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

• ChemBase ID: 471
• Molecular Formular: C20H26N4O
• Molecular Mass: 338.44664
• Monoisotopic Mass: 338.21066147
• SMILES: O=C(N[C@@H]1CN([C@H]2C(=C1)c1c3c(C2)c[nH]c3ccc1)C)N(CC)CC
• Canonical SMILES: CCN(C(=O)N[C@@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3)CC
• 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
• InChIKey: BKRGVLQUQGGVSM-KBXCAEBGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,3-diethyl-1-[(4S,7R)-6-methyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),2,9,12,14-pentaen-4-yl]urea; 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]urea
• IUPAC Traditional name: lisuride
• Brand Name: Lisurida [INN-Spanish]; Lisuride Maleate; Lisuride [INN]; Lisuridum [INN-Latin]; Lysuride
• Synonyms: 1,1-Diethyl-3-((6aR,9S)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinolin-9-yl)urea; N'-[(8α)-9,10-Didehydro-6-methylergolin-8-yl]-N,N-diethylurea; (+)-(5R,8S)-Lisuride; 1,1-Diethyl-3-(D-6-methylisoergolen-8-yl)urea; 3-(9,10-Didehydro-6-methylergolin-8α-yl)-1,1-diethylurea; N-(D-6-Methyl-8-isoergolenyl)-N',N'-diethylurea; Lysuride; Lisurid; 9-(3,3-Diethylureido)-4,6,6a,7,8,9-hexahydro-7-methylindolo[4,3-fg]quinoline; Mesorgydine; Methylergol Carbamide; Lisuride

Database IDs

• CAS Number: 18016-80-3
• PubChem SID: 46505557; 160963934
• PubChem CID: 28864

CALCULATED PROPERTIES

JChem

• Acid pKa: 15.356023
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 0.77861863
• LogD (pH = 7.4): 2.055596
• Log P: 2.1692288
• Molar Refractivity: 101.8121 cm^3
• Polarizability: 39.82207 Å^3
• Polar Surface Area: 51.37 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.37
• LOG S: -3.38
• Solubility (Water): 1.40e-01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 2.2

DETAILS

DrugBank - DB00589

• Drug Groups: approved
• 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]
• Indication: For the management of Parkinson's Disease
• Affected Organisms: Humans and other mammals
• Protein Binding: about 15%
• External Links: Wikipedia

Toronto Research Chemicals - L469075

A 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.

REFERENCES

• De Keyser, J. et al.: Prog. Neuro-Psychopharmacol. Biol. Psych., 19, 1147 (1995)
• Bakker, R.A. et al.: Mol. Pharmacol., 65, 1048 (1995)
• Woitalla, D. et al.: J. Neural Trans. Supp., 68, 89 (1995)