Lisuride

Lisuride

Systematic (IUPAC) name
1,1-diethyl-3-((6aR,9S)-7-methyl-
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy cat.	?
Legal status	Prescription only
Routes	Oral, subcutaneous, transdermal
Pharmacokinetic data
Bioavailability	10-20% for lisuride hydrogen maleate
Protein binding	about 15%
Metabolism	Hepatic
Half-life	2 hours
Excretion	renal and biliary in equal amounts
Identifiers
CAS number	18016-80-3 Y
ATC code	G02CB02 N02CA07
PubChem	CID 28864
IUPHAR ligand	227
DrugBank	APRD00636
ChemSpider	26847 Y
UNII	E0QN3D755O Y
KEGG	D08132 Y
ChEBI	CHEBI:51164 Y
ChEMBL	CHEMBL157138 Y
Chemical data
Formula	C20H26N4O
Mol. mass	338.447 g/mol
SMILES	eMolecules & PubChem
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 Y Key:BKRGVLQUQGGVSM-KBXCAEBGSA-N Y
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Lisuride (Dopergin, Proclacam, 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 that 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 anti-parkinsonian compounds. It is still used clinically in a number of countries in the EU and is still commercially available in the UK and China.

Mode of action

Lisuride is a dopamine and serotonin receptor partial agonist. It has a high affinity for the dopamine D2, D3 and D4 receptors, as well as serotonin 5-HT1A and 5-HT2A/C receptors. While lisuride has a similar receptor binding profile to the more well-known and chemically similar ergoloid N,N-diethyl-lysergamide (LSD), it lacks the psychedelic effects of its sister compound.