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
Migraine 526.32 13.79 298 13208 69728 46602828
Headache 83.66 13.79 315 13191 478037 46194519
Death 45.70 13.79 20 13486 335528 46337028
Gallbladder polyp 44.22 13.79 14 13492 755 46671801
Serotonin syndrome 35.00 13.79 39 13467 24181 46648375
Pre-existing condition improved 33.66 13.79 22 13484 6590 46665966
Cholecystitis chronic 32.88 13.79 26 13480 10473 46662083
Medication overuse headache 32.87 13.79 10 13496 472 46672084
Product substitution issue 32.32 13.79 30 13476 15001 46657555
Dust allergy 31.97 13.79 10 13496 518 46672038
Purpura senile 30.16 13.79 10 13496 625 46671931
Hypermobility syndrome 29.50 13.79 10 13496 669 46671887
Coronary artery dissection 29.34 13.79 10 13496 680 46671876
Multiple sclerosis relapse 28.67 13.79 47 13459 42078 46630478
Product physical issue 26.57 13.79 17 13489 4910 46667646
Allergy to animal 26.45 13.79 9 13497 609 46671947
Anaphylactic reaction 25.60 13.79 51 13455 53061 46619495
Sinusitis 25.46 13.79 89 13417 129679 46542877
Anxiety 25.34 13.79 112 13394 181845 46490711
Colitis ischaemic 23.30 13.79 21 13485 10111 46662445
Nausea 23.01 13.79 301 13205 687153 45985403
Vomiting 22.79 13.79 215 13291 452579 46219977
Vestibular disorder 22.71 13.79 10 13496 1356 46671200
Carotid artery dissection 22.54 13.79 6 13500 174 46672382
Depression 22.40 13.79 103 13403 170001 46502555
Tarsal tunnel syndrome 22.14 13.79 8 13498 647 46671909
Oesophagitis ulcerative 19.80 13.79 7 13499 531 46672025
Injury 19.70 13.79 41 13465 43986 46628570
Acute kidney injury 19.23 13.79 24 13482 235831 46436725
Suicidal ideation 19.09 13.79 47 13459 56335 46616221
Dizziness 18.80 13.79 165 13341 340249 46332307
Vasospasm 18.66 13.79 7 13499 629 46671927
Sepsis 18.64 13.79 8 13498 136006 46536550
Cholelithiasis 18.46 13.79 37 13469 38644 46633912
Sensory level abnormal 18.28 13.79 5 13501 161 46672395
Resorption bone increased 17.93 13.79 8 13498 1119 46671437
Stress 17.48 13.79 43 13463 51508 46621048
Muscle spasms 17.28 13.79 76 13430 123037 46549519
Paraesthesia 16.87 13.79 73 13433 117364 46555192
Toxicity to various agents 16.79 13.79 22 13484 211744 46460812
Pain 16.38 13.79 210 13296 476738 46195818
Anaemia 16.09 13.79 31 13475 255748 46416808
Migraine with aura 15.88 13.79 9 13497 2090 46670466
Oral pruritus 15.80 13.79 8 13498 1483 46671073
Febrile neutropenia 15.70 13.79 4 13502 94623 46577933
Ankylosing spondylitis 15.56 13.79 14 13492 6723 46665833
Muscle twitching 15.26 13.79 20 13486 14652 46657904
Broad ligament tear 15.21 13.79 3 13503 21 46672535
Platelet count decreased 15.18 13.79 5 13501 100019 46572537
Somnolence 15.16 13.79 87 13419 156434 46516122
Cardiac failure congestive 14.99 13.79 4 13502 91746 46580810
Gait inability 14.84 13.79 32 13474 35171 46637385
Thrombophlebitis superficial 14.83 13.79 12 13494 4991 46667565
Pneumonia 14.44 13.79 58 13448 376262 46296294
Feeling of despair 14.36 13.79 8 13498 1797 46670759
Insomnia 14.26 13.79 89 13417 164835 46507721
Emotional distress 14.21 13.79 29 13477 30678 46641878
Sleep apnoea syndrome 14.07 13.79 24 13482 22177 46650379
Gallbladder disorder 13.95 13.79 21 13485 17477 46655079
Completed suicide 13.93 13.79 13 13493 145907 46526649

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 142.23 27.22 43 1344 12831 29938260
Nausea 39.95 27.22 58 1329 296899 29654192
Renal infarct 37.42 27.22 9 1378 1120 29949971
Therapy partial responder 35.02 27.22 11 1376 3680 29947411
Headache 29.47 27.22 39 1348 182267 29768824
Blue toe syndrome 27.29 27.22 5 1382 165 29950926

Pharmacologic Action:

SourceCodeDescription
ATC N02CC04 NERVOUS SYSTEM
ANALGESICS
ANTIMIGRAINE PREPARATIONS
Selective serotonin (5HT1) 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
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018490 Serotonin Agents
MeSH PA D017366 Serotonin Receptor Agonists
CHEBI has role CHEBI:35472 anti-inflammatory drugs
CHEBI has role CHEBI:35941 serotonergic agonists

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
D00675 KEGG_DRUG
145202-66-0 SECONDARY_CAS_RN
4021122 VANDF
4021123 VANDF
C0528321 UMLSCUI
CHEBI:48273 CHEBI
CHEMBL1201032 ChEMBL_ID
CHEMBL905 ChEMBL_ID
DB00953 DRUGBANK_ID
51 IUPHAR_LIGAND_ID
C093622 MESH_SUPPLEMENTAL_RECORD_UI
7474 INN_ID
51086HBW8G UNII
77997 PUBCHEM_CID
237082 RXNORM
196735 MMSL
7484 MMSL
d04328 MMSL
007571 NDDF
007572 NDDF
108411001 SNOMEDCT_US
108412008 SNOMEDCT_US
363573000 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
MAXALT HUMAN PRESCRIPTION DRUG LABEL 1 0006-0266 TABLET 5 mg ORAL NDA 27 sections
MAXALT HUMAN PRESCRIPTION DRUG LABEL 1 0006-0267 TABLET 10 mg ORAL NDA 27 sections
MAXALT-MLT HUMAN PRESCRIPTION DRUG LABEL 1 0006-3800 TABLET, ORALLY DISINTEGRATING 5 mg ORAL NDA 27 sections
MAXALT-MLT HUMAN PRESCRIPTION DRUG LABEL 1 0006-3801 TABLET, ORALLY DISINTEGRATING 10 mg ORAL NDA 27 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 0093-7471 TABLET 5 mg ORAL ANDA 25 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 0093-7472 TABLET 10 mg ORAL ANDA 25 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 0378-1403 TABLET 5 mg ORAL ANDA 28 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 0378-1404 TABLET 10 mg ORAL ANDA 28 sections
MAXALT-MLT HUMAN PRESCRIPTION DRUG LABEL 1 16590-144 TABLET, ORALLY DISINTEGRATING 5 mg ORAL NDA 29 sections
MAXALT HUMAN PRESCRIPTION DRUG LABEL 1 16590-461 TABLET 10 mg ORAL NDA 29 sections
MAXALT HUMAN PRESCRIPTION DRUG LABEL 1 21695-956 TABLET 10 mg ORAL NDA 29 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 29300-268 TABLET, ORALLY DISINTEGRATING 5 mg ORAL ANDA 23 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 29300-269 TABLET, ORALLY DISINTEGRATING 10 mg ORAL ANDA 23 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 29300-316 TABLET 5 mg ORAL ANDA 23 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 29300-317 TABLET 10 mg ORAL ANDA 23 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 31722-462 TABLET 5 mg ORAL ANDA 19 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 31722-463 TABLET 10 mg ORAL ANDA 19 sections
Rizatriptan Human Prescription Drug Label 1 33342-087 TABLET, FILM COATED 5 mg ORAL ANDA 25 sections
Rizatriptan Human Prescription Drug Label 1 33342-088 TABLET, FILM COATED 10 mg ORAL ANDA 25 sections
rizatriptan benzoate Human Prescription Drug Label 1 33342-093 TABLET, ORALLY DISINTEGRATING 5 mg ORAL ANDA 25 sections
rizatriptan benzoate Human Prescription Drug Label 1 33342-094 TABLET, ORALLY DISINTEGRATING 10 mg ORAL ANDA 25 sections
RIZATRIPTAN BENZOATE HUMAN PRESCRIPTION DRUG LABEL 1 43817-133 TABLET, ORALLY DISINTEGRATING 5 mg ORAL ANDA 21 sections
RIZATRIPTAN BENZOATE HUMAN PRESCRIPTION DRUG LABEL 1 43817-135 TABLET, ORALLY DISINTEGRATING 10 mg ORAL ANDA 21 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 45865-825 TABLET 10 mg ORAL ANDA 25 sections
Rizatriptan Benzoate Human Prescription Drug Label 1 50090-3367 TABLET 10 mg ORAL ANDA 25 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 50090-3921 TABLET 10 mg ORAL ANDA 27 sections
rizatriptan benzoate HUMAN PRESCRIPTION DRUG LABEL 1 50090-4619 TABLET 10 mg ORAL ANDA 26 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 51991-354 TABLET 5 mg ORAL ANDA 28 sections
Rizatriptan Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 51991-355 TABLET 10 mg ORAL ANDA 28 sections
RIZATRIPTAN Benzoate HUMAN PRESCRIPTION DRUG LABEL 1 51991-362 TABLET, ORALLY DISINTEGRATING 5 mg ORAL ANDA 28 sections