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
Affected Organisms
Humans and other mammals
ATC Code
G02CB02: Lisuride
G02CB: Prolactine inhibitors
G02C: OTHER GYNECOLOGICALS
G02: OTHER GYNECOLOGICALS
G: GENITO URINARY SYSTEM AND SEX HORMONES
N02CA07: Lisuride
N02CA: Ergot alkaloids
N02C: ANTIMIGRAINE PREPARATIONS
N02: ANALGESICS
N: NERVOUS SYSTEM
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
CHEMBL157138
CAS Number
18016-80-3
UNII
E0QN3D755O
DrugBank ID
DB00589
TTD ID
D0X7KB
INTEDE ID
DR0965
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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]
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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.