Identification

Name
Rizatriptan
Accession Number
DB00953  (APRD00008)
Type
Small Molecule
Groups
Approved
Description

Rizatriptan is a triptan drug used for the treatment of migraine headaches. It is a selective 5-hydroxytryptamine1 receptor subtype agonist.

Structure
Thumb
Synonyms
  • N,N-Dimethyl-2-[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]-ethanamine
  • N,N-Dimethyl-5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indole-3-ethanamine
  • Risatriptan
  • Rizatriptán
  • Rizatriptan
  • Rizatriptanum
External IDs
L-705126 / MK 462 Free Base / MK-462 FREE BASE
Product Ingredients
IngredientUNIICASInChI Key
Rizatriptan benzoateWR978S7QHH145202-66-0JPRXYLQNJJVCMZ-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act RizatriptanTablet5 mgOralActavis Pharma CompanyNot applicableNot applicableCanada
Act RizatriptanTablet10 mgOralActavis Pharma Company2012-06-14Not applicableCanada
Act Rizatriptan ODTTablet, orally disintegrating5 mgOralActavis Pharma Company2012-01-30Not applicableCanada
Act Rizatriptan ODTTablet, orally disintegrating10 mgOralActavis Pharma Company2012-01-30Not applicableCanada
Auro-rizatriptanTablet10 mgOralAuro Pharma Inc2016-04-12Not applicableCanada
Auro-rizatriptan ODTTablet, orally disintegrating5 mgOralAuro Pharma IncNot applicableNot applicableCanada
Auro-rizatriptan ODTTablet, orally disintegrating10 mgOralAuro Pharma IncNot applicableNot applicableCanada
Ccp-rizatriptan ODTTablet, orally disintegrating10 mgOralCellchem Pharmaceuticals Inc.Not applicableNot applicableCanada
Ccp-rizatriptan ODTTablet, orally disintegrating5 mgOralCellchem Pharmaceuticals Inc.Not applicableNot applicableCanada
Dom-rizatriptan RdtTablet, orally disintegrating5 mgOralDominion PharmacalNot applicableNot applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-rizatriptanTablet5 mgOralApotex Corporation2013-03-06Not applicableCanada
Apo-rizatriptanTablet10 mgOralApotex Corporation2012-09-27Not applicableCanada
Apo-rizatriptan RpdTablet, orally disintegrating5 mgOralApotex Corporation2013-09-10Not applicableCanada
Apo-rizatriptan RpdTablet, orally disintegrating10 mgOralApotex Corporation2013-09-10Not applicableCanada
RizatriptanTablet, film coated10 mg/1OralMacleods Pharmaceuticals Limited2014-03-11Not applicableUs
RizatriptanTablet, film coated5 mg/1OralMacleods Pharmaceuticals Limited2014-03-11Not applicableUs
RizatriptanTablet, film coated10 mg/1OralRemedy Repack2015-06-082017-09-01Us
RizatriptanTablet, film coated10 mg/1OralPreferreed Pharmaceuticals Inc.2015-08-18Not applicableUs
Rizatriptan BenzoateTablet10 mg/1OralRemedy Repack2017-05-09Not applicableUs
Rizatriptan BenzoateTablet5 mg/1OralHeritage2013-12-12Not applicableUs
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
RIZATRIPTAN BenzoateTablet, orally disintegrating10 mg/1OralPreferreed Pharmaceuticals Inc.2017-10-31Not applicableUs
International/Other Brands
Maxalt MLT
Categories
UNII
51086HBW8G
CAS number
144034-80-0
Weight
Average: 269.3449
Monoisotopic: 269.164045633
Chemical Formula
C15H19N5
InChI Key
ULFRLSNUDGIQQP-UHFFFAOYSA-N
InChI
InChI=1S/C15H19N5/c1-19(2)6-5-13-8-17-15-4-3-12(7-14(13)15)9-20-11-16-10-18-20/h3-4,7-8,10-11,17H,5-6,9H2,1-2H3
IUPAC Name
dimethyl({2-[5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethyl})amine
SMILES
CN(C)CCC1=CNC2=C1C=C(CN1C=NC=N1)C=C2

Pharmacology

Indication

For treatment of acute migraine attacks with or without aura.

Structured Indications
Pharmacodynamics

Rizatriptan 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 agonists and 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 Rizatriptan 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 Rizatriptan in humans.

Mechanism of action

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.

TargetActionsOrganism
A5-hydroxytryptamine receptor 1D
agonist
Human
A5-hydroxytryptamine receptor 1B
agonist
Human
A5-hydroxytryptamine receptor 1F
agonist
Human
Absorption

Rapid following oral administration. Bioavailability is 45%. Food has no effect on the bioavailability of rizatriptan. However, administering rizatriptan with food will delay by 1 hour the time to reach peak plasma concentration. The rate of absorption is not affected by the presence of a migraine attack.

Volume of distribution
  • 140 L [male]
  • 110 L [female]
Protein binding

14%

Metabolism

Rizatriptan is metabolized by monoamine oxidase A isoenzyme (MAO-A) to an inactive indole acetic acid metabolite. In addition, several other inactive metabolites are formed. An active metabolite, N-monodesmethyl-rizatriptan, with pharmacological activity similar to that of the parent compound has been identified in small concentrations (14%) in the plasma.

Route of elimination

Approximately 14% of an oral dose is excreted in urine as unchanged rizatriptan while 51% is excreted as indole acetic acid metabolite, indicating substantial first pass metabolism.

Half life

2-3 hours

Clearance
Not Available
Toxicity

Symptoms of overdose include dizziness, fainting, heart and blood vessel problems, high blood pressure, loss of bowel and bladder control, slow heartbeat, and vomiting.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Guanine nucleotide-binding protein G(I)/G(S)/G(T) subunit beta-3---(T;T) / (C;T)T AlleleEffect Directly StudiedPatients with this genotype have an increased likelihood of responding to rizatriptan when treating (condition: cluster headache).Details

Interactions

Drug Interactions
DrugInteractionDrug group
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe metabolism of Rizatriptan can be decreased when combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.Experimental
AbirateroneThe serum concentration of Rizatriptan can be increased when it is combined with Abiraterone.Approved
AcepromazineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Acepromazine.Approved, Vet Approved
AceprometazineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Aceprometazine.Approved
AcetophenazineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Acetophenazine.Approved
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Rizatriptan.Approved, Investigational
AmisulprideThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Amisulpride.Approved, Investigational
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Rizatriptan.Approved
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Rizatriptan.Approved
AmperozideThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Amperozide.Experimental
AripiprazoleThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Aripiprazole.Approved, Investigational
AsenapineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Asenapine.Approved
AzaperoneThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Azaperone.Investigational, Vet Approved
AzithromycinThe metabolism of Rizatriptan can be decreased when combined with Azithromycin.Approved
BenmoxinThe metabolism of Rizatriptan can be decreased when combined with Benmoxin.Withdrawn
BenperidolThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Benperidol.Investigational
BifeprunoxThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Bifeprunox.Investigational
BortezomibThe metabolism of Rizatriptan can be decreased when combined with Bortezomib.Approved, Investigational
BrexpiprazoleThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Brexpiprazole.Approved
BrofaromineThe serum concentration of Rizatriptan can be increased when it is combined with Brofaromine.Experimental
BromocriptineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Bromocriptine.Approved, Investigational
BromperidolThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Bromperidol.Investigational
BuspironeThe risk or severity of adverse effects can be increased when Buspirone is combined with Rizatriptan.Approved, Investigational
ButaperazineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Butaperazine.Experimental
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Rizatriptan.Approved
CaffeineThe metabolism of Rizatriptan can be decreased when combined with Caffeine.Approved
CariprazineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Cariprazine.Approved
CaroxazoneThe metabolism of Rizatriptan can be decreased when combined with Caroxazone.Withdrawn
ChlorproethazineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Chlorproethazine.Experimental
ChlorpromazineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Chlorpromazine.Approved, Vet Approved
ChlorprothixeneThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Chlorprothixene.Approved, Investigational, Withdrawn
CitalopramThe risk or severity of adverse effects can be increased when Citalopram is combined with Rizatriptan.Approved
ClomipramineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Clomipramine.Approved, Vet Approved
ClopenthixolThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Clopenthixol.Experimental
ClothiapineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Clothiapine.Experimental
ClotrimazoleThe metabolism of Rizatriptan can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Clozapine.Approved
CyamemazineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Cyamemazine.Approved
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Rizatriptan.Approved
Cyproterone acetateThe serum concentration of Rizatriptan can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
DapiprazoleThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Dapiprazole.Approved
DapoxetineThe risk or severity of adverse effects can be increased when Dapoxetine is combined with Rizatriptan.Investigational
DeferasiroxThe serum concentration of Rizatriptan can be increased when it is combined with Deferasirox.Approved, Investigational
DesipramineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Desipramine.Approved
DesvenlafaxineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Desvenlafaxine.Approved
DextromethorphanThe risk or severity of adverse effects can be increased when Dextromethorphan is combined with Rizatriptan.Approved
DihydroergotamineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Rizatriptan.Approved
DixyrazineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Dixyrazine.Experimental
DolasetronDolasetron may increase the serotonergic activities of Rizatriptan.Approved
DosulepinThe metabolism of Rizatriptan can be decreased when combined with Dosulepin.Approved
DoxepinThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Doxepin.Approved
DroperidolThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Droperidol.Approved, Vet Approved
DroxidopaRizatriptan may increase the hypertensive activities of Droxidopa.Approved, Investigational
DuloxetineThe risk or severity of adverse effects can be increased when Duloxetine is combined with Rizatriptan.Approved
EcopipamThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Ecopipam.Investigational
EletriptanThe risk or severity of adverse effects can be increased when Eletriptan is combined with Rizatriptan.Approved, Investigational
Ergoloid mesylateThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Ergoloid mesylate.Approved
ErgonovineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Ergonovine.Approved
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Rizatriptan.Approved
EscitalopramThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Escitalopram.Approved, Investigational
FencamfamineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Fencamfamine.Approved, Illicit, Withdrawn
FentanylThe risk or severity of adverse effects can be increased when Fentanyl is combined with Rizatriptan.Approved, Illicit, Investigational, Vet Approved
FluanisoneThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Fluanisone.Experimental
FluoxetineThe risk or severity of adverse effects can be increased when Fluoxetine is combined with Rizatriptan.Approved, Vet Approved
FlupentixolThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Flupentixol.Approved, Withdrawn
FluphenazineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Fluphenazine.Approved
FluspirileneThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Fluspirilene.Approved, Investigational
FluvoxamineThe metabolism of Rizatriptan can be decreased when combined with Fluvoxamine.Approved, Investigational
FrovatriptanThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Frovatriptan.Approved, Investigational
FurazolidoneThe metabolism of Rizatriptan can be decreased when combined with Furazolidone.Approved, Investigational, Vet Approved
GranisetronGranisetron may increase the serotonergic activities of Rizatriptan.Approved, Investigational
HaloperidolThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Haloperidol.Approved
HarmalineThe serum concentration of Rizatriptan can be increased when it is combined with Harmaline.Experimental
HydracarbazineThe metabolism of Rizatriptan can be decreased when combined with Hydracarbazine.Experimental
IloperidoneThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Iloperidone.Approved
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Rizatriptan.Approved
IproclozideThe metabolism of Rizatriptan can be decreased when combined with Iproclozide.Withdrawn
IproniazidThe metabolism of Rizatriptan can be decreased when combined with Iproniazid.Withdrawn
IsocarboxazidThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Isocarboxazid.Approved
LevomilnacipranThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Levomilnacipran.Approved
LidocaineThe metabolism of Rizatriptan can be decreased when combined with Lidocaine.Approved, Vet Approved
LinezolidThe risk or severity of adverse effects can be increased when Linezolid is combined with Rizatriptan.Approved, Investigational
LithiumThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Lithium.Approved
LobeglitazoneThe metabolism of Rizatriptan can be decreased when combined with Lobeglitazone.Approved, Investigational
LorcaserinThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Lorcaserin.Approved
LoxapineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Loxapine.Approved
LurasidoneThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Lurasidone.Approved
MaprotilineThe risk or severity of adverse effects can be increased when Maprotiline is combined with Rizatriptan.Approved
MebanazineThe metabolism of Rizatriptan can be decreased when combined with Mebanazine.Withdrawn
MelperoneThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Melperone.Approved, Investigational
MesoridazineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Mesoridazine.Approved, Investigational
MethadoneThe risk or severity of adverse effects can be increased when Methadone is combined with Rizatriptan.Approved
MethotrimeprazineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Methotrimeprazine.Approved
Methylene blueThe metabolism of Rizatriptan can be decreased when combined with Methylene blue.Approved, Investigational
MethylergometrineMethylergometrine may increase the vasoconstricting activities of Rizatriptan.Approved
MetoclopramideThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Metoclopramide.Approved, Investigational
MexiletineThe metabolism of Rizatriptan can be decreased when combined with Mexiletine.Approved
MidostaurinThe metabolism of Rizatriptan can be decreased when combined with Midostaurin.Approved
MilnacipranThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Milnacipran.Approved
MinaprineThe metabolism of Rizatriptan can be decreased when combined with Minaprine.Approved
MirtazapineThe risk or severity of adverse effects can be increased when Mirtazapine is combined with Rizatriptan.Approved
MoclobemideThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Moclobemide.Approved
MolindoneThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Molindone.Approved
MoperoneThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Moperone.Experimental
MosapramineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Mosapramine.Experimental
NaratriptanThe risk or severity of adverse effects can be increased when Naratriptan is combined with Rizatriptan.Approved, Investigational
NefazodoneThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Nefazodone.Approved, Withdrawn
NevirapineThe metabolism of Rizatriptan can be decreased when combined with Nevirapine.Approved
NialamideThe metabolism of Rizatriptan can be decreased when combined with Nialamide.Withdrawn
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Rizatriptan.Approved
OctamoxinThe metabolism of Rizatriptan can be decreased when combined with Octamoxin.Withdrawn
OlanzapineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Olanzapine.Approved, Investigational
OndansetronOndansetron may increase the serotonergic activities of Rizatriptan.Approved
OsanetantThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Osanetant.Investigational
OsimertinibThe serum concentration of Rizatriptan can be decreased when it is combined with Osimertinib.Approved
OxypertineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Oxypertine.Experimental
PaliperidoneThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Paliperidone.Approved
PalonosetronPalonosetron may increase the serotonergic activities of Rizatriptan.Approved, Investigational
PargylineThe metabolism of Rizatriptan can be decreased when combined with Pargyline.Approved
ParoxetineThe risk or severity of adverse effects can be increased when Paroxetine is combined with Rizatriptan.Approved, Investigational
Peginterferon alfa-2bThe serum concentration of Rizatriptan can be increased when it is combined with Peginterferon alfa-2b.Approved
PenfluridolThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Penfluridol.Experimental
PerazineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Perazine.Investigational
PerospironeThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Perospirone.Approved
PerphenazineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Perphenazine.Approved
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Rizatriptan.Approved
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Rizatriptan.Approved
PheniprazineThe metabolism of Rizatriptan can be decreased when combined with Pheniprazine.Withdrawn
PhenoxypropazineThe metabolism of Rizatriptan can be decreased when combined with Phenoxypropazine.Withdrawn
PimozideThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Pimozide.Approved
PipamperoneThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Pipamperone.Approved, Investigational
PipotiazineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Pipotiazine.Approved, Investigational
PirlindoleThe metabolism of Rizatriptan can be decreased when combined with Pirlindole.Approved
PivhydrazineThe metabolism of Rizatriptan can be decreased when combined with Pivhydrazine.Withdrawn
ProcarbazineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Procarbazine.Approved
ProchlorperazineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Prochlorperazine.Approved, Vet Approved
PromazineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Promazine.Approved, Vet Approved
PromethazineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Promethazine.Approved
PropericiazineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Propericiazine.Approved
PropranololThe serum concentration of Rizatriptan can be increased when it is combined with Propranolol.Approved, Investigational
ProthipendylThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Prothipendyl.Investigational
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Rizatriptan.Approved
QuetiapineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Quetiapine.Approved
RacloprideThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Raclopride.Investigational
RasagilineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Rasagiline.Approved
RemoxiprideThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Remoxipride.Approved, Withdrawn
ReserpineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Reserpine.Approved, Investigational
RisperidoneThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Risperidone.Approved, Investigational
RitanserinThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Ritanserin.Investigational
RopiniroleThe metabolism of Rizatriptan can be decreased when combined with Ropinirole.Approved, Investigational
SafrazineThe metabolism of Rizatriptan can be decreased when combined with Safrazine.Withdrawn
SelegilineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Selegiline.Approved, Investigational, Vet Approved
SertindoleThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Sertindole.Approved, Investigational, Withdrawn
SertralineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Sertraline.Approved
SimeprevirThe metabolism of Rizatriptan can be decreased when combined with Simeprevir.Approved
SulpirideThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Sulpiride.Approved, Investigational
SultoprideThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Sultopride.Experimental
SumatriptanThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Rizatriptan.Approved, Investigational
TapentadolThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Tapentadol.Approved
Tedizolid PhosphateTedizolid Phosphate may increase the serotonergic activities of Rizatriptan.Approved
Tenofovir disoproxilThe metabolism of Rizatriptan can be decreased when combined with Tenofovir disoproxil.Approved, Investigational
TeriflunomideThe serum concentration of Rizatriptan can be decreased when it is combined with Teriflunomide.Approved
TetrahydropalmatineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Tetrahydropalmatine.Investigational
TheophyllineThe metabolism of Rizatriptan can be decreased when combined with Theophylline.Approved
ThiopropazateThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Thiopropazate.Experimental
ThioproperazineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Thioproperazine.Approved
ThioridazineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Thioridazine.Approved, Withdrawn
ThiothixeneThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Thiothixene.Approved
TiaprideThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Tiapride.Approved, Investigational
TiclopidineThe metabolism of Rizatriptan can be decreased when combined with Ticlopidine.Approved
ToloxatoneThe metabolism of Rizatriptan can be decreased when combined with Toloxatone.Approved
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Rizatriptan.Approved, Investigational
Trans-2-PhenylcyclopropylamineThe metabolism of Rizatriptan can be decreased when combined with Trans-2-Phenylcyclopropylamine.Experimental
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Rizatriptan.Approved
TrazodoneThe risk or severity of adverse effects can be increased when Trazodone is combined with Rizatriptan.Approved, Investigational
TrifluoperazineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Trifluoperazine.Approved
TrifluperidolThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Trifluperidol.Experimental
TriflupromazineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Triflupromazine.Approved, Vet Approved
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Rizatriptan.Approved
TropisetronTropisetron may increase the serotonergic activities of Rizatriptan.Approved, Investigational
VemurafenibThe serum concentration of Rizatriptan can be increased when it is combined with Vemurafenib.Approved
VenlafaxineThe risk or severity of adverse effects can be increased when Venlafaxine is combined with Rizatriptan.Approved
VeraliprideThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Veralipride.Experimental
VilazodoneThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Vilazodone.Approved
VortioxetineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Vortioxetine.Approved
ZiprasidoneThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Ziprasidone.Approved
ZolmitriptanThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Rizatriptan.Approved, Investigational
ZotepineThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Zotepine.Approved, Investigational
ZucapsaicinThe metabolism of Rizatriptan can be decreased when combined with Zucapsaicin.Approved
ZuclopenthixolThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Zuclopenthixol.Approved, Investigational
Food Interactions
Not Available

References

Synthesis Reference

Montserrat Armengol Asparo, Pere Dalmases Barjoan, "Process for preparing a rizatriptan." U.S. Patent US20050148778, issued July 07, 2005.

US20050148778
General References
  1. Wellington K, Plosker GL: Rizatriptan: an update of its use in the management of migraine. Drugs. 2002;62(10):1539-74. [PubMed:12093318]
  2. Wellington K, Jarvis B: Spotlight on rizatriptan in migraine. CNS Drugs. 2002;16(10):715-20. [PubMed:12269863]
  3. Ikemoto F, Toru T, Aijima H, Natsumeda Y: [Rizatriptan (Maxalt), a new entity of triptan for migraine: pharmacology and therapeutic relevance]. Nihon Yakurigaku Zasshi. 2004 Apr;123(4):295-302. [PubMed:15056946]
  4. 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]
  5. 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]
External Links
Human Metabolome Database
HMDB15088
KEGG Drug
D00675
PubChem Compound
5078
PubChem Substance
46506557
ChemSpider
4900
BindingDB
50033437
ChEBI
48273
ChEMBL
CHEMBL905
Therapeutic Targets Database
DAP000220
PharmGKB
PA451264
IUPHAR
51
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Rizatriptan
ATC Codes
N02CC04 — Rizatriptan
AHFS Codes
  • 28:32.28 — Selective Serotonin Agonists
FDA label
Download (873 KB)
MSDS
Download (57.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentMigraine Disorders1
2CompletedTreatmentMigraines1
2, 3RecruitingTreatmentMigrainous Vertigo / Vestibular Migraine1
3CompletedTreatmentAcute Migraine With or Without Aura in Adolescents1
3CompletedTreatmentMigraine Disorders1
3CompletedTreatmentMigraine, Acute2
3CompletedTreatmentMigraines4
3CompletedTreatmentMigrainous Headache4
4CompletedBasic ScienceEpisodic Migraine1
4CompletedTreatmentMigraines3
4CompletedTreatmentMigrainous Headache1
Not AvailableCompletedBasic ScienceMigraines1
Not AvailableWithdrawnTreatmentChronic Post-traumatic Headache1

Pharmacoeconomics

Manufacturers
  • Merck and co inc
Packagers
Dosage forms
FormRouteStrength
TabletOral5 mg
TabletOral10 mg/1
TabletOral10 mg
Tablet, orally disintegratingOral10 mg
Tablet, orally disintegratingOral5 mg
Film, solubleOral10 1/1
Film, solubleOral5 1/1
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral5 mg/1
TabletOral5 mg/1
Tablet, orally disintegratingOral10 mg/1
Tablet, orally disintegratingOral5 mg/1
Prices
Unit descriptionCostUnit
Maxalt 12 10 mg tablet Box333.27USD box
Maxalt 12 5 mg tablet Box333.27USD box
Maxalt-MLT 3 5 mg Dispersible Tablet Box286.96USD box
Maxalt 9 5 mg tablet Box203.46USD box
Maxalt 6 5 mg tablet Box107.44USD box
Maxalt-MLT 3 10 mg Dispersible Tablet Box83.32USD box
Maxalt mlt 10 mg tablet26.7USD tablet
Maxalt mlt 5 mg tablet26.7USD tablet
Maxalt 10 mg tablet25.31USD tablet
Maxalt 5 mg tablet22.98USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5602162No1994-02-112014-02-11Us
US5298520No1995-06-292012-06-29Us
CA2060139No1998-12-012012-01-28Canada

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)178-180 °CNot Available
water solubility42 mg/mL (for free base)Not Available
logP1.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.338 mg/mLALOGPS
logP1.67ALOGPS
logP1.77ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)17.24ChemAxon
pKa (Strongest Basic)9.56ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.74 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity93.13 m3·mol-1ChemAxon
Polarizability30 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9406
Caco-2 permeable+0.5547
P-glycoprotein substrateSubstrate0.7478
P-glycoprotein inhibitor INon-inhibitor0.8752
P-glycoprotein inhibitor IINon-inhibitor0.7244
Renal organic cation transporterInhibitor0.7394
CYP450 2C9 substrateNon-substrate0.8572
CYP450 2D6 substrateNon-substrate0.6765
CYP450 3A4 substrateSubstrate0.5574
CYP450 1A2 substrateNon-inhibitor0.9149
CYP450 2C9 inhibitorNon-inhibitor0.9063
CYP450 2D6 inhibitorNon-inhibitor0.8913
CYP450 2C19 inhibitorNon-inhibitor0.9515
CYP450 3A4 inhibitorNon-inhibitor0.9688
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.956
Ames testAMES toxic0.5644
CarcinogenicityNon-carcinogens0.9133
BiodegradationNot ready biodegradable0.9439
Rat acute toxicity2.5433 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7051
hERG inhibition (predictor II)Non-inhibitor0.7265
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0udi-0590000000-de0b61f549c5a86c98df

Taxonomy

Description
This compound belongs to the class of organic compounds known as tryptamines and derivatives. These are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Tryptamines and derivatives
Direct Parent
Tryptamines and derivatives
Alternative Parents
3-alkylindoles / Aralkylamines / Substituted pyrroles / Benzenoids / Triazoles / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Tryptamine / 3-alkylindole / Indole / Aralkylamine / Substituted pyrrole / Benzenoid / Azole / Pyrrole / 1,2,4-triazole / Heteroaromatic compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tryptamines (CHEBI:48273)

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 subst...
Gene Name
HTR1D
Uniprot ID
P28221
Uniprot Name
5-hydroxytryptamine receptor 1D
Molecular Weight
41906.38 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. Longmore J, Hargreaves RJ, Boulanger CM, Brown MJ, Desta B, Ferro A, Schofield WN, Taylor AA, Hill RG: Comparison of the vasoconstrictor properties of the 5-HT1D-receptor agonists rizatriptan (MK-462) and sumatriptan in human isolated coronary artery: outcome of two independent studies using different experimental protocols. Funct Neurol. 1997 Jan-Feb;12(1):3-9. [PubMed:9127118]
  3. Longmore J, Boulanger CM, Desta B, Hill RG, Schofield WN, Taylor AA: 5-HT1D receptor agonists and human coronary artery reactivity in vitro: crossover comparisons of 5-HT and sumatriptan with rizatriptan and L-741,519. Br J Clin Pharmacol. 1996 Oct;42(4):431-41. [PubMed:8904614]
  4. Sciberras DG, Polvino WJ, Gertz BJ, Cheng H, Stepanavage M, Wittreich J, Olah T, Edwards M, Mant T: Initial human experience with MK-462 (rizatriptan): a novel 5-HT1D agonist. Br J Clin Pharmacol. 1997 Jan;43(1):49-54. [PubMed:9056052]
  5. Williamson DJ, Hill RG, Shepheard SL, Hargreaves RJ: The anti-migraine 5-HT(1B/1D) agonist rizatriptan inhibits neurogenic dural vasodilation in anaesthetized guinea-pigs. Br J Pharmacol. 2001 Aug;133(7):1029-34. [PubMed:11487512]
  6. Wackenfors A, Jarvius M, Ingemansson R, Edvinsson L, Malmsjo M: Triptans induce vasoconstriction of human arteries and veins from the thoracic wall. J Cardiovasc Pharmacol. 2005 May;45(5):476-84. [PubMed:15821444]
  7. Wellington K, Plosker GL: Rizatriptan: an update of its use in the management of migraine. Drugs. 2002;62(10):1539-74. [PubMed:12093318]
  8. Wellington K, Jarvis B: Spotlight on rizatriptan in migraine. CNS Drugs. 2002;16(10):715-20. [PubMed:12269863]
  9. Ikemoto F, Toru T, Aijima H, Natsumeda Y: [Rizatriptan (Maxalt), a new entity of triptan for migraine: pharmacology and therapeutic relevance]. Nihon Yakurigaku Zasshi. 2004 Apr;123(4):295-302. [PubMed:15056946]
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 subst...
Gene Name
HTR1B
Uniprot ID
P28222
Uniprot Name
5-hydroxytryptamine receptor 1B
Molecular Weight
43567.535 Da
References
  1. Wellington K, Plosker GL: Rizatriptan: an update of its use in the management of migraine. Drugs. 2002;62(10):1539-74. [PubMed:12093318]
  2. Wellington K, Jarvis B: Spotlight on rizatriptan in migraine. CNS Drugs. 2002;16(10):715-20. [PubMed:12269863]
  3. Ikemoto F, Toru T, Aijima H, Natsumeda Y: [Rizatriptan (Maxalt), a new entity of triptan for migraine: pharmacology and therapeutic relevance]. Nihon Yakurigaku Zasshi. 2004 Apr;123(4):295-302. [PubMed:15056946]
  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. Williamson DJ, Hill RG, Shepheard SL, Hargreaves RJ: The anti-migraine 5-HT(1B/1D) agonist rizatriptan inhibits neurogenic dural vasodilation in anaesthetized guinea-pigs. Br J Pharmacol. 2001 Aug;133(7):1029-34. [PubMed:11487512]
  7. Wackenfors A, Jarvius M, Ingemansson R, Edvinsson L, Malmsjo M: Triptans induce vasoconstriction of human arteries and veins from the thoracic wall. J Cardiovasc Pharmacol. 2005 May;45(5):476-84. [PubMed:15821444]
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 trig...
Gene Name
HTR1F
Uniprot ID
P30939
Uniprot Name
5-hydroxytryptamine receptor 1F
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. 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]
  3. 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]
  4. Wainscott DB, Johnson KW, Phebus LA, Schaus JM, Nelson DL: Human 5-HT1F receptor-stimulated [35S]GTPgammaS binding: correlation with inhibition of guinea pig dural plasma protein extravasation. Eur J Pharmacol. 1998 Jul 3;352(1):117-24. [PubMed:9718276]
  5. 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]

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...
Gene Name
MAOA
Uniprot ID
P21397
Uniprot Name
Amine oxidase [flavin-containing] A
Molecular Weight
59681.27 Da
References
  1. Iwasa T, Sano H, Sugiura A, Uchiyama N, Hara K, Okochi H, Nakagawa K, Yasumori T, Ishizaki T: An in vitro interethnic comparison of monoamine oxidase activities between Japanese and Caucasian livers using rizatriptan, a serotonin receptor 1B/1D agonist, as a model drug. Br J Clin Pharmacol. 2003 Nov;56(5):537-44. [PubMed:14651728]
  2. Van Haarst AD, Van Gerven JM, Cohen AF, De Smet M, Sterrett A, Birk KL, Fisher AL, De Puy ME, Goldberg MR, Musson DG: The effects of moclobemide on the pharmacokinetics of the 5-HT1B/1D agonist rizatriptan in healthy volunteers. Br J Clin Pharmacol. 1999 Aug;48(2):190-6. [PubMed:10417495]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Sternieri E, Coccia CP, Pinetti D, Ferrari A: Pharmacokinetics and interactions of headache medications, part I: introduction, pharmacokinetics, metabolism and acute treatments. Expert Opin Drug Metab Toxicol. 2006 Dec;2(6):961-79. [PubMed:17125411]

Drug created on June 13, 2005 07:24 / Updated on November 13, 2017 21:49