Lisurid

Lisuride

HCID 28864CAS 140387-89-9

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Grundinformationen

Standard-SMILES: CCN(CC)C(=O)N[C@H]1C=C2c3cccc4[nH]cc(c34)C[C@H]2N(C)C1
InChIKey: SORAZNWVQFKAFD-IBIFCFAISA-N
Summenformel: C20H26N4O
Durchschnittliche Molmasse: 338,4 g/mol

Überblick

Lisuride is a monocarboxylic acid amide. It has a role as a serotonergic agonist, an antiparkinson drug, a dopamine agonist and an antidyskinesia agent. It derives from a hydride of an ergoline.

Namen und Bezeichner

Bevorzugter Name: Lisuride
IUPAC: 3-[(6aR,9S)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinolin-9-yl]-1,1-diethylurea
Lokaler Name: Lisurid
Englischer Name: S-(-)-LISURIDE
Summenformel: C20H26N4O
Molmasse: 338.45

Namen und Synonyme

LISURIDELysuride18016-80-3LisuridaLisuridumDoperginN'-((8alpha)-9,10-Didehydro-6-methylergolin-8-yl)-N,N-diethylureaE0QN3D755ODTXSID3023217CHEBI:51164Methylergol CarbamideLysurid

Weitere Namen anzeigen

LisuridCABERQOLINEMesorgydinePrestwick_525S-(-)-LISURIDELisuride (S)(-)(+)-(5R,8S)-Lisuride

Urea, N'-((8alpha)-9,10-didehydro-6-methylergolin-8-yl)-N,N-diethyl-3,3-diethyl-1-[(4S,7R)-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaen-4-yl]ureaMesylate, Lisuride3,3-diethyl-1-((4S,7R)-6-methyl-6,11-diazatetracyclo(7.6.1.0^(2,7).0^(12,16))hexadeca-1(16),2,9,12,14-pentaen-4-yl)ureaRevanil 200Carbamide, MethylergolHydrochloride, LisurideRefChem:799371

Datenbank-Bezeichner

CAS: 140387-89-9、18016-80-3
PubChem CID: 28864
DTXSID: DTXSID3023217
ChEMBL: CHEMBL157138
ChEBI: CHEBI:51164
UNII: E0QN3D755O
EC Number: 241-925-1
Nikkaji: J10.957F

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 2,7
Polarare Oberfläche (TPSA): 51,4 Å²
H-Brücken-Donoren: 2
H-Brücken-Akzeptoren: 2
Frei drehbare Bindungen: 3
Schwere Atome: 25
Formalladung: 0
Komplexität: 544

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15

LogP2.2

Solubility1.40e-01 g/L

Human DrugsBreast Feeding; Lactation; Antiparkinson Agents; Dopamine Agonists; Serotonin Receptor Agonists

Physical DescriptionSolid

Physikochemische Eigenschaften

Schmelzpunkt: 186 ° · 186°
Siedepunkt: 603.4 · 603.4±55.0 °C(Predicted)
Dichte: 1.23 · 1.23±0.1 g/cm3(Predicted)
pka: 13.06 · 13.06±0.20(Predicted)
Aggregatzustand: Solid
Farbe: Off-white to light yellow
CAS Datenbank: 18016 · 18016-80-3

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 2 (100%)

Toxikologische Informationen

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Sicherheitsdaten

Alarmwort: Achtung
Gefahrenhinweise: Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H300

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 4 Einträge

G - Genito urinary system and sex hormones

N - Nervous system

QG - Genito urinary system and sex hormones

QN - Nervous system

Protein Bindingabout 15%

PharmacodynamicsThere is evidence that lisuride lowers prolactin levels and, in low doses, prevents migraine attacks.

Mechanism of Action · 1 Eintrag

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.

MeSH Pharmacological Classification · 3 Einträge

Agents used in the treatment of Parkinson's disease. The most commonly used drugs act on the dopaminergic system in the striatum and basal ganglia or are centrally acting muscarinic antagonists.

Endogenous compounds and drugs that bind to and activate SEROTONIN RECEPTORS. Many serotonin receptor agonists are used as ANTIDEPRESSANTS; ANXIOLYTICS; and in the treatment of MIGRAINE DISORDERS.

Drugs that bind to and activate dopamine receptors.

Cellular LocationsMembrane