Rizatriptan - DrugBank

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Targets (3)Enzymes (2)

Targets (3)Enzymes (2)Biointeractions (5)

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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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	Details
Rizatriptan benzoate	WR978S7QHH	145202-66-0	JPRXYLQNJJVCMZ-UHFFFAOYSA-N	Details

Product Images

Approved 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	5 mg	Oral	Actavis Pharma Company	2012-01-30	Not applicable	Canada
Act Rizatriptan ODT	Tablet, orally disintegrating	10 mg	Oral	Actavis Pharma Company	2012-01-30	Not applicable	Canada
Auro-rizatriptan	Tablet	10 mg	Oral	Auro Pharma Inc	2016-04-12	Not applicable	Canada
Auro-rizatriptan ODT	Tablet, orally disintegrating	5 mg	Oral	Auro Pharma Inc	Not applicable	Not applicable	Canada
Auro-rizatriptan ODT	Tablet, orally disintegrating	10 mg	Oral	Auro Pharma Inc	Not applicable	Not applicable	Canada
Ccp-rizatriptan ODT	Tablet, orally disintegrating	5 mg	Oral	Cellchem Pharmaceuticals Inc.	Not applicable	Not applicable	Canada
Ccp-rizatriptan ODT	Tablet, orally disintegrating	10 mg	Oral	Cellchem Pharmaceuticals Inc.	Not applicable	Not applicable	Canada
Dom-rizatriptan Rdt	Tablet, orally disintegrating	10 mg	Oral	Dominion Pharmacal	2013-05-20	Not applicable	Canada
Dom-rizatriptan Rdt	Tablet, orally disintegrating	5 mg	Oral	Dominion Pharmacal	Not applicable	Not applicable	Canada
Ipg-rizatriptan	Tablet	10 mg	Oral	Marcan Pharmaceuticals Inc	Not applicable	Not applicable	Canada
Ipg-rizatriptan	Tablet	5 mg	Oral	Marcan Pharmaceuticals Inc	Not applicable	Not applicable	Canada
Jamp-rizatriptan	Tablet	10 mg	Oral	Jamp Pharma Corporation	2012-03-26	Not applicable	Canada
Jamp-rizatriptan	Tablet	5 mg	Oral	Jamp Pharma Corporation	2012-03-26	Not applicable	Canada
Jamp-rizatriptan Ir	Tablet	10 mg	Oral	Jamp Pharma Corporation	2014-09-25	Not applicable	Canada
Jamp-rizatriptan Ir	Tablet	5 mg	Oral	Jamp Pharma Corporation	2014-09-25	Not applicable	Canada
Jamp-rizatriptan ODT	Tablet, orally disintegrating	5 mg	Oral	Jamp Pharma Corporation	Not applicable	Not applicable	Canada
Jamp-rizatriptan ODT	Tablet, orally disintegrating	10 mg	Oral	Jamp Pharma Corporation	Not applicable	Not applicable	Canada
Mar-rizatriptan	Tablet	10 mg	Oral	Marcan Pharmaceuticals Inc	2012-05-03	Not applicable	Canada
Mar-rizatriptan	Tablet	5 mg	Oral	Marcan Pharmaceuticals Inc	Not applicable	Not applicable	Canada
Mar-rizatriptan ODT	Tablet, orally disintegrating	10 mg	Oral	Marcan Pharmaceuticals Inc	Not applicable	Not applicable	Canada
Mar-rizatriptan ODT	Tablet, orally disintegrating	5 mg	Oral	Marcan Pharmaceuticals Inc	Not applicable	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	Physicians Total Care, Inc.	2007-08-24	Not applicable	US
Maxalt	Tablet	10 mg	Oral	Merck Ltd.	1999-08-31	Not applicable	Canada
Maxalt	Tablet	10 mg/1	Oral	Rebel Distributors	1998-06-29	Not applicable	US
Maxalt	Tablet	10 mg/1	Oral	Merck Sharp & Dohme Limited	1998-06-29	Not applicable	US
Maxalt	Tablet	10 mg/1	Oral	Lake Erie Medical Dba Quality Care Produts Llc	2007-08-24	Not applicable	US
Maxalt	Tablet	10 mg/1	Oral	Stat Rx USA	1998-06-29	Not applicable	US
Maxalt	Tablet	5 mg	Oral	Merck Ltd.	1999-08-31	2013-07-15	Canada
Maxalt Rpd	Tablet, orally disintegrating	10 mg	Oral	Merck Ltd.	1999-08-31	Not applicable	Canada
Maxalt Rpd	Tablet, orally disintegrating	5 mg	Oral	Merck Ltd.	2000-05-05	Not applicable	Canada
Maxalt-mlt	Tablet, orally disintegrating	10 mg/1	Oral	Merck Sharp & Dohme Limited	1998-06-29	Not applicable	US
Maxalt-mlt	Tablet, orally disintegrating	10 mg/1	Oral	Physicians Total Care, Inc.	2009-12-29	Not applicable	US
Maxalt-mlt	Tablet, orally disintegrating	5 mg/1	Oral	Stat Rx USA	1998-06-29	Not applicable	US
Maxalt-mlt	Tablet, orally disintegrating	5 mg/1	Oral	Merck Sharp & Dohme Limited	1998-06-29	Not applicable	US
Mint-rizatriptan ODT	Tablet, orally disintegrating	5 mg	Oral	Mint Pharmaceuticals Inc	2015-06-10	2017-06-19	Canada
Mint-rizatriptan ODT	Tablet, orally disintegrating	10 mg	Oral	Mint Pharmaceuticals Inc	2015-06-10	2017-06-19	Canada
Mylan-rizatriptan	Tablet	5 mg	Oral	Mylan Pharmaceuticals	Not applicable	Not applicable	Canada
Mylan-rizatriptan	Tablet	10 mg	Oral	Mylan Pharmaceuticals	Not applicable	Not applicable	Canada
Mylan-rizatriptan ODT	Tablet, orally disintegrating	10 mg	Oral	Mylan Pharmaceuticals	2012-01-31	Not applicable	Canada
Mylan-rizatriptan ODT	Tablet, orally disintegrating	5 mg	Oral	Mylan Pharmaceuticals	2012-01-31	Not applicable	Canada
Nat-rizatriptan	Tablet	5 mg	Oral	Natco Pharma Limited	Not applicable	Not applicable	Canada
Nat-rizatriptan	Tablet	10 mg	Oral	Natco Pharma Limited	Not applicable	Not applicable	Canada
Nat-rizatriptan ODT	Tablet, orally disintegrating	5 mg	Oral	Natco Pharma Limited	2015-02-17	Not applicable	Canada
Nat-rizatriptan ODT	Tablet, orally disintegrating	10 mg	Oral	Natco Pharma Limited	2015-02-17	Not applicable	Canada
PMS-rizatriptan Rdt	Tablet, orally disintegrating	10 mg	Oral	Pharmascience Inc	2012-10-30	Not applicable	Canada
PMS-rizatriptan Rdt	Tablet, orally disintegrating	5 mg	Oral	Pharmascience Inc	2012-10-30	Not applicable	Canada
Q-rizatriptan ODT	Tablet, orally disintegrating	10 mg	Oral	Qd Pharmaceuticals Ulc	Not applicable	Not applicable	Canada
Q-rizatriptan ODT	Tablet, orally disintegrating	5 mg	Oral	Qd Pharmaceuticals Ulc	Not applicable	Not applicable	Canada
Riva-rizatriptan ODT	Tablet, orally disintegrating	5 mg	Oral	Laboratoire Riva Inc	2014-06-12	Not applicable	Canada
Riva-rizatriptan ODT	Tablet, orally disintegrating	10 mg	Oral	Laboratoire Riva Inc	2014-06-12	Not applicable	Canada
Rizaport	Film, soluble	10 1/1	Oral	Red Hill Biopharma Limited	2016-08-01	2017-06-03	US
Rizaport	Film, soluble	5 1/1	Oral	Red Hill Biopharma Limited	2016-08-01	2017-06-03	US
Rizatriptan	Tablet	10 mg	Oral	Jubilant Generics Limited	Not applicable	Not applicable	Canada
Rizatriptan	Tablet	5 mg	Oral	Jubilant Generics Limited	Not applicable	Not applicable	Canada
Rizatriptan Benzoate	Tablet, orally disintegrating	10 mg/1	Oral	Par Pharmaceutical	1998-06-29	2018-01-31	US
Rizatriptan Benzoate	Tablet	10 mg/1	Oral	Par Pharmaceutical	1998-06-29	2016-09-30	US
Rizatriptan Benzoate	Tablet, orally disintegrating	5 mg/1	Oral	Par Pharmaceutical	1998-06-29	2018-04-30	US
Rizatriptan Benzoate	Tablet	5 mg/1	Oral	Par Pharmaceutical	1998-06-29	2016-09-30	US
Rizatriptan ODT	Tablet, orally disintegrating	5 mg	Oral	Abri Pharmaceuticals Inc	Not applicable	Not applicable	Canada
Rizatriptan ODT	Tablet, orally disintegrating	10 mg	Oral	Sivem Pharmaceuticals Ulc	2015-10-07	Not applicable	Canada
Rizatriptan ODT	Tablet, orally disintegrating	5 mg	Oral	Sivem Pharmaceuticals Ulc	2015-10-07	Not applicable	Canada
Rizatriptan ODT	Tablet, orally disintegrating	5 mg	Oral	Sanis Health Inc	2015-07-23	Not applicable	Canada
Rizatriptan ODT	Tablet, orally disintegrating	10 mg	Oral	Abri Pharmaceuticals Inc	Not applicable	Not applicable	Canada
Rizatriptan ODT	Tablet, orally disintegrating	10 mg	Oral	Sanis Health Inc	2015-07-23	Not applicable	Canada
Rizatriptan Rdt	Tablet, orally disintegrating	10 mg	Oral	Pro Doc Limitee	2013-11-28	Not applicable	Canada
Rizatriptan Rdt	Tablet, orally disintegrating	5 mg	Oral	Pro Doc Limitee	2013-11-28	Not applicable	Canada
Sandoz Rizatriptan ODT	Tablet, orally disintegrating	5 mg	Oral	Sandoz Canada Incorporated	2012-01-30	Not applicable	Canada
Sandoz Rizatriptan ODT	Tablet, orally disintegrating	10 mg	Oral	Sandoz Canada Incorporated	2012-01-30	Not applicable	Canada
Teva-rizatriptan	Tablet	10 mg	Oral	Teva	Not applicable	Not applicable	Canada
Teva-rizatriptan	Tablet	5 mg	Oral	Teva	Not applicable	Not applicable	Canada
Teva-rizatriptan ODT	Tablet, orally disintegrating	5 mg	Oral	Teva	2014-11-04	Not applicable	Canada
Teva-rizatriptan ODT	Tablet, orally disintegrating	10 mg	Oral	Teva	2014-11-04	Not applicable	Canada
Van-rizatriptan	Tablet	5 mg	Oral	Vanc Pharmaceuticals Inc	2015-07-23	Not applicable	Canada
Van-rizatriptan	Tablet	10 mg	Oral	Vanc Pharmaceuticals Inc	2015-07-23	Not applicable	Canada
Van-rizatriptan ODT	Tablet, orally disintegrating	10 mg	Oral	Vanc Pharmaceuticals Inc	2016-04-18	Not applicable	Canada
Van-rizatriptan ODT	Tablet, orally disintegrating	5 mg	Oral	Vanc Pharmaceuticals Inc	Not applicable	Not applicable	Canada

Approved Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-rizatriptan	Tablet	5 mg	Oral	Apotex Corporation	2013-03-06	Not applicable	Canada
Apo-rizatriptan	Tablet	10 mg	Oral	Apotex Corporation	2012-09-27	Not applicable	Canada
Apo-rizatriptan Rpd	Tablet, orally disintegrating	5 mg	Oral	Apotex Corporation	2013-09-10	Not applicable	Canada
Apo-rizatriptan Rpd	Tablet, orally disintegrating	10 mg	Oral	Apotex Corporation	2013-09-10	Not applicable	Canada
Rizatriptan	Tablet, film coated	10 mg/1	Oral	Remedy Repack	2015-06-08	Not applicable	US
Rizatriptan	Tablet, film coated	10 mg/1	Oral	Preferreed Pharmaceuticals Inc.	2015-08-18	Not applicable	US
Rizatriptan	Tablet, film coated	5 mg/1	Oral	Macleods Pharmaceuticals Limited	2014-03-11	Not applicable	US
Rizatriptan	Tablet, film coated	10 mg/1	Oral	Macleods Pharmaceuticals Limited	2014-03-11	Not applicable	US
Rizatriptan Benzoate	Tablet	10 mg/1	Oral	Remedy Repack	2017-05-09	Not applicable	US
Rizatriptan Benzoate	Tablet, orally disintegrating	5 mg/1	Oral	Breckenridge Pharmaceutical, Inc.	2013-07-01	Not applicable	US
Rizatriptan Benzoate	Tablet	5 mg/1	Oral	Teva	2013-02-12	Not applicable	US
Rizatriptan Benzoate	Tablet	10 mg/1	Oral	Glenmark Pharmaceuticals Inc.,Usa	2012-12-31	Not applicable	US
Rizatriptan Benzoate	Tablet, orally disintegrating	5 mg/1	Oral	Citron Pharma LLC	2013-07-01	Not applicable	US
Rizatriptan Benzoate	Tablet	5 mg/1	Oral	Heritage	2013-12-12	Not applicable	US
Rizatriptan Benzoate	Tablet	10 mg/1	Oral	A S Medication Solutions	2013-02-12	2017-06-20	US
Rizatriptan Benzoate	Tablet	10 mg/1	Oral	Aurobindo Pharma	2012-12-31	Not applicable	US
Rizatriptan Benzoate	Tablet, orally disintegrating	5 mg/1	Oral	Glenmark Pharmaceuticals Inc.,Usa	2013-07-01	Not applicable	US
Rizatriptan Benzoate	Tablet	5 mg/1	Oral	Exelan Pharmaceuticals, Inc.	2017-06-06	Not applicable	US
Rizatriptan Benzoate	Tablet, orally disintegrating	5 mg/1	Oral	Macleods Pharmaceuticals Limited	2014-09-23	Not applicable	US
Rizatriptan Benzoate	Tablet, orally disintegrating	10 mg/1	Oral	Remedy Repack	2014-09-09	2016-04-05	US
Rizatriptan Benzoate	Tablet	10 mg/1	Oral	Cipla Limited	2016-07-22	Not applicable	US
Rizatriptan Benzoate	Tablet	10 mg/1	Oral	Citron Pharma LLC	2012-12-31	Not applicable	US
Rizatriptan Benzoate	Tablet	10 mg/1	Oral	Camber Pharmaceuticals	2015-01-29	Not applicable	US
Rizatriptan Benzoate	Tablet	5 mg/1	Oral	Aurobindo Pharma	2012-12-31	Not applicable	US
Rizatriptan Benzoate	Tablet, orally disintegrating	10 mg/1	Oral	Preferreed Pharmaceuticals Inc.	2013-10-22	Not applicable	US
Rizatriptan Benzoate	Tablet, orally disintegrating	10 mg/1	Oral	Bionpharma Inc.,	2017-01-17	Not applicable	US
Rizatriptan Benzoate	Tablet, orally disintegrating	10 mg/1	Oral	Apotex Corporation	2013-07-01	Not applicable	US
Rizatriptan Benzoate	Tablet	5 mg/1	Oral	Mesource Pharmaceuticals	2012-12-31	Not applicable	US
Rizatriptan Benzoate	Tablet	5 mg/1	Oral	Glenmark Pharmaceuticals Inc.,Usa	2012-12-31	Not applicable	US
Rizatriptan Benzoate	Tablet	10 mg/1	Oral	A S Medication Solutions	2012-12-31	2017-06-20	US
Rizatriptan Benzoate	Tablet	10 mg/1	Oral	Apotex Corporation	2012-12-29	2017-06-29	US
Rizatriptan Benzoate	Tablet, orally disintegrating	10 mg/1	Oral	Physicians Total Care, Inc.	2013-01-29	Not applicable	US
Rizatriptan Benzoate	Tablet, orally disintegrating	10 mg/1	Oral	Mylan Pharmaceuticals	2012-12-31	Not applicable	US
Rizatriptan Benzoate	Tablet	10 mg/1	Oral	Cipla Limited	2015-03-20	Not applicable	US
Rizatriptan Benzoate	Tablet	5 mg/1	Oral	Sandoz	2013-02-11	Not applicable	US
Rizatriptan Benzoate	Tablet, orally disintegrating	5 mg/1	Oral	Jubilant Cadista Pharmaceuticals Inc.	2014-03-01	Not applicable	US
Rizatriptan Benzoate	Tablet	10 mg/1	Oral	A S Medication Solutions	2015-01-29	2017-06-20	US
Rizatriptan Benzoate	Tablet, orally disintegrating	5 mg/1	Oral	Unichem Pharmaceuticals (USA), Inc.	2017-03-07	Not applicable	US
Rizatriptan Benzoate	Tablet	5 mg/1	Oral	Breckenridge Pharmaceutical, Inc.	2012-12-31	Not applicable	US
Rizatriptan Benzoate	Tablet	5 mg/1	Oral	Mylan Pharmaceuticals	2012-12-31	Not applicable	US
Rizatriptan Benzoate	Tablet	5 mg/1	Oral	bryant ranch prepack	2015-01-29	Not applicable	US
Rizatriptan Benzoate	Tablet, orally disintegrating	10 mg/1	Oral	Breckenridge Pharmaceutical, Inc.	2013-07-01	Not applicable	US
Rizatriptan Benzoate	Tablet	10 mg/1	Oral	Teva	2013-02-12	Not applicable	US
Rizatriptan Benzoate	Tablet, orally disintegrating	10 mg/1	Oral	Citron Pharma LLC	2013-07-01	Not applicable	US
Rizatriptan Benzoate	Tablet	10 mg/1	Oral	Heritage	2013-12-12	Not applicable	US
Rizatriptan Benzoate	Tablet, orally disintegrating	5 mg/1	Oral	Aurobindo Pharma	2013-07-01	Not applicable	US
Rizatriptan Benzoate	Tablet, orally disintegrating	10 mg/1	Oral	Glenmark Pharmaceuticals Inc.,Usa	2013-07-01	Not applicable	US
Rizatriptan Benzoate	Tablet	10 mg/1	Oral	Exelan Pharmaceuticals, Inc.	2017-06-06	Not applicable	US
Rizatriptan Benzoate	Tablet, orally disintegrating	10 mg/1	Oral	Macleods Pharmaceuticals Limited	2014-09-23	Not applicable	US
Rizatriptan Benzoate	Tablet	5 mg/1	Oral	Jubilant Cadista Pharmaceuticals Inc.	2013-03-01	Not applicable	US
Rizatriptan Benzoate	Tablet	5 mg/1	Oral	Ascend Laboratories, LLC	2012-06-25	Not applicable	US
Rizatriptan Benzoate	Tablet	5 mg/1	Oral	Unichem Pharmaceuticals (USA), Inc.	2017-03-07	Not applicable	US
Rizatriptan Benzoate	Tablet, orally disintegrating	5 mg/1	Oral	Panacea Biotec Ltd	2017-01-17	Not applicable	US
Rizatriptan Benzoate	Tablet	5 mg/1	Oral	Sun Pharma Global FZE	2013-01-12	2017-02-17	US
Rizatriptan Benzoate	Tablet, orally disintegrating	5 mg/1	Oral	Sandoz	2013-07-02	Not applicable	US
Rizatriptan Benzoate	Tablet	10 mg/1	Oral	Breckenridge Pharmaceutical, Inc.	2012-12-31	Not applicable	US
Rizatriptan Benzoate	Tablet	10 mg/1	Oral	Sandoz	2013-02-11	Not applicable	US
Rizatriptan Benzoate	Tablet, orally disintegrating	10 mg/1	Oral	Jubilant Cadista Pharmaceuticals Inc.	2012-03-01	Not applicable	US
Rizatriptan Benzoate	Tablet	5 mg/1	Oral	Cipla Limited	2016-07-22	Not applicable	US
Rizatriptan Benzoate	Tablet, orally disintegrating	10 mg/1	Oral	Unichem Pharmaceuticals (USA), Inc.	2017-03-07	Not applicable	US
Rizatriptan Benzoate	Tablet, orally disintegrating	5 mg/1	Oral	Bionpharma Inc.,	2017-01-17	Not applicable	US
Rizatriptan Benzoate	Tablet, orally disintegrating	5 mg/1	Oral	Apotex Corporation	2013-07-01	Not applicable	US
Rizatriptan Benzoate	Tablet	10 mg/1	Oral	Mesource Pharmaceuticals	2012-12-31	Not applicable	US
Rizatriptan Benzoate	Tablet, orally disintegrating	10 mg/1	Oral	Proficient Rx LP	2013-07-01	Not applicable	US
Rizatriptan Benzoate	Tablet	10 mg/1	Oral	Mylan Pharmaceuticals	2012-12-31	Not applicable	US
Rizatriptan Benzoate	Tablet	5 mg/1	Oral	Apotex Corporation	2012-12-29	2017-06-29	US
Rizatriptan Benzoate	Tablet	10 mg/1	Oral	Physicians Total Care, Inc.	2013-01-23	Not applicable	US
Rizatriptan Benzoate	Tablet, orally disintegrating	5 mg/1	Oral	Mylan Pharmaceuticals	2012-12-31	Not applicable	US
Rizatriptan Benzoate	Tablet	5 mg/1	Oral	Cipla Limited	2013-03-26	Not applicable	US
Rizatriptan Benzoate	Tablet	5 mg/1	Oral	Citron Pharma LLC	2012-12-31	Not applicable	US
Rizatriptan Benzoate	Tablet	5 mg/1	Oral	Camber Pharmaceuticals	2015-01-29	Not applicable	US
Rizatriptan Benzoate	Tablet, orally disintegrating	10 mg/1	Oral	Aurobindo Pharma	2013-07-01	Not applicable	US
Rizatriptan Benzoate	Tablet, orally disintegrating	10 mg/1	Oral	Sandoz	2013-07-02	Not applicable	US
Rizatriptan Benzoate	Tablet	10 mg/1	Oral	Jubilant Cadista Pharmaceuticals Inc.	2014-03-01	Not applicable	US
Rizatriptan Benzoate	Tablet	10 mg/1	Oral	Ascend Laboratories, LLC	2012-06-25	Not applicable	US
Rizatriptan Benzoate	Tablet	10 mg/1	Oral	Unichem Pharmaceuticals (USA), Inc.	2017-03-07	Not applicable	US
Rizatriptan Benzoate	Tablet, orally disintegrating	10 mg/1	Oral	Panacea Biotec Ltd	2017-01-17	Not applicable	US
Rizatriptan Benzoate	Tablet	10 mg/1	Oral	Sun Pharma Global FZE	2013-01-12	2017-02-17	US

Approved Over the Counter Products

Not Available

Unapproved/Other Products

Not Available

International Brands

Name	Company
Maxalt MLT	Not Available

Brand mixtures

Not Available

Categories

UNII

51086HBW8G

CAS number

144034-80-0

Weight

Average: 269.3449
Monoisotopic: 269.164045633

Chemical Formula

C₁₅H₁₉N₅

InChI Key

ULFRLSNUDGIQQP-UHFFFAOYSA-N

InChI

InChI=1S/C15H19N5/c1-19(2)6-5-13-8-17-15-4-3-12(7-14(13)15)9-20-11-16-10-18-20/h3-4,7-8,10-11,17H,5-6,9H2,1-2H3

IUPAC Name

dimethyl({2-[5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethyl})amine

SMILES

CN(C)CCC1=CNC2=C1C=C(CN1C=NC=N1)C=C2

Pharmacology

Indication

For treatment of acute migraine attacks with or without aura.

Structured Indications

Pharmacodynamics

Rizatriptan is a selective agonist of serotonin (5-hydroxytryptamine; 5-HT) type 1B and 1D receptors. It is structurally and pharmacologically related to other selective 5-HT1B/1D receptor agonists and has only a weak affinity for 5-HT_1A, 5-HT_5A, 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	Kind	Pharmacological action	Actions	Organism	UniProt ID
5-hydroxytryptamine receptor 1D	Protein	yes	agonist	Human	P28221	details
5-hydroxytryptamine receptor 1B	Protein	yes	agonist	Human	P28222	details
5-hydroxytryptamine receptor 1F	Protein	yes	agonist	Human	P30939	details

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.

Substrate	Enzymes	Product
Rizatriptan	Not Available	N-monodesmethyl-rizatriptan	Details

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	Better response to drug treatment	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
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
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
Azithromycin	The metabolism of Rizatriptan can be decreased when combined with Azithromycin.	Approved
Benmoxin	The metabolism of Rizatriptan can be decreased when combined with Benmoxin.	Withdrawn
Benperidol	The risk or severity of adverse effects can be increased when Rizatriptan is combined with Benperidol.	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
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.	Investigational
Buspirone	The risk or severity of adverse effects can be increased when Buspirone is combined with Rizatriptan.	Approved, Investigational
Cabergoline	Cabergoline may increase the vasoconstricting activities of Rizatriptan.	Approved
Caffeine	The metabolism of Rizatriptan can be decreased when combined with Caffeine.	Approved
Carbamazepine	The metabolism of Rizatriptan can be increased when combined with Carbamazepine.	Approved, Investigational
Cariprazine	The risk or severity of adverse effects can be increased when Rizatriptan is combined with Cariprazine.	Approved
Caroxazone	The metabolism of Rizatriptan can be decreased when combined with Caroxazone.	Withdrawn
Chlorpromazine	The risk or severity of adverse effects can be increased when Rizatriptan is combined with Chlorpromazine.	Approved, Vet Approved
Chlorprothixene	The risk or severity of adverse effects can be increased when Rizatriptan is combined with Chlorprothixene.	Approved, 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, Vet Approved
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
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
Desvenlafaxine	The risk or severity of adverse effects can be increased when Rizatriptan is combined with Desvenlafaxine.	Approved
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
Dolasetron	Dolasetron may increase the serotonergic activities of Rizatriptan.	Approved
Doxepin	The risk or severity of adverse effects can be increased when Rizatriptan is combined with Doxepin.	Approved
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
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, 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
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, 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
Hydracarbazine	The metabolism of Rizatriptan can be decreased when 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 metabolism of Rizatriptan can be decreased when combined with Iproclozide.	Withdrawn
Iproniazid	The metabolism of Rizatriptan can be decreased when combined with Iproniazid.	Withdrawn
Isocarboxazid	The metabolism of Rizatriptan can be decreased when combined with Isocarboxazid.	Approved
Levomilnacipran	The risk or severity of adverse effects can be increased when Rizatriptan is combined with Levomilnacipran.	Approved
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
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
Maprotiline	The risk or severity of adverse effects can be increased when Maprotiline is combined with Rizatriptan.	Approved
Mebanazine	The metabolism of Rizatriptan can be decreased when combined with Mebanazine.	Withdrawn
Melperone	The risk or severity of adverse effects can be increased when Rizatriptan is combined with Melperone.	Approved
Mesoridazine	The risk or severity of adverse effects can be increased when Rizatriptan is combined with Mesoridazine.	Approved
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
Methylene blue	The metabolism of Rizatriptan can be decreased when combined with Methylene blue.	Investigational
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
Milnacipran	The risk or severity of adverse effects can be increased when Rizatriptan is combined with Milnacipran.	Approved
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 metabolism of Rizatriptan can be decreased when combined with Moclobemide.	Approved
Molindone	The risk or severity of adverse effects can be increased when Rizatriptan is combined with Molindone.	Approved
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 metabolism of Rizatriptan can be decreased when 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
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
Perazine	The risk or severity of adverse effects can be increased when Rizatriptan is combined with Perazine.	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 metabolism of Rizatriptan can be decreased when combined with Phenelzine.	Approved
Pheniprazine	The metabolism of Rizatriptan can be decreased when combined with Pheniprazine.	Withdrawn
Phenobarbital	The metabolism of Rizatriptan can be increased when combined with Phenobarbital.	Approved
Phenoxypropazine	The metabolism of Rizatriptan can be decreased when 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
Pipotiazine	The risk or severity of adverse effects can be increased when Rizatriptan is combined with Pipotiazine.	Approved
Pirlindole	The metabolism of Rizatriptan can be decreased when combined with Pirlindole.	Approved
Pivhydrazine	The metabolism of Rizatriptan can be decreased when combined with Pivhydrazine.	Withdrawn
Primidone	The metabolism of Rizatriptan can be increased when combined with Primidone.	Approved, Vet Approved
Procarbazine	The risk or severity of adverse effects can be increased when Rizatriptan is combined with Procarbazine.	Approved
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
Propericiazine	The risk or severity of adverse effects can be increased when Rizatriptan is combined with Propericiazine.	Approved
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 metabolism of Rizatriptan can be decreased when 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
Rifampicin	The metabolism of Rizatriptan can be increased when combined with Rifampicin.	Approved
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
Safrazine	The metabolism of Rizatriptan can be decreased when combined with Safrazine.	Withdrawn
Selegiline	The metabolism of Rizatriptan can be decreased when 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, 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
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.	Approved, Investigational
Teriflunomide	The serum concentration of Rizatriptan can be decreased when it is combined with Teriflunomide.	Approved
Theophylline	The metabolism of Rizatriptan can be decreased when combined with Theophylline.	Approved
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.	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
Trans-2-Phenylcyclopropylamine	The metabolism of Rizatriptan can be decreased when combined with Trans-2-Phenylcyclopropylamine.	Experimental
Tranylcypromine	The metabolism of Rizatriptan can be decreased when combined with Tranylcypromine.	Approved
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
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
Vilazodone	The risk or severity of adverse effects can be increased when Rizatriptan is combined with Vilazodone.	Approved
Vortioxetine	The risk or severity of adverse effects can be increased when Rizatriptan is combined with Vortioxetine.	Approved
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
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

Resource	Link
Human Metabolome Database (HMDB)	HMDB15088
KEGG Drug	D00675
PubChem Compound	5078
PubChem Substance	46506557
ChemSpider	4900
BindingDB	50033437
ChEBI	48273
ChEMBL	CHEMBL905
Therapeutic Targets Database	DAP000220
PharmGKB	PA451264
IUPHAR	51
Guide to Pharmacology	51
Drug Product Database	11899
RxList	http://www.rxlist.com/cgi/generic2/rizatrip.htm
Drugs.com	http://www.drugs.com/cdi/rizatriptan.html
PDRhealth	http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/max1248.shtml
Wikipedia	Rizatriptan

ATC Codes

N02CC04 — Rizatriptan

AHFS Codes

28:32.28

PDB Entries

Not Available

FDA label

Download (873 KB)

MSDS

Download (57.7 KB)

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
Tablet	Oral	10 mg/1
Tablet	Oral	5 mg/1
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
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

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)
CA2060139	No	1998-12-01	2012-01-28	Canada
US5298520	No	1995-06-29	2012-06-29	US
US5602162	No	1994-02-11	2014-02-11	US

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

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

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum Type	Description	Splash Key
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0udi-0590000000-de0b61f549c5a86c98df	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available

Taxonomy

Description

This compound belongs to the class of chemical entities 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

Chemical entities

Super Class

Organic compounds

Class

Organoheterocyclic compounds

Sub Class

Indoles 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

Details

1. 5-hydroxytryptamine receptor 1D

Kind: Protein
Organism: Human
Pharmacological action: yes
Actions: agonist

General Function:: Serotonin receptor activity
Specific Function:: G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate c...
Gene Name:: HTR1D
Uniprot ID:: P28221
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 ]

Details

2. 5-hydroxytryptamine receptor 1B

Kind: Protein
Organism: Human
Pharmacological action: yes
Actions: agonist

General Function:: Serotonin receptor activity
Specific Function:: G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive substances, such as lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of ...
Gene Name:: HTR1B
Uniprot ID:: P28222
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 ]

Details

3. 5-hydroxytryptamine receptor 1F

Kind: Protein
Organism: Human
Pharmacological action: yes
Actions: agonist

General Function:: Serotonin receptor activity
Specific Function:: G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various alkaloids and psychoactive substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling inhibits adenylate cyclase activity.
Gene Name:: HTR1F
Uniprot ID:: P30939
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

Details

1. Amine oxidase [flavin-containing] A

Kind: Protein
Organism: Human
Pharmacological action: unknown
Actions: substrate

General Function:: Serotonin binding
Specific Function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:: MAOA
Uniprot ID:: P21397
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 ]

Details

2. Cytochrome P450 1A2

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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
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 July 18, 2017 16:54

Get DrugBank to go!

Structure for DB00953 (Rizatriptan)

Targets

References

References

References

Enzymes

References

References