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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

Molecular Formula C20H26N4O
Molecular Weight 338.4466
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
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 No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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
Sleep attacks and Parkinson's disease treatment.
2000 Apr 15
Role of dopamine D3 receptors in thermoregulation: a reappraisal.
2000 Jan 17
Poetic talent unmasked by treatment of Parkinson's disease.
2001 Nov
Dopamine partial agonist reverses amphetamine withdrawal in rats.
2001 Nov
Quantitative analysis of striatal dopamine D2 receptors with 123 I-iodolisuride SPECT in degenerative extrapyramidal diseases.
2001 Nov
[Results of treatment for male prolactinomas].
2002 Dec
Lisuride, a dopamine D2 receptor agonist, and anticraving drug expectancy as modifiers of relapse in alcohol dependence.
2002 Feb
Characterization of phospholipase C activity at h5-HT2C compared with h5-HT2B receptors: influence of novel ligands upon membrane-bound levels of [3H]phosphatidylinositols.
2002 Mar
Is the 5-HT(7) receptor involved in the pathogenesis and prophylactic treatment of migraine?
2002 Mar 29
5-HT2A receptor-stimulated phosphoinositide hydrolysis in the stimulus effects of hallucinogens.
2002 May
Cortisol as an indicator of dopaminergic effects on nicotine craving.
2003 Aug
The primary restless legs syndrome pathogenesis depends on the dysfunction of EEG alpha activity.
2003 Feb
LSD, 5-HT (serotonin), and the evolution of a behavioral assay.
2004 Jan
Familial acromegaly: a familial report and review of the literature.
2004 May
Capillary zone electrophoresis separation of enantiomers of lisuride.
2005 Feb 25
Pharmacokinetic optimisation in the treatment of Parkinson's disease : an update.
2006
Striking differences of action of lisuride stereoisomers at histamine H1 receptors.
2006 Dec
Homology modelling of the serotoninergic 5-HT2c receptor.
2006 Jun
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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 14:58:43 UTC 2023
Edited
by admin
on Fri Dec 15 14:58:43 UTC 2023
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
FDA ORPHAN DRUG 906822
Created by admin on Fri Dec 15 14:58:44 UTC 2023 , Edited by admin on Fri Dec 15 14:58:44 UTC 2023
EU-Orphan Drug EU/3/11/869
Created by admin on Fri Dec 15 14:58:43 UTC 2023 , Edited by admin on Fri Dec 15 14:58:43 UTC 2023
Code System Code Type Description
EVMPD
SUB02940MIG
Created by admin on Fri Dec 15 14:58:43 UTC 2023 , Edited by admin on Fri Dec 15 14:58:43 UTC 2023
PRIMARY
SMS_ID
100000086150
Created by admin on Fri Dec 15 14:58:44 UTC 2023 , Edited by admin on Fri Dec 15 14:58:44 UTC 2023
PRIMARY
CHEBI
31776
Created by admin on Fri Dec 15 14:58:43 UTC 2023 , Edited by admin on Fri Dec 15 14:58:43 UTC 2023
PRIMARY
RXCUI
6553
Created by admin on Fri Dec 15 14:58:44 UTC 2023 , Edited by admin on Fri Dec 15 14:58:44 UTC 2023
PRIMARY RxNorm
DRUG BANK
DBSALT001034
Created by admin on Fri Dec 15 14:58:43 UTC 2023 , Edited by admin on Fri Dec 15 14:58:43 UTC 2023
PRIMARY
EPA CompTox
DTXSID501017378
Created by admin on Fri Dec 15 14:58:43 UTC 2023 , Edited by admin on Fri Dec 15 14:58:43 UTC 2023
PRIMARY
MERCK INDEX
m6844
Created by admin on Fri Dec 15 14:58:44 UTC 2023 , Edited by admin on Fri Dec 15 14:58:44 UTC 2023
PRIMARY Merck Index
PUBCHEM
5282421
Created by admin on Fri Dec 15 14:58:44 UTC 2023 , Edited by admin on Fri Dec 15 14:58:44 UTC 2023
PRIMARY
ECHA (EC/EINECS)
243-387-3
Created by admin on Fri Dec 15 14:58:43 UTC 2023 , Edited by admin on Fri Dec 15 14:58:43 UTC 2023
PRIMARY
CAS
19875-60-6
Created by admin on Fri Dec 15 14:58:43 UTC 2023 , Edited by admin on Fri Dec 15 14:58:43 UTC 2023
PRIMARY
FDA UNII
UV1635N8XW
Created by admin on Fri Dec 15 14:58:44 UTC 2023 , Edited by admin on Fri Dec 15 14:58:44 UTC 2023
PRIMARY
ChEMBL
CHEMBL157138
Created by admin on Fri Dec 15 14:58:43 UTC 2023 , Edited by admin on Fri Dec 15 14:58:43 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY