LISURIDE MALEATE

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

Structure Search

SMILES

OC(=O)\C=C/C(O)=O.CCN(CC)C(=O)N[C@@H]1CN(C)[C@@H]2CC3=CNC4=C3C(=CC=C4)C2=C1

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

HIDE SMILES / InChI

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

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
Sources: https://link.springer.com/chapter/10.1007%2F978-94-015-1308-1_61
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

Approval Year

Targets

Primary Target	Pharmacology	Potency
Dopamine D1 receptor 106 Target ID: CHEMBL2056 Sources: http://www.bayerresources.com.au/resources/uploads/datasheet/file9563.pdf	Agonist 2752	7.19 null [pKi]
Dopamine D2 receptor 311 Target ID: CHEMBL217 Sources: http://www.bayerresources.com.au/resources/uploads/datasheet/file9563.pdf	Agonist 2752	9.47 null [pKi]
Dopamine D3 receptor 97 Target ID: CHEMBL234 Sources: http://www.bayerresources.com.au/resources/uploads/datasheet/file9563.pdf	Agonist 2752	9.55 null [pKi]
Dopamine D4 receptor 76 Target ID: CHEMBL219 Sources: http://www.bayerresources.com.au/resources/uploads/datasheet/file9563.pdf	Agonist 2752	8.34 null [pKi]
Dopamine D5 receptor 15 Target ID: CHEMBL1850 Sources: http://www.bayerresources.com.au/resources/uploads/datasheet/file9563.pdf	Agonist 2752	8.45 null [pKi]

Conditions

Condition	Modality	Highest Phase	Product
Parkinson's disease 232 Sources: http://www.bayerresources.com.au/resources/uploads/datasheet/file9563.pdf	Primary	Approved 8583	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
Lactation 2 Sources: http://www.bayerresources.com.au/resources/uploads/datasheet/file9563.pdf	Preventing	Approved 8583	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
Galactorrhea 2 Sources: http://www.bayerresources.com.au/resources/uploads/datasheet/file9563.pdf	Primary	Approved 8583	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
Postencephalitic parkinsonism 7 Sources: http://www.bayerresources.com.au/resources/uploads/datasheet/file9563.pdf	Primary	Approved 8583	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
Prolactin-induced amenorrhea 2 Sources: http://www.bayerresources.com.au/resources/uploads/datasheet/file9563.pdf	Primary	Approved 8583	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

C_max

Value	Dose	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	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

T_1/2

Value	Dose	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

F_unbound

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: https://pubmed.ncbi.nlm.nih.gov/7241162/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7241162/	DLT: Psychiatric events... Dose limiting toxicities: Psychiatric events (6 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/7241162/
10 mg single, oral Overdose Dose: 10 mg Route: oral Route: single Dose: 10 mg Sources: https://pubmed.ncbi.nlm.nih.gov/23723628/	healthy, CHILD Health Status: healthy Age Group: CHILD Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/23723628/	Other AEs: hypotensia, drowsiness... Other AEs: hypotensia (1 pt) drowsiness (1 pt) Sources: https://pubmed.ncbi.nlm.nih.gov/23723628/

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: https://pubmed.ncbi.nlm.nih.gov/7241162/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7241162/
drowsiness	1 pt	10 mg single, oral Overdose Dose: 10 mg Route: oral Route: single Dose: 10 mg Sources: https://pubmed.ncbi.nlm.nih.gov/23723628/	healthy, CHILD Health Status: healthy Age Group: CHILD Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/23723628/
hypotensia	1 pt	10 mg single, oral Overdose Dose: 10 mg Route: oral Route: single Dose: 10 mg Sources: https://pubmed.ncbi.nlm.nih.gov/23723628/	healthy, CHILD Health Status: healthy Age Group: CHILD Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/23723628/

PubMed

Title	Date	PubMed
In vitro functional characteristics of dopamine D2 receptor partial agonists in second and third messenger-based assays of cloned human dopamine D2Long receptor signalling.	2007-08	17092971
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.	2006-12-15	17001660
Striking differences of action of lisuride stereoisomers at histamine H1 receptors.	2006-12	17106670
Observed smoking in cars: a method and differences by socioeconomic area.	2006-10	16998177
Glutamate-induced cell death and formation of radicals can be reduced by lisuride in mesencephalic primary cell culture.	2006-09	16463121
Dopamine stimulation via infusion in the lateral ventricle.	2006-08	17105930
Ergoline and non-ergoline derivatives in the treatment of Parkinson's disease.	2006-08	16944356
Homology modelling of the serotoninergic 5-HT2c receptor.	2006-06	16918076
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.	2006-04-15	16614540
Potential vascular alpha1-adrenoceptor blocking properties of an array of 5-HT receptor ligands in the rat.	2006-03-27	16545797
Effects of terguride, ropinirole, and acetyl-L-carnitine on methamphetamine withdrawal in the rat.	2006-03	16647107
The partial dopamine D2-like receptor agonist terguride functions as an agonist in preweanling rats after a 5-day reserpine regimen.	2006-03	16447063
Effects of a partial D2-like receptor agonist on striatal dopamine autoreceptor functioning in preweanling rats.	2006-02-16	16427034
Lisuride treatment of restless legs syndrome: first studies with monotherapy in de novo patients and in combination with levodopa in advanced disease.	2006-01	16372146
Transdermal lisuride: short-term efficacy and tolerability study in patients with severe restless legs syndrome.	2006-01	16194624
Transdermal treatment options for neurological disorders: impact on the elderly.	2006	16823990
Pharmacokinetic optimisation in the treatment of Parkinson's disease : an update.	2006	16485914
Mastalgia: a review of management.	2005-12	16444894
Advances in the delivery of treatments for Parkinson's disease.	2005-11	16296809
Treatment of pituitary tumors: dopamine agonists.	2005-10	16311416
Dopamine and serotonin modulate the onset of metamorphosis in the ascidian Phallusia mammillata.	2005-06-01	15936344
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.	2005-06	15952243
Aripiprazole's low intrinsic activities at human dopamine D2L and D2S receptors render it a unique antipsychotic.	2005-05-16	15894311
Influence of steric hindrance on enantioseparation of Dns-amino acids and pesticides on terguride based chiral selectors in capillary electrophoresis.	2005-05	15912739
Evidence-based medical review update: pharmacological and surgical treatments of Parkinson's disease: 2001 to 2004.	2005-05	15818599
Levodopa in the treatment of Parkinson's disease: current controversies.	2005-05	15732130
Agonism at 5-HT2B receptors is not a class effect of the ergolines.	2005-04-25	15862804
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.	2005-04	15765258
Capillary zone electrophoresis separation of enantiomers of lisuride.	2005-02-25	15794580
Buprenorphine and a CRF1 antagonist block the acquisition of opiate withdrawal-induced conditioned place aversion in rats.	2005-01	15138444
D1 but not D2 dopamine receptors or adrenoceptors mediate dopamine-induced potentiation of N-methyl-d-aspartate currents in the rat prefrontal cortex.	2004-11-30	15531094
Regulation of serotonin 5-HT2C receptors by chronic ligand exposure.	2004-09-13	15363976
The effects of dopamine receptor agonists and antagonists on the secretory rate of cockroach (Periplaneta americana) salivary glands.	2004-09	15350502
Familial acromegaly: a familial report and review of the literature.	2004-05	15473133
Evidence for the management of mastalgia.	2004-05	15140333
No evidence of the usefulness of eye blinking as a marker for central dopaminergic activity.	2004-03	15107193
8R-lisuride is a potent stereospecific histamine H1-receptor partial agonist.	2004-03	14978232
Pharmacology of polymorphic variants of the human 5-HT1A receptor.	2004-02-01	15037200
LSD, 5-HT (serotonin), and the evolution of a behavioral assay.	2004-01	15019419
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	15658573
Transdermal lisuride delivery in the treatment of Parkinson's disease.	2004	15354393
Pergolide, terguride and N,N'-spacer-linked oligomers of both interact with 5-HT2A receptors of rat tail artery.	2004	14984312
The dopamine receptor agonist lisuride attenuates iron-mediated dopaminergic neurodegeneration.	2003-11	14637122
Dopamine receptor agonists in current clinical use: comparative dopamine receptor binding profiles defined in the human striatum.	2003-10	14523624
Management of restless legs syndrome by the partial D2-agonist terguride.	2003-09	14592288
Effects of a partial dopamine D2-like agonist on the cocaine-induced behavioral sensitization of preweanling rats.	2003-08	13679214
Cortisol as an indicator of dopaminergic effects on nicotine craving.	2003-08	12923821
Prevention and treatment of motor fluctuations.	2003-08	12915071
Sleep attacks, daytime sleepiness, and dopamine agonists in Parkinson's disease.	2003-06	12784269
Levodopa-induced dyskinesias in Parkinson's disease: clinical and pharmacological classification.	1992	1350058

Patents

Sample Use Guides

In Vivo Use Guide

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 17:33:45 GMT 2025` Edited by `admin` on `Mon Mar 31 17:33:45 GMT 2025`
Record UNII	UV1635N8XW
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LISURIDE MALEATE

Common Name

English

LISURIDE MALEATE [JAN]

Preferred Name

English

Lisuride maleate [WHO-DD]

Common Name

English

LISURIDE MALEATE [MART.]

Common Name

English

LISURIDE MALEATE [MI]

Common Name

English

LYSURIDE MALEATE

Common Name

English

3-(9,10-DIDEHYDRO-6-METHYLERGOLIN-8.ALPHA.-YL)-1,1-DIETHYLUREA MALEATE (1:1)

Systematic Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

906822