METERGOLINE

/static/temp/default.svg Search structure
Synonyms
MCE
Status
Molecule Category Free-form
ATC G02CB05
UNII 1501393LY5
EPA CompTox DTXSID5042584

Structure

InChI Key WZHJKEUHNJHDLS-QTGUNEKASA-N
Smiles CN1C[C@H](CNC(=O)OCc2ccccc2)C[C@@H]2c3cccc4c3c(cn4C)C[C@H]21
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C25H29N3O2
Molecular Weight 403.53
AlogP 4.06
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 4.0
Polar Surface Area 46.5
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 30.0
Assay Description Organism Bioactivity Reference
Evaluated for binding affinity towards rat cortical membranes at 5-hydroxytryptamine 1 receptor binding site by using [3H]-5-HT as a radioligand. None 20.0 nM
Inhibition of [3H]- OH-DPAT binding against 5-hydroxytryptamine 1A receptor from human recombinant None 13.0 nM
Evaluated for the binding affinity to hippocampus striatal membranes at 5-hydroxytryptamine 1A receptor binding site by using [3H]-8-OH- DPAT as a radioligand. None 6.0 nM
Binding affinity (Ki) to rat cortical membranes at 5-HT1B binding site by using [125 I] ICYP as a radioligand. None 25.0 nM
Evaluated for the binding affinity to porcine choroid plexus at 5-hydroxytryptamine 2C receptor binding site by using [3H]-MES as a radioligand. Sus scrofa 0.5 nM
Binding affinity to rat cortical membranes at 5-hydroxytryptamine 2 (5-HT2) receptor using [3H]KET as a radioligand None 0.3 nM
Binding affinity to 5-hydroxytryptamine 2 receptor in rat frontal cortical membranes by [3H]- KET displacement. None 1.0 nM
Binding affinity towards 5-hydroxytryptamine 7 receptor None 6.31 nM
Non-selective inhibitory activity was determined against 5-hydroxytryptamine 7 receptor None 6.31 nM
Displacement of [3H]8-OH-DPAT from human recombinant 5HT1A receptor expressed in CHO cells Homo sapiens 7.5 nM
Inhibition of human FAAH at 1 uM Homo sapiens 5.48 %
Displacement of [3H]5CT from 5HT7 receptor None 6.31 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: [3H] 8-OH-DPAT) None 6.175 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: [3H] 8-OH-DPAT) None 3.528 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1B radioligand binding (ligand: [125I] Cyanopindolol) Rattus norvegicus 19.0 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1B radioligand binding (ligand: [125I] Cyanopindolol) Rattus norvegicus 11.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: [3H] Ketanserin) None 0.395 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: [3H] Ketanserin) None 0.113 nM
DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 95.0 nM DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 38.0 nM
DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 262.0 nM DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 145.0 nM
DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) None 136.0 nM DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) None 67.0 nM
DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) None 58.0 nM DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) None 22.0 nM
DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscine) None 16.0 nM DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscine) None 7.516 nM
DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) None 189.0 nM DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) None 27.0 nM
DRUGMATRIX: Norepinephrine Transporter radioligand binding (ligand: [125I] RTI-55) None 366.0 nM DRUGMATRIX: Norepinephrine Transporter radioligand binding (ligand: [125I] RTI-55) None 363.0 nM
DRUGMATRIX: Calcium Channel Type L, Benzothiazepine radioligand binding (ligand: [3H] Diltiazem) Rattus norvegicus 268.0 nM DRUGMATRIX: Calcium Channel Type L, Benzothiazepine radioligand binding (ligand: [3H] Diltiazem) Rattus norvegicus 238.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 0.442 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 0.281 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: [3H] Mesulergine) None 0.663 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: [3H] Mesulergine) None 0.347 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT4 radioligand binding (ligand: [3H] GR-113808) Cavia porcellus 274.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT6 radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 28.0 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT6 radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 13.0 nM
DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand binding (ligand: [3H] Paroxetine) None 590.0 nM DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand binding (ligand: [3H] Paroxetine) None 313.0 nM
DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotoxin) Rattus norvegicus 792.0 nM DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotoxin) Rattus norvegicus 723.0 nM
DRUGMATRIX: Calcium Channel Type L, Phenylalkylamine radioligand binding (ligand: [3H] (-)-Desmethoxyverapamil (D-888)) Rattus norvegicus 278.0 nM DRUGMATRIX: Calcium Channel Type L, Phenylalkylamine radioligand binding (ligand: [3H] (-)-Desmethoxyverapamil (D-888)) Rattus norvegicus 270.0 nM
DRUGMATRIX: CYP450, 2D6 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) None 200.0 nM
DRUGMATRIX: Dopamine D1 radioligand binding (ligand: [3H] SCH-23390) None 74.0 nM DRUGMATRIX: Dopamine D1 radioligand binding (ligand: [3H] SCH-23390) None 37.0 nM
DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone) None 63.0 nM DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone) None 21.0 nM
DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) None 7.689 nM DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) None 2.611 nM
DRUGMATRIX: Dopamine Transporter radioligand binding (ligand: [125I] RTI-55) None 63.0 nM DRUGMATRIX: Dopamine Transporter radioligand binding (ligand: [125I] RTI-55) None 50.0 nM
DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) None 480.0 nM
DRUGMATRIX: Histamine H2 radioligand binding (ligand: [125I] Aminopotentidine) None 975.0 nM DRUGMATRIX: Histamine H2 radioligand binding (ligand: [125I] Aminopotentidine) None 959.0 nM
TP_TRANSPORTER: increase in Calcein-AM intracellular accumulation (Calcein-AM: ? uM, Metergoline: 100 uM) in MDR1-expressing MDCKII cells None 84.4 %
Displacement of [3H]8-OH-DPAT from human recombinant 5HT1A receptor expressed in CHOK1 cells after 60 mins Homo sapiens 2.3 nM Displacement of [3H]8-OH-DPAT from human recombinant 5HT1A receptor expressed in CHOK1 cells after 60 mins Homo sapiens 4.1 nM
Displacement of [3H]8-OH-DPAT from human recombinant 5HT1A receptor expressed in CHOK1 cells at 10 uM after 60 mins relative to control Homo sapiens -8.0 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 93.79 %
Displacement of [3H]5-HT from recombinant human 5-HT7 receptor expressed in African green monkey COS7 cells Homo sapiens 6.31 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 11.48 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 1.52 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 1.52 %

Cross References

Resources Reference
ChEBI 64216
ChEMBL CHEMBL19215
DrugBank DB13520
DrugCentral 1723
FDA SRS 1501393LY5
Guide to Pharmacology 133
PubChem 28693
SureChEMBL SCHEMBL117882
ZINC ZINC000003812975
CONTENTS