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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.

CNS Activity

Originator

Zikan, V.|Siemonsky, M.
2
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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 7.19 null [pKi]
Agonist
2678
 9.47 null [pKi]
Agonist
2678
 9.55 null [pKi]
Agonist
2678
 8.34 null [pKi]
Agonist
2678
 8.45 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
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
Approved
8429
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
Approved
8429
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
Approved
8429
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
Approved
8429
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
Dopaminergic neurotransmission at the paraventricular nucleus of hypothalamus in central regulation of penile erection in the rat.
1999 Jul
High-affinity agonist binding correlates with efficacy (intrinsic activity) at the human serotonin 5-HT2A and 5-HT2C receptors: evidence favoring the ternary complex and two-state models of agonist action.
1999 May
Terguride attenuates prolactin levels and ameliorates insulin sensitivity and insulin binding in obese spontaneously hypertensive rats.
2001
Clinical features and medical treatment of male prolactinomas.
2001
Atypical polypoid adenomyoma in a patient with hyperprolactinemia.
2001 Jul-Aug
[Parkinson disease: diagnostic and therapeutic criteria].
2001 Mar 3
Dopaminergic modulation of grooming behavior in virgin and pregnant rats.
2001 Nov
[Use of dopamine agonists in the treatment of Parkinson's disease].
2002
DA agonists -- ergot derivatives: bromocriptine: management of Parkinson's disease.
2002
Dopamine agonist and antagonist responders as related to types of nicotine craving and facets of extraversion.
2002 Jun
Sleep attacks in patients taking dopamine agonists: review.
2002 Jun 22
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
Differential actions of antiparkinson agents at multiple classes of monoaminergic receptor. I. A multivariate analysis of the binding profiles of 14 drugs at 21 native and cloned human receptor subtypes.
2002 Nov
An evidence-based review of dopamine receptor agonists in the treatment of Parkinson's disease.
2002 Oct
Re-evaluation of lisuride pharmacology: 5-hydroxytryptamine1A receptor-mediated behavioral effects overlap its other properties in rats.
2002 Oct
Differential activation of Gq/11 and Gi(3) proteins at 5-hydroxytryptamine(2C) receptors revealed by antibody capture assays: influence of receptor reserve and relationship to agonist-directed trafficking.
2002 Sep
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
[Arrest of lactation after 2nd trimester abortion with a single dose of cabergoline in comparison with 10-day administration of teguride].
2003 Jan
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
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
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
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
Capillary zone electrophoresis separation of enantiomers of lisuride.
2005 Feb 25
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
Dopamine stimulation via infusion in the lateral ventricle.
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
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

Patents

JP2011510003A
48
JP2011528275A
455
US3954988
2
US4096266
2

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 Fri Dec 15 14:58:43 GMT 2023
Edited
by admin
on Fri Dec 15 14:58:43 GMT 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 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
Related Record Type Details
Structure of MALEIC ACID
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of LISURIDE
ACTIVE MOIETY
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