eletriptan 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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: 3.36
  • 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 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 50 %
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

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 0.800 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 14.355 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 4.989 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 6.252 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 44.610 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 51.090 % High 1
herg hERG pIC50 5.487 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 2.529 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 30.690 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 40.010 % High 1
kinase-safety-class ACVR2B,AKT1,AKT2,AKT3,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK5,CDK9,DYRK1B,EGFR,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,ITK,MAP3K7,MAPK10,MAPK7,MAPKAPK2,MET,NTRK2,PDK1,PDK2,PDK4,PIK3CA,PIK3CB,PIM2,PRKDC,SIK2,SIK3,TEK,TGFBR1 36
kinase-selectivity-class AXL,CAMK2D,GRK2,PDK4,SIK2,SIK3,TEK 7
mdck-mdr1-bcrp-efflux MDCK-MDR1-BCRP efflux ratio 14.894 High 1
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 9.550 High 1
mh-clint Mouse hepatocyte intrinsic clearance 96.828 High 1
mppb Mouse plasma protein binding (% unbound) 40.450 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 42.855 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 52.700 % High 1
rat-kpuu-brain Rat brain Kpuu 0.027 % High 1
rh-clint Rat hepatocyte intrinsic clearance 90.573 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 73.590 % High 1
rppb Rat plasma protein binding (% unbound) 47.470 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 948.418 uM High 1

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 200.77 15.63 164 9449 190228 90428606
Medication overuse headache 159.38 15.63 36 9577 1465 90617369
Rheumatoid factor negative 83.36 15.63 18 9595 593 90618241
Drug ineffective 82.56 15.63 326 9287 1383972 89234862
Headache 76.38 15.63 232 9381 862514 89756320
Drug dependence 73.13 15.63 43 9570 29284 90589550
Recalled product administered 72.89 15.63 17 9596 798 90618036
Enzyme inhibition 53.19 15.63 8 9605 28 90618806
Rubber sensitivity 51.90 15.63 17 9596 2820 90616014
Communication disorder 49.55 15.63 17 9596 3249 90615585
Feeling abnormal 42.60 15.63 69 9544 167166 90451668
Breast pain 41.96 15.63 21 9592 10397 90608437
Hepatic infiltration eosinophilic 39.67 15.63 6 9607 22 90618812
Paraesthesia 39.47 15.63 84 9529 250242 90368592
Serotonin syndrome 36.39 15.63 31 9582 37856 90580978
Intentional product misuse 36.11 15.63 46 9567 89558 90529276
Joint swelling 34.39 15.63 6 9607 503294 90115540
Throat tightness 32.22 15.63 26 9587 29458 90589376
Withdrawal syndrome 31.50 15.63 23 9590 22501 90596333
Drug ineffective for unapproved indication 29.71 15.63 36 9577 66608 90552226
Chest discomfort 28.53 15.63 52 9561 138313 90480521
Reversible cerebral vasoconstriction syndrome 28.17 15.63 12 9601 4118 90614716
Pleural rub 27.72 15.63 5 9608 63 90618771
Drug abuse 26.65 15.63 38 9575 82309 90536525
Somnolence 26.10 15.63 64 9549 209020 90409814
Oral mucosal exfoliation 25.97 15.63 9 9604 1771 90617063
Lichen planus 25.50 15.63 10 9603 2781 90616053
Product dispensing error 25.45 15.63 16 9597 12257 90606577
Anxiety 24.16 15.63 80 9533 309692 90309142
Stress 24.08 15.63 36 9577 81359 90537475
Glossodynia 23.89 15.63 3 9610 321776 90297058
Disturbance in attention 23.57 15.63 27 9586 47082 90571752
Cholecystitis chronic 23.42 15.63 14 9599 9812 90609022
Vasospasm 22.51 15.63 7 9606 982 90617852
Basilar migraine 22.06 15.63 4 9609 52 90618782
Pain 21.83 15.63 180 9433 996161 89622673
Antisocial behaviour 21.42 15.63 6 9607 586 90618248
Systemic lupus erythematosus 21.31 15.63 6 9607 361890 90256944
Infusion related reaction 20.95 15.63 9 9604 416771 90202063
Inhibitory drug interaction 20.94 15.63 9 9604 3154 90615680
Vomiting 19.77 15.63 147 9466 788146 89830688
Stomatitis 19.35 15.63 3 9610 274695 90344139
Seizure 19.33 15.63 47 9566 152582 90466252
Vasoconstriction 19.04 15.63 6 9607 879 90617955
Drug abuser 18.96 15.63 8 9605 2682 90616152
Nausea 18.92 15.63 190 9423 1110126 89508708
Therapeutic product effect incomplete 18.75 15.63 54 9559 193842 90424992
Death 18.40 15.63 13 9600 456538 90162296
Blindness transient 17.83 15.63 9 9604 4534 90614300
Neck pain 17.65 15.63 38 9575 113925 90504909
Injection site pain 16.43 15.63 48 9565 173651 90445183
Peripheral swelling 16.33 15.63 12 9601 413094 90205740
Vasculitic rash 16.30 15.63 6 9607 1404 90617430
General physical health deterioration 15.83 15.63 9 9604 355106 90263728
Photophobia 15.68 15.63 15 9598 21254 90597580

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 111.53 36.39 53 986 104718 42515578
Medication overuse headache 95.99 36.39 14 1025 210 42620086
Therapy partial responder 74.18 36.39 25 1014 19996 42600300
Insomnia 74.15 36.39 42 997 118211 42502085
Paraesthesia 71.37 36.39 35 1004 73424 42546872
Intentional product misuse 44.15 36.39 24 1015 61876 42558420
Product use in unapproved indication 41.77 36.39 35 1004 184421 42435875
Drug dependence 37.84 36.39 17 1022 29077 42591219

FDA Adverse Event Reporting System (Geriatric)

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
Medication overuse headache 205.65 18.04 42 8172 1521 110579564
Migraine 197.24 18.04 135 8079 171517 110409568
Headache 100.19 18.04 209 8005 882168 109698917
Drug ineffective 92.64 18.04 284 7930 1520256 109060829
Drug abuse 79.55 18.04 81 8133 177330 110403755
Recalled product administered 76.47 18.04 18 8196 1264 110579821
Rheumatoid factor negative 71.02 18.04 17 8197 1283 110579802
Paraesthesia 68.32 18.04 93 8121 276428 110304657
Drug dependence 63.66 18.04 42 8172 49978 110531107
Rubber sensitivity 60.55 18.04 17 8197 2401 110578684
Intentional product misuse 60.13 18.04 61 8153 132843 110448242
Communication disorder 48.26 18.04 17 8197 5022 110576063
Breast pain 46.63 18.04 20 8194 9980 110571105
Enzyme inhibition 44.47 18.04 8 8206 145 110580940
Pain 41.58 18.04 160 8054 954795 109626290
Acute kidney injury 36.05 18.04 3 8211 635427 109945658
Therapy partial responder 35.17 18.04 26 8188 37035 110544050
Feeling abnormal 34.70 18.04 54 8160 180657 110400428
Reversible cerebral vasoconstriction syndrome 30.66 18.04 12 8202 4749 110576336
Stress 29.93 18.04 38 8176 105310 110475775
Pleural rub 29.28 18.04 5 8209 66 110581019
Throat tightness 28.47 18.04 22 8192 33467 110547618
Therapeutic product effect incomplete 27.52 18.04 55 8159 223750 110357335
Oral mucosal exfoliation 25.62 18.04 8 8206 1628 110579457
Chest discomfort 25.42 18.04 46 8168 173802 110407283
Withdrawal syndrome 25.34 18.04 20 8194 31360 110549725
Death 23.94 18.04 11 8203 698858 109882227
Product dispensing error 23.94 18.04 15 8199 16330 110564755
Nausea 23.89 18.04 165 8049 1235525 109345560
Decreased activity 23.83 18.04 13 8201 10961 110570124
Product use in unapproved indication 23.65 18.04 80 8134 447297 110133788
Insomnia 23.19 18.04 69 8145 360521 110220564
Serotonin syndrome 22.89 18.04 25 8189 59128 110521957
Vomiting 22.81 18.04 130 8084 910545 109670540
Joint swelling 22.76 18.04 3 8211 442842 110138243
Basilar migraine 22.65 18.04 4 8210 65 110581020
Somnolence 22.13 18.04 60 8154 297389 110283696
Disturbance in attention 21.93 18.04 25 8189 61970 110519115
Drug ineffective for unapproved indication 21.52 18.04 32 8182 102806 110478279
Antisocial behaviour 21.27 18.04 6 8208 862 110580223
Status migrainosus 20.78 18.04 4 8210 106 110580979
Cholecystitis chronic 19.93 18.04 11 8203 9489 110571596
Lichen planus 19.88 18.04 8 8206 3402 110577683
Coronary artery dissection 19.12 18.04 6 8208 1242 110579843
Anaemia 18.13 18.04 9 8205 547077 110034008

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC N02CC06 NERVOUS SYSTEM
ANALGESICS
ANTIMIGRAINE PREPARATIONS
Selective serotonin (5HT1) agonists
MeSH PA D017366 Serotonin Receptor Agonists
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018490 Serotonin Agents
FDA MoA N0000175763 Serotonin 1b Receptor Agonists
FDA MoA N0000175764 Serotonin 1d Receptor Agonists
FDA EPC N0000175765 Serotonin-1b and Serotonin-1d Receptor Agonist
CHEBI has role CHEBI:35475 non-steroidal anti-inflammatory drug
CHEBI has role CHEBI:35941 serotonergic agonist
CHEBI has role CHEBI:50514 vasoconstrictor agent

Related Drugs by ATC class:

N02CC Selective serotonin (5HT1) agonists 8 drugs
almotriptanfrovatriptanlasmiditannaproxennaratriptanrizatriptansumatriptanzolmitriptan

Drug Use | Suggest Off label Use Form| |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




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

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 1A GPCR AGONIST Ki 7.40 IUPHAR
5-hydroxytryptamine receptor 1F GPCR AGONIST Ki 8 IUPHAR
5-hydroxytryptamine receptor 1E GPCR AGONIST Ki 7.20 IUPHAR

External reference:

IDSource
4021372 VUID
N0000148791 NUI
D01973 KEGG_DRUG
177834-92-3 SECONDARY_CAS_RN
4021372 VANDF
C0759933 UMLSCUI
CHEBI:50922 CHEBI
CHEMBL1510 ChEMBL_ID
CHEMBL1201003 ChEMBL_ID
DB00216 DRUGBANK_ID
C115647 MESH_SUPPLEMENTAL_RECORD_UI
77993 PUBCHEM_CID
40 IUPHAR_LIGAND_ID
7426 INN_ID
22QOO9B8KI UNII
231049 RXNORM
17144 MMSL
260414 MMSL
46299 MMSL
d04849 MMSL
009521 NDDF
009522 NDDF
395255007 SNOMEDCT_US
410843003 SNOMEDCT_US
425436002 SNOMEDCT_US
22QOO9B8KI INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Eletriptan Hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 0093-8310 TABLET, FILM COATED 20 mg ORAL ANDA 25 sections
Eletriptan Hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 0093-8311 TABLET, FILM COATED 40 mg ORAL ANDA 25 sections
Eletriptan Hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 0378-4287 TABLET, FILM COATED 20 mg ORAL ANDA 26 sections
Eletriptan Hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 0378-4288 TABLET, FILM COATED 40 mg ORAL ANDA 26 sections
Relpax HUMAN PRESCRIPTION DRUG LABEL 1 16590-201 TABLET, FILM COATED 40 mg ORAL NDA 28 sections
Relpax HUMAN PRESCRIPTION DRUG LABEL 1 21695-871 TABLET, FILM COATED 40 mg ORAL NDA 28 sections
Eletriptan Hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 24689-167 TABLET, FILM COATED 20 mg ORAL ANDA 29 sections
Eletriptan Hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 24689-168 TABLET, FILM COATED 40 mg ORAL ANDA 29 sections
eletriptan hydrobromide Human Prescription Drug Label 1 27241-039 TABLET, FILM COATED 20 mg ORAL ANDA 24 sections
eletriptan hydrobromide Human Prescription Drug Label 1 27241-040 TABLET, FILM COATED 40 mg ORAL ANDA 24 sections
Eletriptan hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 31722-443 TABLET, FILM COATED 20 mg ORAL ANDA 24 sections
Eletriptan hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 31722-444 TABLET, FILM COATED 40 mg ORAL ANDA 24 sections
Relpax HUMAN PRESCRIPTION DRUG LABEL 1 54868-5528 TABLET, FILM COATED 40 mg ORAL NDA 28 sections
Relpax HUMAN PRESCRIPTION DRUG LABEL 1 58151-367 TABLET 20 mg ORAL NDA 28 sections
Relpax HUMAN PRESCRIPTION DRUG LABEL 1 58151-368 TABLET 40 mg ORAL NDA 28 sections
Eletriptan Hydrobromide Human Prescription Drug Label 1 59651-104 TABLET, FILM COATED 20 mg ORAL ANDA 24 sections
Eletriptan Hydrobromide Human Prescription Drug Label 1 59651-105 TABLET, FILM COATED 40 mg ORAL ANDA 24 sections
Eletriptan Hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 63629-8320 TABLET, FILM COATED 40 mg ORAL ANDA 24 sections
Eletriptan hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 68382-922 TABLET, FILM COATED 20 mg ORAL ANDA 24 sections
Eletriptan hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 68382-923 TABLET, FILM COATED 40 mg ORAL ANDA 24 sections
Eletriptan hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 70771-1107 TABLET, FILM COATED 20 mg ORAL ANDA 1 sections
Eletriptan hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 70771-1108 TABLET, FILM COATED 40 mg ORAL ANDA 1 sections
Eletriptan hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 71335-2983 TABLET, FILM COATED 40 mg ORAL ANDA 2 sections
Eletriptan HBR HUMAN PRESCRIPTION DRUG LABEL 1 72189-439 TABLET, FILM COATED 40 mg ORAL ANDA 17 sections
Eletriptan HBR HUMAN PRESCRIPTION DRUG LABEL 1 72189-517 TABLET, FILM COATED 40 mg ORAL ANDA 17 sections
Eletriptan Hydrobromide HUMAN PRESCRIPTION DRUG LABEL 1 80425-0408 TABLET, FILM COATED 40 mg ORAL ANDA 24 sections