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]
ATC Code
G02CB05: Metergolin
G02CB: Prolactine inhibitors
G02C: OTHER GYNECOLOGICALS
G02: OTHER GYNECOLOGICALS
G: GENITO URINARY SYSTEM AND SEX HORMONES
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
CHEMBL19215
CAS Number
17692-51-2
UNII
1501393LY5
DrugBank ID
DB13520
TTD ID
D0UA0I
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

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.