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

Stem definitionDrug idCAS RN
serotonin (5-HT1) receptor agonists, sumatriptan derivatives 995 143322-58-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • eletriptan
  • eletriptan hydrobromide
  • UK 116044-04
  • UK-116,044
  • relpax
Eletriptan binds with high affinity to 5-HT1B, 5-HT1D and 5-HT1F receptors, has modest affinity for 5-HT1A, 5-HT1E, 5-HT2B and 5-HT7 receptors. Migraines are likely due to local cranial vasodilatation and/or to the release of sensory neuropeptides (vasoactive intestinal peptide, substance P and calcitonin gene-related peptide) through nerve endings in the trigeminal system. The therapeutic activity of Eletriptan for the treatment of migraine headache is thought to be due to the agonist effects at the 5-HT1B/1D receptors on intracranial blood vessels (including the arterio-venous anastomoses) and sensory nerves of the trigeminal system which result in cranial vessel constriction and inhibition of pro-inflammatory neuropeptide release.
  • Molecular weight: 382.52
  • Formula: C22H26N2O2S
  • CLOGP: 3.35
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 1
  • TPSA: 53.17
  • ALOGS: -5.51
  • ROTB: 6

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
40 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 4 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 5 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 1.49 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 1.60 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 5.30 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.15 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 4.20 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Dec. 26, 2002 FDA PFIZER IRELAND

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 414.31 35.11 98 800 10555 2346632
Drug ineffective 206.66 35.11 101 797 101523 2255664
Headache 190.92 35.11 89 809 80090 2277097
Drug dependence 159.89 35.11 36 862 3009 2354178
Drug hypersensitivity 98.45 35.11 48 850 46595 2310592
Drug abuse 94.80 35.11 32 866 11994 2345193
Vomiting 79.12 35.11 48 850 71554 2285633
Chest discomfort 73.94 35.11 28 870 14567 2342620
Intentional product misuse 73.72 35.11 25 873 9464 2347723
Condition aggravated 70.54 35.11 34 864 31945 2325242
Medication overuse headache 70.20 35.11 10 888 53 2357134
Feeling abnormal 67.33 35.11 30 868 23551 2333636
Throat tightness 60.66 35.11 18 880 4418 2352769
Product dispensing error 56.09 35.11 15 883 2526 2354661
Nausea 53.26 35.11 45 853 112144 2245043
Somnolence 48.77 35.11 24 874 23461 2333726
Malaise 48.02 35.11 32 866 55553 2301634
Chest pain 47.50 35.11 25 873 28112 2329075
Serotonin syndrome 46.80 35.11 14 884 3526 2353661
Dizziness 46.45 35.11 32 866 58633 2298554
Disturbance in attention 44.17 35.11 15 883 5670 2351517
Neck pain 43.40 35.11 16 882 7681 2349506
Pain 42.62 35.11 31 867 61826 2295361
Dyspnoea 42.28 35.11 34 864 78699 2278488
Paraesthesia 41.20 35.11 21 877 22067 2335120
Confusional state 39.28 35.11 21 877 24323 2332864
Blindness transient 38.72 35.11 9 889 853 2356334
Recalled product administered 36.24 35.11 5 893 20 2357167

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
Drug abuse 71.17 51.87 20 150 13669 1732942

Pharmacologic Action:

SourceCodeDescription
ATC N02CC06 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:35941 serotonergic agonist
CHEBI has role CHEBI:50514 vasoconstrictor agent
CHEBI has role CHEBI:35475 non-steroidal anti-inflammatory drug

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Migraine indication 37796009 DOID:6364
Hypercholesterolemia contraindication 13644009
Myocardial infarction contraindication 22298006 DOID:5844
Coronary artery spasm contraindication 23687008 DOID:11840
Hypertensive disorder contraindication 38341003 DOID:10763
Hemiplegic migraine contraindication 59292006
Hepatic failure contraindication 59927004
Diabetes mellitus contraindication 73211009 DOID:9351
Vascular insufficiency of intestine contraindication 82196007
Prinzmetal angina contraindication 87343002
Angina pectoris contraindication 194828000
Cerebrovascular accident contraindication 230690007
Disease of liver contraindication 235856003 DOID:409
Transient ischemic attack contraindication 266257000 DOID:224
Raynaud's phenomenon contraindication 266261006
Cerebral ischemia contraindication 287731003
Serotonin syndrome contraindication 371089000
Cardiovascular event risk contraindication 395112001
Peripheral vascular disease contraindication 400047006
Disorder of coronary artery contraindication 414024009
Myocardial ischemia contraindication 414795007 DOID:3393
Obesity contraindication 414916001 DOID:9970
Hypertensive urgency contraindication 443482000
Smokes tobacco daily contraindication 449868002
Familial History of Cardiovascular Disease contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.9 acidic
pKa2 8.57 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 1B GPCR AGONIST Kd 8.52 CHEMBL CHEMBL
5-hydroxytryptamine receptor 1D GPCR AGONIST Kd 9.05 CHEMBL CHEMBL
5-hydroxytryptamine receptor 1F GPCR AGONIST Ki 8 IUPHAR
5-hydroxytryptamine receptor 1A GPCR AGONIST Ki 7.40 IUPHAR
5-hydroxytryptamine receptor 1E GPCR AGONIST Ki 7.20 IUPHAR

External reference:

IDSource
4021372 VUID
N0000148791 NUI
C0759933 UMLSCUI
D01973 KEGG_DRUG
22QOO9B8KI UNII
7426 INN_ID
395255007 SNOMEDCT_US
231049 RXNORM
d04849 MMSL
410843003 SNOMEDCT_US
4021372 VANDF
009521 NDDF
CHEMBL1510 ChEMBL_ID
DB00216 DRUGBANK_ID
177834-92-3 SECONDARY_CAS_RN
CHEBI:50922 CHEBI
40 IUPHAR_LIGAND_ID
CHEMBL1201003 ChEMBL_ID
77993 PUBCHEM_CID
C115647 MESH_SUPPLEMENTAL_RECORD_UI

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Relpax HUMAN PRESCRIPTION DRUG LABEL 1 0049-2330 TABLET, FILM COATED 20 mg ORAL NDA 18 sections
Relpax HUMAN PRESCRIPTION DRUG LABEL 1 0049-2340 TABLET, FILM COATED 40 mg ORAL NDA 18 sections
Eletriptan Hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 0093-8310 TABLET, FILM COATED 20 mg ORAL ANDA 17 sections
Eletriptan Hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 0093-8311 TABLET, FILM COATED 40 mg ORAL ANDA 17 sections
Eletriptan Hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 0378-4287 TABLET, FILM COATED 20 mg ORAL ANDA 18 sections
Eletriptan Hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 0378-4288 TABLET, FILM COATED 40 mg ORAL ANDA 18 sections
Relpax HUMAN PRESCRIPTION DRUG LABEL 1 16590-201 TABLET, FILM COATED 40 mg ORAL NDA 15 sections
Relpax HUMAN PRESCRIPTION DRUG LABEL 1 21695-871 TABLET, FILM COATED 40 mg ORAL NDA 15 sections
eletriptan hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 27241-039 TABLET, FILM COATED 20 mg ORAL ANDA 16 sections
eletriptan hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 27241-040 TABLET, FILM COATED 40 mg ORAL ANDA 16 sections
Relpax HUMAN PRESCRIPTION DRUG LABEL 1 54868-5528 TABLET, FILM COATED 40 mg ORAL NDA 15 sections
eletriptan hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 55700-756 TABLET, FILM COATED 40 mg ORAL ANDA 15 sections
Eletriptan Hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 59651-104 TABLET, FILM COATED 20 mg ORAL ANDA 16 sections
Eletriptan Hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 59651-105 TABLET, FILM COATED 40 mg ORAL ANDA 16 sections
Eletriptan HUMAN PRESCRIPTION DRUG LABEL 1 59762-2321 TABLET, FILM COATED 20 mg ORAL NDA AUTHORIZED GENERIC 18 sections
Eletriptan HUMAN PRESCRIPTION DRUG LABEL 1 59762-2322 TABLET, FILM COATED 40 mg ORAL NDA AUTHORIZED GENERIC 18 sections
Relpax HUMAN PRESCRIPTION DRUG LABEL 1 63539-234 TABLET, FILM COATED 40 mg ORAL NDA 19 sections
Eletriptan hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 68382-922 TABLET, FILM COATED 20 mg ORAL ANDA 17 sections
Eletriptan hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 68382-923 TABLET, FILM COATED 40 mg ORAL ANDA 17 sections
Eletriptan hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 70771-1107 TABLET, FILM COATED 20 mg ORAL ANDA 18 sections
Eletriptan hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 70771-1108 TABLET, FILM COATED 40 mg ORAL ANDA 18 sections