5-HT(1D) receptors and obsessive-compulsive disorder. Eur Neuropsychopharmacol. 2001 Apr;11(2):169-72. [PubMed:11313163]
  2. 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. [PubMed:11641558]
  3. 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. [PubMed:11874390]
  4. 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. [PubMed:12010765]
  5. 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. [PubMed:15554784]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  7. 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. [PubMed:10225363]
  8. 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. [PubMed:10454495]
  9. 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. [PubMed:10772044]
  10. 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. [PubMed:18723285]
  11. 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. [PubMed:12110114]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:10101238]
  2. 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. [PubMed:10225363]
  3. 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. [PubMed:10454495]
  4. 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. [PubMed:10458598]
  5. 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. [PubMed:10513577]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  7. 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. [PubMed:11874390]
  8. 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. [PubMed:12010765]
  9. 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. [PubMed:10772044]
  10. 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. [PubMed:18723285]
  11. 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. [PubMed:12110114]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:10073743]
  2. Pauwels PJ, John GW: Present and future of 5-HT receptor agonists as antimigraine drugs. Clin Neuropharmacol. 1999 May-Jun;22(3):123-36. [PubMed:10367177]
  3. 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. [PubMed:11015308]
  4. 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. [PubMed:15178373]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  6. 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. [PubMed:10225363]
  7. 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. [PubMed:18723285]
  8. 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. [PubMed:12110114]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:11513839]

Enzymes

Kind
Protein
Organism
Human
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
  1. 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. [PubMed:19925626]
  2. Fuseau E, Petricoul O, Moore KH, Barrow A, Ibbotson T: Clinical pharmacokinetics of intranasal sumatriptan. Clin Pharmacokinet. 2002;41(11):801-11. [PubMed:12190330]
  3. Med-Psych Drug-Drug Interactions Update: Triptans [File]

Transporters

Kind
Protein
Organism
Human
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
  1. 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. [PubMed:8779895]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:12438524]
  2. 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. [PubMed:11745719]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:12668685]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:11076394]

Drug created on June 13, 2005 07:24 / Updated on November 17, 2018 04:48