U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C17H25N3O2S
Molecular Weight 335.464
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NARATRIPTAN

SMILES

CNS(=O)(=O)CCC1=CC2=C(NC=C2C3CCN(C)CC3)C=C1

InChI

InChIKey=AMKVXSZCKVJAGH-UHFFFAOYSA-N
InChI=1S/C17H25N3O2S/c1-18-23(21,22)10-7-13-3-4-17-15(11-13)16(12-19-17)14-5-8-20(2)9-6-14/h3-4,11-12,14,18-19H,5-10H2,1-2H3

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/1998/20763lbl.pdf

Naratriptan (trade names include Amerge and Naramig) is a triptan drug marketed by GlaxoSmithKline and is used for the treatment of migraine headaches.Naratriptan is a selective agonist of serotonin (5-hydroxytryptamine; 5-HT) type 1B and 1D receptors. It is structurally and pharmacologically related to other selective 5-HT1B/1D receptor agonist. Naratriptan has only a weak affinity for 5-HT1A, 5-HT5A, and 5-HT7 receptors and no significant affinity or pharmacological activity at 5-HT2, 5-HT3 or 5-HT4 receptor subtypes or at alpha1-, alpha2-, or beta-adrenergic, dopamine1,; dopamine2; muscarinic, or benzodiazepine receptors. This action in humans correlates with the relief of migraine headache. In addition to causing vasoconstriction, experimental data from animal studies show that Naratriptan also activates 5-HT1 receptors on peripheral terminals of the trigeminal nerve innervating cranial blood vessels, which may also contribute to the antimigrainous effect of Naratriptan in humans.Three distinct pharmacological actions have been implicated in the antimigraine effect of the triptans: (1) stimulation of presynaptic 5-HT1D receptors, which serves to inhibit both dural vasodilation and inflammation; (2) direct inhibition of trigeminal nuclei cell excitability via 5-HT1B/1D receptor agonism in the brainstem and (3) vasoconstriction of meningeal, dural, cerebral or pial vessels as a result of vascular 5-HT1B receptor agonism.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
AMERGE

Approved Use

Naratriptan is indicated for the acute treatment of migraine attacks with or without aura in adults.

Launch Date

1998
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
7.97 ng/mL
2.5 mg single, oral
dose: 2.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NARATRIPTAN serum
Homo sapiens
population: UNHEALTHY
age: ADOLESCENT
sex: FEMALE / MALE
food status: FASTED
92 ng/mL
2.5 mg single, oral
dose: 2.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NARATRIPTAN plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
74.6 ng × h/mL
2.5 mg single, oral
dose: 2.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NARATRIPTAN serum
Homo sapiens
population: UNHEALTHY
age: ADOLESCENT
sex: FEMALE / MALE
food status: FASTED
107.97 ng × h/mL
2.5 mg single, oral
dose: 2.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NARATRIPTAN plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.9 h
2.5 mg single, oral
dose: 2.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NARATRIPTAN serum
Homo sapiens
population: UNHEALTHY
age: ADOLESCENT
sex: FEMALE / MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
10 mg 1 times / day single, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: single
Dose: 10 mg, 1 times / day
Sources: Page: Study 2004
unhealthy, 39
n = 96
Health Status: unhealthy
Condition: migraine
Age Group: 39
Sex: M+F
Population Size: 96
Sources: Page: Study 2004
2.5 mg 3 times / day multiple, oral
Recommended
Dose: 2.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 2.5 mg, 3 times / day
Sources: Page: Study 3002
unhealthy, 40.4
n = 127
Health Status: unhealthy
Condition: migraine
Age Group: 40.4
Sex: M+F
Population Size: 127
Sources: Page: Study 3002
Disc. AE: Abdominal pain...
AEs leading to
discontinuation/dose reduction:
Abdominal pain
Sources: Page: Study 3002
AEs

AEs

AESignificanceDosePopulation
Abdominal pain Disc. AE
2.5 mg 3 times / day multiple, oral
Recommended
Dose: 2.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 2.5 mg, 3 times / day
Sources: Page: Study 3002
unhealthy, 40.4
n = 127
Health Status: unhealthy
Condition: migraine
Age Group: 40.4
Sex: M+F
Population Size: 127
Sources: Page: Study 3002
OverviewDrug as perpetrator​Drug as victim
PubMed

PubMed

TitleDatePubMed
Comparison of naratriptan and sumatriptan in recurrence-prone migraine patients. Naratriptan International Recurrence Study Group.
2000 Aug
[Quality of life of migraine patients after treatment with 2.5 mg oral naratriptan].
2000 Dec 9
Are triptans with enhanced lipophilicity used for the acute treatment of migraine associated with an increased consulting rate for depressive illness?
2000 Oct
Naratriptan.
2001
Pharmacokinetics and pharmacodynamics of the triptan antimigraine agents: a comparative review.
2001
[Current topics: expectation for new triptans].
2001 Apr 10
Naratriptan prophylactic treatment in cluster headache.
2001 Feb
A systematic review of the use of triptans in acute migraine.
2001 Feb
Pharmacokinetics of naratriptan in adolescent subjects with a history of migraine.
2001 Feb
Modulation of neuronal activity in the nucleus raphé magnus by the 5-HT(1)-receptor agonist naratriptan in rat.
2001 Feb 15
Headache and female hormones: what you need to know.
2001 Jun
Donitriptan (Pierre Fabre).
2001 Mar
Gastric motor effects of triptans: open questions and future perspectives.
2001 Mar
Naratriptan as short-term prophylaxis of menstrually associated migraine: a randomized, double-blind, placebo-controlled study.
2001 Mar
Patient satisfaction with rizatriptan versus other triptans: direct head-to-head comparisons.
2001 Oct
Effect of rizatriptan and other triptans on the nausea symptom of migraine: a post hoc analysis.
2001 Sep
Have the triptans fulfilled their promise?
2001 Sep
Spotlight on rizatriptan in migraine.
2002
Gateways to Clinical Trials.
2002 Apr
Health needs, drug registration and control in less developed countries--the Peruvian case.
2002 Jan-Feb
Validation of the Patient Perception of Migraine Questionnaire.
2002 Sep-Oct
[Highly selective beginning. Associated symptoms and side effects in retrospect].
2003 May 26
Managing intractable migraine with naratriptan.
2003 Oct
Investigation of the effects of naratriptan, rizatriptan, and sumatriptan on jugular venous oxygen saturation in anesthetized pigs: implications for their mechanism of acute antimigraine action.
2003 Oct
Naratriptan has a selective inhibitory effect on trigeminovascular neurones at central 5-HT1A and 5-HT(1B/1D) receptors in the cat: implications for migraine therapy.
2004 Feb
Involvement of 5-HT1B receptors in triptan-induced contractile responses in guinea-pig isolated iliac artery.
2004 Jul
Patterns of use of triptans and reasons for switching them in a tertiary care migraine population.
2004 Jul-Aug
Triptans and CNS side-effects: pharmacokinetic and metabolic mechanisms.
2004 Jun
Colonic ischemia associated with naratriptan use.
2004 Oct
The use of multiattribute decision models in evaluating triptan treatment options in migraine.
2005 Sep
Patents

Sample Use Guides

Initial dose: 1 mg or 2.5 mg orally, once -Provided there has been some response to first dose, a second dose may be administered at least 4 hours later if migraine returns or symptoms recur. Maximum dose: 5 mg in a 24-hour period
Route of Administration: Oral
Naratriptan (10, 100 uM) inhibited vasocontractile responses in rabbit common carotid artery to sumatriptan with a pKb value of 5.9+0.2 or eletriptan with a pKb value of 5.7+0.7 in CCA
Name Type Language
NARATRIPTAN
INN   MI   ORANGE BOOK   VANDF   WHO-DD  
INN  
Official Name English
1H-INDOLE-5-ETHANESULFONAMIDE, N-METHYL-3-(1-METHYL-4-PIPERIDINYL)-
Systematic Name English
NARATRIPTAN [VANDF]
Common Name English
Naratriptan [WHO-DD]
Common Name English
NARATRIPTAN [MI]
Common Name English
naratriptan [INN]
Common Name English
NARATRIPTAN [ORANGE BOOK]
Common Name English
NARAMIG
Brand Name English
N-METHYL-2-(3-(1-METHYLPIPERIDEN-4-YL)INDOLE-5-YL)ETHANESULFONAMIDE
Common Name English
Classification Tree Code System Code
NDF-RT N0000175763
Created by admin on Sat Dec 16 17:51:59 GMT 2023 , Edited by admin on Sat Dec 16 17:51:59 GMT 2023
NCI_THESAURUS C47794
Created by admin on Sat Dec 16 17:51:59 GMT 2023 , Edited by admin on Sat Dec 16 17:51:59 GMT 2023
WHO-VATC QN02CC02
Created by admin on Sat Dec 16 17:51:59 GMT 2023 , Edited by admin on Sat Dec 16 17:51:59 GMT 2023
WHO-ATC N02CC02
Created by admin on Sat Dec 16 17:51:59 GMT 2023 , Edited by admin on Sat Dec 16 17:51:59 GMT 2023
NDF-RT N0000175765
Created by admin on Sat Dec 16 17:51:59 GMT 2023 , Edited by admin on Sat Dec 16 17:51:59 GMT 2023
LIVERTOX 669
Created by admin on Sat Dec 16 17:51:59 GMT 2023 , Edited by admin on Sat Dec 16 17:51:59 GMT 2023
NDF-RT N0000175764
Created by admin on Sat Dec 16 17:51:59 GMT 2023 , Edited by admin on Sat Dec 16 17:51:59 GMT 2023
Code System Code Type Description
LACTMED
Naratriptan
Created by admin on Sat Dec 16 17:51:59 GMT 2023 , Edited by admin on Sat Dec 16 17:51:59 GMT 2023
PRIMARY
WIKIPEDIA
NARATRIPTAN
Created by admin on Sat Dec 16 17:51:59 GMT 2023 , Edited by admin on Sat Dec 16 17:51:59 GMT 2023
PRIMARY
EVMPD
SUB09164MIG
Created by admin on Sat Dec 16 17:51:59 GMT 2023 , Edited by admin on Sat Dec 16 17:51:59 GMT 2023
PRIMARY
DRUG CENTRAL
1884
Created by admin on Sat Dec 16 17:51:59 GMT 2023 , Edited by admin on Sat Dec 16 17:51:59 GMT 2023
PRIMARY
ChEMBL
CHEMBL1278
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PRIMARY
CAS
121679-13-8
Created by admin on Sat Dec 16 17:51:59 GMT 2023 , Edited by admin on Sat Dec 16 17:51:59 GMT 2023
PRIMARY
CHEBI
7478
Created by admin on Sat Dec 16 17:51:59 GMT 2023 , Edited by admin on Sat Dec 16 17:51:59 GMT 2023
PRIMARY
IUPHAR
45
Created by admin on Sat Dec 16 17:51:59 GMT 2023 , Edited by admin on Sat Dec 16 17:51:59 GMT 2023
PRIMARY
MESH
C106783
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PRIMARY
NCI_THESAURUS
C61857
Created by admin on Sat Dec 16 17:51:59 GMT 2023 , Edited by admin on Sat Dec 16 17:51:59 GMT 2023
PRIMARY
EPA CompTox
DTXSID7023354
Created by admin on Sat Dec 16 17:51:59 GMT 2023 , Edited by admin on Sat Dec 16 17:51:59 GMT 2023
PRIMARY
SMS_ID
100000080321
Created by admin on Sat Dec 16 17:51:59 GMT 2023 , Edited by admin on Sat Dec 16 17:51:59 GMT 2023
PRIMARY
DAILYMED
QX3KXL1ZA2
Created by admin on Sat Dec 16 17:51:59 GMT 2023 , Edited by admin on Sat Dec 16 17:51:59 GMT 2023
PRIMARY
DRUG BANK
DB00952
Created by admin on Sat Dec 16 17:51:59 GMT 2023 , Edited by admin on Sat Dec 16 17:51:59 GMT 2023
PRIMARY
INN
7097
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PRIMARY
PUBCHEM
4440
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PRIMARY
RXCUI
141366
Created by admin on Sat Dec 16 17:51:59 GMT 2023 , Edited by admin on Sat Dec 16 17:51:59 GMT 2023
PRIMARY RxNorm
FDA UNII
QX3KXL1ZA2
Created by admin on Sat Dec 16 17:51:59 GMT 2023 , Edited by admin on Sat Dec 16 17:51:59 GMT 2023
PRIMARY
MERCK INDEX
m7772
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PRIMARY Merck Index