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]
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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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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
UNII: 1501393LY5
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]

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Molecular Interaction Atlas (MIA)

MIA Detail

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.