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
CCN(CC)C(=O)N[C@@H]1CN(C)[C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1
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 | 338.4466 |
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 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
450 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6532807/ |
25 μg single, intravenous dose: 25 μg route of administration: Intravenous experiment type: SINGLE co-administered: |
LISURIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
280 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6532807/ |
200 μg single, intravenous dose: 200 μg route of administration: Intravenous experiment type: SINGLE co-administered: |
LISURIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
307 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2050175/ |
25 μg single, intravenous dose: 25 μg route of administration: Intravenous experiment type: SINGLE co-administered: |
LISURIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
184 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2050175/ |
25 μg single, intramuscular dose: 25 μg route of administration: Intramuscular experiment type: SINGLE co-administered: |
LISURIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
180 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2050175/ |
25 μg single, subcutaneous dose: 25 μg route of administration: Subcutaneous experiment type: SINGLE co-administered: |
LISURIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
450 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6532807/ |
25 μg single, intravenous dose: 25 μg route of administration: Intravenous experiment type: SINGLE co-administered: |
LISURIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
730 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6532807/ |
200 μg single, intravenous dose: 200 μg route of administration: Intravenous experiment type: SINGLE co-administered: |
LISURIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
363 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2050175/ |
25 μg single, intravenous dose: 25 μg route of administration: Intravenous experiment type: SINGLE co-administered: |
LISURIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
321 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2050175/ |
25 μg single, intramuscular dose: 25 μg route of administration: Intramuscular experiment type: SINGLE co-administered: |
LISURIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
326 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2050175/ |
25 μg single, subcutaneous dose: 25 μg route of administration: Subcutaneous experiment type: SINGLE co-administered: |
LISURIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
170 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6532807/ |
25 μg single, intravenous dose: 25 μg route of administration: Intravenous experiment type: SINGLE co-administered: |
LISURIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
14 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2050175/ |
25 μg single, intravenous dose: 25 μg route of administration: Intravenous experiment type: SINGLE co-administered: |
LISURIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
19 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2050175/ |
25 μg single, intramuscular dose: 25 μg route of administration: Intramuscular experiment type: SINGLE co-administered: |
LISURIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
25 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2050175/ |
25 μg single, subcutaneous dose: 25 μg route of administration: Subcutaneous experiment type: SINGLE co-administered: |
LISURIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
34% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6532807/ |
LISURIDE plasma | Homo sapiens |
Doses
Dose | Population | Adverse events |
---|---|---|
2.4 mg 1 times / day steady-state, oral MTD Dose: 2.4 mg, 1 times / day Route: oral Route: steady-state Dose: 2.4 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
DLT: Psychiatric events... Dose limiting toxicities: Psychiatric events (6 patients) Sources: |
10 mg single, oral Overdose |
healthy, CHILD Health Status: healthy Age Group: CHILD Sex: M Food Status: UNKNOWN Sources: |
Other AEs: hypotensia, drowsiness... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Psychiatric events | 6 patients DLT |
2.4 mg 1 times / day steady-state, oral MTD Dose: 2.4 mg, 1 times / day Route: oral Route: steady-state Dose: 2.4 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
drowsiness | 1 pt | 10 mg single, oral Overdose |
healthy, CHILD Health Status: healthy Age Group: CHILD Sex: M Food Status: UNKNOWN Sources: |
hypotensia | 1 pt | 10 mg single, oral Overdose |
healthy, CHILD Health Status: healthy Age Group: CHILD Sex: M Food Status: UNKNOWN Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Levodopa-induced dyskinesias in Parkinson's disease: clinical and pharmacological classification. | 1992 |
|
A dopamine partial agonist and antagonist block amphetamine self-administration in a progressive ratio schedule. | 2001 Apr |
|
Atypical polypoid adenomyoma in a patient with hyperprolactinemia. | 2001 Jul-Aug |
|
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 |
|
Clustered ergot alkaloids modulate cell-mediated cytotoxicity. | 2002 Feb |
|
Terguride treatment attenuated prolactin release and enhanced insulin receptor affinity and GLUT 4 content in obese spontaneously hypertensive female, but not male rats. | 2002 Jun |
|
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 |
|
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 |
|
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 |
|
Effects of a partial dopamine D2-like agonist on the cocaine-induced behavioral sensitization of preweanling rats. | 2003 Aug |
|
Cortisol as an indicator of dopaminergic effects on nicotine craving. | 2003 Aug |
|
Prevention and treatment of motor fluctuations. | 2003 Aug |
|
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 |
|
The partial D2-like dopamine receptor agonist terguride acts as a functional antagonist in states of high and low dopaminergic tone: evidence from preweanling rats. | 2005 Apr |
|
Mastalgia: a review of management. | 2005 Dec |
|
Dopamine stimulation via infusion in the lateral ventricle. | 2006 Aug |
|
Striking differences of action of lisuride stereoisomers at histamine H1 receptors. | 2006 Dec |
|
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 |
|
The partial dopamine D2-like receptor agonist terguride functions as an agonist in preweanling rats after a 5-day reserpine regimen. | 2006 Mar |
|
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 |
|
Observed smoking in cars: a method and differences by socioeconomic area. | 2006 Oct |
|
Glutamate-induced cell death and formation of radicals can be reduced by lisuride in mesencephalic primary cell culture. | 2006 Sep |
|
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
Mon Mar 31 17:34:50 GMT 2025
by
admin
on
Mon Mar 31 17:34:50 GMT 2025
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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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Download
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Official Name | English | ||
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Preferred Name | English | ||
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Common Name | English | ||
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Common Name | English | ||
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Common Name | English | ||
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Systematic Name | English |
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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TARGET -> AGONIST |
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ACTIVE MOIETY |