Identification

Name
Sumatriptan
Accession Number
DB00669
Description

Sumatriptan is a serotonin receptor agonist commonly used to treat migraines and sometimes cluster headaches.5,6,7,8,9,10 Sumatriptan is the first of the triptans and was made available in Europe in 1991 to treat migraines.4 Sumatriptan was granted FDA approval on 28 December 1992.8

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 295.4
Monoisotopic: 295.135447621
Chemical Formula
C14H21N3O2S
Synonyms
  • (3-[2-(dimethylamino)ethyl]-1H-indol-5-yl)-N-methylmethanesulfonamide
  • 1-[3-(2-dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide
  • 3-(2-(dimethylamino)ethyl)-N-methyl-1H-indole-5-methanesulfonamide
  • 3-[2-(dimethylamino)ethyl]-N-methylindole-5-methanesulfonamide
  • Sumatriptan
  • Sumatriptán
  • Sumatriptanum
External IDs
  • GR 43175 A
  • GR 43175 C
  • GR 43175 X
  • NP101
  • SN 308

Pharmacology

Indication

A combination sumatriptan and naproxen tablet is indicated for the treatment of migraines with or without auras in patients 12 years of age and older.5 Sumatriptan nasal powder, nasal spray, subcutaneous injection, and tablets are indicated to treat migraines with or without auras in adults.6,7,8,9,10 One of the subcutaneous formulations of sumatriptan is also indicated to treat cluster headaches in adults8, while the other subcutaneous formulation is not.9

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

Sumatriptan constricts cranial blood vessels and prevents the release of vasoactive peptides.2 The dose of sumatriptan varies widely by route of administration and in most cases, no more than 2 doses should be given daily.5,6,7,8,9,10 Medication overuse headaches may occur in patients who use sumatriptan frequently.5,6,7,8,9,10

Mechanism of action

Sumatriptan is an agonist of 5-HT1B and 5-HT1D.5,6,7,8,9,10 This agonism leads to constriction of cranial blood vessels and inhibits the release of pro-inflammatory neuropeptides.5,6,7,8,9,10 Sumatriptan decreases carotid arterial blood flow, but increases blood flow velocity in the internal carotid artery and middle cerebral artery.2,2,2

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

A 6mg subcutaneous injection of sumatriptan reaches a Cmax of 69.5ng/mL (95% CI of 62.8-76.9ng/mL) with a Tmax of 0.17h (95% CI of 0.08-0.33h), an AUC of 9.0h*ng/mL (95% CI of 7.5-10.9h*ng/mL), and a bioavailability of 100%.3

A 25mg oral dose of sumatriptan reaches a Cmax of 16.5ng/mL (95% CI of 13.5-20.1ng/mL) with a Tmax of 1.50h (95% CI of 0.50-2.00h), an AUC of 8.7h*ng/mL (95% CI of 6.1-12.5h*ng/mL), and a bioavailability of 14.3% (95% CI of 11.4-17.9%).3

A 20mg intranasal dose of sumatriptan reaches a Cmax of 12.9ng/mL (95% CI of 10.5-15.9ng/mL) with a Tmax of 1.50h (95% CI of 0.25-3.00h), an AUC of 7.4h*ng/mL (95% CI of 5.0-10.8h*ng/mL), and a bioavailability of 15.8% (95% CI of 12.6-19.8%).3

A 25mg rectal dose of sumatriptan reaches a Cmax of 22.9ng/mL (95% CI of 18.4-28.6ng/mL) with a Tmax of 1.00h (95% CI of 0.75-3.00h), an AUC of 14.6h*ng/mL (95% CI of 11.3-18.8h*ng/mL), and a bioavailability of 19.2% (95% CI of 15.3-24.1%).3

Volume of distribution

Sumatriptan has a volume of distribution of 50±8L for a 6mg subcutaneous dose7, or 2.7L/kg.10

Protein binding

Sumatriptan is 14%-21% bound to protein in circulation.5,6,7,8,9,10

Metabolism

Sumatriptan is predominantly metabolized by monoamine oxidase A7,10,8,10,5,9. The main metabolites are the inactive indole acetic acid and indole acetic acid glucuronide.7,10,8,10,5,9

Hover over products below to view reaction partners

Route of elimination

22±4% is excreted in the urine as unchanged sumatriptan and 38±7% in urine as indole acetic acid7,8 approximately 40% is excreted in the feces10,5.

Half-life

Subcutaneous sumatriptan has a half life of 1.9h (95% CI of 1.7-2.0h).3 Oral sumatriptan has a half life of 1.7h (95% CI of 1.4-1.9h).3 Rectal sumatriptan has a half life of 1.8h (95% CI of 1.6-2.2h).3 Intrsnasal sumatriptan has a half life of 1.8h (95% CI of 1.7-2.0h).3

Clearance

Subcutaneous sumatriptan has a clearance of 0.22L/min (95% CI of 0.19-0.25L/min).3 Oral sumatriptan has a clearance of 0.17L/min (95% CI of 0.14-0.21L/min).3 Rectal sumatriptan has a clearance of 0.17L/min (95% CI of 0.14-0.21L/min).3 Intrsnasal sumatriptan has a clearance of 0.21L/min (95% CI of 0.18-0.25L/min).3 Total plasma clearance of sumatriptan is approximately 1200mL/min.6

Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
Toxicity

Symptoms of overdose include convulsions, tremor, paralysis, inactivity, ptosis, erythema of the extremities, abnormal respiration, cyanosis, ataxia, mydriasis, salivation, and lacrimation.5,6,7,8,9,10 Overdoses may be fatal and patients should be monitored for 3-5 half lives or while symptoms persist.5,6,7,8,9,10

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
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirSumatriptan may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbemaciclibAbemaciclib may decrease the excretion rate of Sumatriptan which could result in a higher serum level.
AcarboseThe therapeutic efficacy of Acarbose can be increased when used in combination with Sumatriptan.
AcebutololSumatriptan may decrease the antihypertensive activities of Acebutolol.
AceclofenacAceclofenac may decrease the excretion rate of Sumatriptan which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Sumatriptan which could result in a higher serum level.
AcenocoumarolThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Acenocoumarol.
AcetaminophenAcetaminophen may decrease the excretion rate of Sumatriptan which could result in a higher serum level.
AcetazolamideThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Acetazolamide.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be increased when used in combination with Sumatriptan.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Avoid excessive or chronic alcohol consumption. Alcohol increased the risk of GI bleeding, ulcer, and perforation when taken with sumatriptan.
  • Take with or without food.

Products

Product Ingredients
IngredientUNIICASInChI Key
Sumatriptan succinateJ8BDZ68989103628-48-4PORMUFZNYQJOEI-UHFFFAOYSA-N
Product Images
International/Other Brands
Adracon (Inti) / Altaxa (Alapis Pharma) / Apigrane (Advanced Pharmaceutical) / Boots Pharmacy Migraine Relief (Boots) / Cinie (Zentiva) / Frimig (Orion) / Illument (Pliva) / Imigen (Mylan) / Imigran (GlaxoSmithKline) / Imigran mite (GlaxoSmithKline) / Imigran Radis (GlaxoSmithKline) / Imigrane (GlaxoSmithKline) / Imitrex Oral (GlaxoSmithKline) / Migralgin (GMP) / Migraneitor (Driburg) / Nazdav (Dr. Reddy's) / Sapphirex (Hemofarm) / Sumatran (Rowex) / Sumax (Libbs) / Suminat (Sun) / Youshu (Simcere)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Act SumatriptanTabletOralTEVA Canada Limited2005-08-24Not applicableCanada flag
Act SumatriptanTabletOralActavis Pharma Company2005-08-242018-06-19Canada flag
Act SumatriptanTabletOralActavis Pharma Company2005-08-242018-06-19Canada flag
AlsumaInjection, solution6 mg/0.5mLSubcutaneousPfizer Laboratories Div Pfizer Inc.2009-08-312015-08-31US flag
AlsumaInjection, solution6 mg/0.5mLSubcutaneousUs World Meds, Llc2010-10-152013-08-31US flag
ImitrexTablet, film coated50 mg/1OralRebel Distributors2003-12-17Not applicableUS flag
ImitrexTablet, film coated50 mg/1OralPhysicians Total Care, Inc.1996-09-132011-06-30US flag
ImitrexInjection6 mg/0.5mLSubcutaneousGlaxo Operations UK Ltd1997-01-232017-12-21US flag
ImitrexInjection6 mg/0.5mLSubcutaneousSmithKline Beecham Corporation1997-01-302009-11-08US flag
ImitrexInjection6 mg/0.5mLSubcutaneousPhysicians Total Care, Inc.1995-01-262011-03-31US flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-sumatriptanTabletOralApotex CorporationNot applicableNot applicableCanada flag
Apo-sumatriptanTabletOralApotex Corporation2005-08-24Not applicableCanada flag
Apo-sumatriptanSprayNasalApotex CorporationNot applicableNot applicableCanada flag
Apo-sumatriptanTabletOralApotex Corporation2005-08-24Not applicableCanada flag
Apo-sumatriptanSprayNasalApotex CorporationNot applicableNot applicableCanada flag
Ava-sumatriptanTabletOralAvanstra Inc2011-09-192014-08-21Canada flag
Ava-sumatriptanTabletOralAvanstra Inc2011-09-192014-08-21Canada flag
Dom-sumatriptanTabletOralDominion Pharmacal2005-09-29Not applicableCanada flag
Dom-sumatriptanTabletOralDominion Pharmacal2005-09-29Not applicableCanada flag
Dom-sumatriptanTabletOralDominion Pharmacal2005-09-29Not applicableCanada flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Sumatriptan and Naproxen SodiumSumatriptan succinate (85 mg/1) + Naproxen sodium (500 mg/1)Tablet, film coatedOralAurobindo Pharma Limited2018-02-15Not applicableUS flag
Sumatriptan and Naproxen SodiumSumatriptan succinate (85 mg/1) + Naproxen sodium (500 mg/1)Tablet, film coatedOralNorthstar RxLLC2018-11-27Not applicableUS flag
Sumatriptan and Naproxen SodiumSumatriptan succinate (85 mg/1) + Naproxen sodium (500 mg/1)Tablet, film coatedOralSun Pharmaceutical Industries, Inc.2018-07-20Not applicableUS flag
Sumatriptan and Naproxen SodiumSumatriptan succinate (85 mg/1) + Naproxen sodium (500 mg/1)Tablet, film coatedOralMylan Pharmaceuticals Inc.2018-09-04Not applicableUS flag
Sumatriptan Succinate and Naproxen SodiumSumatriptan succinate (85 mg/1) + Naproxen sodium (500 mg/1)TabletOralCurrax Pharmaceuticals LLC dba Cypress, Hawthorn, Macoven2015-05-14Not applicableUS flag
SuvexxSumatriptan (85 mg) + Naproxen sodium (500 mg)TabletOralAralez Pharmaceuticals Canada Inc2020-07-24Not applicableCanada flag
TreximetSumatriptan succinate (85 mg/1) + Naproxen sodium (500 mg/1)Tablet, film coatedOralGlaxo Operations UK Ltd2008-04-252018-02-14US flag
TreximetSumatriptan succinate (10 mg/1) + Naproxen sodium (60 mg/1)Tablet, film coatedOralPernix Therapeutics2015-05-142021-09-30US flag
TreximetSumatriptan succinate (85 mg/1) + Naproxen sodium (500 mg/1)Tablet, film coatedOralGlaxosmithkline Inc2008-04-252018-07-31US flag
TreximetSumatriptan succinate (85 mg/1) + Naproxen sodium (500 mg/1)Tablet, film coatedOralPernix Therapeutics2015-05-142021-09-30US flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
MigranowSumatriptan succinate (50 mg/1) + Levomenthol (10 g/100g) + Synthetic camphor (4 g/100g)KitOral; TopicalPureTek Corporation2016-04-18Not applicableUS flag
SumaChipSumatriptan succinate (100 mg/1) + Capsaicin (0.0375 g/100g) + Levomenthol (5 g/100g)KitOral; TopicalBasiem2015-11-292016-03-04US flag

Categories

ATC Codes
N02CC01 — SumatriptanG01AE10 — Combinations of sulfonamides
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as tryptamines and derivatives. These are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Tryptamines and derivatives
Direct Parent
Tryptamines and derivatives
Alternative Parents
3-alkylindoles / Aralkylamines / Substituted pyrroles / Organosulfonamides / Organic sulfonamides / Benzenoids / Heteroaromatic compounds / Aminosulfonyl compounds / Trialkylamines / Azacyclic compounds
show 3 more
Substituents
3-alkylindole / Amine / Aminosulfonyl compound / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Heteroaromatic compound / Hydrocarbon derivative / Indole
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
sulfonamide, tryptamines (CHEBI:10650)

Chemical Identifiers

UNII
8R78F6L9VO
CAS number
103628-46-2
InChI Key
KQKPFRSPSRPDEB-UHFFFAOYSA-N
InChI
InChI=1S/C14H21N3O2S/c1-15-20(18,19)10-11-4-5-14-13(8-11)12(9-16-14)6-7-17(2)3/h4-5,8-9,15-16H,6-7,10H2,1-3H3
IUPAC Name
1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide
SMILES
CNS(=O)(=O)CC1=CC=C2NC=C(CCN(C)C)C2=C1

References

Synthesis Reference

Rajeev Mathur, T. Kumar, Sunilendu Roy, Rajiv Malik, "Taste masked sumatriptan tablets and processes for their preparation." U.S. Patent US20060233875, issued October 19, 2006.

US20060233875
General References
  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]
  2. Ferrari MD, Saxena PR: Clinical effects and mechanism of action of sumatriptan in migraine. Clin Neurol Neurosurg. 1992;94 Suppl:S73-7. [PubMed:1320526]
  3. Duquesnoy C, Mamet JP, Sumner D, Fuseau E: Comparative clinical pharmacokinetics of single doses of sumatriptan following subcutaneous, oral, rectal and intranasal administration. Eur J Pharm Sci. 1998 Apr;6(2):99-104. [PubMed:9795022]
  4. Humphrey PP: The discovery and development of the triptans, a major therapeutic breakthrough. Headache. 2008 May;48(5):685-7. doi: 10.1111/j.1526-4610.2008.01097.x. [PubMed:18471110]
  5. FDA Approved Drug Products: Sumatriptan and Naproxen Oral Tablets [Link]
  6. FDA Approved Drug Products: Sumatriptan Nasal Powder [Link]
  7. FDA Approved Drug Products: Sumatriptan Nasal Spray [Link]
  8. FDA Approved Drug Products: Sumatriptan Subcutaneous Injection [Link]
  9. FDA Approved Drug Products: Sumatriptan Subcutaneous Solution [Link]
  10. FDA Approved Drug Products: Sumatriptan Oral Tablets [Link]
  11. Sumatriptan Tablets, USP monograph [Link]
Human Metabolome Database
HMDB0005037
KEGG Drug
D00451
KEGG Compound
C07319
PubChem Compound
5358
PubChem Substance
46506520
ChemSpider
5165
BindingDB
50005835
RxNav
37418
ChEBI
10650
ChEMBL
CHEMBL128
ZINC
ZINC000000014360
Therapeutic Targets Database
DNC001649
PharmGKB
PA451566
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Sumatriptan
AHFS Codes
  • 28:32.28 — Selective Serotonin Agonists
MSDS
Download (49.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableMigraine1
4CompletedOtherWorkplace Migraine Treatment1
4CompletedPreventionMigraine2
4CompletedTreatmentAcute Migraine / Migraine / Migraine Disorders / Migraine Headache, With or Without Aura1
4CompletedTreatmentChronic Migraine1
4CompletedTreatmentHeadache Disorders, Primary / Migraine / Tension Headache1
4CompletedTreatmentMenstrual Migraines1
4CompletedTreatmentMigraine5
4CompletedTreatmentPain, Migraine1
4RecruitingTreatmentPost-Dural Puncture Headache1

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
SprayNasal
Injection, solutionCutaneous6 MG/0.5ML
Suppository25 MG
SprayNasal10 mg
Tablet, film coatedOral100 MG
SprayNasal20 mg
Tablet, film coated50 mg
Tablet, film coatedOral50 MG
Tablet
Injection6 mg/0.5ml
LiquidSubcutaneous6 mg
SprayNasal20 mg/1
SprayNasal5 mg/1
TabletOral
LiquidSubcutaneous
KitNasal11 mg/1
CapsuleNasal11 mg/1
SolutionSubcutaneous6 mg
TabletOral100 mg
Tablet, coatedOral500 mg
KitOral; Topical
SprayNasal20 mg/0.1mL
SprayNasal20 mg/100uL
SprayNasal5 mg/100uL
SprayNasal5 mg/0.1mL
TabletOral25 mg
Tablet, coatedOral100 mg/1
Tablet, coatedOral50 mg/1
Tablet100 MG
Tablet50 MG
Tablet, coatedOral50 MG
TabletOral50 MG
SolutionSubcutaneous
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
Injection, solutionParenteral6 MG/0.5ML
Tablet, coatedOral100 mg
SprayNasal10 mg/1
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)Region
US5705520No1998-01-062011-12-10US flag
CA2469019No2005-09-132022-12-04Canada flag
CA2098302No2001-10-162011-12-10Canada flag
US6060499Yes2000-05-092018-02-14US flag
US7332183Yes2008-02-192026-04-02US flag
US6586458Yes2003-07-012018-02-14US flag
US5872145Yes1999-02-162018-02-14US flag
US8022095Yes2011-09-202018-02-14US flag
US8491524No2013-07-232022-11-21US flag
US6681810No2004-01-272015-12-13US flag
US8287489No2012-10-162024-12-06US flag
US6135979No2000-10-242017-03-21US flag
US6280410No2001-08-282017-03-27US flag
US6174304No2001-01-162015-12-13US flag
US8343130No2013-01-012022-10-18US flag
US8241243No2012-08-142023-08-10US flag
US8241244No2012-08-142022-11-21US flag
US5957886No1999-09-282016-03-08US flag
US8267903No2012-09-182023-03-18US flag
US7901385No2011-03-082026-07-31US flag
US6251091No2001-06-262016-12-09US flag
US8118771No2012-02-212023-08-10US flag
US7776007No2010-08-172026-11-22US flag
US7811254No2010-10-122027-08-26US flag
US7973058No2011-07-052027-04-12US flag
US8155737No2012-04-102027-04-12US flag
US8366600No2013-02-052029-04-21US flag
US8470853No2013-06-252027-04-12US flag
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Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)169-170http://www.chemspider.com/Chemical-Structure.5165.html
water solubility54mg/mLSumatriptan Tablets, USP monograph
logP0.93ADLARD,M ET AL. (1995)
pKa4.9Sumatriptan Tablets, USP monograph
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

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive subst...
Gene Name
HTR1D
Uniprot ID
P28221
Uniprot Name
5-hydroxytryptamine receptor 1D
Molecular Weight
41906.38 Da
References
  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
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive subst...
Gene Name
HTR1B
Uniprot ID
P28222
Uniprot Name
5-hydroxytryptamine receptor 1B
Molecular Weight
43567.535 Da
References
  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
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various alkaloids and psychoactive substances. Ligand binding causes a conformation change that trig...
Gene Name
HTR1F
Uniprot ID
P30939
Uniprot Name
5-hydroxytryptamine receptor 1F
Molecular Weight
41708.505 Da
References
  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
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
Gene Name
HTR1A
Uniprot ID
P08908
Uniprot Name
5-hydroxytryptamine receptor 1A
Molecular Weight
46106.335 Da
References
  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
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Serotonin binding
Specific Function
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name
MAOA
Uniprot ID
P21397
Uniprot Name
Amine oxidase [flavin-containing] A
Molecular Weight
59681.27 Da
References
  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
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
Gene Name
SLCO1A2
Uniprot ID
P46721
Uniprot Name
Solute carrier organic anion transporter family member 1A2
Molecular Weight
74144.105 Da
References
  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
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  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
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  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
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  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 September 17, 2020 23:28

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