Basic information
- Standard SMILES
CCN(CC)C(=O)N[C@H]1C=C2c3cccc4[nH]cc(c34)C[C@H]2N(C)C1- InChIKey
SORAZNWVQFKAFD-IBIFCFAISA-N- Molecular formula
- C20H26N4O
- Average molar mass
- 338.4 g/mol
Overview
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.
Names & identifiers
- Preferred name
- Lisuride
- IUPAC
- 3-[(6aR,9S)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinolin-9-yl]-1,1-diethylurea
- English name
- S-(-)-LISURIDE
- Molecular formula
- C20H26N4O
- Molecular weight
- 338.45
Names & synonyms
LISURIDELysuride18016-80-3LisuridaLisuridumDoperginN'-((8alpha)-9,10-Didehydro-6-methylergolin-8-yl)-N,N-diethylureaE0QN3D755ODTXSID3023217CHEBI:51164Methylergol CarbamideLysurid
Show more names
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
Database identifiers
- 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
Properties
Computed structural properties
- XLogP
- 2.7
- Topological polar surface area
- 51.4 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 3
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 544
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP2.2
Solubility1.40e-01 g/L
Human DrugsBreast Feeding; Lactation; Antiparkinson Agents; Dopamine Agonists; Serotonin Receptor Agonists
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 186 ° · 186°
- alpha
- 20 · D20 +313° (c = 0.60 in pyridine)
- Boiling point
- 603.4 · 603.4±55.0 °C(Predicted)
- Density
- 1.23 · 1.23±0.1 g/cm3(Predicted)
- pka
- 13.06 · 13.06±0.20(Predicted)
- form
- Solid
- color
- Off-white to light yellow
- CAS DataBase Reference
- 18016 · 18016-80-3
- FDA UNII
- 0 QN3D755O · E0QN3D755O
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 300 · H300-H330-H310
- Precautionary statements
- 264 · P264-P270-P301+P310-P321-P330-P405-P501-P262-P264-P270-P280-P302+P350-P310-P322-P361-P363-P405-P501-P260-P271-P284-P304+P340-P310-P320-P403+P233-P405-P501
Safety & regulation
GHS classification
GHS Classification
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.
Hazard information
Hazard Classes and CategoriesAcute Tox. 2 (100%)
Toxicology
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- Hazard statements
- H300-H330-H310
- Precautionary statements
- P264-P270-P301+P310-P321-P330-P405-P501-P262-P264-P270-P280-P302+P350-P310-P322-P361-P363-P405-P501-P260-P271-P284-P304+P340-P310-P320-P403+P233-P405-P501
Chemistry & industry
Pharmacology
ATC Code
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
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
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
Applications
UsesA dopamine and serotonin receptor partial agonist with high affinity for the dopamine D2, D3 and D4 receptors, as well as serotonin 5-HT1A and 5-HT2A/C receptors. An anti-parkinson agent (1,2).
Suppliers6 total
中梦研（湖北）科技有限公司0717-6300888 18062399888 · [email protected]
Shaanxi Dideu New Materials Co. Ltd18192503167 · [email protected]
上海知邦生物医药有限公司021-54285032 18116461626 · [email protected]
湖南嘉航医药科技有限公司85567275 15200744171 · [email protected]
湖北凯隆生物科技有限公司19526384105 · [email protected]
DAYANG CHEM (HANGZHOU) CO.,LTD+86-88938639 +86-17705817739 · [email protected]
Additional notes
DefinitionChEBI: Lisuride is a monocarboxylic acid amide. It has a role as an antiparkinson drug, a serotonergic agonist, a dopamine agonist and an antidyskinesia agent. It derives from a hydride of an ergoline.
Related reactions
3 records
Linked notes
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