Rizatriptan

Identification

Summary

Rizatriptan is a triptan used to treat migraines with or without aura.

Brand Names
Maxalt, RizaFilm, Rizaport
Generic Name
Rizatriptan
DrugBank Accession Number
DB00953
Background

Rizatriptan is a second-generation triptan 3 and a selective 5-HT1B and 5-HT1D receptor agonist.9 Used in the treatment of migraines, rizatriptan was first approved in the US in 1998.9 Rizatriptan is available in oral tablets, orally disintegrating tablets (wafers), and oral film formulations.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 269.3449
Monoisotopic: 269.164045633
Chemical Formula
C15H19N5
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

Pharmacology

Indication

Rizatriptan is indicated for the acute treatment of diagnosed migraine with or without aura.9,10,12,13 Rizatriptan is not indicated for the prophylactic therapy of migraine nor the treatment of cluster headache.9

In Canada, rizatriptan is approved in adults.12,13 In the US, the oral tablet formulations are used in patients six years of age and older 9 and the oral film formation is approved for patients 12 years of age and older weighing 40 kg or more.10

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofMigraine with aura••••••••••••••••••••••• ••••••••••• •• •• •• ••••••••
Treatment ofMigraine with aura••••••••••••••••••••••• •••••• •••••••••••••••• ••••••• •••••• ••••••••••••••
Treatment ofMigraine without aura••••••••••••••••••••••• ••••••••••• •• •• •• ••••••••
Treatment ofMigraine without aura••••••••••••••••••••••• •••••• •••••••••••••••• ••••••• •••••• ••••••••••••••
Treatment ofAcute migraine with aura••••••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Rizatriptan relieves migraine-associated symptoms.1,5,9 Rizatriptan is reported to reach the maximum plasma concentrations more quickly and produces a more rapid onset of pain relief than other triptans, such as sumatriptan;2,3,5 however, it has a relatively shorter elimination half-life than other triptans.5 Rizatriptan causes transient increases in blood pressure to some extent.1 In vitro, rizatriptan was shown to contract isolated human coronary arteries; however, since the EC50 for this effect is high, rizatriptan is not expected to cause myocardial ischemia at therapeutic plasma concentrations in patients with normal coronary circulation.3

Rizatriptan has a weak affinity for other 5-HT1 receptor subtypes (5-HT1A, 5-HT1E, 5-HT1F) and the 5-HT7 receptor but has no significant activity at 5-HT2, 5-HT3, alpha- and beta-adrenergic, dopaminergic, histaminergic, muscarinic or benzodiazepine receptors.12

Mechanism of action

There are several physiological and molecular processes implicated in the pathophysiology of migraine. Vasodilation of intracranial extracerebral blood vessels, particularly those supplying the dura mater, has been associated with migraine pain.1,5 Activation of the trigeminovascular system leads to the release of vasoactive neuropeptides (such as substance P, calcitonin gene-related peptide (CGRP), and neurokinin A) from the trigeminal nerve innervating the intracranial vessels and dura mater. Vasoactive neuropeptides cause perivascular inflammation and vasodilation in the periphery. Migraine-associated nausea and vomiting are thought to arise from the activation of central and nociceptive sensory neurons that project to autonomic brain-stem nuclei and higher subcortical and cortical pain processing centres.1 An imbalance in serotonin (5-HT) levels has also been documented: 5-HT binds to 5-HT1B and 5-HT1D receptors to promote trigeminal neuronal firing and vasoconstriction.1,8

Rizatriptan is a selective agonist at the 5-HT1B and 5-HT1D receptors on intracranial blood vessels and sensory nerves of the trigeminal system. It binds to these receptors with high affinity.9 The exact mechanism of action of rizatriptan has not been fully elucidated; however, several documented pharmacological actions of rizatriptan may contribute to its antimigraine effects. Rizatriptan causes vasoconstriction of intracranial extracerebral blood vessels, which is thought to occur primarily via 5-HT1B receptors. Rizatriptan also inhibits nociceptive neurotransmission in trigeminal pain pathways. It attenuates the release of vasoactive neuropeptides by the trigeminal nerve, which is thought to occur via neurogenic and central 5-HT1D receptors.1,3,5 Rizatriptan inhibited neurogenic dural vasodilation and plasma protein extravasation in animal studies.1,7,3,5

TargetActionsOrganism
A5-hydroxytryptamine receptor 1B
agonist
Humans
A5-hydroxytryptamine receptor 1D
agonist
Humans
U5-hydroxytryptamine receptor 1A
agonist
Humans
U5-hydroxytryptamine receptor 1E
agonist
Humans
U5-hydroxytryptamine receptor 1F
agonist
Humans
U5-hydroxytryptamine receptor 7
agonist
Humans
Absorption

Rizatriptan is readily absorbed (approximately 90%) following oral administration;1 however, the mean oral absolute bioavailability of the rizatriptan tablet is about 45%, owing to extensive first-pass metabolism. The Tmax is approximately one to 1.5 hours. The presence of a migraine headache did not appear to affect the absorption or pharmacokinetics of rizatriptan. Food has no significant effect on the bioavailability of rizatriptan but delays the time to reach peak concentration by an hour. In clinical trials, rizatriptan was administered without regard to food.9

The bioavailability and Cmax of rizatriptan were similar following the administration of rizatriptan tablets and rizatriptan orally disintegrating tablets. Still, the absorption rate is somewhat slower with orally disintegrating tablets, with Tmax delayed by up to 0.7 hours. The AUC of rizatriptan is approximately 30% higher in females than males. No accumulation occurred on multiple dosing.9

Volume of distribution

The mean volume of distribution is approximately 140 L in male subjects and 110 L in female subjects.9

Protein binding

Rizatriptan is minimally bound (14%) to plasma proteins.9

Metabolism

Rizatriptan primarily undergoes oxidative deamination mediated by monoamine oxidase-A (MAO-A) to form triazolomethyl-indole-3-acetic acid, which is not pharmacologically active. N-monodesmethyl-rizatriptan is a minor metabolite with a pharmacological activity comparable to the parent compound's. Plasma concentrations of N-monodesmethyl-rizatriptan are approximately 14% of those of the parent compound, which is eliminated at a similar rate. Other pharmacologically inactive minor metabolites include the N-oxide, the 6-hydroxy compound, and the sulfate conjugate of the 6-hydroxy metabolite.1,6,9

Hover over products below to view reaction partners

Route of elimination

Following oral administration of a single 10 mg of 14C-rizatriptan, the total radioactivity of the administered dose recovered over 120 hours in urine and feces was 82% and 12%, respectively. Following oral administration of 14C-rizatriptan, rizatriptan accounted for about 17% of circulating plasma radioactivity. 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.9

Half-life

The plasma half-life of rizatriptan in males and females ranges from two to three hours.9

Clearance

An early study involving healthy subject reported plasma clearance of 1042 mL/min in males and 821 mL/min in females; however, this difference in clearance rates is not thought to be clinically relevant.3,4

Adverse Effects
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Toxicity

The acute oral toxicity (LD50) was 2,227 mg/kg in rats and 700-1,631 mg/kg in mice.11

No overdoses of rizatriptan were reported in clinical trials. Some adult patients who received 40 mg of rizatriptan either a single dose or as two doses with a two-hour interdose interval had dizziness and somnolence. Syncope, dizziness, bradycardia including third degree AV block, vomiting, and/or incontinence were experienced by two adults who received a total cumulative doses of 80 mg (given within four hours) in a clinical pharmacology study. Some adolescent patients (aged 12 to 17 years old) receiving two 10-mg doses of orally disintegrating tablets of rizatriptan experienced abdominal discomfort, fatigue, and dyspnea.9

Based on the pharmacological properties of rizatriptan, hypertension and myocardial ischemia are possible after overdosage. Gastrointestinal decontamination, (i.e., gastric lavage followed by activated charcoal) should be considered in patients suspected of an overdose with rizatriptan. Clinical and electrocardiographic monitoring should be continued for at least 12 hours, even if clinical symptoms are not observed. The effects of hemo- or peritoneal dialysis on serum concentrations of rizatriptan are unknown.9

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
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirRizatriptan may decrease the excretion rate of Abacavir which could result in a higher serum level.
AcebutololRizatriptan may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Rizatriptan is combined with Aceclofenac.
AcemetacinThe risk or severity of hypertension can be increased when Rizatriptan is combined with Acemetacin.
AcetaminophenAcetaminophen may decrease the excretion rate of Rizatriptan which could result in a higher serum level.
Food Interactions
  • Take with or without food. Food has no significant effect on the bioavailability of rizatriptan but delays the time to reach peak concentration by an hour.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Rizatriptan benzoateWR978S7QHH145202-66-0JPRXYLQNJJVCMZ-UHFFFAOYSA-N
Product Images
International/Other Brands
Maxalt MLT / RizaFilm
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Act RizatriptanTablet10 mgOralTEVA Canada Limited2012-06-14Not applicableCanada flag
Act RizatriptanTablet5 mgOralTEVA Canada LimitedNot applicableNot applicableCanada flag
Act Rizatriptan ODTTablet, orally disintegrating5 mgOralActavis Pharma Company2012-01-302019-08-08Canada flag
Act Rizatriptan ODTTablet, orally disintegrating10 mgOralActavis Pharma Company2012-01-302019-08-08Canada flag
MaxaltTablet10 mg/1OralMerck Sharp & Dohme Corp.1998-06-29Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Accel-rizatriptan ODTTablet, orally disintegrating10 mgOralAccel Pharma Inc2019-10-07Not applicableCanada flag
Accel-rizatriptan ODTTablet, orally disintegrating5 mgOralAccel Pharma Inc2019-10-07Not applicableCanada flag
Ag-rizatriptan ODTTablet, orally disintegrating5 mgOralAngita Pharma Inc.2021-08-06Not applicableCanada flag
Ag-rizatriptan ODTTablet, orally disintegrating10 mgOralAngita Pharma Inc.2020-01-27Not applicableCanada flag
Apo-rizatriptanTablet5 mgOralApotex Corporation2013-03-06Not applicableCanada flag

Categories

ATC Codes
N02CC04 — Rizatriptan
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1,2,4-triazole / 3-alkylindole / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Heteroaromatic compound / Hydrocarbon derivative
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tryptamines (CHEBI:48273)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
51086HBW8G
CAS number
144034-80-0
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-yl)methyl]-1H-indol-3-yl}ethyl)amine
SMILES
CN(C)CCC1=CNC2=C1C=C(CN1C=NC=N1)C=C2

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. [Article]
  2. Tfelt-Hansen P, De Vries P, Saxena PR: Triptans in migraine: a comparative review of pharmacology, pharmacokinetics and efficacy. Drugs. 2000 Dec;60(6):1259-87. [Article]
  3. Lainez MJ: Rizatriptan in the treatment of migraine. Neuropsychiatr Dis Treat. 2006 Sep;2(3):247-59. doi: 10.2147/nedt.2006.2.3.247. [Article]
  4. Lee Y, Conroy JA, Stepanavage ME, Mendel CM, Somers G, McLoughlin DA, Olah TV, De Smet M, Keymeulen B, Rogers JD: Pharmacokinetics and tolerability of oral rizatriptan in healthy male and female volunteers. Br J Clin Pharmacol. 1999 Apr;47(4):373-8. doi: 10.1046/j.1365-2125.1999.00917.x. [Article]
  5. Nicolas S, Nicolas D: Triptans. . [Article]
  6. Vyas KP, Halpin RA, Geer LA, Ellis JD, Liu L, Cheng H, Chavez-Eng C, Matuszewski BK, Varga SL, Guiblin AR, Rogers JD: Disposition and pharmacokinetics of the antimigraine drug, rizatriptan, in humans. Drug Metab Dispos. 2000 Jan;28(1):89-95. [Article]
  7. 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. [Article]
  8. Deen M, Christensen CE, Hougaard A, Hansen HD, Knudsen GM, Ashina M: Serotonergic mechanisms in the migraine brain - a systematic review. Cephalalgia. 2017 Mar;37(3):251-264. doi: 10.1177/0333102416640501. Epub 2016 Jul 11. [Article]
  9. FDA Approved Drug Products: MAXALT (rizatriptan benzoate) tablets, for oral use and MAXALT-MLT (rizatriptan benzoate) orally disintegrating tablets (October 2019) [Link]
  10. FDA Approved Drug Products: RizaFilm (rizatriptan) oral film [Link]
  11. Organon: Rizatriptan MSDS [Link]
  12. Health Canada Approved Drug Products: ACT RIZATRIPTAN (Rizatriptan) Oral Tablets [Link]
  13. Health Canada Approved Drug Products: ACCEL-RIZATRIPTAN ODT (Rizatriptan) Orally Disintegrating Tablets [Link]
Human Metabolome Database
HMDB0015088
KEGG Drug
D00675
PubChem Compound
5078
PubChem Substance
46506557
ChemSpider
4900
BindingDB
50033437
RxNav
88014
ChEBI
48273
ChEMBL
CHEMBL905
ZINC
ZINC000000005895
Therapeutic Targets Database
DAP000220
PharmGKB
PA451264
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Rizatriptan
MSDS
Download (57.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceEpisodic Migraine1
4CompletedOtherWorkplace Migraine Treatment1
4CompletedTreatmentMigraine3
3CompletedTreatmentAcute Migraine2
3CompletedTreatmentAcute Migraine With or Without Aura in Adolescents1

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
FormRouteStrength
TabletOral5 mg
Film, solubleOral
TabletOral
TabletOral10 mg
TabletOral10 mg/1
Tablet10 MG
Tablet5 MG
FilmBuccal5.000 mg
Tablet, orally disintegratingOral10 mg
Tablet, orally disintegratingOral5 mg
Tablet, orally disintegratingOral10 mg/1
Tablet, orally disintegratingOral5 mg/1
Tablet, effervescent
Tablet, effervescent10 mg
GelOral10 MG
FilmOral10 mg/1
Film, solubleOral10 mg
Film, solubleOral5 mg
Film, solubleOral10 mg/1
Film, solubleOral5 mg/1
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral5 mg/1
Tablet, orally disintegratingOral
TabletOral5 mg/1
TabletOropharyngeal10 mg/1
Tablet
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)Region
US5602162No1997-02-112014-02-11US flag
US5298520No1994-03-292012-06-29US flag
CA2060139No1998-12-012012-01-28Canada flag
US9301948No2016-04-052034-07-30US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)178-180https://www.fishersci.com/store/msds?partNumber=AC462940010&productDescription=RIZATRIPTAN+BENZOATE+1GR&vendorId=VN00032119&countryCode=US&language=en
water solubility42 mg/mLhttps://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020864s023,020865s024lbl.pdf
Predicted Properties
PropertyValueSource
Water Solubility0.338 mg/mLALOGPS
logP1.67ALOGPS
logP1.77Chemaxon
logS-2.9ALOGPS
pKa (Strongest Acidic)17.23Chemaxon
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-MSsplash10-0a4i-9130000000-5d4f05bf987cb9fd7f28
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0udi-0590000000-de0b61f549c5a86c98df
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0udi-0590000000-de0b61f549c5a86c98df
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-1090000000-4fba948bb941bcc4fc80
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0090000000-c083e6ef59d9fb52fac2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-05di-2190000000-8b71371724a89b1156b4
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-2090000000-a3fa2fb3de7d3df398cf
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-1920000000-5c2be0223ebb76743372
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00xr-1940000000-0ed7cd3ac21ed2133452
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-179.2105007
predicted
DarkChem Lite v0.1.0
[M-H]-179.3003007
predicted
DarkChem Lite v0.1.0
[M-H]-156.72168
predicted
DeepCCS 1.0 (2019)
[M+H]+180.4142007
predicted
DarkChem Lite v0.1.0
[M+H]+181.0856007
predicted
DarkChem Lite v0.1.0
[M+H]+159.07968
predicted
DeepCCS 1.0 (2019)
[M+Na]+179.8996007
predicted
DarkChem Lite v0.1.0
[M+Na]+179.3407007
predicted
DarkChem Lite v0.1.0
[M+Na]+165.17284
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
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. [Article]
  2. Wellington K, Jarvis B: Spotlight on rizatriptan in migraine. CNS Drugs. 2002;16(10):715-20. [Article]
  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. [Article]
  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. [Article]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  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. [Article]
  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. [Article]
  8. Health Canada Approved Drug Products: ACT RIZATRIPTAN (Rizatriptan) Oral Tablets [Link]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  7. Wellington K, Plosker GL: Rizatriptan: an update of its use in the management of migraine. Drugs. 2002;62(10):1539-74. [Article]
  8. Wellington K, Jarvis B: Spotlight on rizatriptan in migraine. CNS Drugs. 2002;16(10):715-20. [Article]
  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. [Article]
  10. Health Canada Approved Drug Products: ACT RIZATRIPTAN (Rizatriptan) Oral Tablets [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
Gene Name
HTR1A
Uniprot ID
P08908
Uniprot Name
5-hydroxytryptamine receptor 1A
Molecular Weight
46106.335 Da
References
  1. Health Canada Approved Drug Products: ACT RIZATRIPTAN (Rizatriptan) Oral Tablets [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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
HTR1E
Uniprot ID
P28566
Uniprot Name
5-hydroxytryptamine receptor 1E
Molecular Weight
41681.57 Da
References
  1. Health Canada Approved Drug Products: ACT RIZATRIPTAN (Rizatriptan) Oral Tablets [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  6. Health Canada Approved Drug Products: ACT RIZATRIPTAN (Rizatriptan) Oral Tablets [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Serotonin receptor activity
Specific Function
This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor ...
Gene Name
HTR7
Uniprot ID
P34969
Uniprot Name
5-hydroxytryptamine receptor 7
Molecular Weight
53554.43 Da
References
  1. Health Canada Approved Drug Products: ACT RIZATRIPTAN (Rizatriptan) Oral Tablets [Link]

Enzymes

Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  3. FDA Approved Drug Products: MAXALT (rizatriptan benzoate) tablets, for oral use and MAXALT-MLT (rizatriptan benzoate) orally disintegrating tablets (October 2019) [Link]
  4. Health Canada Approved Drug Products: ACT RIZATRIPTAN (Rizatriptan) Oral Tablets [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
Curator comments
Rizatriptan is a competitive inhibitor (Ki=1400 nM) of cytochrome P450 2D6, but only at high, clinically irrelevant concentrations.
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Health Canada Approved Drug Products: ACT RIZATRIPTAN (Rizatriptan) Oral Tablets [Link]
  2. FDA Approved Drug Products: MAXALT (rizatriptan benzoate) tablets, for oral use and MAXALT-MLT (rizatriptan benzoate) orally disintegrating tablets (October 2019) [Link]

Drug created at June 13, 2005 13:24 / Updated at April 13, 2024 19:42