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
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
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 |
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 |
---|---|---|
Sleep attacks and Parkinson's disease treatment. | 2000 Apr 15 |
|
Role of dopamine D3 receptors in thermoregulation: a reappraisal. | 2000 Jan 17 |
|
Poetic talent unmasked by treatment of Parkinson's disease. | 2001 Nov |
|
Dopamine partial agonist reverses amphetamine withdrawal in rats. | 2001 Nov |
|
Quantitative analysis of striatal dopamine D2 receptors with 123 I-iodolisuride SPECT in degenerative extrapyramidal diseases. | 2001 Nov |
|
[Results of treatment for male prolactinomas]. | 2002 Dec |
|
Lisuride, a dopamine D2 receptor agonist, and anticraving drug expectancy as modifiers of relapse in alcohol dependence. | 2002 Feb |
|
Characterization of phospholipase C activity at h5-HT2C compared with h5-HT2B receptors: influence of novel ligands upon membrane-bound levels of [3H]phosphatidylinositols. | 2002 Mar |
|
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 |
|
Cortisol as an indicator of dopaminergic effects on nicotine craving. | 2003 Aug |
|
The primary restless legs syndrome pathogenesis depends on the dysfunction of EEG alpha activity. | 2003 Feb |
|
LSD, 5-HT (serotonin), and the evolution of a behavioral assay. | 2004 Jan |
|
Familial acromegaly: a familial report and review of the literature. | 2004 May |
|
Capillary zone electrophoresis separation of enantiomers of lisuride. | 2005 Feb 25 |
|
Pharmacokinetic optimisation in the treatment of Parkinson's disease : an update. | 2006 |
|
Striking differences of action of lisuride stereoisomers at histamine H1 receptors. | 2006 Dec |
|
Homology modelling of the serotoninergic 5-HT2c receptor. | 2006 Jun |
|
The partial dopamine D2-like receptor agonist terguride functions as an agonist in preweanling rats after a 5-day reserpine regimen. | 2006 Mar |
|
Potential vascular alpha1-adrenoceptor blocking properties of an array of 5-HT receptor ligands in the rat. | 2006 Mar 27 |
|
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 14:58:43 UTC 2023
by
admin
on
Fri Dec 15 14:58:43 UTC 2023
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Record UNII |
UV1635N8XW
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Record Status |
Validated (UNII)
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Record Version |
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-
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FDA ORPHAN DRUG |
906822
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EU-Orphan Drug |
EU/3/11/869
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SUB02940MIG
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100000086150
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31776
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6553
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DBSALT001034
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DTXSID501017378
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m6844
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5282421
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243-387-3
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19875-60-6
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UV1635N8XW
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CHEMBL157138
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |