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 |
---|---|---|---|---|
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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Pharmacology in vivo of the phenylindan derivative, Lu 19-005, a new potent inhibitor of dopamine, noradrenaline and 5-hydroxytryptamine uptake in rat brain. | 1985 Apr |
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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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Primary structure and functional characterization of a human 5-HT1D-type serotonin receptor. | 1991 Aug |
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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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Cloning of a novel human serotonin receptor (5-HT7) positively linked to adenylate cyclase. | 1993 Nov 5 |
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Cloning and characterisation of the human 5-HT5A serotonin receptor. | 1994 Dec 5 |
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Gonadal steroids, brain, and behavior: role of context. | 2002 Jun |
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Reproductive hormonal treatments for mood disorders in women. | 2002 Jun |
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Midbrain raphe modulation of nonphotic circadian clock resetting and 5-HT release in the mammalian suprachiasmatic nucleus. | 2003 Aug 20 |
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Treatment of seasonal affective disorders. | 2003 Dec |
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Pharmacological characterization of a serotonin receptor (5-HT7) stimulating cAMP production in human corneal epithelial cells. | 2003 Nov |
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Study of the behavioural responses related to the potential addictive properties of MDMA in mice. | 2004 Mar |
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Updated overview of the putative role of the serotoninergic system in obsessive-compulsive disorder. | 2005 Sep |
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Anoestrus in the dog: a fascinating story. | 2006 Aug |
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Serotonergic mediation of constant light-potentiated nonphotic phase shifting of the circadian locomotor activity rhythm in Syrian hamsters. | 2006 Jul |
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Effects of dopamine D1-like receptor agonists on food-maintained operant behavior in rats. | 2006 Jun |
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Potential vascular alpha1-adrenoceptor blocking properties of an array of 5-HT receptor ligands in the rat. | 2006 Mar 27 |
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Clozapine modulates aromatic L-amino acid decarboxylase activity in mouse striatum. | 2006 May |
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Systemic morphine produce antinociception mediated by spinal 5-HT7, but not 5-HT1A and 5-HT2 receptors in the spinal cord. | 2006 Nov |
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Reanalysis of constitutively active rat and human 5-HT7(a) receptors in HEK-293F cells demonstrates lack of silent properties for reported neutral antagonists. | 2006 Oct |
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Dopamine agonists, anti-progestins, anti-androgens, long-term-release GnRH agonists and anti-estrogens in canine reproduction: a review. | 2006 Oct |
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Serotonin increases the phase shift of the circadian locomotor activity rhythm in mice after dark pulses in constant light conditions. | 2007 |
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In vivo Schild regression analyses using nonselective 5-HT2C receptor antagonists in a rat operant behavioral assay. | 2007 Aug |
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Anxiolytic-like effect of group III mGlu receptor antagonist is serotonin-dependent. | 2007 Feb |
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Feeding behavior after metergoline or GR-46611 injections into the paraventricular nucleus of the hypothalamus in the pigeon. | 2007 May 16 |
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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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Anxiolytic-like action of MTEP expressed in the conflict drinking Vogel test in rats is serotonin dependent. | 2007 Nov |
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The structure of human serotonin 2c G-protein-coupled receptor bound to agonists and antagonists. | 2008 Aug |
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Selective serotonin reuptake inhibitors: a review of its effects on intraocular pressure. | 2008 Dec |
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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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Antidepressant-like effects of glucagon-like peptide-2 in mice occur via monoamine pathways. | 2009 Dec 1 |
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Tonic serotonergic control of ingestive behaviours in the pigeon (Columba livia): the role of the arcopallium. | 2009 Dec 28 |
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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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cis-Urocanic acid stimulates primary human keratinocytes independently of serotonin or platelet-activating factor receptors. | 2009 Nov |
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The bovine mammary gland expresses multiple functional isoforms of serotonin receptors. | 2009 Oct |
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Human 5-HT7 receptor-induced inactivation of forskolin-stimulated adenylate cyclase by risperidone, 9-OH-risperidone and other "inactivating antagonists". | 2009 Sep |
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Serotonergic-postsynaptic receptors modulate gripping-induced immobility episodes in male taiep rats. | 2009 Sep |
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5-hydroxy-L-tryptophan Suppressed Food Intake in Rats Despite an Increase in the Arcuate NPY Expression. | 2010 Dec |
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On the mechanism of the antidepressant-like action of group II mGlu receptor antagonist, MGS0039. | 2010 Dec |
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A role for serotonin in the antidepressant activity of NG-Nitro-L-arginine, in the rat forced swimming test. | 2010 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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In vitro synergistic effects of metergoline and antifungal agents against Candida krusei. | 2010 Nov |
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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