SUMATRIPTAN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H21N3O2S
Molecular Weight	295.4021
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CNS(=O)(=O)Cc1ccc2c(c1)c(CCN(C)C)c[nH]2

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

Molecular Formula	C14H21N3O2S
Molecular Weight	295.4021
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 162 Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8568822	Agonist 2470	330.0 nM [IC50]
Serotonin 1b (5-HT1b) receptor 37 Target ID: CHEMBL1898 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9871581	Agonist 2470	38.3 nM [EC50]
Serotonin 1f (5-HT1f) receptor 11 Target ID: CHEMBL1805 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11708905	Agonist 2470	35.0 nM [EC50]
Serotonin 1d (5-HT1d) receptor 46 Target ID: CHEMBL1983 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14643336	Agonist 2470	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 8043	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 8.7255358E11
Migraine without aura 7 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020080s049lbl.pdf	Primary	Approved 8043	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 8.7255358E11
Cluster headache 10 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020080s049lbl.pdf	Primary	Approved 8043	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 8.7255358E11

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 1601

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MATE1 290 P-gp 1330	OCT1 302 P-gp 1400

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1514	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/28283434/	weak
MATE1 292	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/23241029/	yes [IC50 6.7 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
P-gp 1400	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/12438524/	no
CYP3A4 1601	substrate 3113 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 302	substrate 3113 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 treatment for migraine in a health maintenance organization: economic, humanistic, and clinical outcomes.	1999 Jan	10090435
Fatal cardiac arrhythmia after oral sumatriptan.	1999 Jul-Aug	11279937
Sumatriptan and ergotamine overuse and drug-induced headache: a clinicoepidemiologic study.	1999 Jul-Aug	10442248
An unusual case of renal vein thrombosis in a man taking sumatriptan.	1999 Jun	10368263
Postpartum cerebral angiopathy associated with the administration of sumatriptan and dihydroergotamine--a case report.	1999 May	10401952
Prospective large-scale study of the tolerability of subcutaneous sumatriptan injection for acute treatment of migraine.	1999 May	10376167
Open-labeled long-term study of the efficacy, safety, and tolerability of subcutaneous sumatriptan in acute migraine treatment.	1999 Sep	10524662
Identification of an amino acid residue important for binding of methiothepin and sumatriptan to the human 5-HT(1B) receptor.	1999 Sep 10	10513577
2000 Wolfe Award. Sumatriptan for the range of headaches in migraine sufferers: results of the Spectrum Study.	2000 Nov-Dec	11135021
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
Cluster headache: review of the literature.	2001 Apr	11286443
[Migraine: selection of therapeutic agents to be applied during its attack].	2001 Apr 10	11391906
A comparison of visual analog scale and categorical ratings of headache pain in a randomized controlled clinical trial with migraine patients.	2001 Aug	11427330
A systematic review of the use of triptans in acute migraine.	2001 Feb	11252291
Treatment and management of cluster headache.	2001 Feb	11252143
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
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
Colocalization of CGRP with 5-HT1B/1D receptors and substance P in trigeminal ganglion neurons in rats.	2001 Jun	11422450
Recent development in paediatric headache.	2001 Jun	11371756
Headache and female hormones: what you need to know.	2001 Jun	11371755
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
Sumatriptin vs dihydroergotamine: patient preference.	2001 Mar	11321860
Zolmitriptan versus sumatriptan comparison trial.	2001 Mar	11264695
Naratriptan as short-term prophylaxis of menstrually associated migraine: a randomized, double-blind, placebo-controlled study.	2001 Mar	11264684
4991W93 inhibits release of calcitonin gene-related peptide in the cat but only at doses with 5HT(1B/1D) receptor agonist activity?	2001 Mar	11249961
Cardiovascular effects of SL65.0472, a 5-HT receptor antagonist.	2001 Mar 2	11239927
Serotonin-induced hypercontraction through 5-hydroxytryptamine 1B receptors in atherosclerotic rabbit coronary arteries.	2001 Mar 6	11238275
Effect of MAO-A inhibition on the pharmacokinetics of almotriptan, an antimigraine agent in humans.	2001 May	11422001
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.

Substance Class	Chemical Created by `admin` on `Fri Jun 25 20:55:15 UTC 2021` Edited by `admin` on `Fri Jun 25 20:55:15 UTC 2021`
Record UNII	8R78F6L9VO
Record Status	`Validated (UNII)`
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Name

Type

Language

SUMATRIPTAN

Official Name

English

IMITREX

Brand 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 [WHO-DD]

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