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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.[H][C@@]12CC3=CNC4=C3C(=CC=C4)C1=C[C@@H](CN2C)NC(=O)N(CC)CC

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

Description
Curator's Comment: description was created based on several sources, including http://www.bayerresources.com.au/resources/uploads/datasheet/file9563.pdf | https://www.ncbi.nlm.nih.gov/mesh/68008090

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.

Originator

Curator's Comment: Primary source: Zikan V, Siemonsky M (1960) Mutterkorn alkaloids XVI. Einige N-(D-6-meth-yllisoergolenyl-8)-, N-(D-6-methylergolenyl-8)- und N-(D-6-methylergolin (I)-YL-8)-N’-substitiuerte Harnstoffe. Collect Czech Chem Commun 25:1922–1928.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DOPERGIN

Approved Use

As a Dopamine Agonist in: * Parkinson's disease, postencephalitic parkinsonism, parkinsonism of other origin (with the exception of the medicine-induced form) As a Prolactin Inhibitor in: * Prevention of the onset of lactation in the puerperium (primary ablactation) only for clearly defined medical reasons * Galactorrhea; prolactin-induced amenorrhea; prolactin-induced infertility in women; prolactinomas * Acromegaly
Preventing
DOPERGIN

Approved Use

As a Dopamine Agonist in: * Parkinson's disease, postencephalitic parkinsonism, parkinsonism of other origin (with the exception of the medicine-induced form) As a Prolactin Inhibitor in: * Prevention of the onset of lactation in the puerperium (primary ablactation) only for clearly defined medical reasons * Galactorrhea; prolactin-induced amenorrhea; prolactin-induced infertility in women; prolactinomas * Acromegaly
Primary
DOPERGIN

Approved Use

As a Dopamine Agonist in: * Parkinson's disease, postencephalitic parkinsonism, parkinsonism of other origin (with the exception of the medicine-induced form) As a Prolactin Inhibitor in: * Prevention of the onset of lactation in the puerperium (primary ablactation) only for clearly defined medical reasons * Galactorrhea; prolactin-induced amenorrhea; prolactin-induced infertility in women; prolactinomas * Acromegaly
Primary
DOPERGIN

Approved Use

As a Dopamine Agonist in: * Parkinson's disease, postencephalitic parkinsonism, parkinsonism of other origin (with the exception of the medicine-induced form) As a Prolactin Inhibitor in: * Prevention of the onset of lactation in the puerperium (primary ablactation) only for clearly defined medical reasons * Galactorrhea; prolactin-induced amenorrhea; prolactin-induced infertility in women; prolactinomas * Acromegaly
Primary
DOPERGIN

Approved Use

As a Dopamine Agonist in: * Parkinson's disease, postencephalitic parkinsonism, parkinsonism of other origin (with the exception of the medicine-induced form) As a Prolactin Inhibitor in: * Prevention of the onset of lactation in the puerperium (primary ablactation) only for clearly defined medical reasons * Galactorrhea; prolactin-induced amenorrhea; prolactin-induced infertility in women; prolactinomas * Acromegaly
PubMed

PubMed

TitleDatePubMed
Levodopa-induced dyskinesias in Parkinson's disease: clinical and pharmacological classification.
1992
[Results of treatment for male prolactinomas].
2002 Dec
Differential actions of antiparkinson agents at multiple classes of monoaminergic receptor. III. Agonist and antagonist properties at serotonin, 5-HT(1) and 5-HT(2), receptor subtypes.
2002 Nov
Differential actions of antiparkinson agents at multiple classes of monoaminergic receptor. II. Agonist and antagonist properties at subtypes of dopamine D(2)-like receptor and alpha(1)/alpha(2)-adrenoceptor.
2002 Nov
An evidence-based review of dopamine receptor agonists in the treatment of Parkinson's disease.
2002 Oct
Inhibition of growth hormone excess reduces insulin resistance and ovarian dysfunction in a lean case of polycystic ovary syndrome with a growth-hormone-producing pituitary adenoma.
2003
[Pharmacokinetic/pharmacodynamic analysis of anti-hyperprolactinemic effect of terguride based on dopamine D2 receptor occupancy].
2003 Apr
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
The primary restless legs syndrome pathogenesis depends on the dysfunction of EEG alpha activity.
2003 Feb
[Arrest of lactation after 2nd trimester abortion with a single dose of cabergoline in comparison with 10-day administration of teguride].
2003 Jan
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
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
No evidence of the usefulness of eye blinking as a marker for central dopaminergic activity.
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
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
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
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

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.
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
FDA ORPHAN DRUG 906822
Created by admin on Fri Dec 15 14:58:44 GMT 2023 , Edited by admin on Fri Dec 15 14:58:44 GMT 2023
EU-Orphan Drug EU/3/11/869
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
Code System Code Type Description
EVMPD
SUB02940MIG
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY
SMS_ID
100000086150
Created by admin on Fri Dec 15 14:58:44 GMT 2023 , Edited by admin on Fri Dec 15 14:58:44 GMT 2023
PRIMARY
CHEBI
31776
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY
RXCUI
6553
Created by admin on Fri Dec 15 14:58:44 GMT 2023 , Edited by admin on Fri Dec 15 14:58:44 GMT 2023
PRIMARY RxNorm
DRUG BANK
DBSALT001034
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY
EPA CompTox
DTXSID501017378
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY
MERCK INDEX
m6844
Created by admin on Fri Dec 15 14:58:44 GMT 2023 , Edited by admin on Fri Dec 15 14:58:44 GMT 2023
PRIMARY Merck Index
PUBCHEM
5282421
Created by admin on Fri Dec 15 14:58:44 GMT 2023 , Edited by admin on Fri Dec 15 14:58:44 GMT 2023
PRIMARY
ECHA (EC/EINECS)
243-387-3
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY
CAS
19875-60-6
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY
FDA UNII
UV1635N8XW
Created by admin on Fri Dec 15 14:58:44 GMT 2023 , Edited by admin on Fri Dec 15 14:58:44 GMT 2023
PRIMARY
ChEMBL
CHEMBL157138
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY