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Lisuride, sold under the brand names Dopergin, Proclacam, and Revanil, is an antiparkinson agent of the iso-ergoline class, chemically related to the dopaminergic ergoline Parkinson's drugs. Lisuride is described as free base (see table on the right) and as hydrogen maleate salt.

Lisuride is used to lower prolactin and, in low doses, to prevent migraine attacks. The use of lisuride as initial anti-Parkinsonian treatment has been advocated, delaying the need for levodopa until lisuride becomes insufficient for controlling the parkinsonian disability. Preliminary trials suggest the dermal application of lisuride may be useful in the treatment of Parkinson's disease. As lisuride is very poorly absorbed when take orally and has a short half-life, continuous transdermal administration offers significant advantages and could make the compound a far more consistent therapeutic. Lisuride is not currently available in the US, as the drug was not a commercial success in comparison with other dopamine receptor agonist antiparkinsonian compounds. It is still used clinically in a number of countries in the EU and is still commercially available in the UK and China.

Bromination of Lisuride gives bromerguride.

Mode of action

Lisuride is a dopamine and a partial agonist for several serotonin receptors. It is an antagonist at the serotonin 5-HT2B receptor.^[1] It has a high affinity for the dopamine D2, D3 and D4 receptors, as well as serotonin 5-HT1A^[2] and 5-HT2A/C receptors.^[3] While lisuride has a similar receptor binding profile to the more well-known and chemically similar ergoloid N,N-diethyl-lysergamide (LSD) and inhibits dorsal raphe serotonergic neurons in a similar fashion to LSD, a trait which indicates both drugs in the treatment of Parkinson's disease,^[4] it lacks the psychedelic effects of its sister compound. Newer findings suggest the lack of psychedelic action arises from the phenomenon of biased agonism. Stimulation of the 5-HT2A protomer within the 5-HT2A-mGlu2 receptor complex evokes psychedelic effects, while these effects do not occur during sole stimulation of monomeric 5-HT2A receptors. Accordingly, different G-proteins are involved.^[5]^[6] Lisuride behaves as an agonist at the 5-HT2AR monomer. Since it competitively antagonises the effects of LSD, it may be regarded as a protomer antagonist of the 5-HT2A-mGluR heteromer.^[7] GPCR oligomers are discrete entities and usually possess properties distinct from their parent monomeric receptors.

References

^ Hofmann C, Penner U, Dorow R, Pertz HH, Jähnichen S, Horowski R, Latté KP, Palla D, Schurad B (2006). "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". Clin Neuropharmacol. 29 (2): 80–6. doi:10.1097/00002826-200603000-00005. PMID 16614540.
^ Marona-Lewicka D, Kurrasch-Orbaugh DM, Selken JR, Cumbay MG, Lisnicchia JG, Nichols DE (October 2002). "Re-evaluation of lisuride pharmacology: 5-hydroxytryptamine1A receptor-mediated behavioral effects overlap its other properties in rats". Psychopharmacology. 164 (1): 93–107. doi:10.1007/s00213-002-1141-z. PMID 12373423.
^ Egan CT, Herrick-Davis K, Miller K, Glennon RA, Teitler M (April 1998). "Agonist activity of LSD and lisuride at cloned 5HT2A and 5HT2C receptors". Psychopharmacology. 136 (4): 409–14. doi:10.1007/s002130050585. PMID 9600588.
^ Rogawski MA, Aghajanian GK (1979). "Response of central monoaminergic neurons to lisuride: comparison with LSD". Life Sci. 24 (14): 1289–1297. doi:10.1016/0024-3205(79)90148-6. PMID 470543.
^ Moreno JL, Holloway T, Albizu L, Sealfon SC, González-Maeso J (2011). "Metabotropic glutamate mGlu2 receptor is necessary for the pharmacological and behavioral effects induced by hallucinogenic 5-HT2A receptor agonists". Neurosci. Lett. 493 (3): 76–9. doi:10.1016/j.neulet.2011.01.046. PMC 3064746 . PMID 21276828.
^ González-Maeso J, Ang RL, Yuen T, et al. (2008). "Identification of a serotonin/glutamate receptor complex implicated in psychosis". Nature. 452 (7183): 93–7. doi:10.1038/nature06612. PMC 2743172 . PMID 18297054.
^ González-Maeso J et al. (2007): "Hallucinogens recruit specific cortical 5-HT(2A) receptor-mediated signaling pathways to affect behavior", Neuron, Bd. 53, S. 439. PMID 17270739

UpToDate Contents

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1. パーキンソン病の薬理学的治療 pharmacologic treatment of parkinson disease
2. 尿毒症の男性における性機能障害 sexual dysfunction in uremic men
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English Journal

Feeding condition and the relative contribution of different dopamine receptor subtypes to the discriminative stimulus effects of cocaine in rats.

Baladi MG, Newman AH, France CP.SourceDepartment of Pharmacology, University of Texas Health Science Center at San Antonio, 7703 Floyd Curl Drive, Mail Code 7764, San Antonio, TX, 78229, USA.
Psychopharmacology.Psychopharmacology (Berl).2013 Sep 13. [Epub ahead of print]
RATIONALE: The contribution of dopamine receptor subtypes in mediating the discriminative stimulus effects of cocaine is not fully established. Many drug discrimination studies use food to maintain responding, necessitating food restriction, which can alter drug effects.OBJECTIVE: This study establi
PMID 24030470

Anti-Parkinson's disease drugs and pharmacogenetic considerations.

Agúndez JA, García-Martín E, Alonso-Navarro H, Jiménez-Jiménez FJ.SourceUniversity of Extremadura, Department of Pharmacology, Avda. de la Universidad s/n, E-10071, Cáceres, Spain. jagundez@unex.es
Expert opinion on drug metabolism & toxicology.Expert Opin Drug Metab Toxicol.2013 Jul;9(7):859-74. doi: 10.1517/17425255.2013.789018. Epub 2013 Apr 9.
INTRODUCTION: The development of pharmacogenetic-based clinical practice guidelines for the use of anti-Parkinson's disease drugs requires, as a pre-requisite, the identification and validation of genetic biomarkers. These biomarkers are then used as surrogate endpoints. This review analyzes potenti
PMID 23565891

Characterization of the head-twitch response induced by hallucinogens in mice: detection of the behavior based on the dynamics of head movement.

Halberstadt AL, Geyer MA.SourceDepartment of Psychiatry, University of California San Diego, 9500 Gilman Drive, La Jolla, CA 92093-0804, USA. ahalbers@ucsd.edu
Psychopharmacology.Psychopharmacology (Berl).2013 Jun;227(4):727-39. doi: 10.1007/s00213-013-3006-z. Epub 2013 Feb 14.
RATIONALE: The head-twitch response (HTR) is a rapid side-to-side rotational head movement that occurs in rats and mice after administration of serotonergic hallucinogens and other 5-HT2A agonists. The HTR is widely used as a behavioral assay for 5-HT2A activation and to probe for interactions betwe
PMID 23407781

Japanese Journal

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

HOFMANN C
Clin Neuropharmacol 29, 80-86, 2006
NAID 30018743716

一包化調剤実施による錠剤・カプセル剤の安定性

西岡豊,京谷庄二郎,増井寿,吉岡三郎,宮野望,戸梶志保,尾木恭子,濱田賢邦
病院薬学 25(4), 385-392, 1999-08-10
… A decline in the disintegration time was seen in Lisuride Maleate after 24 hours with (temperature : 26-32℃, RH : 43-70%). …
NAID 110001166897

一包化調剤実施による錠剤・カプセル剤の安定性

西岡豊,京谷庄二郎,増井寿,吉岡三郎,宮野望,戸梶志保,尾木恭子,濱田賢邦
病院薬学 25(4), 385-392, 1999
… A decline in the disintegration time was seen in Lisuride Maleate after 24 hours with (temperature: 26-32°C, RH: 43-70%). …
NAID 130004299708

Related Pictures

lisuride le lisuride dérivé de l ergot Gebruik Lisuride: –behandeling van Lisuride Structural Formulae V.1.svg iprad brand of lisuride maleate; lisuride LISURIDE | 18016-80-3 Lisuride .svg Lisuride maleate Supplier | CAS 19875-60-6

★リンクテーブル★

リンク元	「リスリド」
拡張検索	「lisuride maleate」

「リスリド」

Lisuride
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral, subcutaneous, transdermal
ATC code	G02CB02 (WHO) N02CA07 (WHO);
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	10-20% for lisuride hydrogen maleate
Protein binding	about 15%
Metabolism	Hepatic
Biological half-life	2 hours
Excretion	renal and biliary in equal amounts
Identifiers
	IUPAC name 1,1-Diethyl-3-(7-methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinolin-9-yl)-urea;
CAS Number	18016-80-3 ;
PubChem CID	28864;
IUPHAR/BPS	227;
DrugBank	DB00589 ;
ChemSpider	26847 ;
UNII	E0QN3D755O;
KEGG	D08132 ;
ChEBI	CHEBI:51164 ;
ChEMBL	CHEMBL157138 ;
ECHA InfoCard	100.038.099
Chemical and physical data
Formula	C20H26N4O
Molar mass	338.447 g/mol
3D model (JSmol)	Interactive image;
	SMILES O=C(N(CC)CC)N[C@H]3/C=C2/c4cccc1c4c(cn1)C[C@H]2N(C3)C ;
	InChI 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 ; Key:BKRGVLQUQGGVSM-KBXCAEBGSA-N ;
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　　[★]

英: lisuride、lisuride maleate
関: マレイン酸リスリド

「lisuride maleate」

　　[★]

マレイン酸リスリド

関: lisuride

[pmid16614540-1] Hofmann C, Penner U, Dorow R, Pertz HH, Jähnichen S, Horowski R, Latté KP, Palla D, Schurad B (2006). "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". Clin Neuropharmacol. 29 (2): 80–6. doi:10.1097/00002826-200603000-00005. PMID 16614540.

[pmid12373423-2] Marona-Lewicka D, Kurrasch-Orbaugh DM, Selken JR, Cumbay MG, Lisnicchia JG, Nichols DE (October 2002). "Re-evaluation of lisuride pharmacology: 5-hydroxytryptamine1A receptor-mediated behavioral effects overlap its other properties in rats". Psychopharmacology. 164 (1): 93–107. doi:10.1007/s00213-002-1141-z. PMID 12373423.

[pmid9600588-3] Egan CT, Herrick-Davis K, Miller K, Glennon RA, Teitler M (April 1998). "Agonist activity of LSD and lisuride at cloned 5HT2A and 5HT2C receptors". Psychopharmacology. 136 (4): 409–14. doi:10.1007/s002130050585. PMID 9600588.

[pmid470543-4] Rogawski MA, Aghajanian GK (1979). "Response of central monoaminergic neurons to lisuride: comparison with LSD". Life Sci. 24 (14): 1289–1297. doi:10.1016/0024-3205(79)90148-6. PMID 470543.

[5] Moreno JL, Holloway T, Albizu L, Sealfon SC, González-Maeso J (2011). "Metabotropic glutamate mGlu2 receptor is necessary for the pharmacological and behavioral effects induced by hallucinogenic 5-HT2A receptor agonists". Neurosci. Lett. 493 (3): 76–9. doi:10.1016/j.neulet.2011.01.046. PMC 3064746 . PMID 21276828.

[6] González-Maeso J, Ang RL, Yuen T, et al. (2008). "Identification of a serotonin/glutamate receptor complex implicated in psychosis". Nature. 452 (7183): 93–7. doi:10.1038/nature06612. PMC 2743172 . PMID 18297054.

[7] González-Maeso J et al. (2007): "Hallucinogens recruit specific cortical 5-HT(2A) receptor-mediated signaling pathways to affect behavior", Neuron, Bd. 53, S. 439. PMID 17270739

v t e Tocolytics/labor repressants (G02CA)
β₂ adrenoreceptor agonists	Buphenine Fenoterol Hexoprenaline Ritodrine Terbutaline
Oxytocin antagonists	Atosiban
NSAIDs	Indometacin
Calcium channel blockers	Nifedipine
Myosin inhibitors	Magnesium sulfate

v t e Ergolines
Lysergic acid derivatives	2-Bromo-LSD (BOL-148) Bromocriptine Cabergoline Dihydroergocornine Dihydroergocristine Dihydroergocryptine Dihydroergometrine (Dihydroergonovine, Dihydroergobasine) Dihydroergosine Dihydroergotamine Epicriptine Ergine (LSA; LA-111; Lysergamide) Ergocornine Ergocristine Ergocryptine Ergoloid (Dihydroergotoxine) Ergometrine (Ergonovine, Ergobasine) Ergometrinine Ergotamine Ergotoxine Ergovaline Lisuride LSD LSH Lysergic Acid Lysergic acid cyclobutylamide Lysergic acid cyclopentylamide Lysergic Acid Methyl Ester Lysergol Mesulergine Metergoline Methergine (Methylergometrine, Methylergonovine, Methylergobasine) Methysergide Pergolide Syntometrine
Psychedelic lysergamides	1P-ETH-LAD 1P-LSD AL-LAD ALD-52 BU-LAD CYP-LAD DAL DAM-57 Ergonovine ETH-LAD IP-LAD LAE-32 LSD LPD-824 LSM-775 LSH LSD-Pip Lysergic Acid 2-Butylamide Lysergic Acid 2,4-Dimethylazetidide Lysergic Acid 3-Pentylamide Methylergonovine Methylisopropyllysergamide MLD-41 PARGY-LAD PRO-LAD
Other ergolines	Ergoline
Natural sources	Achnatherum robustum (Sleepy Grass) Claviceps spp. (Ergot) Morning glory: Argyreia nervosa (Hawaiian Baby Woodrose), Ipomoea spp.(Morning Glory, Tlitliltzin, Badoh Negro), Rivea corymbosa (Coaxihuitl, Ololiúqui)

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lisuride