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Details

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

SHOW SMILES / InChI
Structure of LISURIDE

SMILES

[H][C@@]12CC3=CNC4=CC=CC(=C34)C1=C[C@@H](CN2C)NC(=O)N(CC)CC

InChI

InChIKey=BKRGVLQUQGGVSM-KBXCAEBGSA-N
InChI=1S/C20H26N4O/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/h6-8,10-11,14,18,21H,4-5,9,12H2,1-3H3,(H,22,25)/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

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
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
Symptomatic treatment of premenstrual mastalgia in premenopausal women with lisuride maleate: a double-blind placebo-controlled randomized study.
2001 Apr
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: lisuride: management of Parkinson's disease.
2002
DA agonists -- ergot derivatives: bromocriptine: management of Parkinson's disease.
2002
Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease.
2002
[Results of treatment for male prolactinomas].
2002 Dec
Protection of dopaminergic neurons in primary culture by lisuride.
2002 Feb
SUNCT syndrome in two patients with prolactinomas and bromocriptine-induced attacks.
2002 Jun 11
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
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
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
The trigonometric responder approach: a new method for detecting responders to pharmacological or experimental challenges.
2002 Sep
Prospective randomized trial of lisuride infusion versus oral levodopa in patients with Parkinson's disease.
2002 Sep
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
The timing of antiparkinsonian treatment reduction after subthalamic nucleus stimulation.
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
Prevention and treatment of motor fluctuations.
2003 Aug
The primary restless legs syndrome pathogenesis depends on the dysfunction of EEG alpha activity.
2003 Feb
Suppression of cocaine- and food-maintained behavior by the D2-like receptor partial agonist terguride in squirrel monkeys.
2003 Mar
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
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
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
Regulation of serotonin 5-HT2C receptors by chronic ligand exposure.
2004 Sep 13
Agonism at 5-HT2B receptors is not a class effect of the ergolines.
2005 Apr 25
Mastalgia: a review of management.
2005 Dec
Influence of steric hindrance on enantioseparation of Dns-amino acids and pesticides on terguride based chiral selectors in capillary electrophoresis.
2005 May
Levodopa in the treatment of Parkinson's disease: current controversies.
2005 May
Transdermal treatment options for neurological disorders: impact on the elderly.
2006
Pharmacokinetic optimisation in the treatment of Parkinson's disease : an update.
2006
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
Effects of a partial D2-like receptor agonist on striatal dopamine autoreceptor functioning in preweanling rats.
2006 Feb 16
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
Glutamate-induced cell death and formation of radicals can be reduced by lisuride in mesencephalic primary cell culture.
2006 Sep
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 Wed Jul 05 22:32:23 UTC 2023
Edited
by admin
on Wed Jul 05 22:32:23 UTC 2023
Record UNII
E0QN3D755O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LISURIDE
INN   MI   WHO-DD  
INN  
Official Name English
Lisuride [WHO-DD]
Common Name English
LYSURIDE
Common Name English
lisuride [INN]
Common Name English
3-(9,10-DIDEHYDRO-6-METHYLERGOLIN-8.ALPHA.-YL)-1,1-DIETHYLUREA
Systematic Name English
LISURIDE [MI]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 316610
Created by admin on Wed Jul 05 22:32:23 UTC 2023 , Edited by admin on Wed Jul 05 22:32:23 UTC 2023
WHO-VATC QG02CB02
Created by admin on Wed Jul 05 22:32:23 UTC 2023 , Edited by admin on Wed Jul 05 22:32:23 UTC 2023
WHO-ATC G02CB02
Created by admin on Wed Jul 05 22:32:23 UTC 2023 , Edited by admin on Wed Jul 05 22:32:23 UTC 2023
NCI_THESAURUS C38149
Created by admin on Wed Jul 05 22:32:23 UTC 2023 , Edited by admin on Wed Jul 05 22:32:23 UTC 2023
WHO-ATC N02CA07
Created by admin on Wed Jul 05 22:32:23 UTC 2023 , Edited by admin on Wed Jul 05 22:32:23 UTC 2023
WHO-VATC QN02CA07
Created by admin on Wed Jul 05 22:32:23 UTC 2023 , Edited by admin on Wed Jul 05 22:32:23 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C82247
Created by admin on Wed Jul 05 22:32:23 UTC 2023 , Edited by admin on Wed Jul 05 22:32:23 UTC 2023
PRIMARY
EVMPD
SUB08535MIG
Created by admin on Wed Jul 05 22:32:23 UTC 2023 , Edited by admin on Wed Jul 05 22:32:23 UTC 2023
PRIMARY
WIKIPEDIA
LISURIDE
Created by admin on Wed Jul 05 22:32:23 UTC 2023 , Edited by admin on Wed Jul 05 22:32:23 UTC 2023
PRIMARY
PUBCHEM
28864
Created by admin on Wed Jul 05 22:32:23 UTC 2023 , Edited by admin on Wed Jul 05 22:32:23 UTC 2023
PRIMARY
CAS
18016-80-3
Created by admin on Wed Jul 05 22:32:23 UTC 2023 , Edited by admin on Wed Jul 05 22:32:23 UTC 2023
PRIMARY
ECHA (EC/EINECS)
241-925-1
Created by admin on Wed Jul 05 22:32:23 UTC 2023 , Edited by admin on Wed Jul 05 22:32:23 UTC 2023
PRIMARY
DRUG CENTRAL
1588
Created by admin on Wed Jul 05 22:32:23 UTC 2023 , Edited by admin on Wed Jul 05 22:32:23 UTC 2023
PRIMARY
FDA UNII
E0QN3D755O
Created by admin on Wed Jul 05 22:32:23 UTC 2023 , Edited by admin on Wed Jul 05 22:32:23 UTC 2023
PRIMARY
ChEMBL
CHEMBL157138
Created by admin on Wed Jul 05 22:32:23 UTC 2023 , Edited by admin on Wed Jul 05 22:32:23 UTC 2023
PRIMARY
IUPHAR
43
Created by admin on Wed Jul 05 22:32:23 UTC 2023 , Edited by admin on Wed Jul 05 22:32:23 UTC 2023
PRIMARY
LACTMED
Lisuride
Created by admin on Wed Jul 05 22:32:23 UTC 2023 , Edited by admin on Wed Jul 05 22:32:23 UTC 2023
PRIMARY
DRUG BANK
DB00589
Created by admin on Wed Jul 05 22:32:23 UTC 2023 , Edited by admin on Wed Jul 05 22:32:23 UTC 2023
PRIMARY
CHEBI
51164
Created by admin on Wed Jul 05 22:32:23 UTC 2023 , Edited by admin on Wed Jul 05 22:32:23 UTC 2023
PRIMARY
INN
3065
Created by admin on Wed Jul 05 22:32:23 UTC 2023 , Edited by admin on Wed Jul 05 22:32:23 UTC 2023
PRIMARY
MERCK INDEX
M6844
Created by admin on Wed Jul 05 22:32:23 UTC 2023 , Edited by admin on Wed Jul 05 22:32:23 UTC 2023
PRIMARY Merck Index
RXCUI
6446
Created by admin on Wed Jul 05 22:32:23 UTC 2023 , Edited by admin on Wed Jul 05 22:32:23 UTC 2023
PRIMARY RxNorm
MESH
D008090
Created by admin on Wed Jul 05 22:32:23 UTC 2023 , Edited by admin on Wed Jul 05 22:32:23 UTC 2023
PRIMARY
EPA CompTox
DTXSID3023217
Created by admin on Wed Jul 05 22:32:23 UTC 2023 , Edited by admin on Wed Jul 05 22:32:23 UTC 2023
PRIMARY
SMS_ID
100000082525
Created by admin on Wed Jul 05 22:32:23 UTC 2023 , Edited by admin on Wed Jul 05 22:32:23 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY