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
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
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 |
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 |
|||
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 |
---|---|---|
Dopaminergic neurotransmission at the paraventricular nucleus of hypothalamus in central regulation of penile erection in the rat. | 1999 Jul |
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Sleep attacks and Parkinson's disease treatment. | 2000 Apr 15 |
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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 |
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Role of dopamine D3 receptors in thermoregulation: a reappraisal. | 2000 Jan 17 |
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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 |
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Efficacy and tolerability of dopamine agonists in a parkinsonian population. | 2001 Feb |
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Nonlinear analysis of partial dopamine agonist effects on cAMP in C6 glioma cells. | 2001 Jan-Feb |
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Atypical polypoid adenomyoma in a patient with hyperprolactinemia. | 2001 Jul-Aug |
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[Parkinson disease: diagnostic and therapeutic criteria]. | 2001 Mar 3 |
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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 |
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Quantitative analysis of striatal dopamine D2 receptors with 123 I-iodolisuride SPECT in degenerative extrapyramidal diseases. | 2001 Nov |
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Dopamine mediates striatal malonate toxicity via dopamine transporter-dependent generation of reactive oxygen species and D2 but not D1 receptor activation. | 2001 Oct |
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Real-time analysis of dopamine: antagonist interactions at recombinant human D2long receptor upon modulation of its activation state. | 2001 Sep |
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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 |
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 15:38:45 UTC 2021
by
admin
on
Sat Jun 26 15:38:45 UTC 2021
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Record UNII |
E0QN3D755O
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Record Status |
Validated (UNII)
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Record Version |
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-
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Official Name | English | ||
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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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PRIMARY | |||
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SUB08535MIG
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PRIMARY | |||
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LISURIDE
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PRIMARY | |||
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28864
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PRIMARY | |||
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18016-80-3
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PRIMARY | |||
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241-925-1
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PRIMARY | |||
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1588
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PRIMARY | |||
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E0QN3D755O
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PRIMARY | |||
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CHEMBL157138
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PRIMARY | |||
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43
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Lisuride
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DB00589
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3065
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PRIMARY | |||
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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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18016-80-3
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PRIMARY |
Related Record | Type | Details | ||
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TARGET -> AGONIST |
Related Record | Type | Details | ||
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ACTIVE MOIETY |