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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
Structure of LISURIDE

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

HIDE SMILES / InChI

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

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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
450 pg/mL
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
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
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
450 pg × h/mL
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
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
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
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
170 min
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
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
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
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

Funbound

ValueDoseCo-administeredAnalytePopulation
34%
LISURIDE plasma
Homo sapiens
Doses

Doses

DosePopulationAdverse 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
Dose: 10 mg
Route: oral
Route: single
Dose: 10 mg
Sources:
healthy, CHILD
Health Status: healthy
Age Group: CHILD
Sex: M
Food Status: UNKNOWN
Sources:
Other AEs: hypotensia, drowsiness...
Other AEs:
hypotensia (1 pt)
drowsiness (1 pt)
Sources:
AEs

AEs

AESignificanceDosePopulation
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
Dose: 10 mg
Route: oral
Route: single
Dose: 10 mg
Sources:
healthy, CHILD
Health Status: healthy
Age Group: CHILD
Sex: M
Food Status: UNKNOWN
Sources:
hypotensia 1 pt
10 mg single, oral
Overdose
Dose: 10 mg
Route: oral
Route: single
Dose: 10 mg
Sources:
healthy, CHILD
Health Status: healthy
Age Group: CHILD
Sex: M
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
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
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 Mon Mar 31 17:34:50 GMT 2025
Edited
by admin
on Mon Mar 31 17:34:50 GMT 2025
Record UNII
E0QN3D755O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LISURIDE
INN   MI   WHO-DD  
INN  
Official Name English
LISURIDE [MI]
Preferred 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
Classification Tree Code System Code
FDA ORPHAN DRUG 316610
Created by admin on Mon Mar 31 17:34:50 GMT 2025 , Edited by admin on Mon Mar 31 17:34:50 GMT 2025
WHO-VATC QG02CB02
Created by admin on Mon Mar 31 17:34:50 GMT 2025 , Edited by admin on Mon Mar 31 17:34:50 GMT 2025
WHO-ATC G02CB02
Created by admin on Mon Mar 31 17:34:50 GMT 2025 , Edited by admin on Mon Mar 31 17:34:50 GMT 2025
NCI_THESAURUS C38149
Created by admin on Mon Mar 31 17:34:50 GMT 2025 , Edited by admin on Mon Mar 31 17:34:50 GMT 2025
WHO-ATC N02CA07
Created by admin on Mon Mar 31 17:34:50 GMT 2025 , Edited by admin on Mon Mar 31 17:34:50 GMT 2025
WHO-VATC QN02CA07
Created by admin on Mon Mar 31 17:34:50 GMT 2025 , Edited by admin on Mon Mar 31 17:34:50 GMT 2025
Code System Code Type Description
NCI_THESAURUS
C82247
Created by admin on Mon Mar 31 17:34:50 GMT 2025 , Edited by admin on Mon Mar 31 17:34:50 GMT 2025
PRIMARY
EVMPD
SUB08535MIG
Created by admin on Mon Mar 31 17:34:50 GMT 2025 , Edited by admin on Mon Mar 31 17:34:50 GMT 2025
PRIMARY
WIKIPEDIA
LISURIDE
Created by admin on Mon Mar 31 17:34:50 GMT 2025 , Edited by admin on Mon Mar 31 17:34:50 GMT 2025
PRIMARY
PUBCHEM
28864
Created by admin on Mon Mar 31 17:34:50 GMT 2025 , Edited by admin on Mon Mar 31 17:34:50 GMT 2025
PRIMARY
CAS
18016-80-3
Created by admin on Mon Mar 31 17:34:50 GMT 2025 , Edited by admin on Mon Mar 31 17:34:50 GMT 2025
PRIMARY
ECHA (EC/EINECS)
241-925-1
Created by admin on Mon Mar 31 17:34:50 GMT 2025 , Edited by admin on Mon Mar 31 17:34:50 GMT 2025
PRIMARY
DRUG CENTRAL
1588
Created by admin on Mon Mar 31 17:34:50 GMT 2025 , Edited by admin on Mon Mar 31 17:34:50 GMT 2025
PRIMARY
FDA UNII
E0QN3D755O
Created by admin on Mon Mar 31 17:34:50 GMT 2025 , Edited by admin on Mon Mar 31 17:34:50 GMT 2025
PRIMARY
ChEMBL
CHEMBL157138
Created by admin on Mon Mar 31 17:34:50 GMT 2025 , Edited by admin on Mon Mar 31 17:34:50 GMT 2025
PRIMARY
IUPHAR
43
Created by admin on Mon Mar 31 17:34:50 GMT 2025 , Edited by admin on Mon Mar 31 17:34:50 GMT 2025
PRIMARY
LACTMED
Lisuride
Created by admin on Mon Mar 31 17:34:50 GMT 2025 , Edited by admin on Mon Mar 31 17:34:50 GMT 2025
PRIMARY
DRUG BANK
DB00589
Created by admin on Mon Mar 31 17:34:50 GMT 2025 , Edited by admin on Mon Mar 31 17:34:50 GMT 2025
PRIMARY
CHEBI
51164
Created by admin on Mon Mar 31 17:34:50 GMT 2025 , Edited by admin on Mon Mar 31 17:34:50 GMT 2025
PRIMARY
INN
3065
Created by admin on Mon Mar 31 17:34:50 GMT 2025 , Edited by admin on Mon Mar 31 17:34:50 GMT 2025
PRIMARY
MERCK INDEX
m6844
Created by admin on Mon Mar 31 17:34:50 GMT 2025 , Edited by admin on Mon Mar 31 17:34:50 GMT 2025
PRIMARY Merck Index
RXCUI
6446
Created by admin on Mon Mar 31 17:34:50 GMT 2025 , Edited by admin on Mon Mar 31 17:34:50 GMT 2025
PRIMARY RxNorm
MESH
D008090
Created by admin on Mon Mar 31 17:34:50 GMT 2025 , Edited by admin on Mon Mar 31 17:34:50 GMT 2025
PRIMARY
EPA CompTox
DTXSID3023217
Created by admin on Mon Mar 31 17:34:50 GMT 2025 , Edited by admin on Mon Mar 31 17:34:50 GMT 2025
PRIMARY
SMS_ID
100000082525
Created by admin on Mon Mar 31 17:34:50 GMT 2025 , Edited by admin on Mon Mar 31 17:34:50 GMT 2025
PRIMARY
Related Record Type Details
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY