Eletriptan

Identification

Summary

Eletriptan is a triptan used for the treatment of migraines.

Brand Names
Relpax
Generic Name
Eletriptan
DrugBank Accession Number
DB00216
Background

Eletriptan is a second generation triptan drug developed by Pfizer Inc for the treatment of migraine headaches.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 382.519
Monoisotopic: 382.171498776
Chemical Formula
C22H26N2O2S
Synonyms
  • Eletriptán
  • Eletriptan
  • élétriptan
  • Eletriptanum
External IDs
  • UK-116,044
  • UK-116,044-04 FREE BASE
  • UK-116044
  • UK-116044-04 FREE BASE

Pharmacology

Indication

For the acute treatment of migraine with or without aura in adults.

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofMigraine with aura•••••••••••••••••••••••
Treatment ofMigraine without aura•••••••••••••••••••••••
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Eletriptan is a selective 5-hydroxytryptamine 1B/1D receptor agonist. In the anesthetized dog, eletriptan has been shown to reduce carotid arterial blood flow, with only a small increase in arterial blood pressure at high doses. While the effect on blood flow was selective for the carotid arterial bed, decreases in coronary artery diameter were observed. Eletriptan has also been shown to inhibit trigeminal nerve activity in the rat.

Mechanism of action

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, and little or no affinity for 5-HT2A, 5-HT2C, 5-HT3, 5-HT4, 5-HT5A and 5-HT6 receptors. In contrast, eletriptan displays insignificant pharmacological activity at adrenergic alpha1, alpha2, or beta; dopaminergic D1 or D2; muscarinic; or opioid receptors. While the full mechanism of action of 5-HT receptor agonists in relieving migrains is not fully elucidated, it is proposed that the activation of 5-HT1 receptors located on intracranial blood vessels leads to vasoconstriction that correlates with the relief of migraine headaches. It is also proposed that the activation of 5-HT1 receptors on sensory nerve endings in the trigeminal system leads to the inhibition of release of pro-inflammatory neuropeptides.

TargetActionsOrganism
A5-hydroxytryptamine receptor 1D
agonist
Humans
A5-hydroxytryptamine receptor 1B
agonist
Humans
A5-hydroxytryptamine receptor 1F
agonist
Humans
U5-hydroxytryptamine receptor 1A
agonist
Humans
Absorption

Well absorbed after oral administration with a mean absolute bioavailability of approximately 50%.

Volume of distribution
  • 138 L
Protein binding

Plasma protein binding is moderate and approximately 85%.

Metabolism

In vitro studies indicate that eletriptan is primarily metabolized by cytochrome P-450 enzyme CYP3A4. The N-demethylated metabolite of eletriptan is the only known active metabolite.

Hover over products below to view reaction partners

Route of elimination

Not Available

Half-life

The terminal elimination half-life of eletriptan is approximately 4 hours.

Clearance
  • Renal cl=3.9 L/h
Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Based on the pharmacology of the 5-HT1B/1D agonists, hypertension or other more serious cardiovascular symptoms could occur on overdose.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Guanine nucleotide-binding protein G(I)/G(S)/G(T) subunit beta-3---(T;T) / (C;T)T AlleleEffect Directly StudiedPatients with this genotype have an increased likelihood of responding to elitriptan when treating (condition: cluster headache).Details

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Eletriptan is combined with 1,2-Benzodiazepine.
AbametapirThe serum concentration of Eletriptan can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Eletriptan can be increased when combined with Abatacept.
AbirateroneThe metabolism of Eletriptan can be decreased when combined with Abiraterone.
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Eletriptan.
Food Interactions
  • Take with or without food. High-fat meals increase exposure, but not to a clinically relevant extent.

Products

Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
Product Ingredients
IngredientUNIICASInChI Key
Eletriptan hydrobromideM41W832TA3177834-92-3UTINOWOSWSPFLJ-FSRHSHDFSA-N
Eletriptan hydrobromide monohydrate4139X692FA273211-28-2BORDVONYOHPTGR-JQDLGSOUSA-N
Product Images
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
EletriptanTablet40 mgOralSanis Health Inc2021-07-22Not applicableCanada flag
EletriptanTablet20 mgOralPro Doc Limitee2019-07-31Not applicableCanada flag
EletriptanTablet20 mgOralSanis Health Inc2021-07-22Not applicableCanada flag
EletriptanTablet40 mgOralPro Doc Limitee2019-07-31Not applicableCanada flag
RelpaxTablet, film coated40 mg/1OralU.S. Pharmaceuticals2002-12-26Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-eletriptanTablet20 mgOralApotex Corporation2013-09-12Not applicableCanada flag
Apo-eletriptanTablet40 mgOralApotex Corporation2013-09-12Not applicableCanada flag
Apo-eletriptan TabletsTablet40 mgOralApotex Corporation2022-06-01Not applicableCanada flag
Apo-eletriptan TabletsTablet20 mgOralApotex Corporation2022-06-01Not applicableCanada flag
Auro-eletriptanTablet40 mgOralAuro Pharma Inc2019-02-01Not applicableCanada flag

Categories

ATC Codes
N02CC06 — Eletriptan
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 3-alkylindoles. These are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Indoles
Direct Parent
3-alkylindoles
Alternative Parents
Benzenesulfonyl compounds / Aralkylamines / Substituted pyrroles / N-alkylpyrrolidines / Sulfones / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Organic oxides
show 1 more
Substituents
3-alkylindole / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenesulfonyl group / Benzenoid / Heteroaromatic compound / Hydrocarbon derivative / Monocyclic benzene moiety
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
sulfone, indoles, N-alkylpyrrolidine (CHEBI:50922)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
22QOO9B8KI
CAS number
143322-58-1
InChI Key
PWVXXGRKLHYWKM-LJQANCHMSA-N
InChI
InChI=1S/C22H26N2O2S/c1-24-12-5-6-19(24)15-18-16-23-22-10-9-17(14-21(18)22)11-13-27(25,26)20-7-3-2-4-8-20/h2-4,7-10,14,16,19,23H,5-6,11-13,15H2,1H3/t19-/m1/s1
IUPAC Name
5-[2-(benzenesulfonyl)ethyl]-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-1H-indole
SMILES
CN1CCC[C@@H]1CC1=CNC2=C1C=C(CCS(=O)(=O)C1=CC=CC=C1)C=C2

References

Synthesis Reference

Ronald Ogilvie, "Process for the preparation of eletriptan." U.S. Patent US20050059828, issued March 17, 2005.

US20050059828
General References
  1. FDA Approved Drug Products: RELPAX (eletriptan hydrobromide) tablets [Link]
Human Metabolome Database
HMDB0014361
KEGG Drug
D07887
PubChem Compound
77993
PubChem Substance
46506380
ChemSpider
70379
BindingDB
50103594
RxNav
231049
ChEBI
50922
ChEMBL
CHEMBL1510
ZINC
ZINC000003823475
Therapeutic Targets Database
DAP000008
PharmGKB
PA134687947
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Eletriptan
FDA label
Download (148 KB)

Clinical Trials

Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package
PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
Not AvailableCompletedNot AvailableMigraine3somestatusstop reasonjust information to hide
Not AvailableCompletedTreatmentAcute Migraine / Headache Disorders / Migraine1somestatusstop reasonjust information to hide
4CompletedOtherWorkplace Migraine Treatment1somestatusstop reasonjust information to hide
4CompletedPreventionMigraine1somestatusstop reasonjust information to hide
4CompletedTreatmentMigraine3somestatusstop reasonjust information to hide

Pharmacoeconomics

Manufacturers
  • Pfizer ireland pharmaceuticals
Packagers
  • Chunghwa Chemical Synthesis and Biotech Co. Ltd.
  • Pfizer Inc.
  • Physicians Total Care Inc.
  • Rebel Distributors Corp.
  • US Pharmaceutical Group
Dosage Forms
FormRouteStrength
Tablet, film coatedOral20 MG
Tablet, film coatedOral40 MG
Tablet, film coatedOral20 mg/1
TabletOral80.000 mg
TabletOral40.000 mg
TabletOral
TabletOral20 mg/1
TabletOral20 mg
TabletOral40 mg/1
TabletOral40 mg
Tablet, film coatedOral40 mg/1
Tablet, coatedOral40 mg
Tablet, film coatedOral
Tablet, film coatedOral80 mg
Prices
Unit descriptionCostUnit
Relpax 6 20 mg tablet Box156.05USD box
Relpax 6 40 mg tablet Box156.05USD box
Relpax 20 mg tablet25.01USD tablet
Relpax 40 mg tablet25.01USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
CA2352392No2006-01-242019-11-01Canada flag
CA2198599No2000-06-062015-05-17Canada flag
US5545644No1996-08-132016-12-26US flag
US6110940No2000-08-292017-08-29US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilityReadily soluble as hydrobromide formulationNot Available
logP3.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00118 mg/mLALOGPS
logP3.84ALOGPS
logP3.77Chemaxon
logS-5.5ALOGPS
pKa (Strongest Acidic)16.56Chemaxon
pKa (Strongest Basic)8.37Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area53.17 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity110.94 m3·mol-1Chemaxon
Polarizability42.99 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9872
Blood Brain Barrier+0.9774
Caco-2 permeable-0.628
P-glycoprotein substrateSubstrate0.6308
P-glycoprotein inhibitor INon-inhibitor0.8046
P-glycoprotein inhibitor IINon-inhibitor0.8383
Renal organic cation transporterInhibitor0.7
CYP450 2C9 substrateNon-substrate0.6591
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateSubstrate0.643
CYP450 1A2 substrateNon-inhibitor0.7021
CYP450 2C9 inhibitorNon-inhibitor0.8103
CYP450 2D6 inhibitorNon-inhibitor0.7615
CYP450 2C19 inhibitorNon-inhibitor0.7519
CYP450 3A4 inhibitorNon-inhibitor0.6355
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6986
Ames testNon AMES toxic0.5945
CarcinogenicityNon-carcinogens0.8556
BiodegradationNot ready biodegradable0.9883
Rat acute toxicity2.5492 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6436
hERG inhibition (predictor II)Inhibitor0.7581
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-001i-9110000000-bef75cdb82e945554b4a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0009000000-fa579ac6613cd384caea
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0009000000-2842335345e50729f81f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-1049000000-d0631600b8fc7f389120
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0329000000-32fc70bc10331ef74e6c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-003r-5923000000-82431fdde65c0d0e0a8a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0aou-4915000000-6466713f4780366f34b1
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-204.5012312
predicted
DarkChem Lite v0.1.0
[M-H]-205.6329312
predicted
DarkChem Lite v0.1.0
[M-H]-185.27248
predicted
DeepCCS 1.0 (2019)
[M+H]+205.2502312
predicted
DarkChem Lite v0.1.0
[M+H]+206.5549312
predicted
DarkChem Lite v0.1.0
[M+H]+187.76917
predicted
DeepCCS 1.0 (2019)
[M+Na]+204.9878312
predicted
DarkChem Lite v0.1.0
[M+Na]+195.0475
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin) (PubMed:10452531, PubMed:1565658, PubMed:1652050, PubMed:33762731). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive substances (PubMed:10452531, PubMed:1565658, PubMed:1652050, PubMed:33762731). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of downstream effectors, such as adenylate cyclase (PubMed:10452531, PubMed:1565658, PubMed:1652050, PubMed:33762731). HTR1D is coupled to G(i)/G(o) G alpha proteins and mediates inhibitory neurotransmission by inhibiting adenylate cyclase activity (PubMed:33762731). Regulates the release of 5-hydroxytryptamine in the brain, and thereby affects neural activity (PubMed:18476671, PubMed:20945968). May also play a role in regulating the release of other neurotransmitters (PubMed:18476671, PubMed:20945968). May play a role in vasoconstriction (PubMed:18476671, PubMed:20945968)
Specific Function
G protein-coupled serotonin receptor activity
Gene Name
HTR1D
Uniprot ID
P28221
Uniprot Name
5-hydroxytryptamine receptor 1D
Molecular Weight
41906.38 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  2. Napier C, Stewart M, Melrose H, Hopkins B, McHarg A, Wallis R: Characterisation of the 5-HT receptor binding profile of eletriptan and kinetics of [3H]eletriptan binding at human 5-HT1B and 5-HT1D receptors. Eur J Pharmacol. 1999 Mar 5;368(2-3):259-68. [Article]
  3. Wackenfors A, Jarvius M, Ingemansson R, Edvinsson L, Malmsjo M: Triptans induce vasoconstriction of human arteries and veins from the thoracic wall. J Cardiovasc Pharmacol. 2005 May;45(5):476-84. [Article]
  4. Johnson DE, Rollema H, Schmidt AW, McHarg AD: Serotonergic effects and extracellular brain levels of eletriptan, zolmitriptan and sumatriptan in rat brain. Eur J Pharmacol. 2001 Aug 17;425(3):203-10. [Article]
  5. Strijbos PJ, Parsons AA, Fugelli A: Eletriptan Pfizer. Curr Opin Investig Drugs. 2002 Sep;3(9):1359-68. [Article]
  6. Tfelt-Hansen P, De Vries P, Saxena PR: Triptans in migraine: a comparative review of pharmacology, pharmacokinetics and efficacy. Drugs. 2000 Dec;60(6):1259-87. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin) (PubMed:10452531, PubMed:1315531, PubMed:1328844, PubMed:1348246, PubMed:1351684, PubMed:1559993, PubMed:1565658, PubMed:1610347, PubMed:23519210, PubMed:23519215, PubMed:29925951, PubMed:8218242). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive substances, such as lysergic acid diethylamide (LSD) (PubMed:23519210, PubMed:23519215, PubMed:29925951). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of downstream effectors, such as adenylate cyclase (PubMed:10452531, PubMed:1315531, PubMed:1328844, PubMed:1348246, PubMed:1351684, PubMed:1559993, PubMed:1565658, PubMed:1610347, PubMed:23519210, PubMed:23519215, PubMed:29925951, PubMed:8218242). HTR1B is coupled to G(i)/G(o) G alpha proteins and mediates inhibitory neurotransmission by inhibiting adenylate cyclase activity (PubMed:29925951, PubMed:35610220). Arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways (PubMed:29925951). Regulates the release of 5-hydroxytryptamine, dopamine and acetylcholine in the brain, and thereby affects neural activity, nociceptive processing, pain perception, mood and behavior (PubMed:18476671, PubMed:20945968). Besides, plays a role in vasoconstriction of cerebral arteries (PubMed:15853772)
Specific Function
G protein-coupled serotonin receptor activity
Gene Name
HTR1B
Uniprot ID
P28222
Uniprot Name
5-hydroxytryptamine receptor 1B
Molecular Weight
43567.535 Da
References
  1. Napier C, Stewart M, Melrose H, Hopkins B, McHarg A, Wallis R: Characterisation of the 5-HT receptor binding profile of eletriptan and kinetics of [3H]eletriptan binding at human 5-HT1B and 5-HT1D receptors. Eur J Pharmacol. 1999 Mar 5;368(2-3):259-68. [Article]
  2. van den Broek RW, MaassenVanDenBrink A, de Vries R, Bogers AJ, Stegmann AP, Avezaat CJ, Saxena PR: Pharmacological analysis of contractile effects of eletriptan and sumatriptan on human isolated blood vessels. Eur J Pharmacol. 2000 Oct 27;407(1-2):165-73. [Article]
  3. Knyihar-Csillik E, Tajti J, Csillik AE, Chadaide Z, Mihaly A, Vecsei L: Effects of eletriptan on the peptidergic innervation of the cerebral dura mater and trigeminal ganglion, and on the expression of c-fos and c-jun in the trigeminal complex of the rat in an experimental migraine model. Eur J Neurosci. 2000 Nov;12(11):3991-4002. [Article]
  4. Johnson DE, Rollema H, Schmidt AW, McHarg AD: Serotonergic effects and extracellular brain levels of eletriptan, zolmitriptan and sumatriptan in rat brain. Eur J Pharmacol. 2001 Aug 17;425(3):203-10. [Article]
  5. Lambert GA, Boers PM, Hoskin KL, Donaldson C, Zagami AS: Suppression by eletriptan of the activation of trigeminovascular sensory neurons by glyceryl trinitrate. Brain Res. 2002 Oct 25;953(1-2):181-8. [Article]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin) (PubMed:21422162, PubMed:34239069, PubMed:8380639, PubMed:8384716). Also functions as a receptor for various alkaloids and psychoactive substances (PubMed:21422162, PubMed:8380639, PubMed:8384716). Receptor for lasmiditan, a drug for the treatment of acute migraine (PubMed:34239069). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of downstream effectors, such as adenylate cyclase (PubMed:34239069). HTR1F is coupled to G(i)/G(o) G alpha proteins and mediates inhibitory neurotransmission by inhibiting adenylate cyclase activity (PubMed:34239069, PubMed:35610220)
Specific Function
G protein-coupled serotonin receptor activity
Gene Name
HTR1F
Uniprot ID
P30939
Uniprot Name
5-hydroxytryptamine receptor 1F
Molecular Weight
41708.505 Da
References
  1. Napier C, Stewart M, Melrose H, Hopkins B, McHarg A, Wallis R: Characterisation of the 5-HT receptor binding profile of eletriptan and kinetics of [3H]eletriptan binding at human 5-HT1B and 5-HT1D receptors. Eur J Pharmacol. 1999 Mar 5;368(2-3):259-68. [Article]
  2. Bhalla P, Sharma HS, Wurch T, Pauwels PJ, Saxena PR: Molecular cloning and expression of the porcine trigeminal ganglion cDNA encoding a 5-ht(1F) receptor. Eur J Pharmacol. 2002 Feb 1;436(1-2):23-33. [Article]
  3. Jahnichen S, Radtke OA, Pertz HH: Involvement of 5-HT1B receptors in triptan-induced contractile responses in guinea-pig isolated iliac artery. Naunyn Schmiedebergs Arch Pharmacol. 2004 Jul;370(1):54-63. Epub 2004 Jun 8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin) (PubMed:22957663, PubMed:3138543, PubMed:33762731, PubMed:37935376, PubMed:37935377, PubMed:8138923, PubMed:8393041). Also functions as a receptor for various drugs and psychoactive substances (PubMed:22957663, PubMed:3138543, PubMed:33762731, PubMed:38552625, PubMed:8138923, PubMed:8393041). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of downstream effectors, such as adenylate cyclase (PubMed:22957663, PubMed:3138543, PubMed:33762731, PubMed:8138923, PubMed:8393041). HTR1A is coupled to G(i)/G(o) G alpha proteins and mediates inhibitory neurotransmission: signaling inhibits adenylate cyclase activity and activates a phosphatidylinositol-calcium second messenger system that regulates the release of Ca(2+) ions from intracellular stores (PubMed:33762731, PubMed:35610220). Beta-arrestin family members regulate signaling by mediating both receptor desensitization and resensitization processes (PubMed:18476671, PubMed:20363322, PubMed:20945968). Plays a role in the regulation of 5-hydroxytryptamine release and in the regulation of dopamine and 5-hydroxytryptamine metabolism (PubMed:18476671, PubMed:20363322, PubMed:20945968). Plays a role in the regulation of dopamine and 5-hydroxytryptamine levels in the brain, and thereby affects neural activity, mood and behavior (PubMed:18476671, PubMed:20363322, PubMed:20945968). Plays a role in the response to anxiogenic stimuli (PubMed:18476671, PubMed:20363322, PubMed:20945968)
Specific Function
G protein-coupled serotonin receptor activity
Gene Name
HTR1A
Uniprot ID
P08908
Uniprot Name
5-hydroxytryptamine receptor 1A
Molecular Weight
46106.335 Da
References
  1. Johnson DE, Rollema H, Schmidt AW, McHarg AD: Serotonergic effects and extracellular brain levels of eletriptan, zolmitriptan and sumatriptan in rat brain. Eur J Pharmacol. 2001 Aug 17;425(3):203-10. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
Specific Function
anandamide 11,12 epoxidase activity
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Evans DC, O'Connor D, Lake BG, Evers R, Allen C, Hargreaves R: Eletriptan metabolism by human hepatic CYP450 enzymes and transport by human P-glycoprotein. Drug Metab Dispos. 2003 Jul;31(7):861-9. [Article]
  2. Kim YK, Shin KH, Alderman J, Yu KS, Jang IJ, Lee S: Pharmacokinetics and tolerability of eletriptan hydrobromide in healthy Korean subjects. Drug Des Devel Ther. 2018 Feb 19;12:331-337. doi: 10.2147/DDDT.S149119. eCollection 2018. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031)
Specific Function
(R)-limonene 6-monooxygenase activity
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
  2. Capi M, Curto M, Lionetto L, de Andres F, Gentile G, Negro A, Martelletti P: Eletriptan in the management of acute migraine: an update on the evidence for efficacy, safety, and consistent response. Ther Adv Neurol Disord. 2016 Sep;9(5):414-23. doi: 10.1177/1756285616650619. Epub 2016 Jun 3. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
A cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates PUFA specifically at the omega-1 position (PubMed:18577768). Catalyzes the epoxidation of double bonds of PUFA (PubMed:19965576, PubMed:20972997). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine. Hydroxylates fenbendazole at the 4' position (PubMed:23959307)
Specific Function
(R)-limonene 6-monooxygenase activity
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55944.565 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity
Specific Function
arachidonic acid epoxygenase activity
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56517.005 Da
References
  1. Pichard-Garcia L, Hyland R, Baulieu J, Fabre JM, Milton A, Maurel P: Human hepatocytes in primary culture predict lack of cytochrome P-450 3A4 induction by eletriptan in vivo. Drug Metab Dispos. 2000 Jan;28(1):51-7. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Dual cyclooxygenase and peroxidase that plays an important role in the biosynthesis pathway of prostanoids, a class of C20 oxylipins mainly derived from arachidonate ((5Z,8Z,11Z,14Z)-eicosatetraenoate, AA, C20:4(n-6)), with a particular role in the inflammatory response. The cyclooxygenase activity oxygenates AA to the hydroperoxy endoperoxide prostaglandin G2 (PGG2), and the peroxidase activity reduces PGG2 to the hydroxy endoperoxide prostaglandin H2 (PGH2), the precursor of all 2-series prostaglandins and thromboxanes. This complex transformation is initiated by abstraction of hydrogen at carbon 13 (with S-stereochemistry), followed by insertion of molecular O2 to form the endoperoxide bridge between carbon 9 and 11 that defines prostaglandins. The insertion of a second molecule of O2 (bis-oxygenase activity) yields a hydroperoxy group in PGG2 that is then reduced to PGH2 by two electrons (PubMed:7947975). Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the generation of thromboxane A2 (TXA2), which promotes platelet activation and aggregation, vasoconstriction and proliferation of vascular smooth muscle cells (Probable). Can also use linoleate (LA, (9Z,12Z)-octadecadienoate, C18:2(n-6)) as substrate and produce hydroxyoctadecadienoates (HODEs) in a regio- and stereospecific manner, being (9R)-HODE ((9R)-hydroxy-(10E,12Z)-octadecadienoate) and (13S)-HODE ((13S)-hydroxy-(9Z,11E)-octadecadienoate) its major products (By similarity)
Specific Function
heme binding
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
Specific Function
1,8-cineole 2-exo-monooxygenase activity
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
  2. Evans DC, O'Connor D, Lake BG, Evers R, Allen C, Hargreaves R: Eletriptan metabolism by human hepatic CYP450 enzymes and transport by human P-glycoprotein. Drug Metab Dispos. 2003 Jul;31(7):861-9. [Article]
  3. Eletriptan FDA label [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
Specific Function
ABC-type xenobiotic transporter activity
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
ATP-dependent translocase ABCB1
Molecular Weight
141477.255 Da
References
  1. Evans DC, O'Connor D, Lake BG, Evers R, Allen C, Hargreaves R: Eletriptan metabolism by human hepatic CYP450 enzymes and transport by human P-glycoprotein. Drug Metab Dispos. 2003 Jul;31(7):861-9. [Article]
  2. Tepper SJ: Safety and rational use of the triptans. Med Clin North Am. 2001 Jul;85(4):959-70. [Article]

Drug created at June 13, 2005 13:24 / Updated at November 03, 2024 19:35