rizatriptan Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
serotonin (5-HT1) receptor agonists, sumatriptan derivatives 2393 144034-80-0

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • MK-0462
  • rizatriptan
  • risatriptan
  • rizatriptan benzoate
Rizatriptan binds with high affinity to human cloned 5-HT1B/1D receptors. Rizatriptan presumably exerts its therapeutic effects in the treatment of migraine headache by binding to 5-HT1B/1D receptors located on intracranial blood vessels and sensory nerves of the trigeminal system.
  • Molecular weight: 269.35
  • Formula: C15H19N5
  • CLOGP: 1.18
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 1
  • TPSA: 49.74
  • ALOGS: -2.90
  • ROTB: 5

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
10 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 42 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 14 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 1.86 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 45 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 1.90 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 16 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.86 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 2.20 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
June 29, 1998 FDA MERCK

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug ineffective 150.12 34.78 69 471 101555 2255990
Migraine 129.05 34.78 35 505 10618 2346927
Headache 88.76 34.78 45 495 80134 2277411
Serotonin syndrome 79.02 34.78 19 521 3521 2354024
Drug hypersensitivity 78.43 34.78 35 505 46608 2310937
Drug interaction 76.23 34.78 30 510 29133 2328412
Purpura senile 75.15 34.78 9 531 16 2357529
Exposure during pregnancy 66.03 34.78 26 514 25193 2332352
Tarsal tunnel syndrome 61.51 34.78 8 532 35 2357510
Vomiting 55.90 34.78 32 508 71570 2285975
Vestibular disorder 48.10 34.78 8 532 222 2357323
Resorption bone increased 47.70 34.78 8 532 234 2357311
Myocardial infarction 47.56 34.78 19 521 18994 2338551
No adverse event 44.14 34.78 15 525 9513 2348032
Muscle twitching 42.40 34.78 11 529 2754 2354791
Product substitution issue 40.10 34.78 12 528 5057 2352488
Vertigo positional 37.70 34.78 7 533 370 2357175
Chest pain 37.32 34.78 18 522 28119 2329426
Glaucoma 35.36 34.78 9 531 2086 2355459

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Migraine 68.03 55.79 13 108 2298 1744362
Renal infarct 62.02 55.79 9 112 290 1746370

Pharmacologic Action:

SourceCodeDescription
ATC N02CC04 NERVOUS SYSTEM
ANALGESICS
ANTIMIGRAINE PREPARATIONS
Selective serotonin (5HT1) agonists
CHEBI has role CHEBI:50514 vasoconstrictor agent
CHEBI has role CHEBI:35472 anti-inflammatory drug
CHEBI has role CHEBI:35941 serotonergic agonist
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018490 Serotonin Agents
MeSH PA D017366 Serotonin Receptor Agonists
FDA MoA N0000175763 Serotonin 1b Receptor Agonists
FDA MoA N0000175764 Serotonin 1d Receptor Agonists
FDA EPC N0000175765 Serotonin-1b and Serotonin-1d Receptor Agonist

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Migraine indication 37796009 DOID:6364
Myocardial infarction contraindication 22298006 DOID:5844
Hypertensive disorder contraindication 38341003 DOID:10763
Hemiplegic migraine contraindication 59292006
Prinzmetal angina contraindication 87343002
Chronic renal failure syndrome contraindication 90688005
Angina pectoris contraindication 194828000
Cerebrovascular accident contraindication 230690007
Disease of liver contraindication 235856003 DOID:409
Cardiovascular event risk contraindication 395112001
Peripheral vascular disease contraindication 400047006
Myocardial ischemia contraindication 414795007 DOID:3393
Hypertensive urgency contraindication 443482000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.75 acidic
pKa2 8.28 Basic
pKa3 3.56 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
5-hydroxytryptamine receptor 1D GPCR AGONIST Ki 7.90 WOMBAT-PK CHEMBL
5-hydroxytryptamine receptor 1B GPCR AGONIST Ki 6.90 WOMBAT-PK CHEMBL
5-hydroxytryptamine receptor 1F GPCR AGONIST Ki 6.80 IUPHAR
5-hydroxytryptamine receptor 1E GPCR AGONIST Ki 6.80 IUPHAR
5-hydroxytryptamine receptor 2C GPCR IC50 5.10 CHEMBL
5-hydroxytryptamine receptor 2A GPCR IC50 5.10 CHEMBL
5-hydroxytryptamine receptor 1A GPCR Ki 6.85 CHEMBL
Cytochrome P450 2D6 Enzyme Ki 4.85 WOMBAT-PK
Serotonin 3 (5-HT3) receptor Ion channel IC50 5.40 CHEMBL
5-hydroxytryptamine receptor 2A GPCR IC50 5.20 CHEMBL
5-hydroxytryptamine receptor 1D GPCR IC50 7.30 CHEMBL

External reference:

IDSource
4021122 VUID
N0000148576 NUI
C0297635 UMLSCUI
D00675 KEGG_DRUG
51086HBW8G UNII
7474 INN_ID
108411001 SNOMEDCT_US
4021122 VANDF
007571 NDDF
d04328 MMSL
88014 RXNORM
363573000 SNOMEDCT_US
CHEBI:48273 CHEBI
CHEMBL905 ChEMBL_ID
DB00953 DRUGBANK_ID
C093622 MESH_SUPPLEMENTAL_RECORD_UI
145202-66-0 SECONDARY_CAS_RN
5078 PUBCHEM_CID
CHEMBL1201032 ChEMBL_ID
51 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
MAXALT HUMAN PRESCRIPTION DRUG LABEL 1 0006-0266 TABLET 5 mg ORAL NDA 18 sections
MAXALT HUMAN PRESCRIPTION DRUG LABEL 1 0006-0267 TABLET 10 mg ORAL NDA 18 sections
MAXALT-MLT HUMAN PRESCRIPTION DRUG LABEL 1 0006-3800 TABLET, ORALLY DISINTEGRATING 5 mg ORAL NDA 18 sections
MAXALT-MLT HUMAN PRESCRIPTION DRUG LABEL 1 0006-3801 TABLET, ORALLY DISINTEGRATING 10 mg ORAL NDA 18 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 0093-7471 TABLET 5 mg ORAL ANDA 17 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 0093-7472 TABLET 10 mg ORAL ANDA 17 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 0378-1403 TABLET 5 mg ORAL ANDA 17 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 0378-1404 TABLET 10 mg ORAL ANDA 17 sections
MAXALT-MLT HUMAN PRESCRIPTION DRUG LABEL 1 16590-144 TABLET, ORALLY DISINTEGRATING 5 mg ORAL NDA 13 sections
MAXALT HUMAN PRESCRIPTION DRUG LABEL 1 16590-461 TABLET 10 mg ORAL NDA 13 sections
MAXALT HUMAN PRESCRIPTION DRUG LABEL 1 21695-956 TABLET 10 mg ORAL NDA 13 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 23155-244 TABLET 5 mg ORAL ANDA 17 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 23155-245 TABLET 10 mg ORAL ANDA 17 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 29300-268 TABLET, ORALLY DISINTEGRATING 5 mg ORAL ANDA 17 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 29300-269 TABLET, ORALLY DISINTEGRATING 10 mg ORAL ANDA 17 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 29300-316 TABLET 5 mg ORAL ANDA 17 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 29300-317 TABLET 10 mg ORAL ANDA 17 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 31722-462 TABLET 5 mg ORAL ANDA 18 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 31722-463 TABLET 10 mg ORAL ANDA 18 sections
Rizatriptan HUMAN PRESCRIPTION DRUG LABEL 1 33342-087 TABLET, FILM COATED 5 mg ORAL ANDA 18 sections
Rizatriptan HUMAN PRESCRIPTION DRUG LABEL 1 33342-088 TABLET, FILM COATED 10 mg ORAL ANDA 18 sections
rizatriptan benzoate HUMAN PRESCRIPTION DRUG LABEL 1 33342-093 TABLET, ORALLY DISINTEGRATING 5 mg ORAL ANDA 17 sections
rizatriptan benzoate HUMAN PRESCRIPTION DRUG LABEL 1 33342-094 TABLET, ORALLY DISINTEGRATING 10 mg ORAL ANDA 17 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 43817-133 TABLET, ORALLY DISINTEGRATING 5 mg ORAL ANDA 17 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 43817-135 TABLET, ORALLY DISINTEGRATING 10 mg ORAL ANDA 17 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 45865-825 TABLET 10 mg ORAL ANDA 17 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 50090-3367 TABLET 10 mg ORAL ANDA 17 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 50090-3921 TABLET 10 mg ORAL ANDA 19 sections
rizatriptan benzoate HUMAN PRESCRIPTION DRUG LABEL 1 50090-4619 TABLET 10 mg ORAL ANDA 18 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 51991-354 TABLET 5 mg ORAL ANDA 18 sections