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=CC=C2NC=C(CCN(C)C)C2=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 172 Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8568822	Agonist 2678	330.0 nM [IC50]
Serotonin 1b (5-HT1b) receptor 46 Target ID: CHEMBL1898 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9871581	Agonist 2678	38.3 nM [EC50]
Serotonin 1f (5-HT1f) receptor 15 Target ID: CHEMBL1805 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11708905	Agonist 2678	35.0 nM [EC50]
Serotonin 1d (5-HT1d) receptor 52 Target ID: CHEMBL1983 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14643336	Agonist 2678	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 8429	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 8429	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 8429	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
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
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
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
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
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
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
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
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
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

AUC

Value	Dose	Analyte	Population
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
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
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
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
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
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
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
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
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

T_1/2

Value	Dose	Analyte	Population
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
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
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
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
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
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/	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 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
2.1 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

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 n = 94 Health Status: unhealthy Condition: acute migraine with aura Age Group: 18 - 65 years Sex: M+F Population Size: 94 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 Co-administed with:: (SUMATRIPTAN) 12 mg subcutaneous injections Sources: https://pubmed.ncbi.nlm.nih.gov/20051552/	unhealthy, 35 years n = 1 Health Status: unhealthy Condition: migraine Age Group: 35 years Sex: F Population Size: 1 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 n = 1 Health Status: unhealthy Condition: episodic cluster headache Age Group: 36 years Sex: M Population Size: 1 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 n = 437 Health Status: unhealthy Condition: migraine with or without aura Age Group: adult Sex: unknown Population Size: 437 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 Co-administed with:: (SUMATRIPTAN) 12 mg subcutaneous injections Sources: https://pubmed.ncbi.nlm.nih.gov/20051552/	unhealthy, 35 years n = 1 Health Status: unhealthy Condition: migraine Age Group: 35 years Sex: F Population Size: 1 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 n = 437 Health Status: unhealthy Condition: migraine with or without aura Age Group: adult Sex: unknown Population Size: 437 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 n = 437 Health Status: unhealthy Condition: migraine with or without aura Age Group: adult Sex: unknown Population Size: 437 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 n = 437 Health Status: unhealthy Condition: migraine with or without aura Age Group: adult Sex: unknown Population Size: 437 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 n = 437 Health Status: unhealthy Condition: migraine with or without aura Age Group: adult Sex: unknown Population Size: 437 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 n = 437 Health Status: unhealthy Condition: migraine with or without aura Age Group: adult Sex: unknown Population Size: 437 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 n = 437 Health Status: unhealthy Condition: migraine with or without aura Age Group: adult Sex: unknown Population Size: 437 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 n = 437 Health Status: unhealthy Condition: migraine with or without aura Age Group: adult Sex: unknown Population Size: 437 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 n = 437 Health Status: unhealthy Condition: migraine with or without aura Age Group: adult Sex: unknown Population Size: 437 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 n = 437 Health Status: unhealthy Condition: migraine with or without aura Age Group: adult Sex: unknown Population Size: 437 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 n = 437 Health Status: unhealthy Condition: migraine with or without aura Age Group: adult Sex: unknown Population Size: 437 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020132s028,020626s025lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MATE1 306 P-gp 1461	OCT1 327 P-gp 1537

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1650	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/28283434/	weak
MATE1 308	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23241029/	yes [IC50 6.7 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
P-gp 1537	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12438524/	no
CYP3A4 1737	substrate 3367 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 327	substrate 3367 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
ZINC	ZINC000000014360	http://zinc15.docking.org/substances/ZINC000000014360
eMolecules	902519	https://www.emolecules.com/cgi-bin/more?vid=902519

PubMed

Title	Date	PubMed
Sumatriptan and ergotamine overuse and drug-induced headache: a clinicoepidemiologic study.	1999 Jul-Aug	10442248
Postpartum cerebral angiopathy associated with the administration of sumatriptan and dihydroergotamine--a case report.	1999 May	10401952
Open-labeled long-term study of the efficacy, safety, and tolerability of subcutaneous sumatriptan in acute migraine treatment.	1999 Sep	10524662
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	10611634
Comparison of preference for rizatriptan 10-mg wafer versus sumatriptan 50-mg tablet in migraine.	2001	11385269
Irritable bowel syndrome: new agents targeting serotonin receptor subtypes.	2001	11293643
Comparative study of a combination of isometheptene mucate, dichloralphenazone with acetaminophen and sumatriptan succinate in the treatment of migraine.	2001 Apr	11318886
Delivery outcome in women who used drugs for migraine during pregnancy with special reference to sumatriptan.	2001 Apr	11318881
Characterization of 5-HT receptors in the parasitic nematode, Ascaris suum.	2001 Feb	11272652
The impact of pharmacogenetics for migraine.	2001 Feb 9	11173058
Oral almotriptan vs. oral sumatriptan in the abortive treatment of migraine: a double-blind, randomized, parallel-group, optimum-dose comparison.	2001 Jun	11405809
Sumatriptin vs dihydroergotamine: patient preference.	2001 Mar	11321860
Hemodynamic and electrocardiographic effects of almotriptan in healthy volunteers.	2001 Mar	11243418
Characterisation of the effects of a non-peptide CGRP receptor antagonist in SK-N-MC cells and isolated human cerebral arteries.	2001 Mar 9	11245850
Neuroendocrine effects of subcutaneous sumatriptan in patients with migraine.	2001 May	11407649
Treatment of migraine in Canada with naratriptan: a cost-effectiveness analysis.	2001 May	11380643
An in vivo rat model to study calcitonin gene related peptide release following activation of the trigeminal vascular system.	2001 May	11323131

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

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

IMIGRAN

Brand 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