General
Preferred name
SUMATRIPTAN
Synonyms
SUMATRIPTAN SUCCINATE ()
GR 43175 ()
Imitrex / Imigran ()
Sumatriptan succinate ()
[3H]sumatriptan ()
Sumatriptan (succinate) ()
GR 43175 (free base) ()
N02CC01 ()
Dfn-11 (sumatriptan injection) ()
Imitrex ()
Dfn-11 ()
Tosymra ()
Imigran Recovery ()
Treximet ()
Alsuma ()
Imitrex Statdose ()
Imigran ()
GR 43175C ()
NSC-760362 ()
Zembrace symtouch ()
Imigran 50 ()
Sumatriptan (as succinate) ()
Zecuity ()
Sumavel Dosepro ()
Migraitan ()
Onzetra xsail ()
GR-43175C ()
Imigran Radis ()
Sumatriptan galpharm ()
Imigran Subject ()
Migraleve Ultra ()
[3H]sumatriptan ()
Sumatriptan-d6 (succinate) ()
P&D ID
PD000904
CAS
103628-48-4
103628-46-2
1397195-80-0
Tags
drug candidate
natural product
drug
available
Approved by
FDA
First approval
1992
Drug Status
investigational
approved
withdrawn
Drug indication
Migraine
Discovery agent
Antimigraine
Max Phase
Phase 4
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
ROE 22±4% is excreted in the urine as unchanged sumatriptan and 38±7% in urine as indole acetic acid[L6799,L6805] approximately 40% is excreted in the feces[L6811,L6793].; ;
PHARMACODYNAMICS Sumatriptan constricts cranial blood vessels and prevents the release of vasoactive peptides.[A179734] The dose of sumatriptan varies widely by route of administration and in most cases, no more than 2 doses should be given daily.[L6793,L6796,L6799,L6805,L6808,L6811] Medication overuse headaches may occur in patients who use sumatriptan frequently.[L6793,L6796,L6799,L6805,L6808,L6811]
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.[L6793] Sumatriptan nasal powder, nasal spray, subcutaneous injection, and tablets are indicated to treat migraines with or without auras in adults.[L6796,L6799,L6805,L6808,L6811] One of the subcutaneous formulations of sumatriptan is also indicated to treat cluster headaches in adults[L6805], while the other subcutaneous formulation is not.[L6808]
MOA Sumatriptan is an agonist of 5-HT1B and 5-HT1D.[L6793,L6796,L6799,L6805,L6808,L6811] This agonism leads to constriction of cranial blood vessels and inhibits the release of pro-inflammatory neuropeptides.[L6793,L6796,L6799,L6805,L6808,L6811] Sumatriptan decreases carotid arterial blood flow, but increases blood flow velocity in the internal carotid artery and middle cerebral artery.[A179734 Agonism of the 5-HT1B and 5-HT1D receptors also inhibits sensory neurons, preventing the release of vasoactive peptides.[A179734 Sumatriptan does not cross the blood brain barrier.[A179734]
TOXICITY Symptoms of overdose include convulsions, tremor, paralysis, inactivity, ptosis, erythema of the extremities, abnormal respiration, cyanosis, ataxia, mydriasis, salivation, and lacrimation.[L6793,L6796,L6799,L6805,L6808,L6811] Overdoses may be fatal and patients should be monitored for 3-5 half lives or while symptoms persist.[L6793,L6796,L6799,L6805,L6808,L6811]
METABOLISM Sumatriptan is predominantly metabolized by monoamine oxidase A[L6799,L6811,L6805,L6811,L6793,L6808]. The main metabolites are the inactive indole acetic acid and indole acetic acid glucuronide.[L6799,L6811,L6805,L6811,L6793,L6808]
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%.[A179737]; ; 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%).[A179737]; ; 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%).[A179737]; ; 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%).[A179737]
HALF-LIFE Subcutaneous sumatriptan has a half life of 1.9h (95% CI of 1.7-2.0h).[A179737] Oral sumatriptan has a half life of 1.7h (95% CI of 1.4-1.9h).[A179737] Rectal sumatriptan has a half life of 1.8h (95% CI of 1.6-2.2h).[A179737] Intrsnasal sumatriptan has a half life of 1.8h (95% CI of 1.7-2.0h).[A179737]
DESCRIPTION Sumatriptan is a selective serotonin 5-HT1B/ID receptor agonist.
Marketed formulations contain sumatriptan succinate (PubChem CID 59772). (GtoPdb)
DESCRIPTION GnRH receptor agonist (Tocris Bioactive Compound Library)
DESCRIPTION 5-HT1 receptor agonist (Tocriscreen Total)
DESCRIPTION Sumatriptan is a Serotonin-1b and Serotonin-1d Receptor Agonist that acts selectively at 5HT1 receptors. It is a sulfonamide triptan with vasoconstrictor activity. It selectively binds to and activates serotonin 5-HT1D receptors in the central nervous system, thus constricts cerebral blood vessels. It may also relieve vascular headaches by decreasing the release of vasoactive neuropeptides from perivascular trigeminal axons in the dura mater. It is a medication used for the treatment of migraine headaches. (BOC Sciences Bioactive Compounds)
DESCRIPTION 5-HT1A/1B/1D receptor agonist (Tocriscreen Plus)
Cell lines
0
Organisms
3
Compound Sets
38
Axon Medchem Screening Library
1352
BOC Sciences Bioactive Compounds
sumatriptan-cas-103628-46-2-item-53375
Cayman Chemical Bioactives
14600
28202
CeMM library of unique drugs (CLOUD)
ChEMBL Approved Drugs
CHEMBL128
CHEMBL1201150
ChEMBL Drugs
CHEMBL128
CHEMBL1201150
Concise Guide to Pharmacology 2017/18
54
119
Concise Guide to Pharmacology 2019/20
54
119
Concise Guide to Pharmacology 2021/22
54
119
Concise Guide to Pharmacology 2023/24
54
119
Drug Repurposing Hub
DrugBank
DB00669
DrugBank Approved Drugs
DB00669
DrugCentral
2543
DrugCentral Approved Drugs
2543
DrugMAP
DMVYXR8
DM3MBGV
DrugMAP Approved Drugs
DMVYXR8
DrugMatrix
Enamine BioReference Compounds
EU-OPENSCREEN Bioactive Compound Library
EOS100058
Guide to Pharmacology
54
119
Ki Database
SUMATRIPTAN
LSP-MoA library (Laboratory of Systems Pharmacology)
CHEMBL128
MedChem Express Bioactive Compound Library
HY-B0121B
HY-B0121
Natural product-based probes and drugs
NCATS Inxight Approved Drugs
8R78F6L9VO
NIH Clinical Collections (NCC)
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
Sumatriptan-succinate
TargetMol Bioactive Compound Library
T0203
The Spectrum Collection
Tocris Bioactive Compound Library
3586
Tocriscreen Plus
3586
Tocriscreen Total
Withdrawn 2.0
EMA40
External IDs
73
Properties
(calculated by RDKit )
Molecular Weight
295.14
Hydrogen Bond Acceptors
3
Hydrogen Bond Donors
2
Rotatable Bonds
6
Ring Count
2
Aromatic Ring Count
2
cLogP
1.32
TPSA
65.2
Fraction CSP3
0.43
Chiral centers
0.0
Largest ring
6.0
QED
0.84
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Target Type
7-TM Receptors
MOA
serotonin receptor agonist
Agonist
5-HT1B Agonists
5-HT1D Agonists
Target
Serotonin 1d (5-HT1d) receptor
Serotonin 1b (5-HT1b) receptor
5-HT
HTR1A, HTR1B, HTR1D, HTR1E, HTR1F, HTR5A, HTR6, HTR7
5-HT1B/1D agonist
5-HT Receptor
Pathway
GPCR/G protein
Neuroscience
Neuronal Signaling
Primary Target
5-HT1D Receptors
Member status
member
Indication
migraine headache
ATC
N02CC01
Biosynthetic Origin
Alkaloid
Therapeutic Indication
Antimigraine
Therapeutic Class
CNS & PNS
Vasoconstrictor Agents
Solubility
10 mM in DMSO
Source data