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Identification
NameDihydroergotamine
Accession NumberDB00320  (APRD00476)
TypeSmall Molecule
GroupsApproved
Description

A 9,10alpha-dihydro derivative of ergotamine. It is used as a vasoconstrictor, specifically for the therapy of migraine disorders. [PubChem]

Structure
Thumb
Synonyms
(2R,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),9,12,14-tetraene-4-carboxamide
5'-Benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxo-9,10-dihydroergotaman
9,10-dihydro-12'-Hydroxy-2'-methyl-5'-(phenylmethyl)ergotoman-3',6',18-trione
9,10-dihydroergotamine
Dihidroergotamina
Dihydroergotamin
Dihydroergotamine
Dihydroergotaminum
Diidroergotamina
External Identifiers
  • MAP-0004
  • MAP0004
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
D.H.E. 45injection, solution1 mg/mLintramuscular; intravenous; subcutaneousValeant Pharmaceuticals North America2001-10-03Not applicableUs
Dihydroergotamine (dhe), 1mg/mlliquid1 mgintramuscular; intravenous; subcutaneousSterimax Inc1946-12-31Not applicableCanada
Dihydroergotamine Mesylatespray4 mg/mLnasalOceanside Pharmaceuticals2013-03-18Not applicableUs
Dihydroergotamine Mesylate Injection USPliquid1 mgintramuscular; intravenous; subcutaneousSandoz Canada Incorporated1999-12-23Not applicableCanada
Migranalspray4 mg/mLnasalValeant Pharmaceuticals North America LLC1997-12-08Not applicableUs
Migranal Nasal Spray 4mg/mlliquid4 mgnasalSterimax Inc1996-11-05Not applicableCanada
PMS-dihydroergotamineliquid4 mgnasalPharmascience IncNot applicableNot applicableCanada
PMS-dihydroergotamineliquid1 mgintramuscular; intravenous; subcutaneousPharmascience IncNot applicableNot applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dihydroergotamine Mesylateinjection, solution1 mg/mLintramuscular; intravenous; subcutaneousPaddock Laboratories, LLC2003-04-29Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
DihydergotSandoz
ErgontSigmapharm
ErgotoninNot Available
IkaranPierre Fabre
OrstanormAmdipharm
VerladynVerla
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Dihydroergotamine mesylate
6190-39-2
Thumb
  • InChI Key: ADYPXRFPBQGGAH-UMYZUSPBSA-N
  • Monoisotopic Mass: 679.267584474
  • Average Mass: 679.79
DBSALT000997
Dihydroergotamine tartrate
5989-77-5
Thumb
  • InChI Key: FXDJFTCVYTUARH-YZPGULDNSA-N
  • Monoisotopic Mass: 2483.134315159
  • Average Mass: 2484.842
DBSALT001066
Categories
UNII436O5HM03C
CAS number511-12-6
WeightAverage: 583.6774
Monoisotopic: 583.279469319
Chemical FormulaC33H37N5O5
InChI KeyInChIKey=LUZRJRNZXALNLM-JGRZULCMSA-N
InChI
InChI=1S/C33H37N5O5/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/h3-6,8-11,17,21,23,25-27,34,42H,7,12-16,18H2,1-2H3,(H,35,39)/t21-,23-,25-,26+,27+,32-,33+/m1/s1
IUPAC Name
(2R,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),9,12,14-tetraene-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)[C@@]4([H])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
  • Dihydroergotamine
  • Hybrid peptide
  • Lysergic acid amide
  • Indoloquinoline
  • Benzoquinoline
  • Quinoline-3-carboxamide
  • Pyrroloquinoline
  • N-acyl-alpha amino acid or derivatives
  • Quinoline
  • Piperidinecarboxylic acid
  • Piperidinecarboxamide
  • 3-piperidinecarboxamide
  • Isoindole or derivatives
  • Indole or derivatives
  • Indole
  • Aralkylamine
  • N-alkylpiperazine
  • Benzenoid
  • Piperidine
  • 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 the acute treatment of migraine headaches with or without aura and the acute treatment of cluster headache episodes.
PharmacodynamicsDihydroergotamine is indicated for the acute treatment of migraine headaches with or without aura and the acute treatment of cluster headache episodes. Dihydroergotamine binds with high affinity to 5-HT1Da and 5-HT1Db receptors. It also binds with high affinity to serotonin 5-HT1A, 5-HT2A, and 5-HT2C receptors, noradrenaline a2A, a2B and a receptors, and dopamine D2L and D3 receptors. The therapeutic activity of Dihydroergotamine in migraine is generally attributed to the agonist effect at 5-HT1D receptors.
Mechanism of actionTwo theories have been proposed to explain the efficacy of 5-HT1D receptor agonists in migraine: 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
AbsorptionInterpatient variable and may be dependent on the administration technique
Volume of distribution
  • 800 L
Protein binding93% (to plasma proteins)
Metabolism

Hepatic

Route of eliminationThe major excretory route of dihydroergotamine is via the bile in the feces. Only 6%-7% of unchanged dihydroergotamine is excreted in the urine after intramuscular injection.
Half life9 hours
Clearance
  • 1.5 L/min
ToxicitySide effects include abdominal pain, abnormal speech, coma, confusion, convulsions, hallucinations, increase and/or decrease in blood pressure, nausea, numbness, tingling, pain, and a bluish color of your fingersand toes, slowed breathing, vomiting
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+0.8348
Blood Brain Barrier-0.9817
Caco-2 permeable-0.7956
P-glycoprotein substrateSubstrate0.8223
P-glycoprotein inhibitor IInhibitor0.556
P-glycoprotein inhibitor IIInhibitor0.8388
Renal organic cation transporterNon-inhibitor0.8229
CYP450 2C9 substrateNon-substrate0.7897
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.7227
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorInhibitor0.895
CYP450 2D6 inhibitorNon-inhibitor0.8931
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorInhibitor0.712
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.591
Ames testNon AMES toxic0.897
CarcinogenicityNon-carcinogens0.9549
BiodegradationNot ready biodegradable0.9961
Rat acute toxicity2.9503 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9365
hERG inhibition (predictor II)Non-inhibitor0.5788
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Valeant pharmaceuticals international
  • Bedford laboratories
  • Paddock laboratories inc
Packagers
Dosage forms
FormRouteStrength
Liquidintramuscular; intravenous; subcutaneous1 mg
Injection, solutionintramuscular; intravenous; subcutaneous1 mg/mL
Spraynasal4 mg/mL
Liquidnasal4 mg
Prices
Unit descriptionCostUnit
D.H.E. 45 1 mg/ml Solution 1ml Ampule124.61USD ampule
D.H.E. 45 1 mg/ml ampul120.88USD ml
Migranal 4 mg/ml Solution 1ml Glass Container94.46USD container
Migranal nasal spray90.83USD ml
D.h.e.45 1 mg/ml ampul54.46USD ml
Dihydroergotamine 1 mg/ml am38.0USD ml
Dihydroergotamine Mesylate 1 mg/ml Solution 1ml Ampule36.4USD ampule
Migranal 4 mg/ml Spray11.17USD spray
Dihydroergotamine (Dhe) 1 mg/ml4.18USD ml
Dihydroergotamine Mesylate 1 mg/ml3.9USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5169849 No1992-12-082009-12-08Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.229 mg/mLALOGPS
logP3.04ALOGPS
logP2.71ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)9.71ChemAxon
pKa (Strongest Basic)8.39ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area118.21 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity159.39 m3·mol-1ChemAxon
Polarizability63.3 Å3ChemAxon
Number of Rings8ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (10.9 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 ReferencesNot Available
External Links
ATC CodesN02CA01N02CA51
AHFS Codes
  • 12:16.00
PDB EntriesNot Available
FDA labelDownload (412 KB)
MSDSDownload (53.1 KB)
Interactions
Drug Interactions
Drug
AcepromazineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Acepromazine.
AcetophenazineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Acetophenazine.
AmisulprideThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Amisulpride.
AprepitantThe serum concentration of Dihydroergotamine can be increased when it is combined with Aprepitant.
AripiprazoleThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Aripiprazole.
BatimastatThe serum concentration of Dihydroergotamine can be increased when it is combined with Batimastat.
BenzquinamideThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Benzquinamide.
BoceprevirThe serum concentration of Dihydroergotamine can be increased when it is combined with Boceprevir.
CarphenazineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Carphenazine.
ChlormezanoneThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Chlormezanone.
ChlorpromazineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Chlorpromazine.
ChlorprothixeneThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Chlorprothixene.
ClarithromycinThe serum concentration of Dihydroergotamine can be increased when it is combined with Clarithromycin.
ClozapineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Clozapine.
CobicistatThe serum concentration of Dihydroergotamine can be increased when it is combined with Cobicistat.
ConivaptanThe serum concentration of Dihydroergotamine can be increased when it is combined with Conivaptan.
CrizotinibThe serum concentration of Dihydroergotamine can be increased when it is combined with Crizotinib.
DapoxetineThe risk or severity of adverse effects can be increased when Dapoxetine is combined with Dihydroergotamine.
DasatinibThe serum concentration of Dihydroergotamine can be increased when it is combined with Dasatinib.
DipivefrinDihydroergotamine may increase the hypertensive activities of Dipivefrin.
DroperidolThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Droperidol.
EletriptanDihydroergotamine may increase the vasoconstricting activities of Eletriptan.
EnzalutamideThe serum concentration of Dihydroergotamine can be decreased when it is combined with Enzalutamide.
FencamfamineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Fencamfamine.
FluconazoleThe metabolism of Dihydroergotamine can be decreased when combined with Fluconazole.
FlupentixolThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Flupentixol.
FluphenazineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Fluphenazine.
FluspirileneThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Fluspirilene.
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Dihydroergotamine.
FosaprepitantThe serum concentration of Dihydroergotamine can be increased when it is combined with Fosaprepitant.
Fusidic AcidThe serum concentration of Dihydroergotamine can be increased when it is combined with Fusidic Acid.
GranisetronGranisetron may increase the serotonergic activities of Dihydroergotamine.
HaloperidolThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Haloperidol.
IdelalisibThe serum concentration of Dihydroergotamine can be increased when it is combined with Idelalisib.
IsoflurophateThe serum concentration of Dihydroergotamine can be increased when it is combined with Isoflurophate.
ItraconazoleThe serum concentration of Dihydroergotamine can be increased when it is combined with Itraconazole.
IvacaftorThe serum concentration of Dihydroergotamine can be increased when it is combined with Ivacaftor.
KetoconazoleThe serum concentration of Dihydroergotamine can be increased when it is combined with Ketoconazole.
LorcaserinThe risk or severity of adverse effects can be increased when Lorcaserin is combined with Dihydroergotamine.
LoxapineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Loxapine.
LuliconazoleThe serum concentration of Dihydroergotamine can be increased when it is combined with Luliconazole.
MesoridazineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Mesoridazine.
MethotrimeprazineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Methotrimeprazine.
MetoclopramideThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Metoclopramide.
MidodrineDihydroergotamine may increase the hypertensive activities of Midodrine.
MifepristoneThe serum concentration of Dihydroergotamine can be increased when it is combined with Mifepristone.
MolindoneThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Molindone.
NadololNadolol may increase the vasoconstricting activities of Dihydroergotamine.
NelfinavirThe metabolism of Dihydroergotamine can be decreased when combined with Nelfinavir.
NetupitantThe serum concentration of Dihydroergotamine can be increased when it is combined with Netupitant.
NitroglycerinDihydroergotamine may decrease the vasodilatory activities of Nitroglycerin.
OlanzapineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Olanzapine.
OndansetronThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Ondansetron.
PalbociclibThe serum concentration of Dihydroergotamine can be increased when it is combined with Palbociclib.
PaliperidoneThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Paliperidone.
PerphenazineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Perphenazine.
PimozideThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Pimozide.
PiperacetazineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Piperacetazine.
PosaconazoleThe serum concentration of Dihydroergotamine can be increased when it is combined with Posaconazole.
ProchlorperazineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Prochlorperazine.
PromazineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Promazine.
QuetiapineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Quetiapine.
RemoxiprideThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Remoxipride.
ReserpineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Reserpine.
RisperidoneThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Risperidone.
SertindoleThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Sertindole.
SimeprevirThe serum concentration of Dihydroergotamine can be increased when it is combined with Simeprevir.
StiripentolThe serum concentration of Dihydroergotamine can be increased when it is combined with Stiripentol.
SulpirideThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Sulpiride.
Tedizolid PhosphateTedizolid Phosphate may increase the serotonergic activities of Dihydroergotamine.
TelaprevirThe serum concentration of Dihydroergotamine can be increased when it is combined with Telaprevir.
ThioridazineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Thioridazine.
ThiothixeneThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Thiothixene.
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Dihydroergotamine.
TrifluoperazineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Trifluoperazine.
TriflupromazineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Triflupromazine.
VoriconazoleThe serum concentration of Dihydroergotamine can be increased when it is combined with Voriconazole.
ZiprasidoneThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Ziprasidone.
ZuclopenthixolThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Zuclopenthixol.
Food InteractionsNot Available

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. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Lesage AS, Wouters R, Van Gompel P, Heylen L, Vanhoenacker P, Haegeman G, Luyten WH, Leysen JE: Agonistic properties of alniditan, sumatriptan and dihydroergotamine on human 5-HT1B and 5-HT1D receptors expressed in various mammalian cell lines. Br J Pharmacol. 1998 Apr;123(8):1655-65. [PubMed:9605573 ]
  3. Buzzi MG, Moskowitz MA: The trigemino-vascular system and migraine. Pathol Biol (Paris). 1992 Apr;40(4):313-7. [PubMed:1379707 ]
  4. Buzzi MG, Dimitriadou V, Theoharides TC, Moskowitz MA: 5-Hydroxytryptamine receptor agonists for the abortive treatment of vascular headaches block mast cell, endothelial and platelet activation within the rat dura mater after trigeminal stimulation. Brain Res. 1992 Jun 26;583(1-2):137-49. [PubMed:1324091 ]
  5. Silberstein SD, McCrory DC: Ergotamine and dihydroergotamine: history, pharmacology, and efficacy. Headache. 2003 Feb;43(2):144-66. [PubMed:12558771 ]
  6. 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 ]
  7. Villalon CM, Centurion D, Willems EW, Arulmani U, Saxena PR, Valdivia LF: 5-HT1B receptors and alpha 2A/2C-adrenoceptors mediate external carotid vasoconstriction to dihydroergotamine. Eur J Pharmacol. 2004 Jan 26;484(2-3):287-90. [PubMed:14744615 ]
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. 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 ]
  2. Villalon CM, Centurion D, Willems EW, Arulmani U, Saxena PR, Valdivia LF: 5-HT1B receptors and alpha 2A/2C-adrenoceptors mediate external carotid vasoconstriction to dihydroergotamine. Eur J Pharmacol. 2004 Jan 26;484(2-3):287-90. [PubMed:14744615 ]
  3. Buzzi MG, Moskowitz MA: Evidence for 5-HT1B/1D receptors mediating the antimigraine effect of sumatriptan and dihydroergotamine. Cephalalgia. 1991 Sep;11(4):165-8. [PubMed:1660351 ]
  4. Yu XJ, Waeber C, Castanon N, Scearce K, Hen R, Macor JE, Chauveau J, Moskowitz MA: 5-Carboxamido-tryptamine, CP-122,288 and dihydroergotamine but not sumatriptan, CP-93,129, and serotonin-5-O-carboxymethyl-glycyl -tyrosinamide block dural plasma protein extravasation in knockout mice that lack 5-hydroxytryptamine1B receptors. Mol Pharmacol. 1996 May;49(5):761-5. [PubMed:8622623 ]
  5. Pauwels PJ, Palmier C, Dupuis DS, Colpaert FC: Interaction of 5-HT1B/D ligands with recombinant h 5-HT1A receptors: intrinsic activity and modulation by G-protein activation state. Naunyn Schmiedebergs Arch Pharmacol. 1998 May;357(5):490-9. [PubMed:9650800 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
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. Villalon CM, Centurion D, Willems EW, Arulmani U, Saxena PR, Valdivia LF: 5-HT1B receptors and alpha 2A/2C-adrenoceptors mediate external carotid vasoconstriction to dihydroergotamine. Eur J Pharmacol. 2004 Jan 26;484(2-3):287-90. [PubMed:14744615 ]
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 ergot alkaloid derivatives 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. Beta-arrestin family members inhibit signaling via G proteins ...
Gene Name:
HTR2B
Uniprot ID:
P41595
Molecular Weight:
54297.41 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Schaerlinger B, Hickel P, Etienne N, Guesnier L, Maroteaux L: Agonist actions of dihydroergotamine at 5-HT2B and 5-HT2C receptors and their possible relevance to antimigraine efficacy. Br J Pharmacol. 2003 Sep;140(2):277-84. Epub 2003 Aug 11. [PubMed:12970106 ]

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 ]

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