SUMATRIPTAN

Details

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

SHOW SMILES / InChI

Structure Search

SMILES

CNS(=O)(=O)CC1=CC2=C(NC=C2CCN(C)C)C=C1

InChI

InChIKey=KQKPFRSPSRPDEB-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020080s049lbl.pdf

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

Targets

Primary Target	Pharmacology	Potency
Serotonin 1a (5-HT1a) receptor 177 Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8568822	Agonist 2752	330.0 nM [IC50]
Serotonin 1b (5-HT1b) receptor 45 Target ID: CHEMBL1898 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9871581	Agonist 2752	38.3 nM [EC50]
Serotonin 1f (5-HT1f) receptor 15 Target ID: CHEMBL1805 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11708905	Agonist 2752	35.0 nM [EC50]
Serotonin 1d (5-HT1d) receptor 53 Target ID: CHEMBL1983 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14643336	Agonist 2752	5.3 nM [EC50]

Conditions

Condition	Modality	Highest Phase	Product
Migraine with aura 11 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020080s049lbl.pdf	Primary	Approved 8583	IMITREX Approved Use Sumatriptan Injection, USP is indicated in adults for (1) the acute treatment of migraine, with or without aura, and (2) the acute treatment of cluster headache. Limitations of Use: Use only if a clear diagnosis of migraine or cluster headache has been established. If a patient has no response to the first migraine or cluster headache attack treated with Sumatriptan Injection, USP, reconsider the diagnosis before Sumatriptan Injection, USP is administered to treat any subsequent attacks. Sumatriptan Injection, USP is not indicated for the prevention of migraine or cluster headache attacks. Sumatriptan Injection, USP is a serotonin (5-HT1B/1D) receptor agonist (triptan) indicated for: Acute treatment of migraine with or without aura in adults (1) Acute treatment of cluster headache in adults (1) Limitations of Use: Use only if a clear diagnosis of migraine or cluster headache has been established (1) Not indicated for the prophylactic therapy of migraine or cluster headache attacks (1) Launch Date 1997
Migraine without aura 7 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020080s049lbl.pdf	Primary	Approved 8583	IMITREX Approved Use Sumatriptan Injection, USP is indicated in adults for (1) the acute treatment of migraine, with or without aura, and (2) the acute treatment of cluster headache. Limitations of Use: Use only if a clear diagnosis of migraine or cluster headache has been established. If a patient has no response to the first migraine or cluster headache attack treated with Sumatriptan Injection, USP, reconsider the diagnosis before Sumatriptan Injection, USP is administered to treat any subsequent attacks. Sumatriptan Injection, USP is not indicated for the prevention of migraine or cluster headache attacks. Sumatriptan Injection, USP is a serotonin (5-HT1B/1D) receptor agonist (triptan) indicated for: Acute treatment of migraine with or without aura in adults (1) Acute treatment of cluster headache in adults (1) Limitations of Use: Use only if a clear diagnosis of migraine or cluster headache has been established (1) Not indicated for the prophylactic therapy of migraine or cluster headache attacks (1) Launch Date 1997
Cluster headache 10 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020080s049lbl.pdf	Primary	Approved 8583	IMITREX Approved Use Sumatriptan Injection, USP is indicated in adults for (1) the acute treatment of migraine, with or without aura, and (2) the acute treatment of cluster headache. Limitations of Use: Use only if a clear diagnosis of migraine or cluster headache has been established. If a patient has no response to the first migraine or cluster headache attack treated with Sumatriptan Injection, USP, reconsider the diagnosis before Sumatriptan Injection, USP is administered to treat any subsequent attacks. Sumatriptan Injection, USP is not indicated for the prevention of migraine or cluster headache attacks. Sumatriptan Injection, USP is a serotonin (5-HT1B/1D) receptor agonist (triptan) indicated for: Acute treatment of migraine with or without aura in adults (1) Acute treatment of cluster headache in adults (1) Limitations of Use: Use only if a clear diagnosis of migraine or cluster headache has been established (1) Not indicated for the prophylactic therapy of migraine or cluster headache attacks (1) Launch Date 1997

C_max

Value	Dose	Analyte	Population
77 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	3 mg single, intravenous dose: 3 mg route of administration: Intravenous experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
42 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	3 mg single, subcutaneous dose: 3 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
12 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	1 mg single, subcutaneous dose: 1 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
80 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	8 mg single, subcutaneous dose: 8 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
194 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	16 mg single, subcutaneous dose: 16 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
18 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
29 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
49 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
90 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
112 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
144 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
43 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	3 mg single, intravenous dose: 3 mg route of administration: Intravenous experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
41 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	3 mg single, subcutaneous dose: 3 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
14 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	1 mg single, subcutaneous dose: 1 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
105 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	8 mg single, subcutaneous dose: 8 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
239 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	16 mg single, subcutaneous dose: 16 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
44 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
83 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
158 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
380 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
476 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
590 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
1.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	3 mg single, intravenous dose: 3 mg route of administration: Intravenous experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	3 mg single, subcutaneous dose: 3 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	1 mg single, subcutaneous dose: 1 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	8 mg single, subcutaneous dose: 8 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	16 mg single, subcutaneous dose: 16 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
14.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
83 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7768259/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	SUMATRIPTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
200 mg 1 times / month multiple, oral Dose: 200 mg, 1 times / month Route: oral Route: multiple Dose: 200 mg, 1 times / month Sources: https://pubmed.ncbi.nlm.nih.gov/1313746/	unhealthy, 18 - 65 years Health Status: unhealthy Age Group: 18 - 65 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/1313746/	Sources: https://pubmed.ncbi.nlm.nih.gov/1313746/
300 mg single, oral Overdose Dose: 300 mg Route: oral Route: single Dose: 300 mg Sources: https://pubmed.ncbi.nlm.nih.gov/20051552/	unhealthy, 35 years Health Status: unhealthy Age Group: 35 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/20051552/	Disc. AE: Ischemic colitis... AEs leading to discontinuation/dose reduction: Ischemic colitis (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/20051552/
6 mg 2 times / day multiple, subcutaneous Overdose Dose: 6 mg, 2 times / day Route: subcutaneous Route: multiple Dose: 6 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11531904/	unhealthy, 36 years Health Status: unhealthy Age Group: 36 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/11531904/	Sources: https://pubmed.ncbi.nlm.nih.gov/11531904/
100 mg single, oral Highest studied dose Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020132s028,020626s025lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020132s028,020626s025lbl.pdf	Other AEs: Abnormal physical sensation, Abnormal physical sensation... Other AEs: Abnormal physical sensation (6%) Abnormal physical sensation (6%) Abnormal physical sensation (6%) Sensation of pressure (8%) Chest tightness of (2%) Throat tightness (3%) Pain (1%) Pressure (3%) Vertigo (2%) Malaise and fatigue (3%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020132s028,020626s025lbl.pdf

AEs

AE	Significance	Dose	Population
Ischemic colitis	1 patient Disc. AE	300 mg single, oral Overdose Dose: 300 mg Route: oral Route: single Dose: 300 mg Sources: https://pubmed.ncbi.nlm.nih.gov/20051552/	unhealthy, 35 years Health Status: unhealthy Age Group: 35 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/20051552/
Pain	1%	100 mg single, oral Highest studied dose Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020132s028,020626s025lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020132s028,020626s025lbl.pdf
Chest tightness of	2%	100 mg single, oral Highest studied dose Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020132s028,020626s025lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020132s028,020626s025lbl.pdf
Vertigo	2%	100 mg single, oral Highest studied dose Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020132s028,020626s025lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020132s028,020626s025lbl.pdf
Malaise and fatigue	3%	100 mg single, oral Highest studied dose Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020132s028,020626s025lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020132s028,020626s025lbl.pdf
Pressure	3%	100 mg single, oral Highest studied dose Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020132s028,020626s025lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020132s028,020626s025lbl.pdf
Throat tightness	3%	100 mg single, oral Highest studied dose Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020132s028,020626s025lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020132s028,020626s025lbl.pdf
Abnormal physical sensation	6%	100 mg single, oral Highest studied dose Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020132s028,020626s025lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020132s028,020626s025lbl.pdf
Abnormal physical sensation	6%	100 mg single, oral Highest studied dose Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020132s028,020626s025lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020132s028,020626s025lbl.pdf
Abnormal physical sensation	6%	100 mg single, oral Highest studied dose Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020132s028,020626s025lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020132s028,020626s025lbl.pdf
Sensation of pressure	8%	100 mg single, oral Highest studied dose Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020132s028,020626s025lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020132s028,020626s025lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MATE1 415 P-gp 1741	OCT1 393 P-gp 2052

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/28283434/	weak
MATE1 416	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23241029/	yes [IC50 6.7 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12438524/	no
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12017403/	no	weak (co-administration study) Comment: coadministered with clarithromycin: mean sumatriptan AUC(infinity) and Cmax values after administration of combination treatment were 9% and 14% higher, respectively Sources: https://pubmed.ncbi.nlm.nih.gov/12017403/
OCT1 393	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/26659468/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:10650	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:10650
ChemicalBook	CB4135041	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4135041
eMolecules	902519	https://www.emolecules.com/cgi-bin/more?vid=902519
ZINC	ZINC000000014360	http://zinc15.docking.org/substances/ZINC000000014360

PubMed

Title	Date	PubMed
Oral rizatriptan versus oral sumatriptan: a direct comparative study in the acute treatment of migraine. Rizatriptan 030 Study Group.	1998 Nov-Dec	11284463
Fatal cardiac arrhythmia after oral sumatriptan.	1999 Jul-Aug	11279937
Dramatic headache relief after sumatriptan in a patient with a pituitary macroadenoma.	1999 Jun	11279924
Acute abstinence syndrome following abrupt cessation of long-term use of tramadol (Ultram): a case study.	2000	10985875
Comparison of naratriptan and sumatriptan in recurrence-prone migraine patients. Naratriptan International Recurrence Study Group.	2000 Aug	10972634
Atrial fibrillation associated with sumatriptan.	2000 Jul 29	10915131
Sumatriptan overuse in episodic cluster headache: lack of adverse events, rebound syndromes, drug dependence and tachyphylaxis.	2000 Jul-Sep	11062845
Inverse agonism and constitutive activity as functional correlates of serotonin h5-HT(1B) receptor/G-protein stoichiometry.	2000 Nov	11040052
2000 Wolfe Award. Sumatriptan for the range of headaches in migraine sufferers: results of the Spectrum Study.	2000 Nov-Dec	11135021
Are triptans with enhanced lipophilicity used for the acute treatment of migraine associated with an increased consulting rate for depressive illness?	2000 Oct	11167903
Pharmacokinetics and pharmacodynamics of the triptan antimigraine agents: a comparative review.	2001	11327198
Irritable bowel syndrome: new agents targeting serotonin receptor subtypes.	2001	11293643
New abortive agents for the treatment of migraine.	2001	11147249
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	11135422
Comparative study of a combination of isometheptene mucate, dichloralphenazone with acetaminophen and sumatriptan succinate in the treatment of migraine.	2001 Apr	11318886
Sumatriptan nasal spray and cognitive function during migraine: results of an open-label study.	2001 Apr	11318884
Human 5-HT(5) receptors: the 5-HT(5A) receptor is functional but the 5-HT(5B) receptor was lost during mammalian evolution.	2001 Apr 27	11343685
A comparison of visual analog scale and categorical ratings of headache pain in a randomized controlled clinical trial with migraine patients.	2001 Aug	11427330
Economic implications of early treatment of migraine with sumatriptan tablets.	2001 Feb	11293561
Pathophysiology of primary headaches.	2001 Feb	11252141
[Treatment of cluster headache].	2001 Feb	11234673
The impact of pharmacogenetics for migraine.	2001 Feb 9	11173058
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	11164810
Treatment satisfaction, functional status, and health-related quality of life of migraine patients treated with almotriptan or sumatriptan.	2001 Jan	11219473
Effect of sumatriptan on health care resource use among patients with migraine.	2001 Jan	11214537
pH-mediated field-amplified sample stacking of pharmaceutical cations in high-ionic strength samples.	2001 Jan	11197180
Unravelling the pharmacological profile of the canine external carotid vasodilator '5-HT1-like' receptors: coexistence of sympatho-inhibitory 5-HT1B and postjunctional 5-HT7 receptors.	2001 Jan	11191839
Successful use of propranolol in migraine associated with electroconvulsive therapy.	2001 Jan	11168610
Interictal and postictal contingent negative variation in migraine without aura.	2001 Jan	11168606
Long-term efficacy and safety of oral almotriptan: interim analysis of a 1-year open study.	2001 Jan	11168604
Inhibition of inflammation-induced thermal hypersensitivity by sumatriptan through activation of 5-HT(1B/1D) receptors.	2001 Jan	11161594
Sumatriptan elicits both constriction and dilation in human and bovine brain intracortical arterioles.	2001 Jan	11156561
Effect of rizatriptan in the spectrum of headache.	2001 Jun	11437904
Sumatriptan can alleviate headaches due to carotid artery dissection.	2001 Jun	11437896
[Anti-migraine drug sumatriptan succinate, a 5-HT1B/1D-receptor agonist].	2001 Jun	11436516
Oral almotriptan vs. oral sumatriptan in the abortive treatment of migraine: a double-blind, randomized, parallel-group, optimum-dose comparison.	2001 Jun	11405809
Co-localization of 5-HT(1B/1D/1F) receptors and glutamate in trigeminal ganglia in rats.	2001 Jun 13	11409721
Relaxation induced by serotonin and sumatriptan in isolated guinea pig gallbladder strips.	2001 Mar	11426669
Gastric motor effects of triptans: open questions and future perspectives.	2001 Mar	11401410
Complicated migraine and migraine variants.	2001 Mar	11332867
Status migrainosus in children and adolescents.	2001 Mar	11332863
Headaches in children and adolescents: update 2001.	2001 Mar	11332861
Sumatriptin vs dihydroergotamine: patient preference.	2001 Mar	11321860
Multiple 5-HT(1) autoreceptor subtypes govern serotonin release in dorsal and median raphé nuclei.	2001 Mar	11249960
Hemodynamic and electrocardiographic effects of almotriptan in healthy volunteers.	2001 Mar	11243418
Cardiovascular effects of SL65.0472, a 5-HT receptor antagonist.	2001 Mar 2	11239927
Zolmitriptan versus sumatriptan for the acute oral treatment of migraine: a randomized, double-blind, international study.	2001 May	11328332
An in vivo rat model to study calcitonin gene related peptide release following activation of the trigeminal vascular system.	2001 May	11323131
Functional immunohistochemistry of neuropeptides and nitric oxide synthase in the nerve fibers of the supratentorial dura mater in an experimental migraine model.	2001 May 1	11301495
Neurogenic inflammation in the context of migraine.	2001 May 1	11301492

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: Other

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.

Name

Type

Language

SUMATRIPTAN

Official Name

English

IMIGRAN

Preferred Name

English

DFN-11 (SUMATRIPTAN INJECTION)

Common Name

English

DFN-11

Code

English

IMITREX

Brand Name

English

Sumatriptan [WHO-DD]

Common Name

English

TOSYMRA

Brand Name

English

SUMATRIPTAN [USP MONOGRAPH]

Common Name

English

SUMATRIPTAN [MART.]

Common Name

English

SUMATRIPTAN [VANDF]

Common Name

English

N02CC01

Code

English

3-[2-(Dimethylamino)ethyl]-N-methy-1H-indole-5-methanesulfonamide

Common Name

English

SUMATRIPTAN [HSDB]

Common Name

English

SUMATRIPTAN [JAN]

Common Name

English

SUMATRIPTAN [USP-RS]

Common Name

English

SUMATRIPTAN [ORANGE BOOK]

Common Name

English

SUMATRIPTAN [MI]

Common Name

English

1H-INDOLE-5-METHANESULFONAMIDE, 3-(2-(DIMETHYLAMINO)ETHYL)-N-METHYL-

Systematic Name

English

sumatriptan [INN]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QN02CC01