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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H26N4O.C4H4O4
Molecular Weight 454.5188
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of LISURIDE MALEATE

SMILES

OC(=O)\C=C/C(O)=O.CCN(CC)C(=O)N[C@@H]1CN(C)[C@@H]2CC3=CNC4=C3C(=CC=C4)C2=C1

InChI

InChIKey=CVQFAMQDTWVJSV-BAXNFHPCSA-N
InChI=1S/C20H26N4O.C4H4O4/c1-4-24(5-2)20(25)22-14-10-16-15-7-6-8-17-19(15)13(11-21-17)9-18(16)23(3)12-14;5-3(6)1-2-4(7)8/h6-8,10-11,14,18,21H,4-5,9,12H2,1-3H3,(H,22,25);1-2H,(H,5,6)(H,7,8)/b;2-1-/t14-,18+;/m0./s1

HIDE SMILES / InChI

Molecular Formula C20H26N4O
Molecular Weight 338.4466
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Lisuride (DOPERGIN®), a highly active dopaminergic ergot derivative with prolactin-lowering properties, has a pronounced affinity for dopamine receptors. It may also act as an agonist at some serotonin receptors. Lisuride (DOPERGIN®) is concentrated within the pituitary where it acts on dopamine receptors which inhibit prolactin release. It can be used in the clinical conditions where a dopaminergic or prolactin-lowering effect is needed.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Levodopa-induced dyskinesias in Parkinson's disease: clinical and pharmacological classification.
1992
Effects of a partial dopamine D2-like agonist on the cocaine-induced behavioral sensitization of preweanling rats.
2003 Aug
Cortisol as an indicator of dopaminergic effects on nicotine craving.
2003 Aug
Prevention and treatment of motor fluctuations.
2003 Aug
Sleep attacks, daytime sleepiness, and dopamine agonists in Parkinson's disease.
2003 Jun
The dopamine receptor agonist lisuride attenuates iron-mediated dopaminergic neurodegeneration.
2003 Nov
Dopamine receptor agonists in current clinical use: comparative dopamine receptor binding profiles defined in the human striatum.
2003 Oct
Management of restless legs syndrome by the partial D2-agonist terguride.
2003 Sep
Effects of terguride treatment on glucose abnormalities induced by ischemic brain damage in SHR/N-cp lean Koletsky strain and in rats of Wistar strain.
2004
Transdermal lisuride delivery in the treatment of Parkinson's disease.
2004
Pergolide, terguride and N,N'-spacer-linked oligomers of both interact with 5-HT2A receptors of rat tail artery.
2004
Pharmacology of polymorphic variants of the human 5-HT1A receptor.
2004 Feb 1
LSD, 5-HT (serotonin), and the evolution of a behavioral assay.
2004 Jan
No evidence of the usefulness of eye blinking as a marker for central dopaminergic activity.
2004 Mar
8R-lisuride is a potent stereospecific histamine H1-receptor partial agonist.
2004 Mar
Familial acromegaly: a familial report and review of the literature.
2004 May
Evidence for the management of mastalgia.
2004 May
D1 but not D2 dopamine receptors or adrenoceptors mediate dopamine-induced potentiation of N-methyl-d-aspartate currents in the rat prefrontal cortex.
2004 Nov 30
The effects of dopamine receptor agonists and antagonists on the secretory rate of cockroach (Periplaneta americana) salivary glands.
2004 Sep
Regulation of serotonin 5-HT2C receptors by chronic ligand exposure.
2004 Sep 13
The partial D2-like dopamine receptor agonist terguride acts as a functional antagonist in states of high and low dopaminergic tone: evidence from preweanling rats.
2005 Apr
Agonism at 5-HT2B receptors is not a class effect of the ergolines.
2005 Apr 25
Mastalgia: a review of management.
2005 Dec
Capillary zone electrophoresis separation of enantiomers of lisuride.
2005 Feb 25
Buprenorphine and a CRF1 antagonist block the acquisition of opiate withdrawal-induced conditioned place aversion in rats.
2005 Jan
Delineation of receptor-ligand interactions at the human histamine H1 receptor by a combined approach of site-directed mutagenesis and computational techniques - or - how to bind the H1 receptor.
2005 Jun
Dopamine and serotonin modulate the onset of metamorphosis in the ascidian Phallusia mammillata.
2005 Jun 1
Influence of steric hindrance on enantioseparation of Dns-amino acids and pesticides on terguride based chiral selectors in capillary electrophoresis.
2005 May
Evidence-based medical review update: pharmacological and surgical treatments of Parkinson's disease: 2001 to 2004.
2005 May
Levodopa in the treatment of Parkinson's disease: current controversies.
2005 May
Aripiprazole's low intrinsic activities at human dopamine D2L and D2S receptors render it a unique antipsychotic.
2005 May 16
Advances in the delivery of treatments for Parkinson's disease.
2005 Nov
Treatment of pituitary tumors: dopamine agonists.
2005 Oct
Transdermal treatment options for neurological disorders: impact on the elderly.
2006
Pharmacokinetic optimisation in the treatment of Parkinson's disease : an update.
2006
Dopamine stimulation via infusion in the lateral ventricle.
2006 Aug
Ergoline and non-ergoline derivatives in the treatment of Parkinson's disease.
2006 Aug
Striking differences of action of lisuride stereoisomers at histamine H1 receptors.
2006 Dec
In vitro characterization of SLV308 (7-[4-methyl-1-piperazinyl]-2(3H)-benzoxazolone, monohydrochloride): a novel partial dopamine D2 and D3 receptor agonist and serotonin 5-HT1A receptor agonist.
2006 Dec 15
Effects of a partial D2-like receptor agonist on striatal dopamine autoreceptor functioning in preweanling rats.
2006 Feb 16
Lisuride treatment of restless legs syndrome: first studies with monotherapy in de novo patients and in combination with levodopa in advanced disease.
2006 Jan
Transdermal lisuride: short-term efficacy and tolerability study in patients with severe restless legs syndrome.
2006 Jan
Homology modelling of the serotoninergic 5-HT2c receptor.
2006 Jun
Effects of terguride, ropinirole, and acetyl-L-carnitine on methamphetamine withdrawal in the rat.
2006 Mar
The partial dopamine D2-like receptor agonist terguride functions as an agonist in preweanling rats after a 5-day reserpine regimen.
2006 Mar
Potential vascular alpha1-adrenoceptor blocking properties of an array of 5-HT receptor ligands in the rat.
2006 Mar 27
Lisuride, a dopamine receptor agonist with 5-HT2B receptor antagonist properties: absence of cardiac valvulopathy adverse drug reaction reports supports the concept of a crucial role for 5-HT2B receptor agonism in cardiac valvular fibrosis.
2006 Mar-Apr
Observed smoking in cars: a method and differences by socioeconomic area.
2006 Oct
Glutamate-induced cell death and formation of radicals can be reduced by lisuride in mesencephalic primary cell culture.
2006 Sep
In vitro functional characteristics of dopamine D2 receptor partial agonists in second and third messenger-based assays of cloned human dopamine D2Long receptor signalling.
2007 Aug
Patents

Sample Use Guides

In Vivo Use Guide
Parkinsonism: The treatment begins with half of a 0.2 mg DOPERGIN® tablet (0.1 mg) in the evening and should be increased by 0.1 mg weekly until a clinical effect becomes apparent. Endocrine Indications: One DOPERGIN® 0.2 mg tablet should be taken 2 to 3 times daily for 14 days.
Route of Administration: Oral
In Vitro Use Guide
Lysergic acid diethylamide (LSD) and lisuride were potent partial agonists at 5HT2A receptors with EC50 values of 7.2 nM and 17 nM, respectively. Also, LSD and lisuride were partial agonists at 5HT2C receptors with EC50 values of 27 nM and 94 nM, respectively.
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:58:07 UTC 2019
Edited
by admin
on Mon Oct 21 20:58:07 UTC 2019
Record UNII
UV1635N8XW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LISURIDE MALEATE
JAN   MART.   MI   WHO-DD  
Common Name English
LISURIDE MALEATE [WHO-DD]
Common Name English
LISURIDE MALEATE [MART.]
Common Name English
LISURIDE MALEATE [MI]
Common Name English
LISURIDE MALEATE [JAN]
Common Name English
LYSURIDE MALEATE
Common Name English
3-(9,10-DIDEHYDRO-6-METHYLERGOLIN-8.ALPHA.-YL)-1,1-DIETHYLUREA MALEATE (1:1)
Systematic Name English
Classification Tree Code System Code
EU-Orphan Drug EU/3/11/869
Created by admin on Mon Oct 21 20:58:07 UTC 2019 , Edited by admin on Mon Oct 21 20:58:07 UTC 2019
Code System Code Type Description
EVMPD
SUB02940MIG
Created by admin on Mon Oct 21 20:58:07 UTC 2019 , Edited by admin on Mon Oct 21 20:58:07 UTC 2019
PRIMARY
RXCUI
6553
Created by admin on Mon Oct 21 20:58:07 UTC 2019 , Edited by admin on Mon Oct 21 20:58:07 UTC 2019
PRIMARY RxNorm
MERCK INDEX
M6844
Created by admin on Mon Oct 21 20:58:07 UTC 2019 , Edited by admin on Mon Oct 21 20:58:07 UTC 2019
PRIMARY Merck Index
PUBCHEM
5282421
Created by admin on Mon Oct 21 20:58:07 UTC 2019 , Edited by admin on Mon Oct 21 20:58:07 UTC 2019
PRIMARY
ECHA (EC/EINECS)
243-387-3
Created by admin on Mon Oct 21 20:58:07 UTC 2019 , Edited by admin on Mon Oct 21 20:58:07 UTC 2019
PRIMARY
CAS
19875-60-6
Created by admin on Mon Oct 21 20:58:07 UTC 2019 , Edited by admin on Mon Oct 21 20:58:07 UTC 2019
PRIMARY
ChEMBL
CHEMBL157138
Created by admin on Mon Oct 21 20:58:07 UTC 2019 , Edited by admin on Mon Oct 21 20:58:07 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY