Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C25H29N3O2 |
Molecular Weight | 403.5167 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC3=CN(C)C4=CC=CC(=C34)[C@@]1([H])C[C@@H](CNC(=O)OCC5=CC=CC=C5)CN2C
InChI
InChIKey=WZHJKEUHNJHDLS-QTGUNEKASA-N
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
DescriptionSources: https://www.drugbank.ca/drugs/DB13520Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11910270 | https://www.ncbi.nlm.nih.gov/pubmed/12411222 | https://www.ncbi.nlm.nih.gov/pubmed/27251511 | https://www.ncbi.nlm.nih.gov/pubmed/8650684 |
Sources: https://www.drugbank.ca/drugs/DB13520
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11910270 | https://www.ncbi.nlm.nih.gov/pubmed/12411222 | https://www.ncbi.nlm.nih.gov/pubmed/27251511 | https://www.ncbi.nlm.nih.gov/pubmed/8650684 |
Metergoline is a psychoactive drug of the ergoline chemical class which acts as a ligand for various serotonin and dopamine receptors. Metergoline is an antagonist at various 5-HT receptor subtypes at a relatively low concentration and an agonist at dopamine receptors. Its use has been studied in various clinical settings such as a treatment for seasonal affective disorder, prolactin hormone regulation due to its inhibitory effect on prolactin release premenstrual dysphoric disorder in women and antianxiety treatment
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20451398 |
74.0 nM [Ki] | ||
Target ID: CHEMBL1983 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20451398 |
0.9 nM [Ki] | ||
Target ID: CHEMBL1833 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20451398 |
2.6 nM [Ki] | ||
Target ID: CHEMBL245 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20451398 |
3.8 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Determination of the role of serotonergic and cholinergic systems in apomorphine--induced aggressiveness in rats. | 1979 Mar-Apr |
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The influence of 5-HT receptor blocking agents on the behavioral effects of analgesics in rats. | 1980 |
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Central antiserotonergic and antidopaminergic action of pirenperone, a putative 5-HT2 receptor antagonist. | 1985 Mar-Apr |
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Antagonism of drug-induced yawning and penile erections in rats. | 1986 Mar 18 |
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Effect of metergoline, fenfluramine, and 8-OHDPAT on catalepsy induced by haloperidol or morphine. | 1988 Aug |
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Molecular cloning of a serotonin receptor from human brain (5HT1E): a fifth 5HT1-like subtype. | 1992 Jun 15 |
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Cloning of another human serotonin receptor (5-HT1F): a fifth 5-HT1 receptor subtype coupled to the inhibition of adenylate cyclase. | 1993 Jan 15 |
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Cloning and expression of a novel serotonin receptor with high affinity for tricyclic psychotropic drugs. | 1993 Mar |
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Effects of serotoninergic drugs on tremor induced by physostigmine in rats. | 2000 May |
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Discriminative stimulus properties of indorenate, a 5-HT1A, 5-HT1B and 5-HT2C agonist: a study in rats. | 2001 Mar |
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Pregnancy termination in the bitch and queen. | 2002 Aug |
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Pharmacological activity of hyperforin acetate in rats. | 2002 Dec |
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Calcium-antagonistic activity of sumatriptan in the rat anococcygeus muscle. | 2002 Jan |
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Serotonin sets the day state in the neurons that control coupling between the optic lobe circadian pacemakers in the cricket Gryllus bimaculatus. | 2002 May |
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Effects of metergoline on symptoms in women with premenstrual dysphoric disorder. | 2002 Nov |
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Further evidence that the discriminative stimulus properties of indorenate are mediated by 5-HT 1A/1B/2C receptors. | 2003 Jan |
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Effect of fenfluramine on caloric intake and macronutrient selection in Lou/c rats during aging. | 2003 Jan-Feb |
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Serotonin regulates rhythmic whisking. | 2003 Jul 17 |
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Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors. | 2004 Aug |
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Involvement of mast cells in basal and neurotensin-induced intestinal absorption of taurocholate in rats. | 2004 Aug |
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Molecular cloning and pharmacological characterization of the guinea pig 5-HT1E receptor. | 2004 Jan 26 |
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Serotonin reuptake inhibitors do not prevent 5,7-dihydroxytryptamine-induced depletion of serotonin in rat brain. | 2004 May 8 |
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Serotonin-induced enhancement of vasopressin and oxytocin secretion in rat neurohypophyseal tissue culture. | 2005 Apr 15 |
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Anoestrus in the dog: a fascinating story. | 2006 Aug |
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Possible involvement of endogenous 5-HT in aggravation of cerulein-induced acute pancreatitis in mice. | 2007 Nov |
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Physiology of the canine anoestrus and methods for manipulation of its length. | 2008 Jul |
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The effects of metergoline and 8-OH-DPAT injections into arcuate nucleus and lateral hypothalamic area on feeding in female rats during the estrous cycle. | 2008 Oct 20 |
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Panic disorder: is the PAG involved? | 2009 |
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Pharmacological analysis of the novel, rapid, and potent inactivation of the human 5-Hydroxytryptamine7 receptor by risperidone, 9-OH-Risperidone, and other inactivating antagonists. | 2009 Feb |
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On the intrinsic regulation of neuropeptide Y release in the mammalian suprachiasmatic nucleus circadian clock. | 2010 Mar |
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Evaluation of [(11)C]metergoline as a PET radiotracer for 5HTR in nonhuman primates. | 2010 Nov 15 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12411222
from 7.5 mg/day to 40 mg/day
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27251511
Oocytes were injected with human Kv1.4 channel cRNAs and maintained for 2 to 4 d before Kv1.4 channel currents were recorded in ND96 using a two-electrode voltage clamp technique. Original K+ current traces are shown under control conditions, after bath superfusion of metergoline and washout. Voltage pulses of 500-ms duration were applied in 10-mV increments and at 10-s intervals from a holding potential of –80 mV. I–V relationships of human Kv1.4 channels were recorded in the absence or presence of 10 μM metergoline (MG). The current-voltage relationships of Kv1.4 channels were obtained using voltage steps between –80 and +60 mV taken in 10 mV increments.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C66884
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WHO-ATC |
G02CB05
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WHO-VATC |
QG02CB05
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DTXSID5042584
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28693
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CHEMBL19215
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D008711
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m7279
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100000081202
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2378
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METERGOLINE
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SUB08824MIG
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DB13520
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64216
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6834
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1723
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755878
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C91039
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241-686-3
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17692-51-2
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1501393LY5
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ACTIVE MOIETY