LISURIDE

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

Structure Search

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

HIDE SMILES / InChI

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

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 94 Target ID: CHEMBL2056 Sources: http://www.bayerresources.com.au/resources/uploads/datasheet/file9563.pdf	Agonist 2470	7.19 null [pKi]
Dopamine D2 receptor 283 Target ID: CHEMBL217 Sources: http://www.bayerresources.com.au/resources/uploads/datasheet/file9563.pdf	Agonist 2470	9.47 null [pKi]
Dopamine D3 receptor 85 Target ID: CHEMBL234 Sources: http://www.bayerresources.com.au/resources/uploads/datasheet/file9563.pdf	Agonist 2470	9.55 null [pKi]
Dopamine D4 receptor 66 Target ID: CHEMBL219 Sources: http://www.bayerresources.com.au/resources/uploads/datasheet/file9563.pdf	Agonist 2470	8.34 null [pKi]
Dopamine D5 receptor 10 Target ID: CHEMBL1850 Sources: http://www.bayerresources.com.au/resources/uploads/datasheet/file9563.pdf	Agonist 2470	8.45 null [pKi]

Conditions

Condition	Modality	Highest Phase	Product
Parkinson's disease 219 Sources: http://www.bayerresources.com.au/resources/uploads/datasheet/file9563.pdf	Primary	Approved 8043	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 8043	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 8043	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 8043	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 8043	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

PubMed

Title	Date	PubMed
Dopaminergic neurotransmission at the paraventricular nucleus of hypothalamus in central regulation of penile erection in the rat.	1999 Jul	10379793
Sleep attacks and Parkinson's disease treatment.	2000 Apr 15	10776750
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	10611640
Role of dopamine D3 receptors in thermoregulation: a reappraisal.	2000 Jan 17	10683862
Terguride attenuates prolactin levels and ameliorates insulin sensitivity and insulin binding in obese spontaneously hypertensive rats.	2001	11522045
Clinical features and medical treatment of male prolactinomas.	2001	11482696
Efficacy and tolerability of dopamine agonists in a parkinsonian population.	2001 Feb	11487183
Nonlinear analysis of partial dopamine agonist effects on cAMP in C6 glioma cells.	2001 Jan-Feb	11489662
Atypical polypoid adenomyoma in a patient with hyperprolactinemia.	2001 Jul-Aug	11520375
[Parkinson disease: diagnostic and therapeutic criteria].	2001 Mar 3	11268897
Poetic talent unmasked by treatment of Parkinson's disease.	2001 Nov	11748756
Dopamine partial agonist reverses amphetamine withdrawal in rats.	2001 Nov	11682262
Dopaminergic modulation of grooming behavior in virgin and pregnant rats.	2001 Nov	11668358
Quantitative analysis of striatal dopamine D2 receptors with 123 I-iodolisuride SPECT in degenerative extrapyramidal diseases.	2001 Nov	11606886
Dopamine mediates striatal malonate toxicity via dopamine transporter-dependent generation of reactive oxygen species and D2 but not D1 receptor activation.	2001 Oct	11595758
Real-time analysis of dopamine: antagonist interactions at recombinant human D2long receptor upon modulation of its activation state.	2001 Sep	11522600
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	11551517
[Use of dopamine agonists in the treatment of Parkinson's disease].	2002	12378886
Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease.	2002	11978145
Protection of dopaminergic neurons in primary culture by lisuride.	2002 Feb	12075855
Clustered ergot alkaloids modulate cell-mediated cytotoxicity.	2002 Feb	11741789
SUNCT syndrome in two patients with prolactinomas and bromocriptine-induced attacks.	2002 Jun 11	12058109
Is the 5-HT(7) receptor involved in the pathogenesis and prophylactic treatment of migraine?	2002 Mar 29	11937086
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	12388668
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	12388667
Prospective randomized trial of lisuride infusion versus oral levodopa in patients with Parkinson's disease.	2002 Sep	12183351
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	12181434
The timing of antiparkinsonian treatment reduction after subthalamic nucleus stimulation.	2003	12464720
Cortisol as an indicator of dopaminergic effects on nicotine craving.	2003 Aug	12923821
Prevention and treatment of motor fluctuations.	2003 Aug	12915071
The primary restless legs syndrome pathogenesis depends on the dysfunction of EEG alpha activity.	2003 Feb	12606234
Suppression of cocaine- and food-maintained behavior by the D2-like receptor partial agonist terguride in squirrel monkeys.	2003 Mar	12589523
The dopamine receptor agonist lisuride attenuates iron-mediated dopaminergic neurodegeneration.	2003 Nov	14637122
Dopamine receptor agonists in current clinical use: comparative dopamine receptor binding profiles defined in the human striatum.	2003 Oct	14523624
Management of restless legs syndrome by the partial D2-agonist terguride.	2003 Sep	14592288
Pergolide, terguride and N,N'-spacer-linked oligomers of both interact with 5-HT2A receptors of rat tail artery.	2004	14984312
LSD, 5-HT (serotonin), and the evolution of a behavioral assay.	2004 Jan	15019419
No evidence of the usefulness of eye blinking as a marker for central dopaminergic activity.	2004 Mar	15107193
Familial acromegaly: a familial report and review of the literature.	2004 May	15473133
Evidence for the management of mastalgia.	2004 May	15140333
Mastalgia: a review of management.	2005 Dec	16444894
Aripiprazole's low intrinsic activities at human dopamine D2L and D2S receptors render it a unique antipsychotic.	2005 May 16	15894311
Treatment of pituitary tumors: dopamine agonists.	2005 Oct	16311416
Dopamine stimulation via infusion in the lateral ventricle.	2006 Aug	17105930
Lisuride treatment of restless legs syndrome: first studies with monotherapy in de novo patients and in combination with levodopa in advanced disease.	2006 Jan	16372146
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	16614540
Glutamate-induced cell death and formation of radicals can be reduced by lisuride in mesencephalic primary cell culture.	2006 Sep	16463121

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 `Sat Jun 26 15:38:45 UTC 2021` Edited by `admin` on `Sat Jun 26 15:38:45 UTC 2021`
Record UNII	E0QN3D755O
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

LISURIDE

Official 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

LISURIDE [MI]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

316610