Details of the Drug

General Information of Drug (ID: DMJFP6G)

Drug Name
Metergolin
Synonyms
Metergoline; metergoline; Liserdol; 17692-51-2; Methergoline; Metergolina; Metergolinum; Metergolina [DCIT]; Metergolinum [Latin]; Metergolina [Spanish]; Substance 355/255; Metergoline [INN:BAN]; Metergolinum [INN-Latin]; 1-Methyl-N-carbobenzyloxydihydro-D-lysergamin; FI-6337; MLS000069437; UNII-1501393LY5; C25H29N3O2; AHR 3009; 1-Methyl-8-beta-carbobenzyloxyaminomethyl-10-alpha-ergoline; EINECS 241-686-3; 1,6-Dimethyl-8-beta-carbobenzyloxaminomethyl-10-alpha-ergoline; FI 6337; Liserdol (TN)
Indication
Disease Entry ICD 11 Status REF
Hyperprolactinaemia 5A60.1 Approved [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 403.5
Logarithm of the Partition Coefficient (xlogp) 3.8
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
Clearance
The drug present in the plasma can be removed from the body at the rate of 9.6 mL/min/kg [2]
Half-life
The concentration or amount of drug in body reduced by one-half in 0.93 hours [2]
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 0.57 L/kg [2]
Chemical Identifiers
Formula
C25H29N3O2
IUPAC Name
benzyl N-[[(6aR,9S,10aR)-4,7-dimethyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinolin-9-yl]methyl]carbamate
Canonical SMILES
CN1C[C@@H](C[C@H]2[C@H]1CC3=CN(C4=CC=CC2=C34)C)CNC(=O)OCC5=CC=CC=C5
InChI
InChI=1S/C25H29N3O2/c1-27-14-18(13-26-25(29)30-16-17-7-4-3-5-8-17)11-21-20-9-6-10-22-24(20)19(12-23(21)27)15-28(22)2/h3-10,15,18,21,23H,11-14,16H2,1-2H3,(H,26,29)/t18-,21+,23+/m0/s1
InChIKey
WZHJKEUHNJHDLS-QTGUNEKASA-N
Cross-matching ID
PubChem CID
28693
ChEBI ID
CHEBI:64216
CAS Number
17692-51-2
DrugBank ID
DB13520
TTD ID
D0UA0I

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
5-HT 1B receptor (HTR1B) TTK8CXU 5HT1B_HUMAN Antagonist [3]
5-HT 1D receptor (HTR1D) TT6MSOK 5HT1D_HUMAN Antagonist [4]
5-HT 1E receptor (HTR1E) TTCPG9S 5HT1E_HUMAN Antagonist [5]
5-HT 1F receptor (HTR1F) TT0MI3F 5HT1F_HUMAN Antagonist [6]
5-HT 2A receptor (HTR2A) TTJQOD7 5HT2A_HUMAN Antagonist [7]
5-HT 2B receptor (HTR2B) TT0K1SC 5HT2B_HUMAN Antagonist [7]
5-HT 2C receptor (HTR2C) TTWJBZ5 5HT2C_HUMAN Antagonist [7]
5-HT 5A receptor (HTR5A) TTRUFDT 5HT5A_HUMAN Antagonist [8]
5-HT receptor (5HTR) TT85JO3 NOUNIPROTAC Modulator [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3 Two amino acid differences in the sixth transmembrane domain are partially responsible for the pharmacological differences between the 5-HT1D beta and 5-HT1E 5-hydroxytryptamine receptors. J Neurochem. 1996 Nov;67(5):2096-103.
4 Primary structure and functional characterization of a human 5-HT1D-type serotonin receptor. Mol Pharmacol. 1991 Aug;40(2):143-8.
5 Molecular cloning and pharmacological characterization of the guinea pig 5-HT1E receptor. Eur J Pharmacol. 2004 Jan 26;484(2-3):127-39.
6 Cloning and characterization of the guinea pig 5-HT1F receptor subtype: a comparison of the pharmacological profile to the human species homolog. Neuropharmacology. 1997 Apr-May;36(4-5):569-76.
7 Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors. Naunyn Schmiedebergs Arch Pharmacol. 2004 Aug;370(2):114-23.
8 Cloning and characterisation of the human 5-HT5A serotonin receptor. FEBS Lett. 1994 Dec 5;355(3):242-6.
9 Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.