Rizatriptan

Identification

Summary

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

Brand Names

Maxalt, Rizaport

Generic Name

Rizatriptan

DrugBank Accession Number

DB00953

Background

Rizatriptan is a second-generation triptan ³ and a selective 5-HT_{1B 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

Similar Structures

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

Associated Therapies

Acute Treatment of Migraine

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-HT_1A, 5-HT_1E, 5-HT_1F) 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-HT_1B and 5-HT_1D receptors to promote trigeminal neuronal firing and vasoconstriction.^1,8

Rizatriptan is a selective agonist at the 5-HT_1B and 5-HT_1D 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-HT_1B 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-HT_1D receptors.^1,3,5 Rizatriptan inhibited neurogenic dural vasodilation and plasma protein extravasation in animal studies.^1,7,3,5

Target	Actions	Organism
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 T_max 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 C_max 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 T_max 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

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Rizatriptan

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/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	---	(C;T) / (T;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

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.

Drug	Interaction
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Abacavir	Rizatriptan may decrease the excretion rate of Abacavir which could result in a higher serum level.
Acebutolol	Rizatriptan may decrease the antihypertensive activities of Acebutolol.
Aceclofenac	The risk or severity of hypertension can be increased when Rizatriptan is combined with Aceclofenac.
Acemetacin	The risk or severity of hypertension can be increased when Rizatriptan is combined with Acemetacin.
Acetaminophen	Acetaminophen may decrease the excretion rate of Rizatriptan which could result in a higher serum level.
Acetazolamide	Acetazolamide may increase the excretion rate of Rizatriptan which could result in a lower serum level and potentially a reduction in efficacy.
Acetophenazine	The risk or severity of adverse effects can be increased when Rizatriptan is combined with Acetophenazine.
Acetylsalicylic acid	The risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Rizatriptan.
Aclidinium	Rizatriptan may decrease the excretion rate of Aclidinium which could result in a higher serum level.
Acrivastine	Rizatriptan may decrease the excretion rate of Acrivastine which could result in a higher serum level.

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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

Ingredient	UNII	CAS	InChI Key
Rizatriptan benzoate	WR978S7QHH	145202-66-0	JPRXYLQNJJVCMZ-UHFFFAOYSA-N

Product Images

International/Other Brands

Maxalt MLT / RizaFilm

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Act Rizatriptan	Tablet	5 mg	Oral	TEVA Canada Limited	Not applicable	Not applicable
Act Rizatriptan	Tablet	10 mg	Oral	TEVA Canada Limited	2012-06-14	Not applicable
Act Rizatriptan ODT	Tablet, orally disintegrating	10 mg	Oral	Actavis Pharma Company	2012-01-30	2019-08-08
Act Rizatriptan ODT	Tablet, orally disintegrating	5 mg	Oral	Actavis Pharma Company	2012-01-30	2019-08-08
Maxalt	Tablet	10 mg/1	Oral	Stat Rx USA	1998-06-29	Not applicable
Maxalt	Tablet	10 mg/1	Oral	Lake Erie Medical Dba Quality Care Produts Llc	2007-08-24	2014-12-31
Maxalt	Tablet	10 mg/1	Oral	Organon LLC	2021-06-01	Not applicable
Maxalt	Tablet	10 mg/1	Oral	Merck Sharp & Dohme Corp.	1998-06-29	Not applicable
Maxalt	Tablet	5 mg	Oral	Merck Ltd.	1999-08-31	2013-07-15
Maxalt	Tablet	10 mg/1	Oral	Physicians Total Care, Inc.	2007-08-24	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Accel-rizatriptan ODT	Tablet, orally disintegrating	10 mg	Oral	Accel Pharma Inc	2019-10-07	Not applicable
Accel-rizatriptan ODT	Tablet, orally disintegrating	5 mg	Oral	Accel Pharma Inc	2019-10-07	Not applicable
Ag-rizatriptan ODT	Tablet, orally disintegrating	5 mg	Oral	Angita Pharma Inc.	2021-08-06	Not applicable
Ag-rizatriptan ODT	Tablet, orally disintegrating	10 mg	Oral	Angita Pharma Inc.	2020-01-27	Not applicable
Apo-rizatriptan	Tablet	10 mg	Oral	Apotex Corporation	2012-09-27	Not applicable
Apo-rizatriptan	Tablet	5 mg	Oral	Apotex Corporation	2013-03-06	Not applicable
Apo-rizatriptan Rpd	Tablet, orally disintegrating	10 mg	Oral	Apotex Corporation	2013-09-10	Not applicable
Apo-rizatriptan Rpd	Tablet, orally disintegrating	5 mg	Oral	Apotex Corporation	2013-09-10	Not applicable
Auro-rizatriptan	Tablet	10 mg	Oral	Auro Pharma Inc	2016-04-12	Not applicable
Auro-rizatriptan ODT	Tablet, orally disintegrating	5 mg	Oral	Auro Pharma Inc	Not applicable	Not applicable

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

Wellington K, Plosker GL: Rizatriptan: an update of its use in the management of migraine. Drugs. 2002;62(10):1539-74. [Article]
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]
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]
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]
Nicolas S, Nicolas D: Triptans. . [Article]
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]
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]
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]
FDA Approved Drug Products: MAXALT (rizatriptan benzoate) tablets, for oral use and MAXALT-MLT (rizatriptan benzoate) orally disintegrating tablets (October 2019) [Link]
FDA Approved Drug Products: RizaFilm (rizatriptan) oral film [Link]
Organon: Rizatriptan MSDS [Link]
Health Canada Approved Drug Products: ACT RIZATRIPTAN (Rizatriptan) Oral Tablets [Link]
Health Canada Approved Drug Products: ACCEL-RIZATRIPTAN ODT (Rizatriptan) Orally Disintegrating Tablets [Link]

External Links

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

Phase	Status	Purpose	Conditions	Count
4	Completed	Basic Science	Episodic Migraine	1
4	Completed	Other	Workplace Migraine Treatment	1
4	Completed	Treatment	Migraine	3
3	Completed	Treatment	Acute Migraine	2
3	Completed	Treatment	Acute Migraine With or Without Aura in Adolescents	1
3	Completed	Treatment	Migraine	16
3	Completed	Treatment	Migraine With Aura / Migraine Without Aura	1
3	Recruiting	Treatment	Migraine	2
2	Completed	Treatment	Migraine	1
2, 3	Completed	Treatment	Migrainous Vertigo / Vestibular Migraine	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
Film, soluble	Oral
Film, soluble	Oral	10 mg
Film, soluble	Oral	5 mg
Tablet	Oral
Tablet	Oral	10 mg
Tablet	Oral	10 mg/1
Tablet		10 mg
Tablet		5 mg
Film	Buccal	5.000 mg
Tablet, orally disintegrating	Oral	10 mg
Tablet, orally disintegrating	Oral	5 mg
Tablet, orally disintegrating	Oral	10 mg/1
Tablet, orally disintegrating	Oral	5 mg/1
Tablet, effervescent
Tablet, effervescent		10 mg
Gel	Oral	10 MG
Film, soluble	Oral	10 mg/1
Film, soluble	Oral	5 mg/1
Tablet, film coated	Oral	10 mg/1
Tablet, film coated	Oral	5 mg/1
Tablet, orally disintegrating	Oral
Tablet	Oral	5 mg/1
Tablet	Oropharyngeal	10 mg/1
Tablet

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	1997-02-11	2014-02-11
US5298520	No	1994-03-29	2012-06-29
CA2060139	No	1998-12-01	2012-01-28
US9301948	No	2014-07-30	2034-07-30

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	178-180	https://www.fishersci.com/store/msds?partNumber=AC462940010&productDescription=RIZATRIPTAN+BENZOATE+1GR&vendorId=VN00032119&countryCode=US&language=en
water solubility	42 mg/mL	https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020864s023,020865s024lbl.pdf

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)	17.23	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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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

Targets

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Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	41	N/A	N/A	A28746
Ki (nM)	10.1	N/A	N/A	A28741

Details1. 5-hydroxytryptamine receptor 1B

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

Wellington K, Plosker GL: Rizatriptan: an update of its use in the management of migraine. Drugs. 2002;62(10):1539-74. [Article]
Wellington K, Jarvis B: Spotlight on rizatriptan in migraine. CNS Drugs. 2002;16(10):715-20. [Article]
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]
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]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
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]
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]
Health Canada Approved Drug Products: ACT RIZATRIPTAN (Rizatriptan) Oral Tablets [Link]

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	3	N/A	N/A	A28741
EC 50 (nM)	8.4	N/A	N/A	A28746
IC 50 (nM)	11	N/A	N/A	A28746
IC 50 (nM)	79.43	N/A	N/A	A28734
Ki (nM)	14	N/A	N/A	A27734
Ki (nM)	4.3	N/A	N/A	A28741
Ki (nM)	40	N/A	N/A	A27734

Details2. 5-hydroxytryptamine receptor 1D

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

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
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]
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]
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]
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]
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]
Wellington K, Plosker GL: Rizatriptan: an update of its use in the management of migraine. Drugs. 2002;62(10):1539-74. [Article]
Wellington K, Jarvis B: Spotlight on rizatriptan in migraine. CNS Drugs. 2002;16(10):715-20. [Article]
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]
Health Canada Approved Drug Products: ACT RIZATRIPTAN (Rizatriptan) Oral Tablets [Link]

Details3. 5-hydroxytryptamine receptor 1A

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

Health Canada Approved Drug Products: ACT RIZATRIPTAN (Rizatriptan) Oral Tablets [Link]

Details4. 5-hydroxytryptamine receptor 1E

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

Health Canada Approved Drug Products: ACT RIZATRIPTAN (Rizatriptan) Oral Tablets [Link]

Details5. 5-hydroxytryptamine receptor 1F

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

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
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]
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]
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]
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]
Health Canada Approved Drug Products: ACT RIZATRIPTAN (Rizatriptan) Oral Tablets [Link]

Details6. 5-hydroxytryptamine receptor 7

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

Health Canada Approved Drug Products: ACT RIZATRIPTAN (Rizatriptan) Oral Tablets [Link]

Enzymes

Details1. Amine oxidase [flavin-containing] A

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

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]
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]
FDA Approved Drug Products: MAXALT (rizatriptan benzoate) tablets, for oral use and MAXALT-MLT (rizatriptan benzoate) orally disintegrating tablets (October 2019) [Link]
Health Canada Approved Drug Products: ACT RIZATRIPTAN (Rizatriptan) Oral Tablets [Link]

Details2. Cytochrome P450 2D6

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

Health Canada Approved Drug Products: ACT RIZATRIPTAN (Rizatriptan) Oral Tablets [Link]
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 September 30, 2023 15:27

Rizatriptan

Identification

Structure for Rizatriptan (DB00953)

Pharmacology

Interactions

Products

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Chemical Identifiers

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Pharmacoeconomics

Properties

Spectra

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Enzymes

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