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Details

Stereochemistry ACHIRAL
Molecular Formula C14H21N3O2S.C4H6O4
Molecular Weight 413.488
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SUMATRIPTAN SUCCINATE

SMILES

OC(=O)CCC(O)=O.CNS(=O)(=O)CC1=CC2=C(NC=C2CCN(C)C)C=C1

InChI

InChIKey=PORMUFZNYQJOEI-UHFFFAOYSA-N
InChI=1S/C14H21N3O2S.C4H6O4/c1-15-20(18,19)10-11-4-5-14-13(8-11)12(9-16-14)6-7-17(2)3;5-3(6)1-2-4(7)8/h4-5,8-9,15-16H,6-7,10H2,1-3H3;1-2H2,(H,5,6)(H,7,8)

HIDE SMILES / InChI

Molecular Formula C14H21N3O2S
Molecular Weight 295.4
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C4H6O4
Molecular Weight 118.088
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Sumatriptan is a serotonin (5-HT1B/1D) receptor agonist indicated for acute treatment of migraine with or without aura in adults. Sumatriptan is structurally similar to serotonin (5-HT), and is a 5-HT receptor (types 5-HT1D and 5-HT1B) agonist. The specific receptor subtypes it activates are present on the cranial arteries and veins. Acting as an agonist at these receptors, sumatriptan reduces the vascular inflammation associated with migraines. The specific receptor subtype it activates is present in the cranial and basilar arteries. Activation of these receptors causes vasoconstriction of those dilated arteries. Sumatriptan is also shown to decrease the activity of the trigeminal nerve, which presumably accounts for sumatriptan's efficacy in treating cluster headaches. The injectable form of the drug has been shown to abort a cluster headache within 30 minutes in 77% of cases. Sumatriptan is effective for ending or relieving the intensity of migraine and cluster headaches. It is most effective taken early after the start of the pain. Injected sumatriptan is more effective than other formulations. Large doses of sumatriptan can cause sulfhemoglobinemia, a rare condition in which the blood changes from red to greenish-black, due to the integration of sulfur into the hemoglobin molecule. Serious cardiac events, including some that have been fatal, have occurred following the use of sumatriptan injection or tablets. Events reported have included coronary artery vasospasm, transient myocardial ischemia, myocardial infarction, ventricular tachycardia, and ventricular fibrillation (V-Fib).

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Single photon emission computed tomography of the brain with Tc-99m HMPAO during sumatriptan challenge in obsessive-compulsive disorder: investigating the functional role of the serotonin auto-receptor.
1999 Aug
Sumatriptan and ergotamine overuse and drug-induced headache: a clinicoepidemiologic study.
1999 Jul-Aug
Open-labeled long-term study of the efficacy, safety, and tolerability of subcutaneous sumatriptan in acute migraine treatment.
1999 Sep
Identification of an amino acid residue important for binding of methiothepin and sumatriptan to the human 5-HT(1B) receptor.
1999 Sep 10
Acute abstinence syndrome following abrupt cessation of long-term use of tramadol (Ultram): a case study.
2000
Transient global amnesia, migraine, thalamic infarct, dihydroergotamine, and sumatriptan.
2000 Apr
Agonist and antagonist actions of yohimbine as compared to fluparoxan at alpha(2)-adrenergic receptors (AR)s, serotonin (5-HT)(1A), 5-HT(1B), 5-HT(1D) and dopamine D(2) and D(3) receptors. Significance for the modulation of frontocortical monoaminergic transmission and depressive states.
2000 Feb
Alteration in nature of cluster headache during subcutaneous administration of sumatriptan.
2000 Jan
Atrial fibrillation associated with sumatriptan.
2000 Jul 29
Sumatriptan overuse in episodic cluster headache: lack of adverse events, rebound syndromes, drug dependence and tachyphylaxis.
2000 Jul-Sep
Headache relief after sumatriptan in a patient with pituitary macroadenoma.
2000 May
Inverse agonism and constitutive activity as functional correlates of serotonin h5-HT(1B) receptor/G-protein stoichiometry.
2000 Nov
2000 Wolfe Award. Sumatriptan for the range of headaches in migraine sufferers: results of the Spectrum Study.
2000 Nov-Dec
Are triptans with enhanced lipophilicity used for the acute treatment of migraine associated with an increased consulting rate for depressive illness?
2000 Oct
A clinical trial on a plate? The potential of 384-well format solid phase extraction for high-throughput bioanalysis using liquid chromatography/tandem mass spectrometry.
2001
Managing migraine: strategies for successful patient outcomes.
2001 Apr
Sumatriptan nasal spray and cognitive function during migraine: results of an open-label study.
2001 Apr
Delivery outcome in women who used drugs for migraine during pregnancy with special reference to sumatriptan.
2001 Apr
Sumatriptan, 5-HT(1D) receptors and obsessive-compulsive disorder.
2001 Apr
[Migraine: sumatriptan].
2001 Apr 10
[Migraine: selection of therapeutic agents to be applied during its attack].
2001 Apr 10
Sumatriptan: economic evidence for its use in the treatment of migraine, the Canadian comparative economic analysis.
2001 Feb
Efficacy, tolerability, and patient satisfaction with 50- and 100-mg sumatriptan tablets in those initially dissatisfied with the efficacy of 50-mg sumatriptan tablets.
2001 Feb
Effect of encapsulation on absorption of sumatriptan tablets: data from healthy volunteers and patients during a migraine.
2001 Feb
Characterization of 5-HT receptors in the parasitic nematode, Ascaris suum.
2001 Feb
Treatment and management of cluster headache.
2001 Feb
Butterscotch masks the bitter taste of sumatriptan nasal spray.
2001 Feb
[Treatment of cluster headache].
2001 Feb
The impact of pharmacogenetics for migraine.
2001 Feb 9
Cortical spreading depression produces increased cGMP levels in cortex and brain stem that is inhibited by tonabersat (SB-220453) but not sumatriptan.
2001 Feb 9
Treatment satisfaction, functional status, and health-related quality of life of migraine patients treated with almotriptan or sumatriptan.
2001 Jan
Successful use of propranolol in migraine associated with electroconvulsive therapy.
2001 Jan
Inhibition of inflammation-induced thermal hypersensitivity by sumatriptan through activation of 5-HT(1B/1D) receptors.
2001 Jan
[First manifestation of migraine as acute confusional state: "confusional migraine" and diagnostic problems].
2001 Jan-Feb
Sumatriptan can alleviate headaches due to carotid artery dissection.
2001 Jun
[Anti-migraine drug sumatriptan succinate, a 5-HT1B/1D-receptor agonist].
2001 Jun
Recent development in paediatric headache.
2001 Jun
Headache and female hormones: what you need to know.
2001 Jun
Gastric motor effects of triptans: open questions and future perspectives.
2001 Mar
Headaches in children and adolescents: update 2001.
2001 Mar
Zolmitriptan versus sumatriptan comparison trial.
2001 Mar
4991W93 inhibits release of calcitonin gene-related peptide in the cat but only at doses with 5HT(1B/1D) receptor agonist activity?
2001 Mar
Comparative effects of frovatriptan and sumatriptan on coronary and internal carotid vascular haemodynamics in conscious dogs.
2001 Mar
The GR127935-sensitive 5-HT(1) receptors mediating canine internal carotid vasoconstriction: resemblance to the 5-HT(1B), but not to the 5-HT(1D) or 5-ht(1F), receptor subtype.
2001 Mar
Evidence for 5-HT(1B/1D) and 5-HT(2A) receptors mediating constriction of the canine internal carotid circulation.
2001 Mar
Serotonin-induced hypercontraction through 5-hydroxytryptamine 1B receptors in atherosclerotic rabbit coronary arteries.
2001 Mar 6
Effect of MAO-A inhibition on the pharmacokinetics of almotriptan, an antimigraine agent in humans.
2001 May
An in vivo rat model to study calcitonin gene related peptide release following activation of the trigeminal vascular system.
2001 May
Modifications by sumatriptan and acetylcholine of nitric oxide-mediated neurogenic dilatation in dog cerebral arteries.
2001 May 18
Intracranial hemorrhages associated with sumatriptan.
2001 May 8
Patents

Sample Use Guides

In Vivo Use Guide
Migraine Headache. Oral: 25 mg, 50 mg, or 100 mg PO (taken with fluids); Not to exceed 100 mg/dose; additional doses q2hr PRN. Subcutaneous Injection: 6 mg (0.5 mL) SC with autoinjector; may repeat in ≥1 hr; Not to exceed 12 mg SC q24hr Cluster Headache. Subcutaneous Injection: 6 mg (0.5 mL) SC with autoinjector; may repeat in ≥1 hour; Not to exceed 12 mg SC q24hr
Route of Administration: Oral; Subcutaneous
In Vitro Use Guide
The uptake of sumatriptan and other triptans via OCT1 and OCT3 was characterized using HEK293 cells stably transfected to overexpress wild-type OCT1 or OCT3. For measuring the uptake in human hepatocytes, was used cryopreserved human hepatocytes (Gibco Life Technologies, Darmstadt, Germany) obtained from a single donor with two fully active OCT1 alleles. Triptan uptake in OCT1 and OCT3-overexpressing HEK293 cells was measured by incubating the cells with varying concentrations of the substrates in 12-well plates for two minutes at pH 7.4 and 378C. The reaction was stopped with ice-cold buffer, the cells were lysed with 80% acetonitrile, and the intracellularly accumulated triptans were quantified by liquid chromatography coupled to tandem massspectrometry.
Substance Class Chemical
Created
by admin
on Tue Oct 22 05:11:12 UTC 2019
Edited
by admin
on Tue Oct 22 05:11:12 UTC 2019
Record UNII
J8BDZ68989
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SUMATRIPTAN SUCCINATE
EP   JAN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
TREXIMET COMPONENT SUMATRIPTAN SUCCINATE
Common Name English
SUMATRIPTAN SUCCINATE [USP-RS]
Common Name English
ZEMBRACE SYMTOUCH
Brand Name English
SUMATRIPTAN SUCCINATE [MART.]
Common Name English
SUMATRIPTAN SUCCINATE [USAN]
Common Name English
ONZETRA XSAIL
Brand Name English
SUMATRIPTAN SUCCINATE [WHO-DD]
Common Name English
TREXIMET
Common Name English
SUMATRIPTAN SUCCINATE [JAN]
Common Name English
SUMATRIPTAN SUCCINATE [VANDF]
Common Name English
SUMATRIPTAN SUCCINATE [ORANGE BOOK]
Common Name English
SUMATRIPTAN SUCCINATE [EP]
Common Name English
SUMATRIPTAN GALPHARM
Brand Name English
1H-INDOLE-5-METHANESULFONAMIDE, 3-(2-(DIMETHYLAMINO)ETHYL)-N-METHYL-, BUTANEDIOATE (1:1)
Systematic Name English
GR-43175C
Code English
SUMATRIPTAN SUCCINATE [MI]
Common Name English
SUMATRIPTAN SUCCINATE COMPONENT OF TREXIMET
Common Name English
GR 43175C
Code English
SUMATRIPTAN (AS SUCCINATE)
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47794
Created by admin on Tue Oct 22 05:11:12 UTC 2019 , Edited by admin on Tue Oct 22 05:11:12 UTC 2019
EMA ASSESSMENT REPORTS SUMATRIPTAN GALPHARM (REFUSED: MIGRAINE DISORDERS)
Created by admin on Tue Oct 22 05:11:12 UTC 2019 , Edited by admin on Tue Oct 22 05:11:12 UTC 2019
Code System Code Type Description
RXCUI
67158
Created by admin on Tue Oct 22 05:11:12 UTC 2019 , Edited by admin on Tue Oct 22 05:11:12 UTC 2019
PRIMARY RxNorm
PUBCHEM
59772
Created by admin on Tue Oct 22 05:11:12 UTC 2019 , Edited by admin on Tue Oct 22 05:11:12 UTC 2019
PRIMARY
EPA CompTox
103628-48-4
Created by admin on Tue Oct 22 05:11:12 UTC 2019 , Edited by admin on Tue Oct 22 05:11:12 UTC 2019
PRIMARY
EVMPD
SUB15437MIG
Created by admin on Tue Oct 22 05:11:12 UTC 2019 , Edited by admin on Tue Oct 22 05:11:12 UTC 2019
PRIMARY
NCI_THESAURUS
C29470
Created by admin on Tue Oct 22 05:11:12 UTC 2019 , Edited by admin on Tue Oct 22 05:11:12 UTC 2019
PRIMARY
CAS
103628-48-4
Created by admin on Tue Oct 22 05:11:12 UTC 2019 , Edited by admin on Tue Oct 22 05:11:12 UTC 2019
PRIMARY
MERCK INDEX
M10396
Created by admin on Tue Oct 22 05:11:12 UTC 2019 , Edited by admin on Tue Oct 22 05:11:12 UTC 2019
PRIMARY Merck Index
ChEMBL
CHEMBL128
Created by admin on Tue Oct 22 05:11:12 UTC 2019 , Edited by admin on Tue Oct 22 05:11:12 UTC 2019
PRIMARY
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