Dihydro-alpha-ergocryptine

Identification

Name
Dihydro-alpha-ergocryptine
Accession Number
DB11274
Type
Small Molecule
Groups
Approved
Description

Alpha-dihydroergocryptine is usually referred to the mixture of the alpha and beta dihydroergocryptine. These two compounds are differentiated in the position of a methyl group. This structural difference is due to a proteinogenic amino acid replacement from leucine to isoleucine.[16] Both compounds are hydrogenated ergot derivatives. Alpha-dihydroergocryptine approved drug product is as a part of an ergoloid mixture. To know more about this mixture, please visit Ergoloid mesylate

Structure
Thumb
Synonyms
  • 9,10-dihydro-α-ergocryptine
  • Alpha-Dihydroergocriptine
  • dihydro-α-ergocryptine
  • Dihydroergocryptine
  • α-dihydroergocryptine
Product Ingredients
IngredientUNIICASInChI Key
Dihydro-alpha-ergocryptine mesylateZ4I7BU58DN14271-05-7TZGKQIBPZOZAKF-PJLVGBPESA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Ergoloid MesylatesDihydro-alpha-ergocryptine mesylate (0.222 mg/1) + Dihydroergocornine mesylate (0.333 mg/1) + Dihydroergocristine mesylate (0.333 mg/1) + Epicriptine mesilate (0.111 mg/1)TabletOralCarilion Materials Management1991-10-31Not applicableUs
Ergoloid MesylatesDihydro-alpha-ergocryptine mesylate (0.222 mg/1) + Dihydroergocornine mesylate (0.333 mg/1) + Dihydroergocristine mesylate (0.333 mg/1) + Epicriptine mesilate (0.111 mg/1)TabletOralSun Pharmaceutical Industries Limited1991-10-31Not applicableUs
Categories
UNII
202229IR8Y
CAS number
25447-66-9
Weight
Average: 577.726
Monoisotopic: 577.326419505
Chemical Formula
C32H43N5O5
InChI Key
PBUNVLRHZGSROC-VTIMJTGVSA-N
InChI
InChI=1S/C32H43N5O5/c1-17(2)12-25-29(39)36-11-7-10-26(36)32(41)37(25)30(40)31(42-32,18(3)4)34-28(38)20-13-22-21-8-6-9-23-27(21)19(15-33-23)14-24(22)35(5)16-20/h6,8-9,15,17-18,20,22,24-26,33,41H,7,10-14,16H2,1-5H3,(H,34,38)/t20-,22-,24-,25+,26+,31-,32+/m1/s1
IUPAC Name
(2R,4R,7R)-N-[(1S,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-(propan-2-yl)-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),9,12,14-tetraene-4-carboxamide
SMILES
[H][C@@]12CCCN1C(=O)[C@H](CC(C)C)N1C(=O)[C@](NC(=O)[C@H]3CN(C)[C@]4([H])CC5=CNC6=CC=CC(=C56)[C@@]4([H])C3)(O[C@@]21O)C(C)C

Pharmacology

Indication

Alpha-dihydroergocryptine has been studied for the early treatment of Parkinson disease[2] as well as for its use in migraine prophylaxis,[3] treatment of low blood pressure and peripheral vascular disorder. To know more about the ergoloid mesylate mixture and its uses please visit Ergoloid mesylate.

Structured Indications
Not Available
Pharmacodynamics

The effect of alpha-dihydroergocryptine in dopamine receptors was tested in PD patients and seem to generate a significant clinical improvement in the tested patients as well as to reduce motor complications and side effects.[2] In long-term clinical trials with Parkinson disease patients, the administration of alpha-dihydroergocryptine and levodopa, the symptoms were reposted to improve or completely vanish in 80% of the tested individuals.[8] All the registered effects of alpha-dihydroergocryptine suggest a potential neuroprotective effect of this drug and some reports have indicated that this activity may be related to the activation of NF-kB.[10] The effect of alpha-dihydroergocryptine in the dopamine D2 receptor also reduces prolactin plasma levels and induce hypotension.[9] To know more about the ergoloid mesylate mixture please visit Ergoloid mesylate.

Mechanism of action

Alpha-dihydroergocryptine is an established high-affinity ligand to alpha 1 and alpha 2 adrenoreceptors in a number of tissues as well as a dopamine ligand in the brain.[1] It is reported to be a potent agonist of the dopamine D2 receptor and a partial agonist of the dopamine receptors D1 and D3.[4] To know more about the ergoloid mesylate mixture please visit Ergoloid mesylate and to know more about the isomer please visit Epicriptine.

TargetActionsOrganism
AD(2) dopamine receptor
agonist
Human
AD(1) dopamine receptor
partial agonist
Human
AD(3) dopamine receptor
partial agonist
Human
Absorption

Alpha-dihydroergocryptine is rapidly absorbed but it presents a very low bioavailability as it is part of a first-pass hepatic metabolism and thus less of 5% of the administered dose reaches blood circulation. The peak plasma concentration is attained after 30-120 minutes. The absorption of alpha-dihydroergocryptine is not affected by the co-administration with food.[6] When administered in repeated oral doses the Cmax after 1 hour was registered to be 2157 pg/ml.[7] To know more about the ergoloid mesylate mixture please visit Ergoloid mesylate.

Volume of distribution

In preclinical studies, the volume of distribution after intravenous or oral administration was registered to be 11.054 L and 218.630 L respectively.[14] To know more about the ergoloid mesylate mixture please visit Ergoloid mesylate.

Protein binding

Alpha-dihydroergocryptine is highly bound to proteins and it has been reported to present a high affinity for intact human platelets.[1] To know more about the ergoloid mesylate mixture please visit Ergoloid mesylate.

Metabolism

Alpha-dihydroergocryptine presents a linear metabolism with the formation of active metabolites and the metabolism kinetics of this compound has no interference with L-dopa.[9] It is highly metabolized with a rate of 2.4 ng/min/mg protein in the microsomal system and a formation of eight different metabolites.[11] the metabolism of alpha-dihydroergocryptine seems to be highly marked by the action of CYP 3A4.[12] To know more about the ergoloid mesylate mixture please visit Ergoloid mesylate.

Route of elimination

Alpha-dihydroergocryptine is eliminated mainly by feces[9] and to present a very low urinary excretion.[13] To know more about the ergoloid mesylate mixture please visit Ergoloid mesylate.

Half life

Alpha-dihydroergocryptine has been studied in Parkinson disease models and it has shown a half-life of 12-16 hours.[5] To know more about the ergoloid mesylate mixture please visit Ergoloid mesylate.

Clearance

In preclinical studies, the clearance rate after intravenous or oral administration was registered to be 1.129 L/h and 25.98 L/h respectively.[14] To know more about the ergoloid mesylate mixture please visit Ergoloid mesylate.

Toxicity

Alpha-dihydroergocryptine does not have effect in fertility and it does not present mutagenic potential.[15] To know more about the ergoloid mesylate mixture please visit Ergoloid mesylate.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
Acetyl sulfisoxazoleThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Acetyl sulfisoxazole.Approved, Vet Approved
AmiodaroneThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Amiodarone.Approved, Investigational
ApalutamideThe serum concentration of Dihydro-alpha-ergocryptine can be decreased when it is combined with Apalutamide.Approved, Investigational
AprepitantThe serum concentration of Dihydro-alpha-ergocryptine can be increased when it is combined with Aprepitant.Approved, Investigational
AtazanavirThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Atomoxetine.Approved
BoceprevirThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Boceprevir.Approved, Withdrawn
BortezomibThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Dihydro-alpha-ergocryptine can be decreased when it is combined with Bosentan.Approved, Investigational
CarbamazepineThe metabolism of Dihydro-alpha-ergocryptine can be increased when combined with Carbamazepine.Approved, Investigational
CeritinibThe serum concentration of Dihydro-alpha-ergocryptine can be increased when it is combined with Ceritinib.Approved
ClarithromycinThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Clemastine.Approved, Investigational
ClotrimazoleThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Cobicistat.Approved
ConivaptanThe serum concentration of Conivaptan can be increased when it is combined with Dihydro-alpha-ergocryptine.Approved, Investigational
CrizotinibThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Crizotinib.Approved
CyclosporineThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
DabrafenibThe serum concentration of Dihydro-alpha-ergocryptine can be decreased when it is combined with Dabrafenib.Approved, Investigational
DarunavirThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Dihydro-alpha-ergocryptine can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Dihydro-alpha-ergocryptine can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Delavirdine.Approved
DihydroergotamineThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Dihydroergotamine.Approved, Investigational
DiltiazemThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Diltiazem.Approved, Investigational
DoxycyclineThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Dronedarone.Approved
EnzalutamideThe serum concentration of Dihydro-alpha-ergocryptine can be decreased when it is combined with Enzalutamide.Approved
ErythromycinThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Erythromycin.Approved, Investigational, Vet Approved
FluconazoleThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Fluconazole.Approved, Investigational
FluvoxamineThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Dihydro-alpha-ergocryptine can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Dihydro-alpha-ergocryptine can be increased when combined with Fosphenytoin.Approved, Investigational
Fusidic AcidThe serum concentration of Dihydro-alpha-ergocryptine can be increased when it is combined with Fusidic Acid.Approved, Investigational
IdelalisibThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Idelalisib.Approved
ImatinibThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Imatinib.Approved
IndinavirThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Indinavir.Approved
IsavuconazoleThe serum concentration of Dihydro-alpha-ergocryptine can be increased when it is combined with Isavuconazole.Approved, Investigational
IsavuconazoniumThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Isavuconazonium.Approved, Investigational
IsradipineThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Isradipine.Approved, Investigational
ItraconazoleThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Dihydro-alpha-ergocryptine can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Ketoconazole.Approved, Investigational
LopinavirThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Lopinavir.Approved
LorpiprazoleThe serum concentration of Dihydro-alpha-ergocryptine can be increased when it is combined with Lorpiprazole.Approved
LovastatinThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Dihydro-alpha-ergocryptine can be increased when it is combined with Luliconazole.Approved
LumacaftorThe metabolism of Dihydro-alpha-ergocryptine can be increased when combined with Lumacaftor.Approved
MifepristoneThe serum concentration of Dihydro-alpha-ergocryptine can be increased when it is combined with Mifepristone.Approved, Investigational
MitotaneThe serum concentration of Dihydro-alpha-ergocryptine can be decreased when it is combined with Mitotane.Approved
NefazodoneThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Dihydro-alpha-ergocryptine can be increased when it is combined with Netupitant.Approved, Investigational
NevirapineThe metabolism of Dihydro-alpha-ergocryptine can be increased when combined with Nevirapine.Approved
NilotinibThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Olaparib.Approved
OsimertinibThe serum concentration of Dihydro-alpha-ergocryptine can be increased when it is combined with Osimertinib.Approved
PalbociclibThe serum concentration of Dihydro-alpha-ergocryptine can be increased when it is combined with Palbociclib.Approved, Investigational
PentobarbitalThe metabolism of Dihydro-alpha-ergocryptine can be increased when combined with Pentobarbital.Approved, Investigational, Vet Approved
PhenobarbitalThe metabolism of Dihydro-alpha-ergocryptine can be increased when combined with Phenobarbital.Approved, Investigational
PhenytoinThe metabolism of Dihydro-alpha-ergocryptine can be increased when combined with Phenytoin.Approved, Vet Approved
PitolisantThe serum concentration of Dihydro-alpha-ergocryptine can be decreased when it is combined with Pitolisant.Approved, Investigational
PosaconazoleThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrimidoneThe metabolism of Dihydro-alpha-ergocryptine can be increased when combined with Primidone.Approved, Vet Approved
RanolazineThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Ranolazine.Approved, Investigational
RifabutinThe metabolism of Dihydro-alpha-ergocryptine can be increased when combined with Rifabutin.Approved, Investigational
RifampicinThe metabolism of Dihydro-alpha-ergocryptine can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Dihydro-alpha-ergocryptine can be increased when combined with Rifapentine.Approved, Investigational
RucaparibThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Rucaparib.Approved, Investigational
SaquinavirThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Saquinavir.Approved, Investigational
SarilumabThe therapeutic efficacy of Dihydro-alpha-ergocryptine can be decreased when used in combination with Sarilumab.Approved, Investigational
SildenafilThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Dihydro-alpha-ergocryptine can be decreased when it is combined with Siltuximab.Approved, Investigational
SimeprevirThe serum concentration of Dihydro-alpha-ergocryptine can be increased when it is combined with Simeprevir.Approved
St. John's WortThe serum concentration of Dihydro-alpha-ergocryptine can be decreased when it is combined with St. John's Wort.Approved, Investigational, Nutraceutical
StiripentolThe serum concentration of Dihydro-alpha-ergocryptine can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TelaprevirThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Telithromycin.Approved
TiclopidineThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Ticlopidine.Approved
TocilizumabThe serum concentration of Dihydro-alpha-ergocryptine can be decreased when it is combined with Tocilizumab.Approved
VemurafenibThe serum concentration of Dihydro-alpha-ergocryptine can be decreased when it is combined with Vemurafenib.Approved
VenlafaxineThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Verapamil.Approved
VoriconazoleThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Voriconazole.Approved, Investigational
ZiprasidoneThe metabolism of Dihydro-alpha-ergocryptine can be decreased when combined with Ziprasidone.Approved
Food Interactions
Not Available

References

General References
  1. Elliott JM, Grahame-Smith DG: The binding characteristics of [3H]-dihydroergocryptine on intact human platelets. Br J Pharmacol. 1982 May;76(1):121-30. [PubMed:6805543]
  2. Battistin L, Bardin PG, Ferro-Milone F, Ravenna C, Toso V, Reboldi G: Alpha-dihydroergocryptine in Parkinson's disease: a multicentre randomized double blind parallel group study. Acta Neurol Scand. 1999 Jan;99(1):36-42. [PubMed:9925236]
  3. Micieli G, Cavallini A, Marcheselli S, Mailland F, Ambrosoli L, Nappi G: Alpha-dihydroergocryptine and predictive factors in migraine prophylaxis. Int J Clin Pharmacol Ther. 2001 Apr;39(4):144-51. [PubMed:11332869]
  4. Gerlach M, Double K, Arzberger T, Leblhuber F, Tatschner T, Riederer P: Dopamine receptor agonists in current clinical use: comparative dopamine receptor binding profiles defined in the human striatum. J Neural Transm (Vienna). 2003 Oct;110(10):1119-27. doi: 10.1007/s00702-003-0027-5. [PubMed:14523624]
  5. Antonini A, Tolosa E, Mizuno Y, Yamamoto M, Poewe WH: A reassessment of risks and benefits of dopamine agonists in Parkinson's disease. Lancet Neurol. 2009 Oct;8(10):929-37. doi: 10.1016/S1474-4422(09)70225-X. Epub 2009 Aug 24. [PubMed:19709931]
  6. Albanese A, Colosimo C: Dihydroergocriptine in Parkinson's disease: clinical efficacy and comparison with other dopamine agonists. Acta Neurol Scand. 2003 May;107(5):349-55. [PubMed:12713527]
  7. de Mey C, Stamenova P, Daskalov M, Orozova M, Staikov I, Vlahov V, Wangemann M: Bioequivalence of a novel high-dose oral formulation of alpha-dihydroergocryptine. Arzneimittelforschung. 2006;56(3):205-11. doi: 10.1055/s-0031-1296712. [PubMed:16618013]
  8. Mailland E, Magnani P, Ottillinger B: Alpha-dihydroergocryptine in the long-term therapy of Parkinson's disease. Arzneimittelforschung. 2004;54(10):647-54. doi: 10.1055/s-0031-1297016. [PubMed:15553103]
  9. Authors unspecified: DA agonists -- ergot derivatives: dihydroergocryptine (DHEC): management of Parkinson's disease. Mov Disord. 2002;17 Suppl 4:S72-3. doi: 10.1002/mds.5564. [PubMed:12211143]
  10. Zheng SQ, Li T, Xuan YX, Lin SZ, Chen LJ, Yan GM: [Neuroprotective effect of alpha-dihydroergocryptine depends on activation of nuclear factor kappa B]. Yao Xue Xue Bao. 2000 Dec;35(12):898-901. [PubMed:12567910]
  11. Mas-Chamberlin C, Bromet N, Olgiati V, Girardello R, Lowenthal DT: Metabolism study of dihydro-alpha-ergocryptine,9,10-[9,10-3H(N)] in rat and human hepatocyte cultures and rat, monkey, and human microsomes. Am J Ther. 1997 Sep-Oct;4(9-10):291-9. [PubMed:10423622]
  12. de Mey C, Althaus M, Ezan E, Retzow A: Erythromycin increases plasma concentrations of alpha-dihydroergocryptine in humans. Clin Pharmacol Ther. 2001 Aug;70(2):142-8. doi: 10.1067/mcp.2001.117286. [PubMed:11503008]
  13. Grognet JM, Istin M, Zanotti A, Mailland F, Coppi G: Pharmacokinetics of alpha-dihydroergokryptine in monkeys after oral administration. Drugs Exp Clin Res. 1991;17(6):309-12. [PubMed:1769319]
  14. Coppi G, Silingardi S: Pharmacokinetics of alpha-dihydroergocriptine in rats after single intravenous and single and repeated oral administrations. Biopharm Drug Dispos. 1995 May;16(4):333-42. [PubMed:7548782]
  15. Adams K, Allen JA, Brooker PC, Jones E, Proudlock RJ, Mailland F, Coppi G: Evaluation of the mutagenicity of a-dihydroergocryptine in vitro and in vivo. Arzneimittelforschung. 1993 Dec;43(12):1253-7. [PubMed:8141809]
  16. Steinhilber, D., Schubert M. and Roth H. (2005). Medizinische Chemie. Deutscher Apotheker Verlag. [ISBN:3-7692-3483-9]
External Links
ChemSpider
102887
BindingDB
50390994
ChEBI
59919
ChEMBL
CHEMBL1743263

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
TabletOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)117 ºCLabNetwork
boiling point (°C)DecomposesLabNetwork
logP5.90Yasuda, et al. The Journal of Pharmacology and Experimental Therapeutics. (2002)
Predicted Properties
PropertyValueSource
Water Solubility0.264 mg/mLALOGPS
logP3.28ALOGPS
logP3.43ChemAxon
logS-3.3ALOGPS
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 Count5ChemAxon
Refractivity157.33 m3·mol-1ChemAxon
Polarizability63.78 Å3ChemAxon
Number of Rings7ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as lysergamides. These are amides of Lysergic acids.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Ergoline and derivatives
Sub Class
Lysergic acids and derivatives
Direct Parent
Lysergamides
Alternative Parents
Indoloquinolines / Benzoquinolines / Pyrroloquinolines / N-acyl-alpha amino acids and derivatives / 3-alkylindoles / Isoindoles and derivatives / Piperidinecarboxamides / Aralkylamines / N-alkylpiperazines / Benzenoids
show 17 more
Substituents
Lysergic acid amide / Indoloquinoline / Benzoquinoline / N-acyl-alpha amino acid or derivatives / Pyrroloquinoline / Alpha-amino acid or derivatives / Quinoline / 3-alkylindole / Indole / Indole or derivatives
show 40 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
ergot alkaloid (CHEBI:59919)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
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. Gerlach M, Double K, Arzberger T, Leblhuber F, Tatschner T, Riederer P: Dopamine receptor agonists in current clinical use: comparative dopamine receptor binding profiles defined in the human striatum. J Neural Transm (Vienna). 2003 Oct;110(10):1119-27. doi: 10.1007/s00702-003-0027-5. [PubMed:14523624]
Kind
Protein group
Organism
Human
Pharmacological action
Yes
Actions
Partial 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. Gerlach M, Double K, Arzberger T, Leblhuber F, Tatschner T, Riederer P: Dopamine receptor agonists in current clinical use: comparative dopamine receptor binding profiles defined in the human striatum. J Neural Transm (Vienna). 2003 Oct;110(10):1119-27. doi: 10.1007/s00702-003-0027-5. [PubMed:14523624]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Partial agonist
General Function
G-protein coupled amine receptor activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase. Promotes cell proliferation.
Gene Name
DRD3
Uniprot ID
P35462
Uniprot Name
D(3) dopamine receptor
Molecular Weight
44224.335 Da
References
  1. Gerlach M, Double K, Arzberger T, Leblhuber F, Tatschner T, Riederer P: Dopamine receptor agonists in current clinical use: comparative dopamine receptor binding profiles defined in the human striatum. J Neural Transm (Vienna). 2003 Oct;110(10):1119-27. doi: 10.1007/s00702-003-0027-5. [PubMed:14523624]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
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. de Mey C, Althaus M, Ezan E, Retzow A: Erythromycin increases plasma concentrations of alpha-dihydroergocryptine in humans. Clin Pharmacol Ther. 2001 Aug;70(2):142-8. doi: 10.1067/mcp.2001.117286. [PubMed:11503008]

Drug created on December 03, 2015 09:52 / Updated on May 09, 2018 14:59