Ergotamine

Identification

Summary

Ergotamine is an alpha-1 selective adrenergic agonist vasoconstrictor used to treat migraines with or without aura and cluster headaches.

Brand Names
Ergomar, Migergot
Generic Name
Ergotamine
DrugBank Accession Number
DB00696
Background

A vasoconstrictor found in ergot of Central Europe. It is an alpha-1 selective adrenergic agonist and is commonly used in the treatment of migraine disorders.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 581.6615
Monoisotopic: 581.263819255
Chemical Formula
C33H35N5O5
Synonyms
  • (5'α)-12'-hydroxy-2'-methyl-5'-(phenylmethyl)ergotoman-3',6',18-trione
  • 12'-Hydroxy-2'-methyl-5'alpha-(phenylmethyl)ergotaman-3',6',18-trione
  • 12'-hydroxy-2'-methyl-5'α-(phenylmethyl)ergotaman-3',6',18-trione
  • Ergotamin
  • Ergotamina
  • Ergotamine
  • Ergotaminum

Pharmacology

Indication

For use as therapy to abort or prevent vascular headache, e.g., migraine, migraine variants, or so called "histaminic cephalalgia".

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofCluster headache••••••••••••
Prevention ofCluster headache••••••••••••
Prevention ofMigraine••••••••••••
Treatment ofMigraine••••••••••••
Used in combination to treatUterine atonyCombination Product in combination with: Ergometrine (DB01253)••••••••••••••••••••••••••••• ••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Ergotamine is a vasoconstrictor and alpha adrenoreceptor antagonist. The pharmacological properties of ergotamine are extremely complex; some of its actions are unrelated to each other, and even mutually antagonistic. The drug has partial agonist and/or antagonist activity against tryptaminergic, dopaminergic and alpha adrenergic receptors depending upon their site, and it is a highly active uterine stimulant. It causes constriction of peripheral and cranial blood vessels and produces depression of central vasomotor centers. The pain of a migraine attack is believed to be due to greatly increased amplitude of pulsations in the cranial arteries, especially the meningeal branches of the external carotid artery. Ergotamine reduces extracranial blood flow, causes a decline in the amplitude of pulsation in the cranial arteries, and decreases hyperperfusion of the territory of the basilar artery. It does not reduce cerebral hemispheric blood flow.

Mechanism of action

Ergotamine acts on migraine by one of two proposed mechanisms: 1) activation of 5-HT1D receptors located on intracranial blood vessels, including those on arterio-venous anastomoses, leads to vasoconstriction, which correlates with the relief of migraine headache, and 2) activation of 5-HT1D receptors on sensory nerve endings of the trigeminal system results in the inhibition of pro-inflammatory neuropeptide release.

TargetActionsOrganism
A5-hydroxytryptamine receptor 1D
agonist
Humans
A5-hydroxytryptamine receptor 1B
agonist
Humans
A5-hydroxytryptamine receptor 2A
agonist
Humans
AAlpha-1A adrenergic receptor
partial agonist
Humans
AAlpha-1B adrenergic receptor
partial agonist
Humans
AAlpha-1D adrenergic receptor
partial agonist
Humans
UDopamine D2 receptor
agonist
Humans
UAlpha-2A adrenergic receptor
partial agonist
Humans
UD(1) dopamine receptor
agonist
Humans
U5-hydroxytryptamine receptor 1A
agonist
Humans
U5-hydroxytryptamine receptor 1F
agonist
Humans
U5-hydroxytryptamine receptor 2C
agonist
Humans
U5-hydroxytryptamine receptor 2BNot AvailableHumans
UAlpha-2C adrenergic receptorNot AvailableHumans
Absorption

The bioavailability of sublingually administered ergotamine has not been determined.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Hepatic. Ergotamine is metabolized by the liver by largely undefined pathways, and 90% of the metabolites are excreted in the bile.

Route of elimination

Not Available

Half-life

2 hours

Clearance

Not Available

Adverse Effects
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Toxicity

Signs of overexposure include irritation, nausea, vomiting, headache, diarrhea, thirst, coldness of skin, pruritus, weak pulse, numbness, tingling of extremities, and confusion.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

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 metabolism of 1,2-Benzodiazepine can be decreased when combined with Ergotamine.
AbametapirThe serum concentration of Ergotamine can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Ergotamine can be increased when combined with Abatacept.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Ergotamine.
AbirateroneThe metabolism of Abiraterone can be decreased when combined with Ergotamine.
Food Interactions
  • Take with or without food. The absorption is unaffected by food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Ergotamine tartrateMRU5XH3B48379-79-3CJMJLDQKTOJACI-BGQAIRJTSA-N
Product Images
International/Other Brands
Anervan (Recip) / Antimigraine (Ta Fong) / Enxak (Cazi) / Ergam (Gedeon Richter) / Ergo-Kranit (Krewel Meuselbach) / Gynaemine (Sriprasit Dispensary) / Gynergen / Wigrettes
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ergomar Slt 2mgTablet2 mg / sltSublingualAventis Pharma Ltd.1975-12-312003-07-22Canada flag
Medihaler-ErgotamineAerosol9.0 mg/1mLOral3M Company1960-01-142006-12-29US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ErgomarTablet, orally disintegrating2 mg/1SublingualRosedale Therapeutics2012-08-31Not applicableUS flag
Ergomar SublingualTablet2 mg/1OralTerSera Therapeutics, LLC2016-09-20Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AVMIGRAN FİLM TABLET, 20 ADETErgotamine tartrate (0.75 mg) + Acetaminophen (325 mg) + Caffeine (80 mg) + Mecloxamine citrate (20 mg)TabletMENARİNİ SAĞLIK VE İLAÇ SAN. VE TİC. A.Ş.1974-01-15Not applicableTurkey flag
Bellergal SpacetabsErgotamine tartrate (0.6 mg) + Belladonna (0.2 mg) + Phenobarbital (40.0 mg)Tablet, extended releaseOralPaladin Labs Inc1959-01-012018-06-05Canada flag
Bellergal TabErgotamine tartrate (.3 mg / tab) + Belladonna (.1 mg / tab) + Phenobarbital (20 mg / tab)TabletOralSandoz1951-12-311997-08-12Canada flag
CAFERGOTErgotamine tartrate (2 MG) + Caffeine (100 MG)SuppositoryRectalAmdipharm Ltd2014-07-08Not applicableItaly flag
CAFERGOTErgotamine tartrate (1 MG) + Caffeine (100 MG)TabletOralAmdipharm Ltd2014-07-08Not applicableItaly flag

Categories

ATC Codes
N02CA02 — ErgotamineN02CA52 — Ergotamine, combinations excl. psycholepticsN02CA72 — Ergotamine, combinations with psycholeptics
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as ergotamines, dihydroergotamines, and derivatives. These are organic compounds containing an ergotamine moiety, which is structurally characterized by a benzyl substituent attached to the piperazine ring of the ergopeptine backbone.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Ergoline and derivatives
Sub Class
Lysergic acids and derivatives
Direct Parent
Ergotamines, dihydroergotamines, and derivatives
Alternative Parents
Hybrid peptides / Dipeptides / Lysergamides / Indoloquinolines / Benzoquinolines / Quinoline-3-carboxamides / Pyrroloquinolines / N-acyl-alpha amino acids and derivatives / 3-alkylindoles / Isoindoles and derivatives
show 19 more
Substituents
1,4-diazinane / 3-alkylindole / Alkanolamine / Alpha-amino acid or derivatives / Alpha-dipeptide / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle
show 39 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
peptide ergot alkaloid (CHEBI:64318)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
PR834Q503T
CAS number
113-15-5
InChI Key
XCGSFFUVFURLIX-VFGNJEKYSA-N
InChI
InChI=1S/C33H35N5O5/c1-32(35-29(39)21-15-23-22-10-6-11-24-28(22)20(17-34-24)16-25(23)36(2)18-21)31(41)38-26(14-19-8-4-3-5-9-19)30(40)37-13-7-12-27(37)33(38,42)43-32/h3-6,8-11,15,17,21,25-27,34,42H,7,12-14,16,18H2,1-2H3,(H,35,39)/t21-,25-,26+,27+,32-,33+/m1/s1
IUPAC Name
(4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0^{2,6}]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
SMILES
[H][C@@]12CCCN1C(=O)[C@H](CC1=CC=CC=C1)N1C(=O)[C@](C)(NC(=O)[C@H]3CN(C)[C@]4([H])CC5=CNC6=CC=CC(=C56)C4=C3)O[C@@]21O

References

General References
  1. Tfelt-Hansen P, Saxena PR, Dahlof C, Pascual J, Lainez M, Henry P, Diener H, Schoenen J, Ferrari MD, Goadsby PJ: Ergotamine in the acute treatment of migraine: a review and European consensus. Brain. 2000 Jan;123 ( Pt 1):9-18. [Article]
  2. Schardl CL, Panaccione DG, Tudzynski P: Ergot alkaloids--biology and molecular biology. Alkaloids Chem Biol. 2006;63:45-86. [Article]
Human Metabolome Database
HMDB0014834
KEGG Drug
D07906
KEGG Compound
C07544
PubChem Compound
8223
PubChem Substance
46507632
ChemSpider
7930
BindingDB
50027065
RxNav
4025
ChEBI
64318
ChEMBL
CHEMBL442
ZINC
ZINC000052955754
Therapeutic Targets Database
DAP000141
PharmGKB
PA164747651
PDBe Ligand
ERM
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Ergotamine
PDB Entries
4iar / 4ib4 / 4nc3 / 5tud / 6bqg / 7c61
MSDS
Download (53.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableAutonomic Failure / Orthostatic Hypotension1

Pharmacoeconomics

Manufacturers
  • 3m pharmaceuticals inc
  • Rosedale therapeutics
  • Parke davis div warner lambert co
  • Organon usa inc
Packagers
  • Cypress Pharmaceutical Inc.
  • G & W Labs
  • Harvest Pharmaceuticals Inc.
  • Kaiser Foundation Hospital
  • Mikart Inc.
  • Novartis AG
  • Nucare Pharmaceuticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Physicians Total Care Inc.
  • Rosedale Therapeutics
  • Sandoz
  • Spectrum Pharmaceuticals
  • West-Ward Pharmaceuticals
Dosage Forms
FormRouteStrength
Tablet
Tablet, extended releaseOral
SuppositoryRectal
TabletOral100 mg
Tablet, film coatedOral
Tablet, coatedOral150 mg
Tablet, coated
CapsuleOral
Tablet, orally disintegratingSublingual2 mg/1
TabletSublingual2 mg / slt
TabletOral2 mg/1
TabletOral
AerosolOral9.0 mg/1mL
Tablet, coatedOral1 mg
Tablet, film coated1 mg
Tablet, sugar coatedOral
Tablet, coatedOral
Prices
Unit descriptionCostUnit
Ergotamine tartrate powder224.35USD powder
Ergomar 2 mg tablet sl8.97USD tablet
Migergot suppository7.39USD suppository
Cafergot tablet1.89USD tablet
Ergotamine-caffeine tablet1.14USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)213.5 dec °CPhysProp
water solubilitySlightNot Available
logP2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.223 mg/mLALOGPS
logP2.95ALOGPS
logP2.6Chemaxon
logS-3.4ALOGPS
pKa (Strongest Acidic)9.7Chemaxon
pKa (Strongest Basic)7.78Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area118.21 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity160.17 m3·mol-1Chemaxon
Polarizability62.23 Å3Chemaxon
Number of Rings8Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9311
Blood Brain Barrier-0.9644
Caco-2 permeable-0.7317
P-glycoprotein substrateSubstrate0.8678
P-glycoprotein inhibitor IInhibitor0.7801
P-glycoprotein inhibitor IIInhibitor0.6032
Renal organic cation transporterNon-inhibitor0.8178
CYP450 2C9 substrateNon-substrate0.8205
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.7408
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.8849
CYP450 3A4 inhibitorInhibitor0.7959
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6759
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9604
BiodegradationNot ready biodegradable0.99
Rat acute toxicity2.9840 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8701
hERG inhibition (predictor II)Non-inhibitor0.6708
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (12 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0gi0-6692120000-7fabddfa08a8dd219bc3
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0001090000-a2cdce08b3be2daaa9a5
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0044090000-7b21b23d2b4d4dc9dfd8
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-003r-0100490000-0a77812c3cc70d6fde38
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ff0-1191040000-ef7cebf34263dabe0c06
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-003r-0116890000-c5d61816e08e0d15e2fd
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-5837940000-576e797a4aa80b716786
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-245.830042
predicted
DarkChem Lite v0.1.0
[M-H]-252.533842
predicted
DarkChem Lite v0.1.0
[M-H]-262.236342
predicted
DarkChem Lite v0.1.0
[M-H]-231.34007
predicted
DeepCCS 1.0 (2019)
[M+H]+244.265042
predicted
DarkChem Lite v0.1.0
[M+H]+248.727842
predicted
DarkChem Lite v0.1.0
[M+H]+263.748142
predicted
DarkChem Lite v0.1.0
[M+H]+233.23547
predicted
DeepCCS 1.0 (2019)
[M+Na]+245.600842
predicted
DarkChem Lite v0.1.0
[M+Na]+248.640842
predicted
DarkChem Lite v0.1.0
[M+Na]+238.93083
predicted
DeepCCS 1.0 (2019)

Targets

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Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive subst...
Gene Name
HTR1D
Uniprot ID
P28221
Uniprot Name
5-hydroxytryptamine receptor 1D
Molecular Weight
41906.38 Da
References
  1. Silberstein SD, McCrory DC: Ergotamine and dihydroergotamine: history, pharmacology, and efficacy. Headache. 2003 Feb;43(2):144-66. [Article]
  2. Lovenberg TW, Erlander MG, Baron BM, Racke M, Slone AL, Siegel BW, Craft CM, Burns JE, Danielson PE, Sutcliffe JG: Molecular cloning and functional expression of 5-HT1E-like rat and human 5-hydroxytryptamine receptor genes. Proc Natl Acad Sci U S A. 1993 Mar 15;90(6):2184-8. [Article]
  3. Hoyer D, Lery H, Waeber C, Bruinvels AT, Nozulak J, Palacios JM: "5-HT1R" or 5-HT1D sites? Evidence for 5-HT1D binding sites in rabbit brain. Naunyn Schmiedebergs Arch Pharmacol. 1992 Sep;346(3):249-54. [Article]
  4. Sanchez-Lopez A, Centurion D, Vazquez E, Arulmani U, Saxena PR, Villalon CM: Pharmacological profile of the 5-HT-induced inhibition of cardioaccelerator sympathetic outflow in pithed rats: correlation with 5-HT1 and putative 5-ht5A/5B receptors. Br J Pharmacol. 2003 Oct;140(4):725-35. Epub 2003 Sep 22. [Article]
  5. Deliganis AV, Peroutka SJ: 5-Hydroxtryptamine1D receptor agonism predicts antimigraine efficacy. Headache. 1991 Apr;31(4):228-31. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive subst...
Gene Name
HTR1B
Uniprot ID
P28222
Uniprot Name
5-hydroxytryptamine receptor 1B
Molecular Weight
43567.535 Da
References
  1. Villalon CM, De Vries P, Rabelo G, Centurion D, Sanchez-Lopez A, Saxena P: Canine external carotid vasoconstriction to methysergide, ergotamine and dihydroergotamine: role of 5-HT1B/1D receptors and alpha2-adrenoceptors. Br J Pharmacol. 1999 Feb;126(3):585-94. [Article]
  2. Willems EW, Trion M, De Vries P, Heiligers JP, Villalon CM, Saxena PR: Pharmacological evidence that alpha1-and alpha2-adrenoceptors mediate vasoconstriction of carotid arteriovenous anastomoses in anaesthetized pigs. Br J Pharmacol. 1999 Jul;127(5):1263-71. [Article]
  3. Cohen ML, Schenck K: Contractile responses to sumatriptan and ergotamine in the rabbit saphenous vein: effect of selective 5-HT(1F) receptor agonists and PGF(2alpha). Br J Pharmacol. 2000 Oct;131(3):562-8. [Article]
  4. Valdivia LF, Centurion D, Arulmani U, Saxena PR, Villalon CM: 5-HT1B receptors, alpha2A/2C- and, to a lesser extent, alpha1-adrenoceptors mediate the external carotid vasoconstriction to ergotamine in vagosympathectomised dogs. Naunyn Schmiedebergs Arch Pharmacol. 2004 Jul;370(1):46-53. Epub 2004 Jun 29. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Virus receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
Gene Name
HTR2A
Uniprot ID
P28223
Uniprot Name
5-hydroxytryptamine receptor 2A
Molecular Weight
52602.58 Da
References
  1. Bom AH, Heiligers JP, Saxena PR, Verdouw PD: Reduction of cephalic arteriovenous shunting by ergotamine is not mediated by 5-HT1-like or 5-HT2 receptors. Br J Pharmacol. 1989 Jun;97(2):383-90. [Article]
  2. Panconesi A, Anselmi B, Curradi C, Perfetto F, Piluso A, Franchi G: Comparison between venoconstrictor effects of sumatriptan and ergotamine in migraine patients. Headache. 1994 Apr;34(4):194-7. [Article]
  3. 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
Partial agonist
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
Molecular Weight
51486.005 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Gornemann T, Jahnichen S, Schurad B, Latte KP, Horowski R, Tack J, Flieger M, Pertz HH: Pharmacological properties of a wide array of ergolines at functional alpha(1)-adrenoceptor subtypes. Naunyn Schmiedebergs Arch Pharmacol. 2008 Jan;376(5):321-30. Epub 2007 Dec 8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Partial agonist
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1B
Uniprot ID
P35368
Uniprot Name
Alpha-1B adrenergic receptor
Molecular Weight
56835.375 Da
References
  1. Gornemann T, Jahnichen S, Schurad B, Latte KP, Horowski R, Tack J, Flieger M, Pertz HH: Pharmacological properties of a wide array of ergolines at functional alpha(1)-adrenoceptor subtypes. Naunyn Schmiedebergs Arch Pharmacol. 2008 Jan;376(5):321-30. Epub 2007 Dec 8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Partial agonist
General Function
Alpha1-adrenergic receptor activity
Specific Function
This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium.
Gene Name
ADRA1D
Uniprot ID
P25100
Uniprot Name
Alpha-1D adrenergic receptor
Molecular Weight
60462.205 Da
References
  1. Gornemann T, Jahnichen S, Schurad B, Latte KP, Horowski R, Tack J, Flieger M, Pertz HH: Pharmacological properties of a wide array of ergolines at functional alpha(1)-adrenoceptor subtypes. Naunyn Schmiedebergs Arch Pharmacol. 2008 Jan;376(5):321-30. Epub 2007 Dec 8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Potassium channel regulator activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name
DRD2
Uniprot ID
P14416
Uniprot Name
D(2) dopamine receptor
Molecular Weight
50618.91 Da
References
  1. Verhoeff NP, Visser WH, Ferrari MD, Saxena PR, van Royen EA: Dopamine D2-receptor imaging with 123I-iodobenzamide SPECT in migraine patients abusing ergotamine: does ergotamine cross the blood brain barrier? Cephalalgia. 1993 Oct;13(5):325-9. [Article]
  2. Larson BT, Samford MD, Camden JM, Piper EL, Kerley MS, Paterson JA, Turner JT: Ergovaline binding and activation of D2 dopamine receptors in GH4ZR7 cells. J Anim Sci. 1995 May;73(5):1396-400. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Partial agonist
General Function
Thioesterase binding
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
Gene Name
ADRA2A
Uniprot ID
P08913
Uniprot Name
Alpha-2A adrenergic receptor
Molecular Weight
48956.275 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Gornemann T, Jahnichen S, Schurad B, Latte KP, Horowski R, Tack J, Flieger M, Pertz HH: Pharmacological properties of a wide array of ergolines at functional alpha(1)-adrenoceptor subtypes. Naunyn Schmiedebergs Arch Pharmacol. 2008 Jan;376(5):321-30. Epub 2007 Dec 8. [Article]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
G-protein coupled amine receptor activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.

Components:
References
  1. Bigal ME, Tepper SJ: Ergotamine and dihydroergotamine: a review. Curr Pain Headache Rep. 2003 Feb;7(1):55-62. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
Gene Name
HTR1A
Uniprot ID
P08908
Uniprot Name
5-hydroxytryptamine receptor 1A
Molecular Weight
46106.335 Da
References
  1. Bigal ME, Tepper SJ: Ergotamine and dihydroergotamine: a review. Curr Pain Headache Rep. 2003 Feb;7(1):55-62. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various alkaloids and psychoactive substances. Ligand binding causes a conformation change that trig...
Gene Name
HTR1F
Uniprot ID
P30939
Uniprot Name
5-hydroxytryptamine receptor 1F
Molecular Weight
41708.505 Da
References
  1. Bigal ME, Tepper SJ: Ergotamine and dihydroergotamine: a review. Curr Pain Headache Rep. 2003 Feb;7(1):55-62. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-...
Gene Name
HTR2C
Uniprot ID
P28335
Uniprot Name
5-hydroxytryptamine receptor 2C
Molecular Weight
51820.705 Da
References
  1. Bigal ME, Tepper SJ: Ergotamine and dihydroergotamine: a review. Curr Pain Headache Rep. 2003 Feb;7(1):55-62. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various ergot alkaloid derivatives and psychoactive substances. Ligand binding causes a conformation...
Gene Name
HTR2B
Uniprot ID
P41595
Uniprot Name
5-hydroxytryptamine receptor 2B
Molecular Weight
54297.41 Da
References
  1. Rothman RB, Baumann MH, Savage JE, Rauser L, McBride A, Hufeisen SJ, Roth BL: Evidence for possible involvement of 5-HT(2B) receptors in the cardiac valvulopathy associated with fenfluramine and other serotonergic medications. Circulation. 2000 Dec 5;102(23):2836-41. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein homodimerization activity
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins.
Gene Name
ADRA2C
Uniprot ID
P18825
Uniprot Name
Alpha-2C adrenergic receptor
Molecular Weight
49521.585 Da
References
  1. Villamil-Hernandez MT, Alcantara-Vazquez O, Sanchez-Lopez A, Centurion D: Pharmacological identification of alpha1- and alpha2-adrenoceptor subtypes involved in the vasopressor responses induced by ergotamine in pithed rats. Eur J Pharmacol. 2013 Sep 5;715(1-3):262-9. doi: 10.1016/j.ejphar.2013.05.011. Epub 2013 May 22. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Ladona MG, Gonzalez ML, Rane A, Peter RM, de la Torre R: Cocaine metabolism in human fetal and adult liver microsomes is related to cytochrome P450 3A expression. Life Sci. 2000 Dec 15;68(4):431-43. [Article]
  2. Moubarak AS, Rosenkrans CF Jr, Johnson ZB: Modulation of cytochrome P450 metabolism by ergonovine and dihydroergotamine. Vet Hum Toxicol. 2003 Feb;45(1):6-9. [Article]
  3. Wooltorton E: Risk of stroke, gangrene from ergot drug interactions. CMAJ. 2003 Apr 15;168(8):1015. [Article]
  4. Zhou SF, Xue CC, Yu XQ, Li C, Wang G: Clinically important drug interactions potentially involving mechanism-based inhibition of cytochrome P450 3A4 and the role of therapeutic drug monitoring. Ther Drug Monit. 2007 Dec;29(6):687-710. doi: 10.1097/FTD.0b013e31815c16f5. [Article]
  5. Cafergot (Ergotamine tartrate and Caffeine) FDA Label [Link]

Transporters

Details
1. P-glycoprotein 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Ekins S, Kim RB, Leake BF, Dantzig AH, Schuetz EG, Lan LB, Yasuda K, Shepard RL, Winter MA, Schuetz JD, Wikel JH, Wrighton SA: Three-dimensional quantitative structure-activity relationships of inhibitors of P-glycoprotein. Mol Pharmacol. 2002 May;61(5):964-73. [Article]
  2. Yasuda K, Lan LB, Sanglard D, Furuya K, Schuetz JD, Schuetz EG: Interaction of cytochrome P450 3A inhibitors with P-glycoprotein. J Pharmacol Exp Ther. 2002 Oct;303(1):323-32. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48