Details of the Drug

General Information of Drug (ID: DMCME17)

Drug Name
Lisuride
Synonyms
Lisurida; Lisuridum; Lysurid; Lysuride; Lisuride [INN]; Lysuride Hydrogen Maleate; Methylergol Carbamide; Arolac (TN); Cuvalit (TN); Dipergon (TN); Dopergin (TN); Dopergine (TN); Lisurida [INN-Spanish]; Lisuride (INN); Lisuridum [INN-Latin]; Lysenyl Forte (TN); Prolacam (TN); Revanil (TN); Lisuride Maleate (1:1); N'-((8alpha)-9,10-Didehydro-6-methylergolin-8-yl)-N,N-diethylurea; 1,1-diethyl-3-[(8alpha)-6-methyl-9,10-didehydroergolin-8-yl]urea; 3-(9,10-Didehydro-6-methylergolin-8alpha-yl)-1,1-diethylurea
Indication
Disease Entry ICD 11 Status REF
Acromegaly 5A60.0 Approved [1]
Amenorrhea GA20.0 Approved [2]
Migraine disorder N.A. Approved [3]
Parkinson disease 8A00.0 Approved [4]
Fibrosis GA14-GC01 Phase 3 [5]
Therapeutic Class
Antiparkinson Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 338.4
Logarithm of the Partition Coefficient (xlogp) 2.7
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
Clearance
The drug present in the plasma can be removed from the body at the rate of 13.3 mL/min/kg [6]
Half-life
The concentration or amount of drug in body reduced by one-half in 1.8 hours [6]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.24612 micromolar/kg/day [7]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 1.73 L/kg [6]
Chemical Identifiers
Formula
C20H26N4O
IUPAC Name
3-[(6aR,9S)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinolin-9-yl]-1,1-diethylurea
Canonical SMILES
CCN(CC)C(=O)N[C@@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C
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
Cross-matching ID
PubChem CID
28864
ChEBI ID
CHEBI:51164
CAS Number
18016-80-3
DrugBank ID
DB00589
TTD ID
D0X7KB
INTEDE ID
DR0965
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Dopamine D2 receptor (D2R) TTEX248 DRD2_HUMAN Agonist [8]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [9]
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [9]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Interferon gamma (IFNG) OTXG9JM7 IFNG_HUMAN Gene/Protein Processing [10]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Acromegaly
ICD Disease Classification 5A60.0
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Dopamine D2 receptor (D2R) DTT DRD2 2.50E-02 -0.08 -0.49
Cytochrome P450 2D6 (CYP2D6) DME CYP2D6 7.30E-01 -1.91E-02 -1.41E-01
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 1.04E-02 6.29E-02 3.54E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 [Treatment of hyperprolactinemia and acromegaly with lisuride]. Harefuah. 1989 Jun 15;116(12):634-7.
2 Pregnancy with macroprolactinoma. J Coll Physicians Surg Pak. 2008 Dec;18(12):787-8.
3 Is the 5-HT(7) receptor involved in the pathogenesis and prophylactic treatment of migraine?. Eur J Pharmacol. 2002 Mar 29;439(1-3):1-11.
4 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 43).
5 ClinicalTrials.gov (NCT00408915) Continuous Application of Lisuride in Parkinson's Disease by Subcutaneous Infusion. U.S. National Institutes of Health.
6 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
7 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
8 Fibrotic heart-valve reactions to dopamine-agonist treatment in Parkinson's disease. Lancet Neurol. 2007 Sep;6(9):826-9.
9 Stable expression of human cytochrome P450 3A4 in V79 cells and its application for metabolic profiling of ergot derivatives. Eur J Pharmacol. 1995 Oct 6;293(3):183-90.
10 Is alpha-methyldopa-type autoimmune hemolytic anemia mediated by interferon-gamma?. Ann Hematol. 1994 Nov;69(5):249-51. doi: 10.1007/BF01700279.