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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyRizatriptan
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
Structure for DB00953 (Rizatriptan)
- 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
Ingredient UNII CAS InChI Key Rizatriptan benzoate WR978S7QHH 145202-66-0 JPRXYLQNJJVCMZ-UHFFFAOYSA-N - Product Images
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Act Rizatriptan Tablet 5 mg Oral Actavis Pharma Company Not applicable Not applicable Canada 
Act Rizatriptan Tablet 10 mg Oral Actavis Pharma Company 2012-06-14 Not applicable Canada Act Rizatriptan ODT Tablet, orally disintegrating 10 mg Oral Actavis Pharma Company 2012-01-30 Not applicable Canada Act Rizatriptan ODT Tablet, orally disintegrating 5 mg Oral Actavis Pharma Company 2012-01-30 Not applicable Canada Maxalt Tablet 5 mg/1 Oral Merck Sharp & Dohme Limited 1998-06-29 Not applicable US 
Maxalt Tablet 10 mg/1 Oral Rebel Distributors 1998-06-29 Not applicable US Maxalt Tablet 10 mg/1 Oral Stat Rx USA 1998-06-29 2018-02-08 US Maxalt Tablet 10 mg/1 Oral Physicians Total Care, Inc. 2007-08-24 Not applicable US Maxalt Tablet 5 mg Oral Merck Ltd. 1999-08-31 2013-07-15 Canada Maxalt Tablet 10 mg/1 Oral Merck Sharp & Dohme Limited 1998-06-29 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Apo-rizatriptan Tablet 10 mg Oral Apotex Corporation 2012-09-27 Not applicable Canada Apo-rizatriptan Tablet 5 mg Oral Apotex Corporation 2013-03-06 Not applicable Canada Apo-rizatriptan Rpd Tablet, orally disintegrating 10 mg Oral Apotex Corporation 2013-09-10 Not applicable Canada Apo-rizatriptan Rpd Tablet, orally disintegrating 5 mg Oral Apotex Corporation 2013-09-10 Not applicable Canada Auro-rizatriptan Tablet 10 mg Oral Auro Pharma Inc 2016-04-12 Not applicable Canada Auro-rizatriptan ODT Tablet, orally disintegrating 10 mg Oral Auro Pharma Inc Not applicable Not applicable Canada Auro-rizatriptan ODT Tablet, orally disintegrating 5 mg Oral Auro Pharma Inc Not applicable Not applicable Canada Ccp-rizatriptan ODT Tablet, orally disintegrating 10 mg Oral Cellchem Pharmaceuticals Inc. Not applicable Not applicable Canada Ccp-rizatriptan ODT Tablet, orally disintegrating 5 mg Oral Cellchem Pharmaceuticals Inc. Not applicable Not applicable Canada Dom-rizatriptan Rdt Tablet, orally disintegrating 5 mg Oral Dominion Pharmacal Not applicable Not applicable Canada - International/Other Brands
- Maxalt MLT
- Categories
- Amines
- Analgesics
- Antimigraine Preparations
- Biogenic Amines
- Biogenic Monoamines
- Indoles
- Migraine Disorders
- Nervous System
- Neurotransmitter Agents
- Selective Serotonin 5-HT1 Receptor Agonists
- Selective Serotonin Agonists
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Serotonin 5-HT1 Receptor Agonists
- Serotonin Agents
- Serotonin Modulators
- Serotonin Receptor Agonists
- Serotonin-1b and Serotonin-1d Receptor Agonist
- Triptans
- 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.
- Associated Conditions
- 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.
Target Actions Organism A5-hydroxytryptamine receptor 1D agonistHuman A5-hydroxytryptamine receptor 1B agonistHuman A5-hydroxytryptamine receptor 1F agonistHuman - 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/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Guanine nucleotide-binding protein G(I)/G(S)/G(T) subunit beta-3 --- (T;T) / (C;T) T Allele Effect Directly Studied Patients with this genotype have an increased likelihood of responding to rizatriptan when treating (condition: cluster headache). Details
Interactions
- Drug Interactions
Drug Interaction Drug group 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline The metabolism of Rizatriptan can be decreased when combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline. Experimental Abiraterone The serum concentration of Rizatriptan can be increased when it is combined with Abiraterone. Approved Acepromazine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Acepromazine. Approved, Vet Approved Aceprometazine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Aceprometazine. Approved Acetophenazine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Acetophenazine. Approved Almotriptan The risk or severity of adverse effects can be increased when Almotriptan is combined with Rizatriptan. Approved, Investigational Alosetron Alosetron may increase the serotonergic activities of Rizatriptan. Approved, Withdrawn Amisulpride The risk or severity of adverse effects can be increased when Rizatriptan is combined with Amisulpride. Approved, Investigational Amitriptyline The risk or severity of adverse effects can be increased when Amitriptyline is combined with Rizatriptan. Approved Amoxapine The risk or severity of adverse effects can be increased when Amoxapine is combined with Rizatriptan. Approved Amperozide The risk or severity of adverse effects can be increased when Rizatriptan is combined with Amperozide. Experimental Amphetamine The serum concentration of Rizatriptan can be increased when it is combined with Amphetamine. Approved, Illicit, Investigational Aripiprazole The risk or severity of adverse effects can be increased when Rizatriptan is combined with Aripiprazole. Approved, Investigational Asenapine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Asenapine. Approved Azaperone The risk or severity of adverse effects can be increased when Rizatriptan is combined with Azaperone. Investigational, Vet Approved Azithromycin The metabolism of Rizatriptan can be decreased when combined with Azithromycin. Approved Benmoxin The serum concentration of Rizatriptan can be increased when it is combined with Benmoxin. Withdrawn Benperidol The risk or severity of adverse effects can be increased when Rizatriptan is combined with Benperidol. Approved, Investigational Bifeprunox The risk or severity of adverse effects can be increased when Rizatriptan is combined with Bifeprunox. Investigational Bortezomib The metabolism of Rizatriptan can be decreased when combined with Bortezomib. Approved, Investigational Brexpiprazole The risk or severity of adverse effects can be increased when Rizatriptan is combined with Brexpiprazole. Approved, Investigational Brofaromine The serum concentration of Rizatriptan can be increased when it is combined with Brofaromine. Experimental Bromocriptine Bromocriptine may increase the vasoconstricting activities of Rizatriptan. Approved, Investigational Bromperidol The risk or severity of adverse effects can be increased when Rizatriptan is combined with Bromperidol. Approved, Investigational Buspirone The risk or severity of adverse effects can be increased when Buspirone is combined with Rizatriptan. Approved, Investigational Butaperazine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Butaperazine. Experimental Cabergoline Cabergoline may increase the vasoconstricting activities of Rizatriptan. Approved Caffeine The metabolism of Rizatriptan can be decreased when combined with Caffeine. Approved Cariprazine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Cariprazine. Approved, Investigational Caroxazone The serum concentration of Rizatriptan can be increased when it is combined with Caroxazone. Withdrawn Chlorproethazine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Chlorproethazine. Experimental Chlorpromazine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Chlorpromazine. Approved, Investigational, Vet Approved Chlorprothixene The risk or severity of adverse effects can be increased when Rizatriptan is combined with Chlorprothixene. Approved, Investigational, Withdrawn Citalopram The risk or severity of adverse effects can be increased when Citalopram is combined with Rizatriptan. Approved Clomipramine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Clomipramine. Approved, Investigational, Vet Approved Clopenthixol The risk or severity of adverse effects can be increased when Rizatriptan is combined with Clopenthixol. Experimental Clothiapine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Clothiapine. Experimental Clotrimazole The metabolism of Rizatriptan can be decreased when combined with Clotrimazole. Approved, Vet Approved Clozapine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Clozapine. Approved Curcumin The metabolism of Rizatriptan can be decreased when combined with Curcumin. Approved, Investigational Cyamemazine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Cyamemazine. Approved Cyclobenzaprine The risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Rizatriptan. Approved Cyproterone acetate The serum concentration of Rizatriptan can be decreased when it is combined with Cyproterone acetate. Approved, Investigational Dapiprazole The risk or severity of adverse effects can be increased when Rizatriptan is combined with Dapiprazole. Approved Dapoxetine The risk or severity of adverse effects can be increased when Dapoxetine is combined with Rizatriptan. Investigational Deferasirox The serum concentration of Rizatriptan can be increased when it is combined with Deferasirox. Approved, Investigational Desipramine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Desipramine. Approved, Investigational Desvenlafaxine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Desvenlafaxine. Approved, Investigational Dextromethorphan The risk or severity of adverse effects can be increased when Dextromethorphan is combined with Rizatriptan. Approved Dihydroergotamine Dihydroergotamine may increase the vasoconstricting activities of Rizatriptan. Approved, Investigational Dixyrazine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Dixyrazine. Experimental Dolasetron Dolasetron may increase the serotonergic activities of Rizatriptan. Approved, Investigational Dosulepin The metabolism of Rizatriptan can be decreased when combined with Dosulepin. Approved Doxepin The risk or severity of adverse effects can be increased when Rizatriptan is combined with Doxepin. Approved, Investigational Droperidol The risk or severity of adverse effects can be increased when Rizatriptan is combined with Droperidol. Approved, Vet Approved Droxidopa Rizatriptan may increase the hypertensive activities of Droxidopa. Approved, Investigational Duloxetine The risk or severity of adverse effects can be increased when Duloxetine is combined with Rizatriptan. Approved Ecopipam The risk or severity of adverse effects can be increased when Rizatriptan is combined with Ecopipam. Investigational Eletriptan The risk or severity of adverse effects can be increased when Eletriptan is combined with Rizatriptan. Approved, Investigational Ergoloid mesylate Ergoloid mesylate may increase the vasoconstricting activities of Rizatriptan. Approved Ergonovine Ergonovine may increase the vasoconstricting activities of Rizatriptan. Approved Ergotamine Ergotamine may increase the vasoconstricting activities of Rizatriptan. Approved Escitalopram The risk or severity of adverse effects can be increased when Rizatriptan is combined with Escitalopram. Approved, Investigational Fencamfamine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Fencamfamine. Approved, Illicit, Withdrawn Fentanyl The risk or severity of adverse effects can be increased when Fentanyl is combined with Rizatriptan. Approved, Illicit, Investigational, Vet Approved Fluanisone The risk or severity of adverse effects can be increased when Rizatriptan is combined with Fluanisone. Experimental Fluoxetine The risk or severity of adverse effects can be increased when Fluoxetine is combined with Rizatriptan. Approved, Vet Approved Flupentixol The risk or severity of adverse effects can be increased when Rizatriptan is combined with Flupentixol. Approved, Investigational, Withdrawn Fluphenazine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Fluphenazine. Approved Fluspirilene The risk or severity of adverse effects can be increased when Rizatriptan is combined with Fluspirilene. Approved, Investigational Fluvoxamine The metabolism of Rizatriptan can be decreased when combined with Fluvoxamine. Approved, Investigational Frovatriptan The risk or severity of adverse effects can be increased when Rizatriptan is combined with Frovatriptan. Approved, Investigational Furazolidone The metabolism of Rizatriptan can be decreased when combined with Furazolidone. Approved, Investigational, Vet Approved Granisetron Granisetron may increase the serotonergic activities of Rizatriptan. Approved, Investigational Haloperidol The risk or severity of adverse effects can be increased when Rizatriptan is combined with Haloperidol. Approved Harmaline The serum concentration of Rizatriptan can be increased when it is combined with Harmaline. Experimental Hydracarbazine The serum concentration of Rizatriptan can be increased when it is combined with Hydracarbazine. Experimental Iloperidone The risk or severity of adverse effects can be increased when Rizatriptan is combined with Iloperidone. Approved Imipramine The risk or severity of adverse effects can be increased when Imipramine is combined with Rizatriptan. Approved Iproclozide The serum concentration of Rizatriptan can be increased when it is combined with Iproclozide. Withdrawn Iproniazid The metabolism of Rizatriptan can be decreased when combined with Iproniazid. Withdrawn Isocarboxazid The serum concentration of Rizatriptan can be increased when it is combined with Isocarboxazid. Approved L-Tryptophan L-Tryptophan may increase the serotonergic activities of Rizatriptan. Approved, Nutraceutical, Withdrawn Lamotrigine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Lamotrigine. Approved, Investigational Levomilnacipran The risk or severity of adverse effects can be increased when Rizatriptan is combined with Levomilnacipran. Approved, Investigational Lidocaine The metabolism of Rizatriptan can be decreased when combined with Lidocaine. Approved, Vet Approved Linezolid The risk or severity of adverse effects can be increased when Linezolid is combined with Rizatriptan. Approved, Investigational Lithium The risk or severity of adverse effects can be increased when Rizatriptan is combined with Lithium. Approved Lobeglitazone The metabolism of Rizatriptan can be decreased when combined with Lobeglitazone. Approved, Investigational Lorcaserin The risk or severity of adverse effects can be increased when Rizatriptan is combined with Lorcaserin. Approved Loxapine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Loxapine. Approved Lurasidone The risk or severity of adverse effects can be increased when Rizatriptan is combined with Lurasidone. Approved, Investigational Maprotiline The risk or severity of adverse effects can be increased when Maprotiline is combined with Rizatriptan. Approved, Investigational Mebanazine The serum concentration of Rizatriptan can be increased when it is combined with Mebanazine. Withdrawn Melperone The risk or severity of adverse effects can be increased when Rizatriptan is combined with Melperone. Approved, Investigational Mesoridazine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Mesoridazine. Approved, Investigational Methadone The risk or severity of adverse effects can be increased when Methadone is combined with Rizatriptan. Approved Methotrimeprazine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Methotrimeprazine. Approved, Investigational Methylene blue The serum concentration of Rizatriptan can be increased when it is combined with Methylene blue. Approved, Investigational Methylergometrine Methylergometrine may increase the vasoconstricting activities of Rizatriptan. Approved Metoclopramide The risk or severity of adverse effects can be increased when Rizatriptan is combined with Metoclopramide. Approved, Investigational Mexiletine The metabolism of Rizatriptan can be decreased when combined with Mexiletine. Approved, Investigational Midostaurin The metabolism of Rizatriptan can be decreased when combined with Midostaurin. Approved, Investigational Milnacipran The risk or severity of adverse effects can be increased when Rizatriptan is combined with Milnacipran. Approved, Investigational Minaprine The metabolism of Rizatriptan can be decreased when combined with Minaprine. Approved Mirtazapine The risk or severity of adverse effects can be increased when Mirtazapine is combined with Rizatriptan. Approved Moclobemide The serum concentration of Rizatriptan can be increased when it is combined with Moclobemide. Approved, Investigational Molindone The risk or severity of adverse effects can be increased when Rizatriptan is combined with Molindone. Approved Moperone The risk or severity of adverse effects can be increased when Rizatriptan is combined with Moperone. Experimental Mosapramine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Mosapramine. Experimental Naratriptan The risk or severity of adverse effects can be increased when Naratriptan is combined with Rizatriptan. Approved, Investigational Nefazodone The risk or severity of adverse effects can be increased when Rizatriptan is combined with Nefazodone. Approved, Withdrawn Nevirapine The metabolism of Rizatriptan can be decreased when combined with Nevirapine. Approved Nialamide The metabolism of Rizatriptan can be decreased when combined with Nialamide. Withdrawn Nortriptyline The risk or severity of adverse effects can be increased when Nortriptyline is combined with Rizatriptan. Approved Octamoxin The serum concentration of Rizatriptan can be increased when it is combined with Octamoxin. Withdrawn Olanzapine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Olanzapine. Approved, Investigational Ondansetron Ondansetron may increase the serotonergic activities of Rizatriptan. Approved Osanetant The risk or severity of adverse effects can be increased when Rizatriptan is combined with Osanetant. Investigational Osimertinib The serum concentration of Rizatriptan can be decreased when it is combined with Osimertinib. Approved Oxypertine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Oxypertine. Experimental Paliperidone The risk or severity of adverse effects can be increased when Rizatriptan is combined with Paliperidone. Approved Palonosetron Palonosetron may increase the serotonergic activities of Rizatriptan. Approved, Investigational Pargyline The metabolism of Rizatriptan can be decreased when combined with Pargyline. Approved Paroxetine The risk or severity of adverse effects can be increased when Paroxetine is combined with Rizatriptan. Approved, Investigational Peginterferon alfa-2b The serum concentration of Rizatriptan can be increased when it is combined with Peginterferon alfa-2b. Approved Penfluridol The risk or severity of adverse effects can be increased when Rizatriptan is combined with Penfluridol. Experimental Perazine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Perazine. Approved, Investigational Perospirone The risk or severity of adverse effects can be increased when Rizatriptan is combined with Perospirone. Approved Perphenazine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Perphenazine. Approved Pethidine The risk or severity of adverse effects can be increased when Pethidine is combined with Rizatriptan. Approved Phenelzine The serum concentration of Rizatriptan can be increased when it is combined with Phenelzine. Approved Pheniprazine The serum concentration of Rizatriptan can be increased when it is combined with Pheniprazine. Withdrawn Phenoxypropazine The serum concentration of Rizatriptan can be increased when it is combined with Phenoxypropazine. Withdrawn Pimozide The risk or severity of adverse effects can be increased when Rizatriptan is combined with Pimozide. Approved Pipamperone The risk or severity of adverse effects can be increased when Rizatriptan is combined with Pipamperone. Approved, Investigational Pipotiazine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Pipotiazine. Approved, Investigational Pirlindole The metabolism of Rizatriptan can be decreased when combined with Pirlindole. Approved Pivhydrazine The serum concentration of Rizatriptan can be increased when it is combined with Pivhydrazine. Withdrawn Procaine The serum concentration of Rizatriptan can be increased when it is combined with Procaine. Approved, Investigational, Vet Approved Procarbazine The serum concentration of Rizatriptan can be increased when it is combined with Procarbazine. Approved, Investigational Prochlorperazine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Prochlorperazine. Approved, Vet Approved Promazine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Promazine. Approved, Vet Approved Promethazine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Promethazine. Approved, Investigational Propericiazine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Propericiazine. Approved, Investigational Propranolol The serum concentration of Rizatriptan can be increased when it is combined with Propranolol. Approved, Investigational Prothipendyl The risk or severity of adverse effects can be increased when Rizatriptan is combined with Prothipendyl. Investigational Protriptyline The risk or severity of adverse effects can be increased when Protriptyline is combined with Rizatriptan. Approved Quetiapine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Quetiapine. Approved Raclopride The risk or severity of adverse effects can be increased when Rizatriptan is combined with Raclopride. Investigational Rasagiline The serum concentration of Rizatriptan can be increased when it is combined with Rasagiline. Approved Remoxipride The risk or severity of adverse effects can be increased when Rizatriptan is combined with Remoxipride. Approved, Withdrawn Reserpine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Reserpine. Approved, Investigational Risperidone The risk or severity of adverse effects can be increased when Rizatriptan is combined with Risperidone. Approved, Investigational Ritanserin The risk or severity of adverse effects can be increased when Rizatriptan is combined with Ritanserin. Investigational Ropinirole The metabolism of Rizatriptan can be decreased when combined with Ropinirole. Approved, Investigational Rucaparib The metabolism of Rizatriptan can be decreased when combined with Rucaparib. Approved, Investigational Safrazine The serum concentration of Rizatriptan can be increased when it is combined with Safrazine. Withdrawn Selegiline The serum concentration of Rizatriptan can be increased when it is combined with Selegiline. Approved, Investigational, Vet Approved Sertindole The risk or severity of adverse effects can be increased when Rizatriptan is combined with Sertindole. Approved, Investigational, Withdrawn Sertraline The risk or severity of adverse effects can be increased when Rizatriptan is combined with Sertraline. Approved Simeprevir The metabolism of Rizatriptan can be decreased when combined with Simeprevir. Approved Sulpiride The risk or severity of adverse effects can be increased when Rizatriptan is combined with Sulpiride. Approved, Investigational Sultopride The risk or severity of adverse effects can be increased when Rizatriptan is combined with Sultopride. Experimental Sumatriptan The risk or severity of adverse effects can be increased when Sumatriptan is combined with Rizatriptan. Approved, Investigational Tapentadol The risk or severity of adverse effects can be increased when Rizatriptan is combined with Tapentadol. Approved Tedizolid Phosphate Tedizolid Phosphate may increase the serotonergic activities of Rizatriptan. Approved Tenofovir disoproxil The metabolism of Rizatriptan can be decreased when combined with Tenofovir disoproxil. Approved, Investigational Teriflunomide The serum concentration of Rizatriptan can be decreased when it is combined with Teriflunomide. Approved Tetrahydropalmatine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Tetrahydropalmatine. Investigational Theophylline The metabolism of Rizatriptan can be decreased when combined with Theophylline. Approved Thiopropazate The risk or severity of adverse effects can be increased when Rizatriptan is combined with Thiopropazate. Experimental Thioproperazine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Thioproperazine. Approved Thioridazine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Thioridazine. Approved, Withdrawn Thiothixene The risk or severity of adverse effects can be increased when Rizatriptan is combined with Thiothixene. Approved Tiapride The risk or severity of adverse effects can be increased when Rizatriptan is combined with Tiapride. Approved, Investigational Ticlopidine The metabolism of Rizatriptan can be decreased when combined with Ticlopidine. Approved Toloxatone The metabolism of Rizatriptan can be decreased when combined with Toloxatone. Approved Tramadol The risk or severity of adverse effects can be increased when Tramadol is combined with Rizatriptan. Approved, Investigational Tranylcypromine The serum concentration of Rizatriptan can be increased when it is combined with Tranylcypromine. Approved, Investigational Trazodone The risk or severity of adverse effects can be increased when Trazodone is combined with Rizatriptan. Approved, Investigational Trifluoperazine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Trifluoperazine. Approved, Investigational Trifluperidol The risk or severity of adverse effects can be increased when Rizatriptan is combined with Trifluperidol. Experimental Triflupromazine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Triflupromazine. Approved, Vet Approved Trimipramine The risk or severity of adverse effects can be increased when Trimipramine is combined with Rizatriptan. Approved Tropisetron Tropisetron may increase the serotonergic activities of Rizatriptan. Approved, Investigational Vemurafenib The serum concentration of Rizatriptan can be increased when it is combined with Vemurafenib. Approved Venlafaxine The risk or severity of adverse effects can be increased when Venlafaxine is combined with Rizatriptan. Approved Veralipride The risk or severity of adverse effects can be increased when Rizatriptan is combined with Veralipride. Experimental Vilazodone The risk or severity of adverse effects can be increased when Vilazodone is combined with Rizatriptan. Approved Vortioxetine The risk or severity of adverse effects can be increased when Vortioxetine is combined with Rizatriptan. Approved, Investigational Ziprasidone The risk or severity of adverse effects can be increased when Rizatriptan is combined with Ziprasidone. Approved Zolmitriptan The risk or severity of adverse effects can be increased when Zolmitriptan is combined with Rizatriptan. Approved, Investigational Zotepine The risk or severity of adverse effects can be increased when Rizatriptan is combined with Zotepine. Approved, Investigational, Withdrawn Zucapsaicin The metabolism of Rizatriptan can be decreased when combined with Zucapsaicin. Approved, Investigational Zuclopenthixol The 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
- Wellington K, Plosker GL: Rizatriptan: an update of its use in the management of migraine. Drugs. 2002;62(10):1539-74. [PubMed:12093318]
- Wellington K, Jarvis B: Spotlight on rizatriptan in migraine. CNS Drugs. 2002;16(10):715-20. [PubMed:12269863]
- 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]
- 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]
- 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
- HMDB0015088
- 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
Phase Status Purpose Conditions Count 1 Completed Treatment Migraine Disorders 1 2 Completed Treatment Migraines 1 2, 3 Recruiting Treatment Migrainous Vertigo / Vestibular Migraine 1 3 Completed Treatment Acute Migraine With or Without Aura in Adolescents 1 3 Completed Treatment Migraine Disorders 1 3 Completed Treatment Migraine, Acute 2 3 Completed Treatment Migraines 4 3 Completed Treatment Migrainous Headache 4 4 Completed Basic Science Episodic Migraine 1 4 Completed Treatment Migraines 3 4 Completed Treatment Migrainous Headache 1 Not Available Completed Basic Science Migraines 1 Not Available Withdrawn Treatment Chronic Post-traumatic Headache 1
Pharmacoeconomics
- Manufacturers
- Merck and co inc
- Packagers
- Catalent Pharma Solutions
- Chunghwa Chemical Synthesis and Biotech Co. Ltd.
- Diversified Healthcare Services Inc.
- Lake Erie Medical and Surgical Supply
- Merck & Co.
- Nucare Pharmaceuticals Inc.
- Physicians Total Care Inc.
- Scherer Drug Delivery Systems Ltd.
- Dosage forms
Form Route Strength Tablet Oral 5 mg Tablet Oral 10 mg/1 Tablet Oral 10 mg Tablet, orally disintegrating Oral 10 mg Tablet, orally disintegrating Oral 5 mg Film, soluble Oral 10 1/1 Film, soluble Oral 5 1/1 Tablet, film coated Oral 10 mg/1 Tablet, film coated Oral 5 mg/1 Tablet Oral 5 mg/1 Tablet, orally disintegrating Oral 10 mg/1 Tablet, orally disintegrating Oral 5 mg/1 - Prices
Unit description Cost Unit Maxalt 12 10 mg tablet Box 333.27USD box Maxalt 12 5 mg tablet Box 333.27USD box Maxalt-MLT 3 5 mg Dispersible Tablet Box 286.96USD box Maxalt 9 5 mg tablet Box 203.46USD box Maxalt 6 5 mg tablet Box 107.44USD box Maxalt-MLT 3 10 mg Dispersible Tablet Box 83.32USD box Maxalt mlt 10 mg tablet 26.7USD tablet Maxalt mlt 5 mg tablet 26.7USD tablet Maxalt 10 mg tablet 25.31USD tablet Maxalt 5 mg tablet 22.98USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) US5602162 No 1994-02-11 2014-02-11 US US5298520 No 1995-06-29 2012-06-29 US CA2060139 No 1998-12-01 2012-01-28 Canada
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 178-180 °C Not Available water solubility 42 mg/mL (for free base) Not Available logP 1.4 Not Available - Predicted Properties
Property Value Source Water Solubility 0.338 mg/mL ALOGPS logP 1.67 ALOGPS logP 1.77 ChemAxon logS -2.9 ALOGPS pKa (Strongest Acidic) 17.24 ChemAxon pKa (Strongest Basic) 9.56 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 49.74 Å2 ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 93.13 m3·mol-1 ChemAxon Polarizability 30 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9406 Caco-2 permeable + 0.5547 P-glycoprotein substrate Substrate 0.7478 P-glycoprotein inhibitor I Non-inhibitor 0.8752 P-glycoprotein inhibitor II Non-inhibitor 0.7244 Renal organic cation transporter Inhibitor 0.7394 CYP450 2C9 substrate Non-substrate 0.8572 CYP450 2D6 substrate Non-substrate 0.6765 CYP450 3A4 substrate Substrate 0.5574 CYP450 1A2 substrate Non-inhibitor 0.9149 CYP450 2C9 inhibitor Non-inhibitor 0.9063 CYP450 2D6 inhibitor Non-inhibitor 0.8913 CYP450 2C19 inhibitor Non-inhibitor 0.9515 CYP450 3A4 inhibitor Non-inhibitor 0.9688 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.956 Ames test AMES toxic 0.5644 Carcinogenicity Non-carcinogens 0.9133 Biodegradation Not ready biodegradable 0.9439 Rat acute toxicity 2.5433 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7051 hERG inhibition (predictor II) Non-inhibitor 0.7265
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-0udi-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
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- 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]
- 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]
- 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]
- 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]
- 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]
- Wellington K, Plosker GL: Rizatriptan: an update of its use in the management of migraine. Drugs. 2002;62(10):1539-74. [PubMed:12093318]
- Wellington K, Jarvis B: Spotlight on rizatriptan in migraine. CNS Drugs. 2002;16(10):715-20. [PubMed:12269863]
- 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
- Wellington K, Plosker GL: Rizatriptan: an update of its use in the management of migraine. Drugs. 2002;62(10):1539-74. [PubMed:12093318]
- Wellington K, Jarvis B: Spotlight on rizatriptan in migraine. CNS Drugs. 2002;16(10):715-20. [PubMed:12269863]
- 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]
- 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]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- 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]
- 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
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- 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]
- 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]
- 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]
- 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
- 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]
- 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
- 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 June 17, 2018 20:13