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
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
DescriptionCurator'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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12373423
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2056 |
7.19 null [pKi] | ||
Target ID: CHEMBL217 |
9.47 null [pKi] | ||
Target ID: CHEMBL234 |
9.55 null [pKi] | ||
Target ID: CHEMBL219 |
8.34 null [pKi] | ||
Target ID: CHEMBL1850 |
8.45 null [pKi] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | DOPERGIN Approved UseAs 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 |
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Preventing | DOPERGIN Approved UseAs 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 UseAs 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 UseAs 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 UseAs 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
Title | Date | PubMed |
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Levodopa-induced dyskinesias in Parkinson's disease: clinical and pharmacological classification. | 1992 |
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[Results of treatment for male prolactinomas]. | 2002 Dec |
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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 |
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An evidence-based review of dopamine receptor agonists in the treatment of Parkinson's disease. | 2002 Oct |
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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 |
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The timing of antiparkinsonian treatment reduction after subthalamic nucleus stimulation. | 2003 |
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[Pharmacokinetic/pharmacodynamic analysis of anti-hyperprolactinemic effect of terguride based on dopamine D2 receptor occupancy]. | 2003 Apr |
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Effects of a partial dopamine D2-like agonist on the cocaine-induced behavioral sensitization of preweanling rats. | 2003 Aug |
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Cortisol as an indicator of dopaminergic effects on nicotine craving. | 2003 Aug |
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Prevention and treatment of motor fluctuations. | 2003 Aug |
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The primary restless legs syndrome pathogenesis depends on the dysfunction of EEG alpha activity. | 2003 Feb |
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[Arrest of lactation after 2nd trimester abortion with a single dose of cabergoline in comparison with 10-day administration of teguride]. | 2003 Jan |
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Sleep attacks, daytime sleepiness, and dopamine agonists in Parkinson's disease. | 2003 Jun |
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Suppression of cocaine- and food-maintained behavior by the D2-like receptor partial agonist terguride in squirrel monkeys. | 2003 Mar |
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The dopamine receptor agonist lisuride attenuates iron-mediated dopaminergic neurodegeneration. | 2003 Nov |
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Dopamine receptor agonists in current clinical use: comparative dopamine receptor binding profiles defined in the human striatum. | 2003 Oct |
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Management of restless legs syndrome by the partial D2-agonist terguride. | 2003 Sep |
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Effects of terguride treatment on glucose abnormalities induced by ischemic brain damage in SHR/N-cp lean Koletsky strain and in rats of Wistar strain. | 2004 |
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Transdermal lisuride delivery in the treatment of Parkinson's disease. | 2004 |
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Pergolide, terguride and N,N'-spacer-linked oligomers of both interact with 5-HT2A receptors of rat tail artery. | 2004 |
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Pharmacology of polymorphic variants of the human 5-HT1A receptor. | 2004 Feb 1 |
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LSD, 5-HT (serotonin), and the evolution of a behavioral assay. | 2004 Jan |
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No evidence of the usefulness of eye blinking as a marker for central dopaminergic activity. | 2004 Mar |
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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 |
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Evidence for the management of mastalgia. | 2004 May |
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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 |
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The effects of dopamine receptor agonists and antagonists on the secretory rate of cockroach (Periplaneta americana) salivary glands. | 2004 Sep |
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Regulation of serotonin 5-HT2C receptors by chronic ligand exposure. | 2004 Sep 13 |
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Agonism at 5-HT2B receptors is not a class effect of the ergolines. | 2005 Apr 25 |
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Mastalgia: a review of management. | 2005 Dec |
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Buprenorphine and a CRF1 antagonist block the acquisition of opiate withdrawal-induced conditioned place aversion in rats. | 2005 Jan |
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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 |
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Evidence-based medical review update: pharmacological and surgical treatments of Parkinson's disease: 2001 to 2004. | 2005 May |
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Levodopa in the treatment of Parkinson's disease: current controversies. | 2005 May |
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Transdermal treatment options for neurological disorders: impact on the elderly. | 2006 |
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Pharmacokinetic optimisation in the treatment of Parkinson's disease : an update. | 2006 |
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Dopamine stimulation via infusion in the lateral ventricle. | 2006 Aug |
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Ergoline and non-ergoline derivatives in the treatment of Parkinson's disease. | 2006 Aug |
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Striking differences of action of lisuride stereoisomers at histamine H1 receptors. | 2006 Dec |
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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 |
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Homology modelling of the serotoninergic 5-HT2c receptor. | 2006 Jun |
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Effects of terguride, ropinirole, and acetyl-L-carnitine on methamphetamine withdrawal in the rat. | 2006 Mar |
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The partial dopamine D2-like receptor agonist terguride functions as an agonist in preweanling rats after a 5-day reserpine regimen. | 2006 Mar |
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Potential vascular alpha1-adrenoceptor blocking properties of an array of 5-HT receptor ligands in the rat. | 2006 Mar 27 |
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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 |
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Observed smoking in cars: a method and differences by socioeconomic area. | 2006 Oct |
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Glutamate-induced cell death and formation of radicals can be reduced by lisuride in mesencephalic primary cell culture. | 2006 Sep |
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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 |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9600588
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.
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
316610
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WHO-VATC |
QG02CB02
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WHO-ATC |
G02CB02
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NCI_THESAURUS |
C38149
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WHO-ATC |
N02CA07
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WHO-VATC |
QN02CA07
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Code System | Code | Type | Description | ||
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C82247
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SUB08535MIG
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LISURIDE
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28864
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18016-80-3
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241-925-1
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1588
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E0QN3D755O
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CHEMBL157138
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43
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Lisuride
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DB00589
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51164
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3065
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m6844
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PRIMARY | Merck Index | ||
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6446
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PRIMARY | RxNorm | ||
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D008090
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DTXSID3023217
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100000082525
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ACTIVE MOIETY