Lisuride

Synonyms :
Lisurid, Lisurida, Lisuride, Lisuridum, N’-((8alpha)-9,10-didehydro-6-methylergolin-8-yl)-N,N-diethylurea

Status : approved

Category

Antiparkinson Agents

Therapeutic Classification

OTHER GYNECOLOGICALS

GENITO URINARY SYSTEM AND SEX HORMONES
OTHER GYNECOLOGICALS
OTHER GYNECOLOGICALS
Dopamine Agonists

Description

An ergot derivative that acts as an agonist at dopamine D2 receptors (dopamine agonists). It may also act as an antagonist at dopamine D1 receptors, and as an agonist at some serotonin receptors (serotonin agonists). [PubChem]

Used

For the management of Parkinson’s Disease

Mechanism Of Action

Lisuride is an anti-Parkinson drug chemically related to the dopaminergic ergoline Parkinson’s drugs. Lisuride binds to the 5-HT(1A) and 5-HT(2A/2C) receptors. It is also thought to bind to the dopamine receptor and to act as a dopamine agonist. Evidence has also emerged that Lisuride also binds to the Histamine H1 receptor. Lisuride is also used to lower prolactin and, in low doses, to prevent migraine attacks.

Protein Binding

about 15%

Chemical Classification

This compound belongs to the class of organic compounds known as indoloquinolines. These are polycyclic aromatic compounds containing an indole fused to a quinoline.

Indoloquinolines

Organic compounds

Organoheterocyclic compounds

Quinolines and derivatives

Indoloquinolines

Salt : Lysuride Maleate

Chemical Name

Lisurid

Calculated Property

kind Value Source
logP 2.37 ALOGPS
logS -3.4 ALOGPS
Water Solubility 1.40e-01 g/l ALOGPS
logP 2.17 ChemAxon
IUPAC Name 3,3-diethyl-1-[(4S,7R)-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaen-4-yl]urea ChemAxon
Traditional IUPAC Name lisuride ChemAxon
Molecular Weight 338.4466 ChemAxon
Monoisotopic Weight 338.210661474 ChemAxon
SMILES [H][C@@]12CC3=CNC4=CC=CC(=C34)C1=C[C@@H](CN2C)NC(=O)N(CC)CC ChemAxon
Molecular Formula C20H26N4O ChemAxon
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 ChemAxon
InChIKey InChIKey=BKRGVLQUQGGVSM-KBXCAEBGSA-N ChemAxon
Polar Surface Area (PSA) 51.37 ChemAxon
Refractivity 101.81 ChemAxon
Polarizability 38.81 ChemAxon
Rotatable Bond Count 3 ChemAxon
H Bond Acceptor Count 2 ChemAxon
H Bond Donor Count 2 ChemAxon
pKa (strongest acidic) 15.36 ChemAxon
pKa (strongest basic) 6.88 ChemAxon
Physiological Charge 0 ChemAxon
Number of Rings 4 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five 1 ChemAxon
Ghose Filter 1 ChemAxon
MDDR-Like Rule 0 ChemAxon

Affected organism

Humans and other mammals

Target within organism

  • D(2) dopamine receptor : in Human
  • D(3) dopamine receptor : in Human
  • D(4) dopamine receptor : in Human
  • D(1A) dopamine receptor : in Human
  • D(1B) dopamine receptor : in Human
  • 5-hydroxytryptamine receptor 1A : in Human
  • 5-hydroxytryptamine receptor 1D : in Human
  • 5-hydroxytryptamine receptor 2B : in Human
  • 5-hydroxytryptamine receptor 2A : in Human
  • 5-hydroxytryptamine receptor 2C : in Human
  • 5-hydroxytryptamine receptor 1B : in Human
  • Alpha-2A adrenergic receptor : in Human
  • Alpha-2B adrenergic receptor : in Human
  • Alpha-2C adrenergic receptor : in Human