eletriptan indications/contra

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

Drug dosage:

DoseUnitRoute
40 mg O

Approvals:

DateAgencyCompanyOrphan
Dec. 26, 2002 FDA PFIZER IRELAND

FDA Adverse Event Reporting System

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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 473.40 38.73 105 917 9911 3374926
Headache 217.53 38.73 97 925 91883 3292954
Drug ineffective 169.26 38.73 88 934 116002 3268835
Drug abuse 109.08 38.73 38 984 18292 3366545
Drug hypersensitivity 100.85 38.73 43 979 35637 3349200
Medication overuse headache 93.15 38.73 12 1010 30 3384807
Drug dependence 86.96 38.73 23 999 4353 3380484
Vomiting 81.04 38.73 50 972 89481 3295356
Chest discomfort 77.13 38.73 29 993 17256 3367581
Throat tightness 75.27 38.73 21 1001 4847 3379990
Condition aggravated 74.91 38.73 36 986 39197 3345640
Intentional product misuse 66.56 38.73 24 998 12677 3372160
Nausea 62.07 38.73 49 973 129596 3255241
Somnolence 56.73 38.73 28 994 32176 3352661
Muscle tightness 54.43 38.73 14 1008 2367 3382470
Chest pain 53.60 38.73 29 993 40246 3344591
Drug interaction 52.19 38.73 30 992 46782 3338055
Feeling abnormal 51.65 38.73 25 997 27500 3357337
Serotonin syndrome 51.30 38.73 16 1006 5407 3379430
Disturbance in attention 48.73 38.73 17 1005 8131 3376706
Dizziness 47.79 38.73 34 988 76478 3308359
Pain 45.13 38.73 32 990 71525 3313312
Hypoaesthesia 44.82 38.73 22 1000 24917 3359920
Confusional state 44.05 38.73 25 997 37973 3346864
Drug dispensing error 43.20 38.73 13 1009 3895 3380942
Malaise 43.07 38.73 30 992 65147 3319690
Dyspnoea 42.96 38.73 36 986 102898 3281939
Blindness transient 41.24 38.73 10 1012 1328 3383509
Paraesthesia 39.87 38.73 21 1001 27527 3357310
Drug abuser 38.74 38.73 11 1011 2692 3382145

Pharmacologic Action:

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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)

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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 DOID:6713
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

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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:

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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:

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IDSource
DB00216 DRUGBANK_ID
40 IUPHAR_LIGAND_ID
4021372 VUID
N0000148791 NUI
C0759933 UMLSCUI
D01973 KEGG_DRUG
22QOO9B8KI UNII
7426 INN_ID
231049 RXNORM
d04849 MMSL
395255007 SNOMEDCT_US
410843003 SNOMEDCT_US
4021372 VANDF
N0000148791 NDFRT
N0000010109 NDFRT
009521 NDDF
CHEMBL1510 ChEMBL_ID
77993 PUBCHEM_CID
CHEMBL1201003 ChEMBL_ID
177834-92-3 SECONDARY_CAS_RN
C115647 MESH_SUPPLEMENTAL_RECORD_UI
CHEBI:50922 CHEBI

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Relpax HUMAN PRESCRIPTION DRUG LABEL 1 0049-2330 TABLET, FILM COATED 20 mg ORAL NDA 19 sections
Relpax HUMAN PRESCRIPTION DRUG LABEL 1 0049-2340 TABLET, FILM COATED 40 mg ORAL NDA 19 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 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 68382-923 TABLET, FILM COATED 40 mg ORAL ANDA 18 sections
Eletriptan hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 70771-1108 TABLET, FILM COATED 40 mg ORAL ANDA 18 sections