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Identification
NameNaratriptan
Accession NumberDB00952  (APRD00220)
TypeSmall Molecule
GroupsApproved, Investigational
DescriptionNaratriptan is a triptan drug used for the treatment of migraine headaches. It is a selective 5-hydroxytryptamine1 receptor subtype agonist.
Structure
Thumb
Synonyms
N-Methyl-2-(3-(1-methylpiperiden-4-yl)indole-5-yl)ethanesulfonamide
N-Methyl-2-[3-(1-methyl-4-piperidyl)-1H-indol-5-yl]-ethanesulfonamide
Naratriptanum
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AmergeTablet1 mgOralGlaxosmithkline Inc1998-05-05Not applicableCanada
AmergeTablet2.5 mgOralGlaxosmithkline Inc1998-05-05Not applicableCanada
AmergeTablet, film coated1 mg/1OralGlaxo Smith Kline Llc1998-02-26Not applicableUs
AmergeTablet, film coated2.5 mg/1OralGlaxo Smith Kline Llc1998-02-26Not applicableUs
Sandoz NaratriptanTablet2.5 mgOralSandoz Canada Incorporated2010-04-08Not applicableCanada
Teva-naratriptanTablet1 mgOralTeva Canada Limited2009-12-02Not applicableCanada
Teva-naratriptanTablet2.5 mgOralTeva Canada Limited2009-12-01Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-naratriptanTablet1 mgOralApotex IncNot applicableNot applicableCanada
Apo-naratriptanTablet2.5 mgOralApotex IncNot applicableNot applicableCanada
NaratriptanTablet, film coated2.5 mg/1OralOrchid Pharma Inc2012-12-12Not applicableUs
NaratriptanTablet, film coated1 mg/1OralMylan Pharmaceuticals Inc.2012-06-13Not applicableUs
NaratriptanTablet1 mg/1OralHeritage Pharmaceuticals Inc.2011-03-15Not applicableUs
NaratriptanTablet, film coated2.5 mg/1OralSun Pharmaceutical Industries Limited2011-02-22Not applicableUs
NaratriptanTablet, film coated2.5 mg/1OralMylan Pharmaceuticals Inc.2012-06-13Not applicableUs
NaratriptanTablet2.5 mg/1OralHeritage Pharmaceuticals Inc.2011-03-15Not applicableUs
NaratriptanTablet, film coated1 mg/1OralTeva Pharmaceuticals USA Inc2013-08-122015-11-30Us
NaratriptanTablet, coated1 mg/1OralSandoz Inc2010-07-07Not applicableUs
NaratriptanTablet1 mg/1OralWest Ward Pharmaceuticals Corp.2010-07-07Not applicableUs
NaratriptanTablet, film coated1 mg/1OralOrchid Pharma Inc2012-12-12Not applicableUs
NaratriptanTablet, film coated2.5 mg/1OralTeva Pharmaceuticals USA Inc2013-08-092015-10-31Us
NaratriptanTablet, coated2.5 mg/1OralSandoz Inc2010-07-07Not applicableUs
NaratriptanTablet2.5 mg/1OralWest Ward Pharmaceuticals Corp.2010-07-07Not applicableUs
Naratriptan HydrochlorideTablet, film coated1 mg/1OralPaddock Laboratories, LLC2010-07-08Not applicableUs
Naratriptan HydrochlorideTablet, film coated2.5 mg/1OralPaddock Laboratories, LLC2010-07-08Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
NaramigNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Naratriptan hydrochloride
143388-64-1
Thumb
  • InChI Key: AWEZYKMQFAUBTD-UHFFFAOYSA-N
  • Monoisotopic Mass: 371.143426
  • Average Mass: 371.92
DBSALT001246
Categories
UNIIQX3KXL1ZA2
CAS number121679-13-8
WeightAverage: 335.464
Monoisotopic: 335.166747749
Chemical FormulaC17H25N3O2S
InChI KeyAMKVXSZCKVJAGH-UHFFFAOYSA-N
InChI
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
IUPAC Name
N-methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethane-1-sulfonamide
SMILES
CNS(=O)(=O)CCC1=CC2=C(NC=C2C2CCN(C)CC2)C=C1
Pharmacology
IndicationFor the acute treatment of migraine attacks with or without aura in adults.
Structured Indications
PharmacodynamicsNaratriptan 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.
Mechanism of actionThree 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
5-hydroxytryptamine receptor 1DProteinyes
agonist
HumanP28221 details
5-hydroxytryptamine receptor 1BProteinyes
agonist
HumanP28222 details
5-hydroxytryptamine receptor 1FProteinyes
agonist
HumanP30939 details
5-hydroxytryptamine receptor 1AProteinyes
agonist
HumanP08908 details
Related Articles
AbsorptionWell absorbed (74% oral biovaility), absorption is rapid with peak plasma concentrations after 2-5 hours. The rate of absorption is slower during a migraine attack.
Volume of distribution
  • 170 L
Protein binding28%-31% (over the concentration range of 50 to 1000 ng/mL)
Metabolism

Primarily hepatic. In vitro, naratriptan is metabolized by a wide range of cytochrome P450 isoenzymes into a number of inactive metabolites.

Route of eliminationNot Available
Half life5-8 hours
Clearance
  • 6.6 mL/min/kg
ToxicitySymptoms of overdose include light-headedness, loss of coordination, tension in the neck, and tiredness.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated Effects
Interacting Gene/EnzymeSNP RS IDAllele nameDefining changeEffectReference(s)
Guanine nucleotide-binding protein G(I)/G(S)/G(T) subunit beta-3
Gene symbol: GNB3
UniProt: P16520
rs5443 Not AvailableT AlleleBetter response to drug treatment17361120
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINEThe metabolism of Naratriptan can be decreased when combined with 7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE.Experimental
AcepromazineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Acepromazine.Approved, Vet Approved
AceprometazineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Aceprometazine.Approved
AcetophenazineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Acetophenazine.Approved
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Naratriptan.Approved, Investigational
AmisulprideThe risk or severity of adverse effects can be increased when Naratriptan is combined with Amisulpride.Approved, Investigational
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Naratriptan.Approved
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Naratriptan.Approved
AmperozideThe risk or severity of adverse effects can be increased when Naratriptan is combined with Amperozide.Experimental
AripiprazoleThe risk or severity of adverse effects can be increased when Naratriptan is combined with Aripiprazole.Approved, Investigational
AsenapineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Asenapine.Approved
AzaperoneThe risk or severity of adverse effects can be increased when Naratriptan is combined with Azaperone.Vet Approved
BenmoxinThe metabolism of Naratriptan can be decreased when combined with Benmoxin.Withdrawn
BenperidolThe risk or severity of adverse effects can be increased when Naratriptan is combined with Benperidol.Investigational
BifeprunoxThe risk or severity of adverse effects can be increased when Naratriptan is combined with Bifeprunox.Investigational
BrexpiprazoleThe risk or severity of adverse effects can be increased when Naratriptan is combined with Brexpiprazole.Approved
BromocriptineBromocriptine may increase the vasoconstricting activities of Naratriptan.Approved, Investigational
BromperidolThe risk or severity of adverse effects can be increased when Naratriptan is combined with Bromperidol.Investigational
BuspironeThe risk or severity of adverse effects can be increased when Buspirone is combined with Naratriptan.Approved, Investigational
CabergolineCabergoline may increase the vasoconstricting activities of Naratriptan.Approved
CariprazineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Cariprazine.Approved
CaroxazoneThe metabolism of Naratriptan can be decreased when combined with Caroxazone.Withdrawn
ChlorpromazineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Chlorpromazine.Approved, Vet Approved
ChlorprothixeneThe risk or severity of adverse effects can be increased when Naratriptan is combined with Chlorprothixene.Approved, Withdrawn
CitalopramThe risk or severity of adverse effects can be increased when Citalopram is combined with Naratriptan.Approved
ClomipramineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Clomipramine.Approved, Vet Approved
ClozapineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Clozapine.Approved
CyamemazineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Cyamemazine.Approved
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Naratriptan.Approved
DapiprazoleThe risk or severity of adverse effects can be increased when Naratriptan is combined with Dapiprazole.Approved
DapoxetineThe risk or severity of adverse effects can be increased when Dapoxetine is combined with Naratriptan.Investigational
DesipramineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Desipramine.Approved
DesvenlafaxineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Desvenlafaxine.Approved
DextromethorphanThe risk or severity of adverse effects can be increased when Dextromethorphan is combined with Naratriptan.Approved
DihydroergotamineDihydroergotamine may increase the vasoconstricting activities of Naratriptan.Approved
DolasetronDolasetron may increase the serotonergic activities of Naratriptan.Approved
DoxepinThe risk or severity of adverse effects can be increased when Naratriptan is combined with Doxepin.Approved
DroperidolThe risk or severity of adverse effects can be increased when Naratriptan is combined with Droperidol.Approved, Vet Approved
DroxidopaNaratriptan may increase the hypertensive activities of Droxidopa.Approved, Investigational
DuloxetineThe risk or severity of adverse effects can be increased when Duloxetine is combined with Naratriptan.Approved
EcopipamThe risk or severity of adverse effects can be increased when Naratriptan is combined with Ecopipam.Investigational
EletriptanThe risk or severity of adverse effects can be increased when Eletriptan is combined with Naratriptan.Approved, Investigational
Ergoloid mesylateErgoloid mesylate may increase the vasoconstricting activities of Naratriptan.Approved
ErgonovineErgonovine may increase the vasoconstricting activities of Naratriptan.Approved
ErgotamineErgotamine may increase the vasoconstricting activities of Naratriptan.Approved
EscitalopramThe risk or severity of adverse effects can be increased when Naratriptan is combined with Escitalopram.Approved, Investigational
FencamfamineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Fencamfamine.Approved, Illicit, Withdrawn
FentanylThe risk or severity of adverse effects can be increased when Fentanyl is combined with Naratriptan.Approved, Illicit, Investigational, Vet Approved
FluoxetineThe risk or severity of adverse effects can be increased when Fluoxetine is combined with Naratriptan.Approved, Vet Approved
FlupentixolThe risk or severity of adverse effects can be increased when Naratriptan is combined with Flupentixol.Approved, Withdrawn
FluphenazineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Fluphenazine.Approved
FluspirileneThe risk or severity of adverse effects can be increased when Naratriptan is combined with Fluspirilene.Approved
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Naratriptan.Approved, Investigational
FrovatriptanThe risk or severity of adverse effects can be increased when Naratriptan is combined with Frovatriptan.Approved, Investigational
FurazolidoneThe metabolism of Naratriptan can be decreased when combined with Furazolidone.Approved, Vet Approved
GranisetronGranisetron may increase the serotonergic activities of Naratriptan.Approved, Investigational
HaloperidolThe risk or severity of adverse effects can be increased when Naratriptan is combined with Haloperidol.Approved
HydracarbazineThe metabolism of Naratriptan can be decreased when combined with Hydracarbazine.Approved
IloperidoneThe risk or severity of adverse effects can be increased when Naratriptan is combined with Iloperidone.Approved
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Naratriptan.Approved
IproclozideThe metabolism of Naratriptan can be decreased when combined with Iproclozide.Withdrawn
IproniazidThe metabolism of Naratriptan can be decreased when combined with Iproniazid.Withdrawn
IsocarboxazidThe metabolism of Naratriptan can be decreased when combined with Isocarboxazid.Approved
LevomilnacipranThe risk or severity of adverse effects can be increased when Naratriptan is combined with Levomilnacipran.Approved
LinezolidThe risk or severity of adverse effects can be increased when Linezolid is combined with Naratriptan.Approved, Investigational
LithiumThe risk or severity of adverse effects can be increased when Naratriptan is combined with Lithium.Approved
LorcaserinThe risk or severity of adverse effects can be increased when Naratriptan is combined with Lorcaserin.Approved
LoxapineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Loxapine.Approved
LurasidoneThe risk or severity of adverse effects can be increased when Naratriptan is combined with Lurasidone.Approved
MaprotilineThe risk or severity of adverse effects can be increased when Maprotiline is combined with Naratriptan.Approved
MebanazineThe metabolism of Naratriptan can be decreased when combined with Mebanazine.Withdrawn
MelperoneThe risk or severity of adverse effects can be increased when Naratriptan is combined with Melperone.Approved
MesoridazineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Mesoridazine.Approved
MethadoneThe risk or severity of adverse effects can be increased when Methadone is combined with Naratriptan.Approved
MethotrimeprazineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Methotrimeprazine.Approved
Methylene blueThe metabolism of Naratriptan can be decreased when combined with Methylene blue.Investigational
MetoclopramideThe risk or severity of adverse effects can be increased when Naratriptan is combined with Metoclopramide.Approved, Investigational
MilnacipranThe risk or severity of adverse effects can be increased when Naratriptan is combined with Milnacipran.Approved
MinaprineThe metabolism of Naratriptan can be decreased when combined with Minaprine.Approved
MirtazapineThe risk or severity of adverse effects can be increased when Mirtazapine is combined with Naratriptan.Approved
MoclobemideThe metabolism of Naratriptan can be decreased when combined with Moclobemide.Approved
MolindoneThe risk or severity of adverse effects can be increased when Naratriptan is combined with Molindone.Approved
NefazodoneThe risk or severity of adverse effects can be increased when Naratriptan is combined with Nefazodone.Approved, Withdrawn
NialamideThe metabolism of Naratriptan can be decreased when combined with Nialamide.Withdrawn
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Naratriptan.Approved
OctamoxinThe metabolism of Naratriptan can be decreased when combined with Octamoxin.Withdrawn
OlanzapineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Olanzapine.Approved, Investigational
OndansetronOndansetron may increase the serotonergic activities of Naratriptan.Approved
OsanetantThe risk or severity of adverse effects can be increased when Naratriptan is combined with Osanetant.Investigational
PaliperidoneThe risk or severity of adverse effects can be increased when Naratriptan is combined with Paliperidone.Approved
PalonosetronPalonosetron may increase the serotonergic activities of Naratriptan.Approved, Investigational
PargylineThe metabolism of Naratriptan can be decreased when combined with Pargyline.Approved
ParoxetineThe risk or severity of adverse effects can be increased when Paroxetine is combined with Naratriptan.Approved, Investigational
PerazineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Perazine.Investigational
PerospironeThe risk or severity of adverse effects can be increased when Naratriptan is combined with Perospirone.Approved
PerphenazineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Perphenazine.Approved
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Naratriptan.Approved
PhenelzineThe metabolism of Naratriptan can be decreased when combined with Phenelzine.Approved
PheniprazineThe metabolism of Naratriptan can be decreased when combined with Pheniprazine.Withdrawn
PhenoxypropazineThe metabolism of Naratriptan can be decreased when combined with Phenoxypropazine.Withdrawn
PimozideThe risk or severity of adverse effects can be increased when Naratriptan is combined with Pimozide.Approved
PipamperoneThe risk or severity of adverse effects can be increased when Naratriptan is combined with Pipamperone.Approved
PipotiazineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Pipotiazine.Approved
PirlindoleThe metabolism of Naratriptan can be decreased when combined with Pirlindole.Approved
PivhydrazineThe metabolism of Naratriptan can be decreased when combined with Pivhydrazine.Withdrawn
ProcarbazineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Procarbazine.Approved
ProchlorperazineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Prochlorperazine.Approved, Vet Approved
PromazineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Promazine.Approved, Vet Approved
PromethazineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Promethazine.Approved
PropericiazineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Propericiazine.Approved
ProthipendylThe risk or severity of adverse effects can be increased when Naratriptan is combined with Prothipendyl.Investigational
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Naratriptan.Approved
QuetiapineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Quetiapine.Approved
RacloprideThe risk or severity of adverse effects can be increased when Naratriptan is combined with Raclopride.Investigational
RasagilineThe metabolism of Naratriptan can be decreased when combined with Rasagiline.Approved
RemoxiprideThe risk or severity of adverse effects can be increased when Naratriptan is combined with Remoxipride.Approved, Withdrawn
ReserpineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Reserpine.Approved
RisperidoneThe risk or severity of adverse effects can be increased when Naratriptan is combined with Risperidone.Approved, Investigational
RitanserinThe risk or severity of adverse effects can be increased when Naratriptan is combined with Ritanserin.Investigational
RizatriptanThe risk or severity of adverse effects can be increased when Naratriptan is combined with Rizatriptan.Approved
SafrazineThe metabolism of Naratriptan can be decreased when combined with Safrazine.Withdrawn
SelegilineThe metabolism of Naratriptan can be decreased when combined with Selegiline.Approved, Investigational, Vet Approved
SertindoleThe risk or severity of adverse effects can be increased when Naratriptan is combined with Sertindole.Approved, Withdrawn
SertralineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Sertraline.Approved
SulpirideThe risk or severity of adverse effects can be increased when Naratriptan is combined with Sulpiride.Approved
SumatriptanThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Naratriptan.Approved, Investigational
TapentadolThe risk or severity of adverse effects can be increased when Naratriptan is combined with Tapentadol.Approved
Tedizolid PhosphateTedizolid Phosphate may increase the serotonergic activities of Naratriptan.Approved
ThioproperazineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Thioproperazine.Approved
ThioridazineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Thioridazine.Approved
ThiothixeneThe risk or severity of adverse effects can be increased when Naratriptan is combined with Thiothixene.Approved
TiaprideThe risk or severity of adverse effects can be increased when Naratriptan is combined with Tiapride.Investigational
ToloxatoneThe metabolism of Naratriptan can be decreased when combined with Toloxatone.Approved
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Naratriptan.Approved, Investigational
Trans-2-PhenylcyclopropylamineThe metabolism of Naratriptan can be decreased when combined with Trans-2-Phenylcyclopropylamine.Experimental
TranylcypromineThe metabolism of Naratriptan can be decreased when combined with Tranylcypromine.Approved
TrazodoneThe risk or severity of adverse effects can be increased when Trazodone is combined with Naratriptan.Approved, Investigational
TrifluoperazineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Trifluoperazine.Approved
TriflupromazineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Triflupromazine.Approved, Vet Approved
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Naratriptan.Approved
TropisetronTropisetron may increase the serotonergic activities of Naratriptan.Investigational
VenlafaxineThe risk or severity of adverse effects can be increased when Venlafaxine is combined with Naratriptan.Approved
VilazodoneThe risk or severity of adverse effects can be increased when Naratriptan is combined with Vilazodone.Approved
VortioxetineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Vortioxetine.Approved
ZiprasidoneThe risk or severity of adverse effects can be increased when Naratriptan is combined with Ziprasidone.Approved
ZolmitriptanThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Naratriptan.Approved, Investigational
ZotepineThe risk or severity of adverse effects can be increased when Naratriptan is combined with Zotepine.Approved
ZuclopenthixolThe risk or severity of adverse effects can be increased when Naratriptan is combined with Zuclopenthixol.Approved, Investigational
Food Interactions
  • Take without regard to meals.
References
Synthesis Reference

Dharmaraj Ramachandra Rao, Rajendra Narayanrao Kankan, Sandip Vasant Chikhalikar, Maruti Ghagare, “Process for the synthesis of naratriptan.” U.S. Patent US20120220778, issued August 30, 2012.

US20120220778
General References
  1. Massiou H: Naratriptan. Curr Med Res Opin. 2001;17 Suppl 1:s51-3. [PubMed:12463278 ]
  2. Lambert GA: Preclinical neuropharmacology of naratriptan. CNS Drug Rev. 2005 Autumn;11(3):289-316. [PubMed:16389295 ]
  3. Villalon CM, Centurion D, Valdivia LF, de Vries P, Saxena PR: Migraine: pathophysiology, pharmacology, treatment and future trends. Curr Vasc Pharmacol. 2003 Mar;1(1):71-84. [PubMed:15320857 ]
External Links
ATC CodesN02CC02
AHFS Codes
  • 28:32.28
PDB EntriesNot Available
FDA labelDownload (1.93 MB)
MSDSDownload (29.8 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9668
Caco-2 permeable-0.7657
P-glycoprotein substrateSubstrate0.6958
P-glycoprotein inhibitor INon-inhibitor0.6055
P-glycoprotein inhibitor IINon-inhibitor0.8139
Renal organic cation transporterNon-inhibitor0.5982
CYP450 2C9 substrateNon-substrate0.8257
CYP450 2D6 substrateNon-substrate0.5565
CYP450 3A4 substrateSubstrate0.6693
CYP450 1A2 substrateInhibitor0.5521
CYP450 2C9 inhibitorNon-inhibitor0.9034
CYP450 2D6 inhibitorNon-inhibitor0.6785
CYP450 2C19 inhibitorNon-inhibitor0.804
CYP450 3A4 inhibitorNon-inhibitor0.5914
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.707
Ames testNon AMES toxic0.6042
CarcinogenicityNon-carcinogens0.8226
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5630 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.608
hERG inhibition (predictor II)Inhibitor0.6772
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Glaxosmithkline
  • Paddock laboratories inc
  • Roxane laboratories inc
  • Sandoz inc
  • Teva pharmaceuticals usa
Packagers
Dosage forms
FormRouteStrength
TabletOral1 mg
TabletOral1 mg/1
TabletOral2.5 mg/1
Tablet, coatedOral1 mg/1
Tablet, coatedOral2.5 mg/1
Tablet, film coatedOral1 mg/1
Tablet, film coatedOral2.5 mg/1
TabletOral2.5 mg
Prices
Unit descriptionCostUnit
Amerge 9 2.5 mg tablet Box277.47USD box
Amerge 9 1 mg tablet Box275.67USD box
Amerge 1 mg tablet32.77USD tablet
Amerge 2.5 mg tablet32.77USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US4997841 No1993-07-072010-07-07Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point246 °C (HCl salt)Not Available
water solubility35 mg/mLNot Available
logP1.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.114 mg/mLALOGPS
logP2.16ALOGPS
logP1.44ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)11.55ChemAxon
pKa (Strongest Basic)9.18ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area65.2 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity94.26 m3·mol-1ChemAxon
Polarizability38 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as indoles. These are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct ParentIndoles
Alternative Parents
Substituents
  • Indole
  • Aralkylamine
  • Benzenoid
  • Substituted pyrrole
  • Piperidine
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Pyrrole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Serotonin receptor activity
Specific Function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate c...
Gene Name:
HTR1D
Uniprot ID:
P28221
Molecular Weight:
41906.38 Da
References
  1. Hargreaves RJ, Shepheard SL: Pathophysiology of migraine--new insights. Can J Neurol Sci. 1999 Nov;26 Suppl 3:S12-9. [PubMed:10563228 ]
  2. Donaldson C, Boers PM, Hoskin KL, Zagami AS, Lambert GA: The role of 5-HT1B and 5-HT1D receptors in the selective inhibitory effect of naratriptan on trigeminovascular neurons. Neuropharmacology. 2002 Mar;42(3):374-85. [PubMed:11897116 ]
  3. Pauwels PJ, Colpaert FC: Selective antagonism of human 5-HT1D and 5-HT1B receptor-mediated responses in stably transfected C6-glial cells by ketanserin and GR 127,935. Eur J Pharmacol. 1996 Apr 4;300(1-2):141-5. [PubMed:8741180 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  5. Akin D, Onaran HO, Gurdal H: Agonist-directed trafficking explaining the difference between response pattern of naratriptan and sumatriptan in rabbit common carotid artery. Br J Pharmacol. 2002 May;136(2):171-6. [PubMed:12010764 ]
  6. Hoskin KL, Lambert GA, Donaldson C, Zagami AS: The 5-hydroxytryptamine1B/1D/1F receptor agonists eletriptan and naratriptan inhibit trigeminovascular input to the nucleus tractus solitarius in the cat. Brain Res. 2004 Feb 13;998(1):91-9. [PubMed:14725972 ]
  7. Boers PM, Donaldson C, Zagami AS, Lambert GA: 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. Cephalalgia. 2004 Feb;24(2):99-109. [PubMed:14728705 ]
  8. Johnston MM, Rapoport AM: Triptans for the management of migraine. Drugs. 2010 Aug 20;70(12):1505-18. doi: 10.2165/11537990-000000000-00000. [PubMed:20687618 ]
  9. Dulli DA: Naratriptan: an alternative for migraine. Ann Pharmacother. 1999 Jun;33(6):704-11. [PubMed:10410185 ]
  10. Tfelt-Hansen P, De Vries P, Saxena PR: Triptans in migraine: a comparative review of pharmacology, pharmacokinetics and efficacy. Drugs. 2000 Dec;60(6):1259-87. [PubMed:11152011 ]
  11. Massiou H: Naratriptan. Curr Med Res Opin. 2001;17 Suppl 1:s51-3. [PubMed:12463278 ]
  12. Lambert GA: Preclinical neuropharmacology of naratriptan. CNS Drug Rev. 2005 Autumn;11(3):289-316. [PubMed:16389295 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Serotonin receptor activity
Specific Function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive substances, such as lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of ...
Gene Name:
HTR1B
Uniprot ID:
P28222
Molecular Weight:
43567.535 Da
References
  1. Akin D, Onaran HO, Gurdal H: Agonist-directed trafficking explaining the difference between response pattern of naratriptan and sumatriptan in rabbit common carotid artery. Br J Pharmacol. 2002 May;136(2):171-6. [PubMed:12010764 ]
  2. Hoskin KL, Lambert GA, Donaldson C, Zagami AS: The 5-hydroxytryptamine1B/1D/1F receptor agonists eletriptan and naratriptan inhibit trigeminovascular input to the nucleus tractus solitarius in the cat. Brain Res. 2004 Feb 13;998(1):91-9. [PubMed:14725972 ]
  3. Boers PM, Donaldson C, Zagami AS, Lambert GA: 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. Cephalalgia. 2004 Feb;24(2):99-109. [PubMed:14728705 ]
  4. Pauwels PJ, Palmier C, Dupuis DS, Colpaert FC: Interaction of 5-HT1B/D ligands with recombinant h 5-HT1A receptors: intrinsic activity and modulation by G-protein activation state. Naunyn Schmiedebergs Arch Pharmacol. 1998 May;357(5):490-9. [PubMed:9650800 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  6. Johnston MM, Rapoport AM: Triptans for the management of migraine. Drugs. 2010 Aug 20;70(12):1505-18. doi: 10.2165/11537990-000000000-00000. [PubMed:20687618 ]
  7. Dulli DA: Naratriptan: an alternative for migraine. Ann Pharmacother. 1999 Jun;33(6):704-11. [PubMed:10410185 ]
  8. Tfelt-Hansen P, De Vries P, Saxena PR: Triptans in migraine: a comparative review of pharmacology, pharmacokinetics and efficacy. Drugs. 2000 Dec;60(6):1259-87. [PubMed:11152011 ]
  9. Massiou H: Naratriptan. Curr Med Res Opin. 2001;17 Suppl 1:s51-3. [PubMed:12463278 ]
  10. Lambert GA: Preclinical neuropharmacology of naratriptan. CNS Drug Rev. 2005 Autumn;11(3):289-316. [PubMed:16389295 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Serotonin receptor activity
Specific Function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various alkaloids and psychoactive substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling inhibits adenylate cyclase activity.
Gene Name:
HTR1F
Uniprot ID:
P30939
Molecular Weight:
41708.505 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Hoskin KL, Lambert GA, Donaldson C, Zagami AS: The 5-hydroxytryptamine1B/1D/1F receptor agonists eletriptan and naratriptan inhibit trigeminovascular input to the nucleus tractus solitarius in the cat. Brain Res. 2004 Feb 13;998(1):91-9. [PubMed:14725972 ]
  3. Tfelt-Hansen P, De Vries P, Saxena PR: Triptans in migraine: a comparative review of pharmacology, pharmacokinetics and efficacy. Drugs. 2000 Dec;60(6):1259-87. [PubMed:11152011 ]
  4. Massiou H: Naratriptan. Curr Med Res Opin. 2001;17 Suppl 1:s51-3. [PubMed:12463278 ]
  5. Villalon CM, Centurion D, Valdivia LF, de Vries P, Saxena PR: Migraine: pathophysiology, pharmacology, treatment and future trends. Curr Vasc Pharmacol. 2003 Mar;1(1):71-84. [PubMed:15320857 ]
  6. Goadsby PJ, Classey JD: Evidence for serotonin (5-HT)1B, 5-HT1D and 5-HT1F receptor inhibitory effects on trigeminal neurons with craniovascular input. Neuroscience. 2003;122(2):491-8. [PubMed:14614913 ]
  7. Villalon CM, Centurion D, Valdivia LF, De Vries P, Saxena PR: An introduction to migraine: from ancient treatment to functional pharmacology and antimigraine therapy. Proc West Pharmacol Soc. 2002;45:199-210. [PubMed:12434581 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Serotonin receptor activity
Specific Function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Beta-arrestin family members inhibit signaling via G pro...
Gene Name:
HTR1A
Uniprot ID:
P08908
Molecular Weight:
46106.335 Da
References
  1. Boers PM, Donaldson C, Zagami AS, Lambert GA: 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. Cephalalgia. 2004 Feb;24(2):99-109. [PubMed:14728705 ]
  2. Tfelt-Hansen P, De Vries P, Saxena PR: Triptans in migraine: a comparative review of pharmacology, pharmacokinetics and efficacy. Drugs. 2000 Dec;60(6):1259-87. [PubMed:11152011 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Serotonin binding
Specific Function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular Weight:
59681.27 Da
References
  1. Millson DS, Tepper SJ, Rapoport AM: Migraine pharmacotherapy with oral triptans: a rational approach to clinical management. Expert Opin Pharmacother. 2000 Mar;1(3):391-404. [PubMed:11249525 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on December 08, 2016 11:46