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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H26N4O
Molecular Weight 338.4474
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LISURIDE

SMILES

CCN(CC)C(=N[C@@]1([H])C=C2c3cccc4c3c(C[C@@]2([H])N(C)C1)c[nH]4)O

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 338.4474
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
Dopaminergic neurotransmission at the paraventricular nucleus of hypothalamus in central regulation of penile erection in the rat.
1999 Jul
Sleep attacks and Parkinson's disease treatment.
2000 Apr 15
Agonist high and low affinity state ratios predict drug intrinsic activity and a revised ternary complex mechanism at serotonin 5-HT(2A) and 5-HT(2C) receptors.
2000 Feb
Role of dopamine D3 receptors in thermoregulation: a reappraisal.
2000 Jan 17
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
Efficacy and tolerability of dopamine agonists in a parkinsonian population.
2001 Feb
Nonlinear analysis of partial dopamine agonist effects on cAMP in C6 glioma cells.
2001 Jan-Feb
Atypical polypoid adenomyoma in a patient with hyperprolactinemia.
2001 Jul-Aug
[Parkinson disease: diagnostic and therapeutic criteria].
2001 Mar 3
Poetic talent unmasked by treatment of Parkinson's disease.
2001 Nov
Dopamine partial agonist reverses amphetamine withdrawal in rats.
2001 Nov
Dopaminergic modulation of grooming behavior in virgin and pregnant rats.
2001 Nov
Quantitative analysis of striatal dopamine D2 receptors with 123 I-iodolisuride SPECT in degenerative extrapyramidal diseases.
2001 Nov
Dopamine mediates striatal malonate toxicity via dopamine transporter-dependent generation of reactive oxygen species and D2 but not D1 receptor activation.
2001 Oct
Real-time analysis of dopamine: antagonist interactions at recombinant human D2long receptor upon modulation of its activation state.
2001 Sep
Differential signalling of both wild-type and Thr(343)Arg dopamine D(2short) receptor by partial agonists in a G-protein-dependent manner.
2001 Sep 15
[Use of dopamine agonists in the treatment of Parkinson's disease].
2002
Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease.
2002
Protection of dopaminergic neurons in primary culture by lisuride.
2002 Feb
Clustered ergot alkaloids modulate cell-mediated cytotoxicity.
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
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
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
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
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
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
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
Mastalgia: a review of management.
2005 Dec
Aripiprazole's low intrinsic activities at human dopamine D2L and D2S receptors render it a unique antipsychotic.
2005 May 16
Treatment of pituitary tumors: dopamine agonists.
2005 Oct
Dopamine stimulation via infusion in the lateral ventricle.
2006 Aug
Lisuride treatment of restless legs syndrome: first studies with monotherapy in de novo patients and in combination with levodopa in advanced disease.
2006 Jan
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
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 Sat Jun 26 15:38:45 UTC 2021
Edited
by admin
on Sat Jun 26 15:38:45 UTC 2021
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 Sat Jun 26 15:38:45 UTC 2021 , Edited by admin on Sat Jun 26 15:38:45 UTC 2021
WHO-VATC QG02CB02
Created by admin on Sat Jun 26 15:38:45 UTC 2021 , Edited by admin on Sat Jun 26 15:38:45 UTC 2021
WHO-ATC G02CB02
Created by admin on Sat Jun 26 15:38:45 UTC 2021 , Edited by admin on Sat Jun 26 15:38:45 UTC 2021
NCI_THESAURUS C38149
Created by admin on Sat Jun 26 15:38:45 UTC 2021 , Edited by admin on Sat Jun 26 15:38:45 UTC 2021
WHO-ATC N02CA07
Created by admin on Sat Jun 26 15:38:45 UTC 2021 , Edited by admin on Sat Jun 26 15:38:45 UTC 2021
WHO-VATC QN02CA07
Created by admin on Sat Jun 26 15:38:45 UTC 2021 , Edited by admin on Sat Jun 26 15:38:45 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C82247
Created by admin on Sat Jun 26 15:38:45 UTC 2021 , Edited by admin on Sat Jun 26 15:38:45 UTC 2021
PRIMARY
EVMPD
SUB08535MIG
Created by admin on Sat Jun 26 15:38:45 UTC 2021 , Edited by admin on Sat Jun 26 15:38:45 UTC 2021
PRIMARY
WIKIPEDIA
LISURIDE
Created by admin on Sat Jun 26 15:38:45 UTC 2021 , Edited by admin on Sat Jun 26 15:38:45 UTC 2021
PRIMARY
PUBCHEM
28864
Created by admin on Sat Jun 26 15:38:45 UTC 2021 , Edited by admin on Sat Jun 26 15:38:45 UTC 2021
PRIMARY
CAS
18016-80-3
Created by admin on Sat Jun 26 15:38:45 UTC 2021 , Edited by admin on Sat Jun 26 15:38:45 UTC 2021
PRIMARY
ECHA (EC/EINECS)
241-925-1
Created by admin on Sat Jun 26 15:38:45 UTC 2021 , Edited by admin on Sat Jun 26 15:38:45 UTC 2021
PRIMARY
DRUG CENTRAL
1588
Created by admin on Sat Jun 26 15:38:45 UTC 2021 , Edited by admin on Sat Jun 26 15:38:45 UTC 2021
PRIMARY
FDA UNII
E0QN3D755O
Created by admin on Sat Jun 26 15:38:45 UTC 2021 , Edited by admin on Sat Jun 26 15:38:45 UTC 2021
PRIMARY
ChEMBL
CHEMBL157138
Created by admin on Sat Jun 26 15:38:45 UTC 2021 , Edited by admin on Sat Jun 26 15:38:45 UTC 2021
PRIMARY
IUPHAR
43
Created by admin on Sat Jun 26 15:38:45 UTC 2021 , Edited by admin on Sat Jun 26 15:38:45 UTC 2021
PRIMARY
LACTMED
Lisuride
Created by admin on Sat Jun 26 15:38:45 UTC 2021 , Edited by admin on Sat Jun 26 15:38:45 UTC 2021
PRIMARY
DRUG BANK
DB00589
Created by admin on Sat Jun 26 15:38:45 UTC 2021 , Edited by admin on Sat Jun 26 15:38:45 UTC 2021
PRIMARY
INN
3065
Created by admin on Sat Jun 26 15:38:45 UTC 2021 , Edited by admin on Sat Jun 26 15:38:45 UTC 2021
PRIMARY
MERCK INDEX
M6844
Created by admin on Sat Jun 26 15:38:45 UTC 2021 , Edited by admin on Sat Jun 26 15:38:45 UTC 2021
PRIMARY Merck Index
RXCUI
6446
Created by admin on Sat Jun 26 15:38:45 UTC 2021 , Edited by admin on Sat Jun 26 15:38:45 UTC 2021
PRIMARY RxNorm
MESH
D008090
Created by admin on Sat Jun 26 15:38:45 UTC 2021 , Edited by admin on Sat Jun 26 15:38:45 UTC 2021
PRIMARY
EPA CompTox
18016-80-3
Created by admin on Sat Jun 26 15:38:45 UTC 2021 , Edited by admin on Sat Jun 26 15:38:45 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY