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
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
DescriptionCurator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/1998/20763lbl.pdf
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.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1983 |
1.6 nM [EC50] | ||
Target ID: CHEMBL1898 |
23.0 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | AMERGE Approved UseNaratriptan is indicated for the acute treatment of migraine attacks with or without aura in adults. Launch Date1998 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7.97 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11210397/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
74.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11210397/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11210397/ |
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
Dose | Population | Adverse 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 |
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
AE | Significance | Dose | Population |
---|---|---|---|
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 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/12814962/ Page: - |
no [IC50 >100 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12814962/ Page: - |
no [IC50 >100 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12814962/ Page: - |
no [IC50 >100 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12814962/ Page: - |
no [IC50 >100 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12814962/ Page: - |
no [IC50 >100 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12814962/ Page: - |
weak [IC50 40 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12814962/ Page: - |
weak [IC50 84 uM] | |||
yes [IC50 5.5 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/12814962/ Page: - |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12814962/ Page: - |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12814962/ Page: - |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12814962/ Page: - |
poor | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12814962/ Page: - |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12814962/ Page: - |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12814962/ Page: - |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12814962/ Page: - |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12814962/ Page: - |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/26659468/ Page: - |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12814962/ Page: - |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
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
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/naratriptan.html
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12010764
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
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175763
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NCI_THESAURUS |
C47794
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WHO-VATC |
QN02CC02
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WHO-ATC |
N02CC02
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NDF-RT |
N0000175765
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LIVERTOX |
669
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NDF-RT |
N0000175764
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Naratriptan
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NARATRIPTAN
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SUB09164MIG
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CHEMBL1278
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C61857
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m7772
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PRIMARY | Merck Index |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)