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Identification
NameErgotamine
Accession NumberDB00696  (APRD00677)
TypeSmall Molecule
GroupsApproved
Description

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. [PubChem]

Structure
Thumb
Synonyms
(5'alpha)-12'-hydroxy-2'-methyl-5'-(phenylmethyl)ergotoman-3',6',18-trione
12'-Hydroxy-2'-methyl-5'alpha-(phenylmethyl)ergotaman-3',6',18-trione
Ergotamin
Ergotamina
Ergotamine
Ergotaminum
Gynergen
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ergomar Slt 2mgtablet2 mgsublingualAventis Pharma Inc1975-12-312003-07-22Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ergomartablet, orally disintegrating2 mg/1sublingualRosedale Therapeutics2012-08-31Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AnervanRecip
AntimigraineTa Fong
EnxakCazi
ErgamGedeon Richter
Ergo-KranitKrewel Meuselbach
GynaemineSriprasit Dispensary
WigrettesNot Available
Brand mixtures
NameLabellerIngredients
CafergotKAISER FOUNDATION HOSPITALS
Cafergot SupNovartis Pharmaceuticals Canada Inc
Cafergot TabNovartis Pharmaceuticals Canada Inc
Ergodryl CapErfa Canada 2012 Inc
ErgotamineWest ward Pharmaceutical Corp
Ergotamine Tartrate and CaffeineKAISER FOUNDATION HOSPITALS
Gravergol CapsulesCan Med Pharma Inc.
Megral TabsGlaxo Wellcome Inc.
MigergotG&W Laboratories, Inc.
Salts
Name/CASStructureProperties
Ergotamine Tartrate
ThumbNot applicableDBSALT000979
Categories
UNIIPR834Q503T
CAS number113-15-5
WeightAverage: 581.6615
Monoisotopic: 581.263819255
Chemical FormulaC33H35N5O5
InChI KeyInChIKey=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[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
SMILES
[H][C@@]12CCCN1C(=O)[[email protected]](CC1=CC=CC=C1)N1C(=O)[C@](C)(NC(=O)[[email protected]]3CN(C)[C@]4([H])CC5=CNC6=CC=CC(=C56)C4=C3)O[C@@]21O
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassErgoline and derivatives
Sub ClassLysergic acids and derivatives
Direct ParentErgotamines, dihydroergotamines, and derivatives
Alternative Parents
Substituents
  • Ergotamine
  • Hybrid peptide
  • Lysergic acid amide
  • Indoloquinoline
  • Benzoquinoline
  • Quinoline-3-carboxamide
  • Pyrroloquinoline
  • N-acyl-alpha amino acid or derivatives
  • Quinoline
  • Isoindole or derivatives
  • Indole or derivatives
  • Indole
  • Aralkylamine
  • N-alkylpiperazine
  • Tetrahydropyridine
  • Benzenoid
  • Piperazine
  • Oxazolidinone
  • 1,4-diazinane
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Pyrrole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Orthocarboxylic acid derivative
  • Lactam
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Alkanolamine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor use as therapy to abort or prevent vascular headache, e.g., migraine, migraine variants, or so called "histaminic cephalalgia".
PharmacodynamicsErgotamine 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 actionErgotamine 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.
Related Articles
AbsorptionThe bioavailability of sublingually administered ergotamine has not been determined.
Volume of distributionNot Available
Protein bindingNot 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 eliminationNot Available
Half life2 hours
ClearanceNot Available
ToxicitySigns of overexposure include irritation, nausea, vomiting, headache, diarrhea, thirst, coldness of skin, pruritus, weak pulse, numbness, tingling of extremities, and confusion.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
Manufacturers
  • 3m pharmaceuticals inc
  • Rosedale therapeutics
  • Parke davis div warner lambert co
  • Organon usa inc
Packagers
Dosage forms
FormRouteStrength
Capsuleoral
Tablet, orally disintegratingsublingual2 mg/1
Tabletsublingual2 mg
Tablet, film coatedoral
Tabletoral
Capsule
Suppositoryrectal
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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point213.5 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
Polarizability61.69 Å3ChemAxon
Number of Rings8ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (12 KB)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
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. [PubMed:10611116 ]
  2. Schardl CL, Panaccione DG, Tudzynski P: Ergot alkaloids--biology and molecular biology. Alkaloids Chem Biol. 2006;63:45-86. [PubMed:17133714 ]
External Links
ATC CodesN02CA52N02CA72N02CA02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (53.1 KB)
Interactions
Drug Interactions
Drug
AcepromazineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Acepromazine.
AcetophenazineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Acetophenazine.
AmisulprideThe risk or severity of adverse effects can be increased when Ergotamine is combined with Amisulpride.
AprepitantThe serum concentration of Ergotamine can be increased when it is combined with Aprepitant.
AripiprazoleThe risk or severity of adverse effects can be increased when Ergotamine is combined with Aripiprazole.
BatimastatThe serum concentration of Ergotamine can be increased when it is combined with Batimastat.
BenzquinamideThe risk or severity of adverse effects can be increased when Ergotamine is combined with Benzquinamide.
BoceprevirThe serum concentration of Ergotamine can be increased when it is combined with Boceprevir.
CarphenazineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Carphenazine.
ChlormezanoneThe risk or severity of adverse effects can be increased when Ergotamine is combined with Chlormezanone.
ChlorpromazineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Chlorpromazine.
ChlorprothixeneThe risk or severity of adverse effects can be increased when Ergotamine is combined with Chlorprothixene.
ClarithromycinThe serum concentration of Ergotamine can be increased when it is combined with Clarithromycin.
ClozapineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Clozapine.
CobicistatThe serum concentration of Ergotamine can be increased when it is combined with Cobicistat.
ConivaptanThe serum concentration of Ergotamine can be increased when it is combined with Conivaptan.
CrizotinibThe serum concentration of Ergotamine can be increased when it is combined with Crizotinib.
DapoxetineThe risk or severity of adverse effects can be increased when Dapoxetine is combined with Ergotamine.
DasatinibThe serum concentration of Ergotamine can be increased when it is combined with Dasatinib.
DipivefrinErgotamine may increase the hypertensive activities of Dipivefrin.
DroperidolThe risk or severity of adverse effects can be increased when Ergotamine is combined with Droperidol.
EletriptanErgotamine may increase the vasoconstricting activities of Eletriptan.
EnzalutamideThe serum concentration of Ergotamine can be decreased when it is combined with Enzalutamide.
FencamfamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Fencamfamine.
FluconazoleThe metabolism of Ergotamine can be decreased when combined with Fluconazole.
FlupentixolThe risk or severity of adverse effects can be increased when Ergotamine is combined with Flupentixol.
FluphenazineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Fluphenazine.
FluspirileneThe risk or severity of adverse effects can be increased when Ergotamine is combined with Fluspirilene.
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Ergotamine.
FosaprepitantThe serum concentration of Ergotamine can be increased when it is combined with Fosaprepitant.
Fusidic AcidThe serum concentration of Ergotamine can be increased when it is combined with Fusidic Acid.
GranisetronGranisetron may increase the serotonergic activities of Ergotamine.
HaloperidolThe risk or severity of adverse effects can be increased when Ergotamine is combined with Haloperidol.
IdelalisibThe serum concentration of Ergotamine can be increased when it is combined with Idelalisib.
IsoflurophateThe serum concentration of Ergotamine can be increased when it is combined with Isoflurophate.
ItraconazoleThe serum concentration of Ergotamine can be increased when it is combined with Itraconazole.
IvacaftorThe serum concentration of Ergotamine can be increased when it is combined with Ivacaftor.
KetoconazoleThe serum concentration of Ergotamine can be increased when it is combined with Ketoconazole.
LorcaserinThe risk or severity of adverse effects can be increased when Lorcaserin is combined with Ergotamine.
LoxapineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Loxapine.
LuliconazoleThe serum concentration of Ergotamine can be increased when it is combined with Luliconazole.
MesoridazineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Mesoridazine.
MethotrimeprazineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Methotrimeprazine.
MetoclopramideThe risk or severity of adverse effects can be increased when Ergotamine is combined with Metoclopramide.
MidodrineErgotamine may increase the hypertensive activities of Midodrine.
MifepristoneThe serum concentration of Ergotamine can be increased when it is combined with Mifepristone.
MolindoneThe risk or severity of adverse effects can be increased when Ergotamine is combined with Molindone.
NadololNadolol may increase the vasoconstricting activities of Ergotamine.
NelfinavirThe metabolism of Ergotamine can be decreased when combined with Nelfinavir.
NetupitantThe serum concentration of Ergotamine can be increased when it is combined with Netupitant.
NitroglycerinErgotamine may decrease the vasodilatory activities of Nitroglycerin.
OlanzapineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Olanzapine.
OndansetronThe risk or severity of adverse effects can be increased when Ergotamine is combined with Ondansetron.
PalbociclibThe serum concentration of Ergotamine can be increased when it is combined with Palbociclib.
PaliperidoneThe risk or severity of adverse effects can be increased when Ergotamine is combined with Paliperidone.
PerphenazineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Perphenazine.
PimozideThe risk or severity of adverse effects can be increased when Ergotamine is combined with Pimozide.
PiperacetazineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Piperacetazine.
PosaconazoleThe serum concentration of Ergotamine can be increased when it is combined with Posaconazole.
ProchlorperazineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Prochlorperazine.
PromazineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Promazine.
QuetiapineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Quetiapine.
RemoxiprideThe risk or severity of adverse effects can be increased when Ergotamine is combined with Remoxipride.
ReserpineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Reserpine.
RisperidoneThe risk or severity of adverse effects can be increased when Ergotamine is combined with Risperidone.
SertindoleThe risk or severity of adverse effects can be increased when Ergotamine is combined with Sertindole.
SimeprevirThe serum concentration of Ergotamine can be increased when it is combined with Simeprevir.
StiripentolThe serum concentration of Ergotamine can be increased when it is combined with Stiripentol.
SulpirideThe risk or severity of adverse effects can be increased when Ergotamine is combined with Sulpiride.
Tedizolid PhosphateTedizolid Phosphate may increase the serotonergic activities of Ergotamine.
TelaprevirThe serum concentration of Ergotamine can be increased when it is combined with Telaprevir.
ThioridazineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Thioridazine.
ThiothixeneThe risk or severity of adverse effects can be increased when Ergotamine is combined with Thiothixene.
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Ergotamine.
TrifluoperazineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Trifluoperazine.
TriflupromazineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Triflupromazine.
VoriconazoleThe serum concentration of Ergotamine can be increased when it is combined with Voriconazole.
ZiprasidoneThe risk or severity of adverse effects can be increased when Ergotamine is combined with Ziprasidone.
ZuclopenthixolThe risk or severity of adverse effects can be increased when Ergotamine is combined with Zuclopenthixol.
Food Interactions
  • Caffeine increases absorption.
  • Take without regard to meals.

Targets

Kind
Protein
Organism
Human
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 substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate c...
Gene Name:
HTR1D
Uniprot ID:
P28221
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. [PubMed:12558771 ]
  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. [PubMed:8384716 ]
  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. [PubMed:1407010 ]
  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. [PubMed:14504136 ]
  5. Deliganis AV, Peroutka SJ: 5-Hydroxtryptamine1D receptor agonism predicts antimigraine efficacy. Headache. 1991 Apr;31(4):228-31. [PubMed:1646776 ]
Kind
Protein
Organism
Human
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 substances, such as lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of ...
Gene Name:
HTR1B
Uniprot ID:
P28222
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. [PubMed:10188968 ]
  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. [PubMed:10455274 ]
  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. [PubMed:11015308 ]
  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. [PubMed:15224175 ]
Kind
Protein
Organism
Human
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-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates...
Gene Name:
HTR2A
Uniprot ID:
P28223
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. [PubMed:2758221 ]
  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. [PubMed:8014033 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
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
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. [PubMed:8242725 ]
  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. [PubMed:7665369 ]
Kind
Protein
Organism
Human
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) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine(PE)-stimulated ERK signaling in cardiac myocytes.
Gene Name:
ADRA1A
Uniprot ID:
P35348
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. [PubMed:17139284 ]
  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. [PubMed:17016423 ]
  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. [PubMed:18066532 ]
Kind
Protein
Organism
Human
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) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine (PE)-stimulated ERK signaling in cardiac myocytes.
Gene Name:
ADRA1B
Uniprot ID:
P35368
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. [PubMed:18066532 ]
Kind
Protein
Organism
Human
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
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. [PubMed:18066532 ]
Kind
Protein
Organism
Human
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 oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianser...
Gene Name:
ADRA2A
Uniprot ID:
P08913
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. [PubMed:17139284 ]
  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. [PubMed:17016423 ]
  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. [PubMed:18066532 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonistpartial agonist
General Function:
Epinephrine 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 clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phent...
Gene Name:
ADRA2B
Uniprot ID:
P18089
Molecular Weight:
49565.8 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. [PubMed:17139284 ]
  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. [PubMed:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Norepinephrine:sodium symporter activity
Specific Function:
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A2
Uniprot ID:
P23975
Molecular Weight:
69331.42 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. [PubMed:17139284 ]
  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. [PubMed:17016423 ]
Kind
Protein group
Organism
Human
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:
NameUniProt IDDetails
D(1A) dopamine receptorP21728 Details
D(1B) dopamine receptorP21918 Details
References
  1. Bigal ME, Tepper SJ: Ergotamine and dihydroergotamine: a review. Curr Pain Headache Rep. 2003 Feb;7(1):55-62. [PubMed:12525272 ]
Kind
Protein
Organism
Human
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 signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Beta-arrestin family members inhibit signaling via G pro...
Gene Name:
HTR1A
Uniprot ID:
P08908
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. [PubMed:12525272 ]
Kind
Protein
Organism
Human
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 triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling inhibits adenylate cyclase activity.
Gene Name:
HTR1F
Uniprot ID:
P30939
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. [PubMed:12525272 ]
Kind
Protein
Organism
Human
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-iodophenyl-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modul...
Gene Name:
HTR2C
Uniprot ID:
P28335
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. [PubMed:12525272 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Kind
Protein
Organism
Human
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
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. [PubMed:11961113 ]
  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. [PubMed:12235267 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23