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Identification
NameSumatriptan
Accession NumberDB00669  (APRD00379)
TypeSmall Molecule
GroupsApproved, Investigational
DescriptionA 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
Imigran
Imitrex
NP101
Sumatran
Sumatriptan
Sumatriptán
Sumatriptan Succinate
Sumatriptanum
Sumax
triptan
External Identifiers
  • GR 43175 A
  • GR 43175 C
  • GR 43175 X
  • SN 308
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act SumatriptanTablet25 mgOralActavis Pharma Company2005-08-24Not applicableCanada
Act SumatriptanTablet50 mgOralActavis Pharma Company2005-08-24Not applicableCanada
Act SumatriptanTablet100 mgOralActavis Pharma Company2005-08-24Not applicableCanada
AlsumaInjection, solution6 mg/.5mLSubcutaneousUs World Meds, Llc2010-10-152016-03-29Us
AlsumaInjection, solution6 mg/.5mLSubcutaneousPfizer Laboratories Div Pfizer Inc2009-08-312016-10-13Us
Ava-sumatriptanTablet50 mgOralAvanstra Inc2011-09-192014-08-21Canada
Ava-sumatriptanTablet100 mgOralAvanstra Inc2011-09-192014-08-21Canada
Dom-sumatriptanTablet25 mgOralDominion Pharmacal2005-09-29Not applicableCanada
Dom-sumatriptanTablet50 mgOralDominion Pharmacal2005-09-29Not applicableCanada
Dom-sumatriptanTablet100 mgOralDominion Pharmacal2005-09-29Not applicableCanada
ImitrexSpray20 mg/1NasalGlaxo Smith Kline Llc1997-09-18Not applicableUs
ImitrexInjection6 mg/.5mLSubcutaneousPhysicians Total Care, Inc.1995-01-26Not applicableUs
ImitrexTablet, film coated100 mg/1OralGlaxo Smith Kline Llc2003-12-19Not applicableUs
ImitrexInjection6 mg/.5mLSubcutaneousGlaxo Smith Kline Llc1993-02-23Not applicableUs
ImitrexTablet, film coated100 mg/1OralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2012-03-28Not applicableUs
ImitrexTablet, film coated100 mg/1OralPhysicians Total Care, Inc.2004-07-14Not applicableUs
ImitrexSpray5 mg/1NasalGlaxo Smith Kline Llc1997-10-10Not applicableUs
ImitrexTablet, film coated50 mg/1OralRebel Distributors Corp2003-12-17Not applicableUs
ImitrexInjection4 mg/.5mLSubcutaneousGlaxo Smith Kline Llc2006-04-06Not applicableUs
ImitrexInjection6 mg/.5mLSubcutaneousGlaxo Smith Kline Llc1997-01-27Not applicableUs
ImitrexTablet, film coated25 mg/1OralGlaxo Smith Kline Llc2003-12-17Not applicableUs
ImitrexInjection6 mg/.5mLSubcutaneousGlaxo Smith Kline Llc1997-01-23Not applicableUs
ImitrexTablet, film coated50 mg/1OralGlaxo Smith Kline Llc2003-12-17Not applicableUs
ImitrexTablet, film coated50 mg/1OralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2012-03-28Not applicableUs
Imitrex - Tab 50mgTablet50 mgOralGlaxo Canada Inc1995-12-311998-07-30Canada
Imitrex Df - Tab 100mgTablet100 mgOralGlaxosmithkline Inc1997-02-11Not applicableCanada
Imitrex Df - Tab 25mgTablet25 mgOralGlaxosmithkline Inc1999-12-232009-01-19Canada
Imitrex Df - Tab 50mgTablet50 mgOralGlaxosmithkline Inc1998-02-11Not applicableCanada
Imitrex Inj 12mg/mlLiquid12 mgSubcutaneousGlaxo Canada Inc1992-12-312000-08-02Canada
Imitrex Injection 12mg/mlLiquid12 mgSubcutaneousGlaxosmithkline Inc1999-08-30Not applicableCanada
Imitrex Nasal SpraySpray5 mgNasalGlaxosmithkline Inc1997-02-19Not applicableCanada
Imitrex Nasal SpraySpray20 mgNasalGlaxosmithkline Inc1997-02-19Not applicableCanada
Imitrex Tab 100mgTablet100 mgOralGlaxo Canada Inc1992-12-311998-07-30Canada
Mylan-sumatriptanTablet100 mgOralMylan Pharmaceuticals Ulc2005-08-24Not applicableCanada
Mylan-sumatriptanTablet25 mgOralMylan Pharmaceuticals Ulc2005-08-24Not applicableCanada
Mylan-sumatriptanTablet50 mgOralMylan Pharmaceuticals Ulc2005-08-24Not applicableCanada
Ntp-sumatriptan DFTablet100 mgOralTeva Canada LimitedNot applicableNot applicableCanada
Ntp-sumatriptan DFTablet25 mgOralTeva Canada LimitedNot applicableNot applicableCanada
Ntp-sumatriptan DFTablet50 mgOralTeva Canada LimitedNot applicableNot applicableCanada
Nu-sumatriptanTablet50 mgOralNu Pharm IncNot applicableNot applicableCanada
Nu-sumatriptanTablet100 mgOralNu Pharm IncNot applicableNot applicableCanada
Nu-sumatriptanTablet25 mgOralNu Pharm IncNot applicableNot applicableCanada
OnzetraKitNasalAvanir Pharmaceuticals, Inc.2015-10-01Not applicableUs
PHL-sumatriptanTablet25 mgOralPharmel Inc2005-09-27Not applicableCanada
PHL-sumatriptanTablet50 mgOralPharmel Inc2005-09-27Not applicableCanada
PHL-sumatriptanTablet100 mgOralPharmel Inc2005-09-27Not applicableCanada
PMS-sumatriptanTablet100 mgOralPharmascience Inc2005-08-24Not applicableCanada
PMS-sumatriptanTablet25 mgOralPharmascience Inc2005-08-24Not applicableCanada
PMS-sumatriptanTablet50 mgOralPharmascience Inc2005-08-24Not applicableCanada
Q-sumatriptanTablet25 mgOralQd Pharmaceuticals UlcNot applicableNot applicableCanada
Q-sumatriptanTablet50 mgOralQd Pharmaceuticals UlcNot applicableNot applicableCanada
Q-sumatriptanTablet100 mgOralQd Pharmaceuticals UlcNot applicableNot applicableCanada
Ratio-sumatriptanTablet50 mgOralRatiopharm Inc Division Of Teva Canada Limited2005-12-062010-08-02Canada
Ratio-sumatriptanTablet100 mgOralRatiopharm Inc Division Of Teva Canada Limited2005-12-062010-08-02Canada
Riva-sumatriptanTablet100 mgOralLaboratoire Riva Inc2005-09-152013-07-31Canada
Riva-sumatriptanTablet25 mgOralLaboratoire Riva IncNot applicableNot applicableCanada
Riva-sumatriptanTablet50 mgOralLaboratoire Riva Inc2005-09-152013-07-31Canada
Sandoz SumatriptanTablet50 mgOralSandoz Canada Incorporated2005-08-24Not applicableCanada
Sandoz SumatriptanTablet100 mgOralSandoz Canada Incorporated2005-08-24Not applicableCanada
Sdz-sumatriptanTablet50 mgOralSandoz Canada IncorporatedNot applicableNot applicableCanada
Sdz-sumatriptanTablet100 mgOralSandoz Canada IncorporatedNot applicableNot applicableCanada
SumatriptanTablet50 mgOralSanis Health Inc2010-04-05Not applicableCanada
SumatriptanSpray20 mg/100uLNasalPhysicians Total Care, Inc.2009-07-23Not applicableUs
SumatriptanSpray5 mg/100uLNasalSandoz Inc2008-09-11Not applicableUs
SumatriptanTablet100 mgOralCobalt Pharmaceuticals CompanyNot applicableNot applicableCanada
SumatriptanTablet100 mgOralSanis Health Inc2010-04-05Not applicableCanada
SumatriptanTablet50 mgOralPro Doc Limitee2009-06-15Not applicableCanada
SumatriptanTablet25 mgOralCobalt Pharmaceuticals CompanyNot applicableNot applicableCanada
SumatriptanTablet100 mgOralPro Doc Limitee2009-06-15Not applicableCanada
SumatriptanTablet25 mgOralSanis Health Inc2010-04-052014-08-01Canada
SumatriptanTablet50 mgOralCobalt Pharmaceuticals CompanyNot applicableNot applicableCanada
SumatriptanSpray20 mg/100uLNasalSandoz Inc2008-09-11Not applicableUs
Sumatriptan DFTablet50 mgOralSivem Pharmaceuticals Ulc2012-06-10Not applicableCanada
Sumatriptan DFTablet25 mgOralSivem Pharmaceuticals UlcNot applicableNot applicableCanada
Sumatriptan DFTablet100 mgOralSivem Pharmaceuticals Ulc2012-06-10Not applicableCanada
Sumatriptan InjectionSolution12 mgSubcutaneousTeva Canada LimitedNot applicableNot applicableCanada
Sumatriptan Injection, USPSolution6 mgSubcutaneousMylan Pharmaceuticals UlcNot applicableNot applicableCanada
Sumatriptan SuccinateInjection, solution6 mg/.5mLSubcutaneousSandoz Inc2012-01-12Not applicableUs
Sumatriptan SuccinateTablet, film coated100 mg/1OralStat Rx USA2008-07-01Not applicableUs
Sumatriptan SuccinateInjection, solution6 mg/.5mLSubcutaneousSandoz Inc2008-09-09Not applicableUs
Sumatriptan SuccinateTablet, film coated50 mg/1OralDispensing Solutions Inc.2009-03-03Not applicableUs
Sumatriptan SuccinateTablet, film coated100 mg/1OralPhysicians Total Care, Inc.2009-01-20Not applicableUs
Sumatriptan SuccinateInjection, solution6 mg/.5mLSubcutaneousSandoz Inc2008-09-09Not applicableUs
Sumatriptan SuccinateInjection, solution4 mg/.5mLSubcutaneousSandoz Inc2012-01-12Not applicableUs
Sumatriptan SuccinateTablet, film coated100 mg/1OralDispensing Solutions Inc.2009-03-03Not applicableUs
Sumatriptan SuccinateTablet, film coated50 mg/1OralPhysicians Total Care, Inc.2009-04-16Not applicableUs
Sumatriptan SuccinateInjection, solution4 mg/.5mLSubcutaneousSandoz Inc2012-01-12Not applicableUs
Sumavel DoseproInjection4 mg/.5mLSubcutaneousEndo Pharmaceuticals2015-06-08Not applicableUs
Sumavel DoseproInjection4 mg/.5mLSubcutaneousZogenix, Inc.2013-12-04Not applicableUs
Sumavel DoseproInjection6 mg/.5mLSubcutaneousEndo Pharmaceuticals2015-06-08Not applicableUs
Sumavel DoseproInjection6 mg/.5mLSubcutaneousZogenix, Inc.2009-07-15Not applicableUs
Taro-sumatriptanSolution6 mgSubcutaneousTaro Pharmaceuticals Inc2011-06-06Not applicableCanada
Teva-sumatriptanTablet100 mgOralTeva Canada Limited2005-09-30Not applicableCanada
Teva-sumatriptan DFTablet100 mgOralTeva Canada Limited2006-10-30Not applicableCanada
Teva-sumatriptan DFTablet25 mgOralTeva Canada Limited2006-10-30Not applicableCanada
Teva-sumatriptan DFTablet50 mgOralTeva Canada Limited2006-10-30Not applicableCanada
ZecuityPatch, extended release, electrically controlled6.5 mg/4hTransdermalTeva Pharmaceuticals Usa, Inc.2015-08-25Not applicableUs
Zembrace SymtouchInjection, solution3 mg/1SubcutaneousPromius Pharma, LLC2016-02-22Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-sumatriptanTablet100 mgOralApotex Inc2005-08-24Not applicableCanada
Apo-sumatriptanTablet25 mgOralApotex IncNot applicableNot applicableCanada
Apo-sumatriptanSpray5 mgNasalApotex IncNot applicableNot applicableCanada
Apo-sumatriptanSpray20 mgNasalApotex IncNot applicableNot applicableCanada
Apo-sumatriptanTablet50 mgOralApotex Inc2005-08-24Not applicableCanada
ImitrexTablet25 mg/1OralDirectrx2016-05-13Not applicableUs
ImitrexTablet50 mg/1OralDIRECT RX2016-06-06Not applicableUs
SumatriptanTablet50 mg/1OralGreenstone LLC2009-08-172015-11-30Us
SumatriptanTablet25 mg/1OralA S Medication Solutions2009-08-13Not applicableUs
SumatriptanTablet100 mg/1OralActavis Pharma, Inc.2009-08-10Not applicableUs
SumatriptanTablet50 mg/1OralUnit Dose Services2009-08-13Not applicableUs
SumatriptanInjection, solution6 mg/.5mLSubcutaneousA S Medication Solutions2011-01-01Not applicableUs
SumatriptanTablet25 mg/1OralAurobindo Pharma Limited2009-08-17Not applicableUs
SumatriptanTablet50 mg/1OralPreferred Pharmaceuticals, Inc.2013-10-24Not applicableUs
SumatriptanInjection6 mg/.5mLSubcutaneousWest Ward Pharmaceuticals Corp2013-09-16Not applicableUs
SumatriptanTablet50 mg/1OralRanbaxy Pharmaceuticals Inc.2009-08-13Not applicableUs
SumatriptanSpray5 mg/.1mLNasalLannett Company, Inc.2016-02-19Not applicableUs
SumatriptanTablet50 mg/1OralA S Medication Solutions2009-08-172016-10-26Us
SumatriptanTablet25 mg/1OralProficient Rx LP2009-08-13Not applicableUs
SumatriptanTablet100 mg/1OralGreenstone LLC2009-08-172015-12-31Us
SumatriptanTablet, film coated25 mg/1OralNorthstar Rx LLC2011-01-03Not applicableUs
SumatriptanTablet50 mg/1OralA S Medication Solutions2009-08-17Not applicableUs
SumatriptanTablet50 mg/1OralAurobindo Pharma Limited2009-08-17Not applicableUs
SumatriptanTablet25 mg/1OralPreferred Pharmaceuticals, Inc.2012-06-04Not applicableUs
SumatriptanInjection, solution6 mg/.5mLSubcutaneousAuro Medics Pharma Llc2013-04-23Not applicableUs
SumatriptanTablet25 mg/1OralA S Medication Solutions2009-08-17Not applicableUs
SumatriptanTablet25 mg/1OralPhysicians Total Care, Inc.2009-08-13Not applicableUs
SumatriptanTablet100 mg/1OralRanbaxy Pharmaceuticals Inc.2009-02-10Not applicableUs
SumatriptanSpray20 mg/.1mLNasalLannett Company, Inc.2016-02-19Not applicableUs
SumatriptanTablet100 mg/1OralA S Medication Solutions2009-08-17Not applicableUs
SumatriptanTablet25 mg/1OralActavis Pharma, Inc.2009-08-10Not applicableUs
SumatriptanTablet50 mg/1OralREMEDYREPACK INC.2012-03-05Not applicableUs
SumatriptanTablet100 mg/1OralProficient Rx LP2009-02-10Not applicableUs
SumatriptanTablet, film coated50 mg/1OralNorthstar Rx LLC2011-01-03Not applicableUs
SumatriptanTablet100 mg/1OralA S Medication Solutions2009-08-17Not applicableUs
SumatriptanTablet100 mg/1OralAurobindo Pharma Limited2009-08-17Not applicableUs
SumatriptanInjection4 mg/.5mLSubcutaneousTeva Pharmaceuticals USA Inc2016-06-01Not applicableUs
SumatriptanTablet25 mg/1OralPreferred Pharmaceuticals Inc.2016-10-24Not applicableUs
SumatriptanInjection, solution6 mg/.5mLSubcutaneousSagent Pharmaceuticals2011-01-01Not applicableUs
SumatriptanInjection6 mg/.5mLSubcutaneousAGILA SPECIALTIES PRIVATE LIMITED2014-04-15Not applicableUs
SumatriptanInjection, solution6 mg/.5mLSubcutaneousA S Medication Solutions2013-04-23Not applicableUs
SumatriptanTablet50 mg/1OralActavis Pharma, Inc.2009-08-10Not applicableUs
SumatriptanTablet25 mg/1OralUnit Dose Services2009-08-13Not applicableUs
SumatriptanTablet50 mg/1OralREMEDYREPACK INC.2014-08-01Not applicableUs
SumatriptanTablet25 mg/1OralRanbaxy Pharmaceuticals Inc.2009-08-13Not applicableUs
SumatriptanTablet, film coated100 mg/1OralNorthstar Rx LLC2011-01-03Not applicableUs
SumatriptanInjection6 mg/.5mLSubcutaneousTeva Pharmaceuticals USA Inc2016-06-01Not applicableUs
SumatriptanTablet100 mg/1OralDIRECT RX2015-01-01Not applicableUs
SumatriptanTablet50 mg/1OralPreferred Pharmaceuticals, Inc.2015-03-26Not applicableUs
SumatriptanTablet100 mg/1OralPreferred Pharmaceuticals, Inc.2016-10-24Not applicableUs
Sumatriptan SuccinateTablet50 mg/1OralProficient Rx LP2009-11-17Not applicableUs
Sumatriptan SuccinateTablet100 mg/1OralPreferred Pharmaceuticals, Inc2011-06-08Not applicableUs
Sumatriptan SuccinateTablet50 mg/1OralLake Erie Medical DBA Quality Care Products LLC2009-11-17Not applicableUs
Sumatriptan SuccinateTablet100 mg/1OralDr. Reddy's Laboratories Limited2009-11-17Not applicableUs
Sumatriptan SuccinateTablet, coated100 mg/1OralAmerican Health Packaging2013-07-052016-01-05Us
Sumatriptan SuccinateInjection6 mg/.5mLSubcutaneousDr. Reddy's Laboratories Limited2014-02-24Not applicableUs
Sumatriptan SuccinateTablet50 mg/1OralRebel Distributors Corp2009-11-17Not applicableUs
Sumatriptan SuccinateTablet100 mg/1OralH.J. Harkins Company, Inc.2009-11-17Not applicableUs
Sumatriptan SuccinateTablet, film coated25 mg/1OralCarilion Materials Management2009-08-10Not applicableUs
Sumatriptan SuccinateInjection, solution6 mg/.5mLSubcutaneousTeva Parenteral Medicines, Inc.2009-02-06Not applicableUs
Sumatriptan SuccinateInjection6 mg/.5mLSubcutaneousSun Pharma Global FZE2011-06-22Not applicableUs
Sumatriptan SuccinateTablet, film coated25 mg/1OralSun Pharmaceutical Industries Limited2009-08-10Not applicableUs
Sumatriptan SuccinateTablet50 mg/1OralSTAT Rx USA LLC2009-11-17Not applicableUs
Sumatriptan SuccinateTablet100 mg/1OralUnit Dose Services2009-11-17Not applicableUs
Sumatriptan SuccinateTablet, film coated25 mg/1OralMylan Pharmaceuticals Inc.2009-08-10Not applicableUs
Sumatriptan SuccinateInjection6 mg/.5mLSubcutaneousJHP Pharmaceuticals LLC2009-08-06Not applicableUs
Sumatriptan SuccinateInjection6 mg/.5mLSubcutaneousWockhardt Limited2009-02-06Not applicableUs
Sumatriptan SuccinateTablet25 mg/1OralLake Erie Medical DBA Quality Care Products LLC2009-11-17Not applicableUs
Sumatriptan SuccinateTablet100 mg/1OralProficient Rx LP2009-11-17Not applicableUs
Sumatriptan SuccinateTablet100 mg/1OralRebel Distributors Corp2009-11-17Not applicableUs
Sumatriptan SuccinateTablet, film coated50 mg/1OralDispensing Solutions, Inc.2009-08-10Not applicableUs
Sumatriptan SuccinateTablet, film coated50 mg/1OralSun Pharmaceutical Industries Limited2009-08-10Not applicableUs
Sumatriptan SuccinateTablet25 mg/1OralSTAT Rx USA LLC2009-11-17Not applicableUs
Sumatriptan SuccinateTablet50 mg/1OralREMEDYREPACK INC.2013-12-05Not applicableUs
Sumatriptan SuccinateTablet, coated25 mg/1OralAmerican Health Packaging2013-07-052016-01-05Us
Sumatriptan SuccinateTablet, film coated50 mg/1OralMylan Pharmaceuticals Inc.2009-08-10Not applicableUs
Sumatriptan SuccinateTablet, coated25 mg/1OralRebel Distributors Corp2009-08-10Not applicableUs
Sumatriptan SuccinateTablet, film coated50 mg/1OralLake Erie Medical DBA Quality Care Products LLC2009-08-10Not applicableUs
Sumatriptan SuccinateTablet25 mg/1OralProficient Rx LP2009-11-17Not applicableUs
Sumatriptan SuccinateTablet, film coated25 mg/1OralLake Erie Medical DBA Quality Care Products LLC2009-08-10Not applicableUs
Sumatriptan SuccinateTablet25 mg/1OralDr. Reddy's Laboratories Limited2009-11-17Not applicableUs
Sumatriptan SuccinateInjection6 mg/.5mLSubcutaneousFresenius Kabi USA, LLC2011-04-12Not applicableUs
Sumatriptan SuccinateTablet25 mg/1OralPreferred Pharmaceuticals, Inc2011-06-08Not applicableUs
Sumatriptan SuccinateTablet, film coated100 mg/1OralSun Pharmaceutical Industries Limited2009-08-10Not applicableUs
Sumatriptan SuccinateTablet25 mg/1OralRebel Distributors Corp2009-11-17Not applicableUs
Sumatriptan SuccinateTablet, coated50 mg/1OralAmerican Health Packaging2013-07-052016-01-05Us
Sumatriptan SuccinateTablet, film coated100 mg/1OralMylan Pharmaceuticals Inc.2009-08-10Not applicableUs
Sumatriptan SuccinateTablet25 mg/1OralMedsource Pharmaceuticals2009-11-17Not applicableUs
Sumatriptan SuccinateTablet, film coated50 mg/1OralMed Vantx, Inc.2010-09-22Not applicableUs
Sumatriptan SuccinateTablet100 mg/1OralLake Erie Medical DBA Quality Care Products LLC2009-11-17Not applicableUs
Sumatriptan SuccinateTablet50 mg/1OralDr. Reddy's Laboratories Limited2009-11-17Not applicableUs
Sumatriptan SuccinateInjection6 mg/.5mLSubcutaneousWockhardt USA LLC.2009-02-06Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AdraconInti
AltaxaAlapis Pharma
ApigraneAdvanced Pharmaceutical
Boots Pharmacy Migraine ReliefBoots
CinieZentiva
FrimigOrion
IllumentPliva
ImigenMylan
ImigranGlaxoSmithKline
Imigran miteGlaxoSmithKline
Imigran RadisGlaxoSmithKline
ImigraneGlaxoSmithKline
Imitrex OralGlaxoSmithKline
MigralginGMP
MigraneitorDriburg
NazdavDr. Reddy's
SapphirexHemofarm
SumatranRowex
SumaxLibbs
SuminatSun
YoushuSimcere
Brand mixtures
NameLabellerIngredients
TreximetGlaxo Smith Kline Llc
Salts
Name/CASStructureProperties
Sumatriptan Succinate
ThumbNot applicableDBSALT001003
Categories
UNII8R78F6L9VO
CAS number103628-46-2
WeightAverage: 295.4
Monoisotopic: 295.135447621
Chemical FormulaC14H21N3O2S
InChI KeyKQKPFRSPSRPDEB-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
IndicationFor the treatment of migraine attacks with or without aura.
Structured Indications
PharmacodynamicsSumatriptan, 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 actionThe 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
5-hydroxytryptamine receptor 1DProteinyes
agonist
HumanP28221 details
5-hydroxytryptamine receptor 1BProteinyes
agonist
HumanP28222 details
5-hydroxytryptamine receptor 1FProteinyes
agonist
HumanP30939 details
5-hydroxytryptamine receptor 1AProteinyes
agonist
HumanP08908 details
Related Articles
AbsorptionApproximately 15%
Volume of distribution
  • 2.7 L/kg [subcutaneous dosing]
Protein binding14%-21%
Metabolism

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

Route of eliminationOnly 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 life2.5 hours
Clearance
  • 1200 mL/min [Following a 6-mg SC injection]
ToxicitySymptoms 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
PathwaysNot Available
SNP Mediated Effects
Interacting Gene/EnzymeSNP RS IDAllele nameDefining changeEffectReference(s)
Guanine nucleotide-binding protein G(I)/G(S)/G(T) subunit beta-3
Gene symbol: GNB3
UniProt: P16520
rs5443 Not AvailableT AlleleBetter response to drug treatment17361120
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINEThe metabolism of Sumatriptan can be decreased when combined with 7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE.Experimental
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Sumatriptan.Approved
AcepromazineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Acepromazine.Approved, Vet Approved
AceprometazineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Aceprometazine.Approved
AcetaminophenThe serum concentration of Acetaminophen can be increased when it is combined with Sumatriptan.Approved
AcetophenazineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Acetophenazine.Approved
Acetylsalicylic acidThe serum concentration of Acetylsalicylic acid can be increased when it is combined with Sumatriptan.Approved, Vet Approved
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Sumatriptan.Approved
AldosteroneThe serum concentration of Aldosterone can be increased when it is combined with Sumatriptan.Experimental
AlitretinoinThe serum concentration of Alitretinoin can be increased when it is combined with Sumatriptan.Approved, Investigational
AlmotriptanThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Almotriptan.Approved, Investigational
AmbrisentanThe serum concentration of Ambrisentan can be increased when it is combined with Sumatriptan.Approved, Investigational
AmisulprideThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Amisulpride.Approved, Investigational
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Sumatriptan.Approved
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Sumatriptan.Approved
AmperozideThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Amperozide.Experimental
ApixabanThe serum concentration of Apixaban can be increased when it is combined with Sumatriptan.Approved
AripiprazoleThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Aripiprazole.Approved, Investigational
Arsenic trioxideThe serum concentration of Arsenic trioxide can be increased when it is combined with Sumatriptan.Approved, Investigational
AsenapineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Asenapine.Approved
AtazanavirThe serum concentration of Atazanavir can be increased when it is combined with Sumatriptan.Approved, Investigational
AtenololThe serum concentration of Atenolol can be increased when it is combined with Sumatriptan.Approved
AxitinibThe serum concentration of Axitinib can be increased when it is combined with Sumatriptan.Approved, Investigational
AzaperoneThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Azaperone.Vet Approved
BenmoxinThe metabolism of Sumatriptan can be decreased when combined with Benmoxin.Withdrawn
BenperidolThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Benperidol.Investigational
BetamethasoneThe serum concentration of Betamethasone can be increased when it is combined with Sumatriptan.Approved, Vet Approved
BifeprunoxThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Bifeprunox.Investigational
BoceprevirThe serum concentration of Boceprevir can be increased when it is combined with Sumatriptan.Approved
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Sumatriptan.Approved
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Sumatriptan.Approved
BrexpiprazoleThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Brexpiprazole.Approved
BromocriptineBromocriptine may increase the vasoconstricting activities of Sumatriptan.Approved, Investigational
BromperidolThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Bromperidol.Investigational
BuspironeThe risk or severity of adverse effects can be increased when Buspirone is combined with Sumatriptan.Approved, Investigational
CabazitaxelThe serum concentration of Cabazitaxel can be increased when it is combined with Sumatriptan.Approved
CabergolineCabergoline may increase the vasoconstricting activities of Sumatriptan.Approved
CaffeineThe serum concentration of Caffeine can be increased when it is combined with Sumatriptan.Approved
CamptothecinThe serum concentration of Camptothecin can be increased when it is combined with Sumatriptan.Experimental
CanagliflozinThe serum concentration of Canagliflozin can be increased when it is combined with Sumatriptan.Approved
CarbamazepineThe serum concentration of Carbamazepine can be increased when it is combined with Sumatriptan.Approved, Investigational
CarfilzomibThe serum concentration of Carfilzomib can be increased when it is combined with Sumatriptan.Approved
CariprazineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Cariprazine.Approved
CaroxazoneThe metabolism of Sumatriptan can be decreased when combined with Caroxazone.Withdrawn
CeritinibThe serum concentration of Ceritinib can be increased when it is combined with Sumatriptan.Approved
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Sumatriptan.Withdrawn
ChlorpromazineThe serum concentration of Chlorpromazine can be increased when it is combined with Sumatriptan.Approved, Vet Approved
ChlorprothixeneThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Chlorprothixene.Approved, Withdrawn
CimetidineThe serum concentration of Cimetidine can be increased when it is combined with Sumatriptan.Approved
CiprofloxacinThe serum concentration of Ciprofloxacin can be increased when it is combined with Sumatriptan.Approved, Investigational
CisplatinThe serum concentration of Cisplatin can be increased when it is combined with Sumatriptan.Approved
CitalopramThe risk or severity of adverse effects can be increased when Citalopram is combined with Sumatriptan.Approved
ClarithromycinThe serum concentration of Clarithromycin can be increased when it is combined with Sumatriptan.Approved
ClobazamThe serum concentration of Clobazam can be increased when it is combined with Sumatriptan.Approved, Illicit
ClomifeneThe serum concentration of Clomifene can be increased when it is combined with Sumatriptan.Approved, Investigational
ClomipramineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Clomipramine.Approved, Vet Approved
ClonidineThe serum concentration of Clonidine can be increased when it is combined with Sumatriptan.Approved
ClopidogrelThe serum concentration of Clopidogrel can be increased when it is combined with Sumatriptan.Approved, Nutraceutical
ClozapineThe serum concentration of Clozapine can be increased when it is combined with Sumatriptan.Approved
CobimetinibThe serum concentration of Cobimetinib can be increased when it is combined with Sumatriptan.Approved
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Sumatriptan.Approved
Conjugated Equine EstrogensThe serum concentration of Conjugated Equine Estrogens can be increased when it is combined with Sumatriptan.Approved
CrizotinibThe serum concentration of Crizotinib can be increased when it is combined with Sumatriptan.Approved
CyamemazineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Cyamemazine.Approved
CyclobenzaprineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Cyclobenzaprine.Approved
CyclosporineThe serum concentration of Cyclosporine can be increased when it is combined with Sumatriptan.Approved, Investigational, Vet Approved
Dabigatran etexilateThe serum concentration of the active metabolites of Dabigatran etexilate can be increased when Dabigatran etexilate is used in combination with Sumatriptan.Approved
DabrafenibThe serum concentration of Dabrafenib can be increased when it is combined with Sumatriptan.Approved
DactinomycinThe serum concentration of Dactinomycin can be increased when it is combined with Sumatriptan.Approved
DapagliflozinThe serum concentration of Dapagliflozin can be increased when it is combined with Sumatriptan.Approved
DapiprazoleThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Dapiprazole.Approved
DapoxetineThe risk or severity of adverse effects can be increased when Dapoxetine is combined with Sumatriptan.Investigational
DasatinibThe serum concentration of Dasatinib can be increased when it is combined with Sumatriptan.Approved, Investigational
DaunorubicinThe serum concentration of Daunorubicin can be increased when it is combined with Sumatriptan.Approved
DebrisoquinThe serum concentration of Debrisoquin can be increased when it is combined with Sumatriptan.Approved
DesipramineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Desipramine.Approved
DesvenlafaxineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Desvenlafaxine.Approved
DexamethasoneThe serum concentration of Dexamethasone can be increased when it is combined with Sumatriptan.Approved, Investigational, Vet Approved
DexketoprofenThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with Sumatriptan.Approved
DextromethorphanThe risk or severity of adverse effects can be increased when Dextromethorphan is combined with Sumatriptan.Approved
DiazepamThe serum concentration of Diazepam can be increased when it is combined with Sumatriptan.Approved, Illicit, Vet Approved
DiethylstilbestrolThe serum concentration of Diethylstilbestrol can be increased when it is combined with Sumatriptan.Approved
DigitoxinThe serum concentration of Digitoxin can be increased when it is combined with Sumatriptan.Approved
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Sumatriptan.Approved
DihydroergotamineDihydroergotamine may increase the vasoconstricting activities of Sumatriptan.Approved
DihydrotestosteroneThe serum concentration of Dihydrotestosterone can be increased when it is combined with Sumatriptan.Illicit
DiltiazemThe serum concentration of Diltiazem can be increased when it is combined with Sumatriptan.Approved
DipyridamoleThe serum concentration of Dipyridamole can be increased when it is combined with Sumatriptan.Approved
DocetaxelThe serum concentration of Docetaxel can be increased when it is combined with Sumatriptan.Approved, Investigational
DolasetronDolasetron may increase the serotonergic activities of Sumatriptan.Approved
DomperidoneThe serum concentration of Domperidone can be increased when it is combined with Sumatriptan.Approved, Investigational, Vet Approved
DoxepinThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Doxepin.Approved
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Sumatriptan.Approved, Investigational
DroperidolThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Droperidol.Approved, Vet Approved
DroxidopaSumatriptan may increase the hypertensive activities of Droxidopa.Approved, Investigational
DuloxetineThe risk or severity of adverse effects can be increased when Duloxetine is combined with Sumatriptan.Approved
EcopipamThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Ecopipam.Investigational
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Sumatriptan.Approved
EletriptanThe risk or severity of adverse effects can be increased when Eletriptan is combined with Sumatriptan.Approved, Investigational
EltrombopagThe serum concentration of Sumatriptan can be increased when it is combined with Eltrombopag.Approved
EpinastineThe serum concentration of Epinastine can be increased when it is combined with Sumatriptan.Approved, Investigational
Ergoloid mesylateErgoloid mesylate may increase the vasoconstricting activities of Sumatriptan.Approved
ErgonovineErgonovine may increase the vasoconstricting activities of Sumatriptan.Approved
ErgotamineErgotamine may increase the vasoconstricting activities of Sumatriptan.Approved
ErlotinibThe serum concentration of Erlotinib can be increased when it is combined with Sumatriptan.Approved, Investigational
ErythromycinThe serum concentration of Erythromycin can be increased when it is combined with Sumatriptan.Approved, Vet Approved
EscitalopramThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Escitalopram.Approved, Investigational
EstradiolThe serum concentration of Estradiol can be increased when it is combined with Sumatriptan.Approved, Investigational, Vet Approved
EstriolThe serum concentration of Estriol can be increased when it is combined with Sumatriptan.Approved, Vet Approved
EstroneThe serum concentration of Estrone can be increased when it is combined with Sumatriptan.Approved
Ethinyl EstradiolThe serum concentration of Ethinyl Estradiol can be increased when it is combined with Sumatriptan.Approved
EtoposideThe serum concentration of Etoposide can be increased when it is combined with Sumatriptan.Approved
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Sumatriptan.Approved
EzetimibeThe serum concentration of Ezetimibe can be increased when it is combined with Sumatriptan.Approved
FencamfamineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Fencamfamine.Approved, Illicit, Withdrawn
FentanylThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Fentanyl.Approved, Illicit, Investigational, Vet Approved
FesoterodineThe serum concentration of Fesoterodine can be increased when it is combined with Sumatriptan.Approved
FexofenadineThe serum concentration of Fexofenadine can be increased when it is combined with Sumatriptan.Approved
FidaxomicinThe serum concentration of Fidaxomicin can be increased when it is combined with Sumatriptan.Approved
FluoxetineThe risk or severity of adverse effects can be increased when Fluoxetine is combined with Sumatriptan.Approved, Vet Approved
FlupentixolThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Flupentixol.Approved, Withdrawn
FluphenazineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Fluphenazine.Approved
FluspirileneThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Fluspirilene.Approved
Fluticasone furoateThe serum concentration of Fluticasone furoate can be increased when it is combined with Sumatriptan.Approved
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Sumatriptan.Approved, Investigational
FrovatriptanThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Frovatriptan.Approved, Investigational
FurazolidoneThe metabolism of Sumatriptan can be decreased when combined with Furazolidone.Approved, Vet Approved
GefitinibThe serum concentration of Gefitinib can be increased when it is combined with Sumatriptan.Approved, Investigational
GemcitabineThe serum concentration of Gemcitabine can be increased when it is combined with Sumatriptan.Approved
GranisetronGranisetron may increase the serotonergic activities of Sumatriptan.Approved, Investigational
GrazoprevirThe serum concentration of Grazoprevir can be increased when it is combined with Sumatriptan.Approved
GrepafloxacinThe serum concentration of Grepafloxacin can be increased when it is combined with Sumatriptan.Withdrawn
HaloperidolThe serum concentration of Haloperidol can be increased when it is combined with Sumatriptan.Approved
HydracarbazineThe metabolism of Sumatriptan can be decreased when combined with Hydracarbazine.Approved
HydrocortisoneThe serum concentration of Hydrocortisone can be increased when it is combined with Sumatriptan.Approved, Vet Approved
IbuprofenThe serum concentration of Ibuprofen can be increased when it is combined with Sumatriptan.Approved
IdelalisibThe serum concentration of Idelalisib can be increased when it is combined with Sumatriptan.Approved
IloperidoneThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Iloperidone.Approved
ImatinibThe serum concentration of Imatinib can be increased when it is combined with Sumatriptan.Approved
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Sumatriptan.Approved
IndacaterolThe serum concentration of Indacaterol can be increased when it is combined with Sumatriptan.Approved
IndinavirThe serum concentration of Indinavir can be increased when it is combined with Sumatriptan.Approved
IndomethacinThe serum concentration of Indomethacin can be increased when it is combined with Sumatriptan.Approved, Investigational
IproclozideThe metabolism of Sumatriptan can be decreased when combined with Iproclozide.Withdrawn
IproniazidThe metabolism of Sumatriptan can be decreased when combined with Iproniazid.Withdrawn
IrinotecanThe serum concentration of Irinotecan can be increased when it is combined with Sumatriptan.Approved, Investigational
IsocarboxazidThe metabolism of Sumatriptan can be decreased when combined with Isocarboxazid.Approved
IvermectinThe serum concentration of Ivermectin can be increased when it is combined with Sumatriptan.Approved, Vet Approved
KetazolamThe serum concentration of Ketazolam can be increased when it is combined with Sumatriptan.Approved
KetoconazoleThe serum concentration of Ketoconazole can be increased when it is combined with Sumatriptan.Approved, Investigational
LamivudineThe serum concentration of Lamivudine can be increased when it is combined with Sumatriptan.Approved, Investigational
LamotrigineThe serum concentration of Lamotrigine can be increased when it is combined with Sumatriptan.Approved, Investigational
LansoprazoleThe serum concentration of Lansoprazole can be increased when it is combined with Sumatriptan.Approved, Investigational
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Sumatriptan.Approved
LenalidomideThe serum concentration of Lenalidomide can be increased when it is combined with Sumatriptan.Approved
LenvatinibThe serum concentration of Lenvatinib can be increased when it is combined with Sumatriptan.Approved
LevetiracetamThe serum concentration of Levetiracetam can be increased when it is combined with Sumatriptan.Approved, Investigational
LevofloxacinThe serum concentration of Levofloxacin can be increased when it is combined with Sumatriptan.Approved, Investigational
LevomilnacipranThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Levomilnacipran.Approved
LinagliptinThe serum concentration of Linagliptin can be increased when it is combined with Sumatriptan.Approved
LinezolidThe risk or severity of adverse effects can be increased when Linezolid is combined with Sumatriptan.Approved, Investigational
LithiumThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Lithium.Approved
LoperamideThe serum concentration of Loperamide can be increased when it is combined with Sumatriptan.Approved
LorcaserinThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Lorcaserin.Approved
LosartanThe serum concentration of Losartan can be increased when it is combined with Sumatriptan.Approved
LoxapineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Loxapine.Approved
LurasidoneThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Lurasidone.Approved
MannitolThe serum concentration of Mannitol can be increased when it is combined with Sumatriptan.Approved, Investigational
MaprotilineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Maprotiline.Approved
MebanazineThe metabolism of Sumatriptan can be decreased when combined with Mebanazine.Withdrawn
MecamylamineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Mecamylamine.Approved
MelperoneThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Melperone.Approved
MesoridazineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Mesoridazine.Approved
MethadoneThe risk or severity of adverse effects can be increased when Methadone is combined with Sumatriptan.Approved
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Sumatriptan.Approved
MethotrimeprazineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Methotrimeprazine.Approved
Methylene blueThe metabolism of Sumatriptan can be decreased when combined with Methylene blue.Investigational
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Sumatriptan.Approved, Vet Approved
MetoclopramideThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Metoclopramide.Approved, Investigational
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Sumatriptan.Approved, Investigational
MidazolamThe serum concentration of Midazolam can be increased when it is combined with Sumatriptan.Approved, Illicit
MilnacipranThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Milnacipran.Approved
MinaprineThe metabolism of Sumatriptan can be decreased when combined with Minaprine.Approved
MirabegronThe serum concentration of Mirabegron can be increased when it is combined with Sumatriptan.Approved
MirtazapineThe risk or severity of adverse effects can be increased when Mirtazapine is combined with Sumatriptan.Approved
MitoxantroneThe serum concentration of Mitoxantrone can be increased when it is combined with Sumatriptan.Approved, Investigational
MoclobemideThe metabolism of Sumatriptan can be decreased when combined with Moclobemide.Approved
MolindoneThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Molindone.Approved
MorphineThe serum concentration of Morphine can be increased when it is combined with Sumatriptan.Approved, Investigational
Mycophenolate mofetilThe serum concentration of Mycophenolate mofetil can be increased when it is combined with Sumatriptan.Approved, Investigational
NadololThe serum concentration of Nadolol can be increased when it is combined with Sumatriptan.Approved
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Sumatriptan.Approved
NaloxoneThe serum concentration of Naloxone can be increased when it is combined with Sumatriptan.Approved, Vet Approved
NaratriptanThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Naratriptan.Approved, Investigational
NefazodoneThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Nefazodone.Approved, Withdrawn
NelfinavirThe serum concentration of Nelfinavir can be increased when it is combined with Sumatriptan.Approved
NialamideThe metabolism of Sumatriptan can be decreased when combined with Nialamide.Withdrawn
NicardipineThe serum concentration of Nicardipine can be increased when it is combined with Sumatriptan.Approved
NifedipineThe serum concentration of Nifedipine can be increased when it is combined with Sumatriptan.Approved
NilotinibThe serum concentration of Nilotinib can be increased when it is combined with Sumatriptan.Approved, Investigational
NintedanibThe serum concentration of Nintedanib can be increased when it is combined with Sumatriptan.Approved
NizatidineThe serum concentration of Nizatidine can be increased when it is combined with Sumatriptan.Approved
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Sumatriptan.Approved
OctamoxinThe metabolism of Sumatriptan can be decreased when combined with Octamoxin.Withdrawn
OlanzapineThe serum concentration of Olanzapine can be increased when it is combined with Sumatriptan.Approved, Investigational
OmbitasvirThe serum concentration of Ombitasvir can be increased when it is combined with Sumatriptan.Approved
OndansetronOndansetron may increase the serotonergic activities of Sumatriptan.Approved
OsanetantThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Osanetant.Investigational
OsimertinibThe serum concentration of Osimertinib can be increased when it is combined with Sumatriptan.Approved
PaclitaxelThe serum concentration of Paclitaxel can be increased when it is combined with Sumatriptan.Approved, Vet Approved
PaliperidoneThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Paliperidone.Approved
PalonosetronPalonosetron may increase the serotonergic activities of Sumatriptan.Approved, Investigational
PanobinostatThe serum concentration of Panobinostat can be increased when it is combined with Sumatriptan.Approved, Investigational
PargylineThe metabolism of Sumatriptan can be decreased when combined with Pargyline.Approved
ParoxetineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Paroxetine.Approved, Investigational
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Sumatriptan.Approved
PerazineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Perazine.Investigational
PerospironeThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Perospirone.Approved
PerphenazineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Perphenazine.Approved
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Sumatriptan.Approved
PhenelzineThe metabolism of Sumatriptan can be decreased when combined with Phenelzine.Approved
PheniprazineThe metabolism of Sumatriptan can be decreased when combined with Pheniprazine.Withdrawn
PhenobarbitalThe serum concentration of Phenobarbital can be increased when it is combined with Sumatriptan.Approved
PhenoxypropazineThe metabolism of Sumatriptan can be decreased when combined with Phenoxypropazine.Withdrawn
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Sumatriptan.Approved, Vet Approved
PimozideThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Pimozide.Approved
PipamperoneThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Pipamperone.Approved
PipotiazineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Pipotiazine.Approved
PirlindoleThe metabolism of Sumatriptan can be decreased when combined with Pirlindole.Approved
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Sumatriptan.Approved
PivhydrazineThe metabolism of Sumatriptan can be decreased when combined with Pivhydrazine.Withdrawn
PomalidomideThe serum concentration of Pomalidomide can be increased when it is combined with Sumatriptan.Approved
PonatinibThe serum concentration of Ponatinib can be increased when it is combined with Sumatriptan.Approved
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Sumatriptan.Approved
PrazosinThe serum concentration of Prazosin can be increased when it is combined with Sumatriptan.Approved
PrednisoloneThe serum concentration of Prednisolone can be increased when it is combined with Sumatriptan.Approved, Vet Approved
PrednisoneThe serum concentration of Prednisone can be increased when it is combined with Sumatriptan.Approved, Vet Approved
ProcarbazineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Procarbazine.Approved
ProchlorperazineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Prochlorperazine.Approved, Vet Approved
ProgesteroneThe serum concentration of Progesterone can be increased when it is combined with Sumatriptan.Approved, Vet Approved
PromazineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Promazine.Approved, Vet Approved
PromethazineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Promethazine.Approved
PropericiazineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Propericiazine.Approved
PropranololThe serum concentration of Propranolol can be increased when it is combined with Sumatriptan.Approved, Investigational
ProthipendylThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Prothipendyl.Investigational
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Sumatriptan.Approved
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Sumatriptan.Approved
QuetiapineThe serum concentration of Quetiapine can be increased when it is combined with Sumatriptan.Approved
QuinidineThe serum concentration of Quinidine can be increased when it is combined with Sumatriptan.Approved
QuinineThe serum concentration of Quinine can be increased when it is combined with Sumatriptan.Approved
RacloprideThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Raclopride.Investigational
RanitidineThe serum concentration of Ranitidine can be increased when it is combined with Sumatriptan.Approved
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Sumatriptan.Approved, Investigational
RasagilineThe metabolism of Sumatriptan can be decreased when combined with Rasagiline.Approved
RemoxiprideThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Remoxipride.Approved, Withdrawn
ReserpineThe serum concentration of Reserpine can be increased when it is combined with Sumatriptan.Approved
RifampicinThe serum concentration of Rifampicin can be increased when it is combined with Sumatriptan.Approved
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Sumatriptan.Approved, Investigational
RisperidoneThe serum concentration of Risperidone can be increased when it is combined with Sumatriptan.Approved, Investigational
RitanserinThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Ritanserin.Investigational
RitonavirThe serum concentration of Ritonavir can be increased when it is combined with Sumatriptan.Approved, Investigational
RivaroxabanThe serum concentration of Rivaroxaban can be increased when it is combined with Sumatriptan.Approved
RizatriptanThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Rizatriptan.Approved
RolapitantThe serum concentration of Sumatriptan can be increased when it is combined with Rolapitant.Approved
RomidepsinThe serum concentration of Romidepsin can be increased when it is combined with Sumatriptan.Approved, Investigational
SafrazineThe metabolism of Sumatriptan can be decreased when combined with Safrazine.Withdrawn
Salicylic acidThe serum concentration of Salicylic acid can be increased when it is combined with Sumatriptan.Approved, Vet Approved
SaquinavirThe serum concentration of Saquinavir can be increased when it is combined with Sumatriptan.Approved, Investigational
SelegilineThe metabolism of Sumatriptan can be decreased when combined with Selegiline.Approved, Investigational, Vet Approved
SelexipagThe serum concentration of Selexipag can be increased when it is combined with Sumatriptan.Approved
SertindoleThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Sertindole.Approved, Withdrawn
SertralineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Sertraline.Approved
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Sumatriptan.Approved
SimeprevirThe serum concentration of Simeprevir can be increased when it is combined with Sumatriptan.Approved
SitagliptinThe serum concentration of Sitagliptin can be increased when it is combined with Sumatriptan.Approved, Investigational
SofosbuvirThe serum concentration of Sofosbuvir can be increased when it is combined with Sumatriptan.Approved
SorafenibThe serum concentration of Sorafenib can be increased when it is combined with Sumatriptan.Approved, Investigational
SparfloxacinThe serum concentration of Sparfloxacin can be increased when it is combined with Sumatriptan.Approved
SphingosineThe serum concentration of Sphingosine can be increased when it is combined with Sumatriptan.Experimental
SulpirideThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Sulpiride.Approved
TacrolimusThe serum concentration of Tacrolimus can be increased when it is combined with Sumatriptan.Approved, Investigational
TamoxifenThe serum concentration of Tamoxifen can be increased when it is combined with Sumatriptan.Approved
TapentadolThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Tapentadol.Approved
Taurocholic AcidThe serum concentration of Taurocholic Acid can be increased when it is combined with Sumatriptan.Experimental
Technetium Tc-99m sestamibiThe serum concentration of Technetium Tc-99m sestamibi can be increased when it is combined with Sumatriptan.Approved
Tedizolid PhosphateTedizolid Phosphate may increase the serotonergic activities of Sumatriptan.Approved
TelaprevirThe serum concentration of Telaprevir can be increased when it is combined with Sumatriptan.Approved
TemsirolimusThe serum concentration of Temsirolimus can be increased when it is combined with Sumatriptan.Approved
TeriflunomideThe serum concentration of Sumatriptan can be increased when it is combined with Teriflunomide.Approved
ThioproperazineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Thioproperazine.Approved
ThioridazineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Thioridazine.Approved
ThiothixeneThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Thiothixene.Approved
TiaprideThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Tiapride.Investigational
TicagrelorThe serum concentration of Ticagrelor can be increased when it is combined with Sumatriptan.Approved
TimololThe serum concentration of Timolol can be increased when it is combined with Sumatriptan.Approved
ToloxatoneThe metabolism of Sumatriptan can be decreased when combined with Toloxatone.Approved
TolvaptanThe serum concentration of Tolvaptan can be increased when it is combined with Sumatriptan.Approved
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Sumatriptan.Approved, Investigational
ToremifeneThe serum concentration of Toremifene can be increased when it is combined with Sumatriptan.Approved, Investigational
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Sumatriptan.Approved, Investigational
Trans-2-PhenylcyclopropylamineThe metabolism of Sumatriptan can be decreased when combined with Trans-2-Phenylcyclopropylamine.Experimental
TranylcypromineThe metabolism of Sumatriptan can be decreased when combined with Tranylcypromine.Approved
Trastuzumab emtansineThe serum concentration of Trastuzumab emtansine can be increased when it is combined with Sumatriptan.Approved
TrazodoneThe risk or severity of adverse effects can be increased when Trazodone is combined with Sumatriptan.Approved, Investigational
TrifluoperazineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Trifluoperazine.Approved
TriflupromazineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Triflupromazine.Approved, Vet Approved
TrimipramineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Trimipramine.Approved
TropisetronTropisetron may increase the serotonergic activities of Sumatriptan.Investigational
UlipristalThe serum concentration of Ulipristal can be increased when it is combined with Sumatriptan.Approved
UmeclidiniumThe serum concentration of Umeclidinium can be increased when it is combined with Sumatriptan.Approved
VecuroniumThe serum concentration of Vecuronium can be increased when it is combined with Sumatriptan.Approved
VenetoclaxThe serum concentration of Venetoclax can be increased when it is combined with Sumatriptan.Approved
VenlafaxineThe risk or severity of adverse effects can be increased when Venlafaxine is combined with Sumatriptan.Approved
VerapamilThe serum concentration of Verapamil can be increased when it is combined with Sumatriptan.Approved
VilazodoneThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Vilazodone.Approved
VinblastineThe serum concentration of Vinblastine can be increased when it is combined with Sumatriptan.Approved
VincristineThe serum concentration of Vincristine can be increased when it is combined with Sumatriptan.Approved, Investigational
VismodegibThe serum concentration of Vismodegib can be increased when it is combined with Sumatriptan.Approved
VortioxetineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Vortioxetine.Approved
ZidovudineThe serum concentration of Zidovudine can be increased when it is combined with Sumatriptan.Approved
ZiprasidoneThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Ziprasidone.Approved
ZolmitriptanThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Sumatriptan.Approved, Investigational
ZotepineThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Zotepine.Approved
ZuclopenthixolThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Zuclopenthixol.Approved, Investigational
Food InteractionsNot 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
ATC CodesN02CC01
AHFS Codes
  • 28:32.28
PDB EntriesNot Available
FDA labelDownload (142 KB)
MSDSDownload (49.9 KB)
ADMET
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 )
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
Dosage forms
FormRouteStrength
SprayNasal20 mg/1
SprayNasal5 mg/1
TabletOral100 mg
TabletOral50 mg
LiquidSubcutaneous12 mg
SprayNasal20 mg
SprayNasal5 mg
KitNasal
TabletOral25 mg
InjectionSubcutaneous6 mg/.5mL
SprayNasal20 mg/.1mL
SprayNasal20 mg/100uL
SprayNasal5 mg/.1mL
SprayNasal5 mg/100uL
TabletOral100 mg/1
TabletOral25 mg/1
TabletOral50 mg/1
SolutionSubcutaneous12 mg
Injection, solutionSubcutaneous4 mg/.5mL
Injection, solutionSubcutaneous6 mg/.5mL
Tablet, coatedOral100 mg/1
Tablet, coatedOral25 mg/1
Tablet, coatedOral50 mg/1
Tablet, film coatedOral100 mg/1
Tablet, film coatedOral25 mg/1
Tablet, film coatedOral50 mg/1
InjectionSubcutaneous4 mg/.5mL
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)
CA2098302 No2001-10-162011-12-10Canada
CA2469019 No2005-09-132022-12-04Canada
US5705520 No1994-12-102011-12-10Us
US5872145 Yes1998-02-142018-02-14Us
US5957886 No1996-03-082016-03-08Us
US6060499 Yes1998-02-142018-02-14Us
US6135979 No1997-03-212017-03-21Us
US6174304 No1995-12-132015-12-13Us
US6251091 No1996-12-092016-12-09Us
US6280410 No1997-03-272017-03-27Us
US6586458 Yes1998-02-142018-02-14Us
US6681810 No1995-12-132015-12-13Us
US6715485 No2000-03-032020-03-03Us
US6745071 No2003-02-212023-02-21Us
US7332183 Yes2006-04-022026-04-02Us
US7776007 No2006-11-222026-11-22Us
US7811254 No2007-08-262027-08-26Us
US7901385 No2006-07-312026-07-31Us
US7973058 No2007-04-122027-04-12Us
US7975690 No2005-08-182025-08-18Us
US8022095 Yes1998-02-142018-02-14Us
US8047202 No2003-07-022023-07-02Us
US8118771 No2003-08-102023-08-10Us
US8155737 No2007-04-122027-04-12Us
US8241243 No2003-08-102023-08-10Us
US8241244 No2002-11-212022-11-21Us
US8267903 No2003-03-182023-03-18Us
US8287489 No2004-12-062024-12-06Us
US8327844 No2003-10-032023-10-03Us
US8343130 No2002-10-182022-10-18Us
US8366600 No2009-04-212029-04-21Us
US8470853 No2007-04-122027-04-12Us
US8491524 No2002-11-212022-11-21Us
US8550073 No2009-10-222029-10-22Us
US8555877 No2000-03-032020-03-03Us
US8590530 No2005-09-152025-09-15Us
US8597272 No2007-04-122027-04-12Us
US8875704 No2008-04-072028-04-07Us
US8899229 No2010-08-182030-08-18Us
US8978647 No2010-12-062030-12-06Us
US8983594 No2010-11-192030-11-19Us
US9108015 No2005-09-152025-09-15Us
US9119932 No2004-04-232024-04-23Us
US9272137 No2007-09-072027-09-07Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point169-171 °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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0a4i-9400000000-93cc7dc7e521f98aa292View in MoNA
Taxonomy
DescriptionThis 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 subsituted at the 3-position by an ethanamine.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassTryptamines and derivatives
Direct ParentTryptamines and derivatives
Alternative Parents
Substituents
  • Tryptamine
  • Indole
  • Aralkylamine
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Pyrrole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

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 substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate c...
Gene Name:
HTR1D
Uniprot ID:
P28221
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 substances, such as lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of ...
Gene Name:
HTR1B
Uniprot ID:
P28222
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 triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling inhibits adenylate cyclase activity.
Gene Name:
HTR1F
Uniprot ID:
P30939
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 signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Beta-arrestin family members inhibit signaling via G pro...
Gene Name:
HTR1A
Uniprot ID:
P08908
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 tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
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 ]

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 inhibited by the grapefruit juice component naringin.
Gene Name:
SLCO1A2
Uniprot ID:
P46721
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
inhibitor
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
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 ]
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 from mitochondria to cytosol and from cytosol to extracellular space, and cellular export of hemin, and heme. Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from t...
Gene Name:
ABCG2
Uniprot ID:
Q9UNQ0
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, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. Involved in the clearance of bile acids and organic anions from the liver.
Gene Name:
SLCO1B1
Uniprot ID:
Q9Y6L6
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 ]
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Drug created on June 13, 2005 07:24 / Updated on December 07, 2016 03:54