Details of the Drug-Related molecule(s) Interaction Atlas

General Information of Drug (ID: DMJFP6G)

• Drug Name: Metergolin Drug Info
• 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]

• Cross-matching ID:
  PubChem CID: 28693
  ChEBI ID: CHEBI:64216
  CAS Number: CAS 17692-51-2
  TTD Drug ID: DMJFP6G

Molecule-Related Drug Atlas

Drug(s) Targeting 5-HT 1B receptor (HTR1B)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Eletriptan	DMW649X	Migraine	8A80	Approved	[9]
Zolmitriptan	DM1IB4Q	Migraine	8A80	Approved	[9]
Frovatriptan	DM7RE8P	Migraine	8A80	Approved	[9]
Fluphenazine	DMIT8LX	Psychotic disorder	6A20-6A25	Approved	[9]
Naratriptan	DMO50U2	Headache	8A80-8A84	Approved	[10]
Prolixin decanoate	DMMJ1IS	Schizophrenia	6A20	Approved	[9]
Eltoprazine	DMW6C81	Attention deficit hyperactivity disorder	6A05.Z	Phase 3	[11]
NXN-188	DMMBAIH	Migraine	8A80	Phase 2	[12]
[N-methyl-3H(3)]AZ-10419369	DMSCV02	Mood disorder	6A60-6E23	Phase 1	[13]
Alniditan	DMFE3CT	Migraine	8A80	Discontinued in Phase 3	[14]

Drug(s) Targeting 5-HT 1D receptor (HTR1D)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Eletriptan	DMW649X	Migraine	8A80	Approved	[9]
Zolmitriptan	DM1IB4Q	Migraine	8A80	Approved	[9]
Frovatriptan	DM7RE8P	Migraine	8A80	Approved	[9]
Sumatriptan	DMVYXR8	Cluster headache	8A81.0	Approved	[15]
Rizatriptan	DMDJMA3	Migraine	8A80	Approved	[16]
Almogran	DM7I64Z	Migraine	8A80	Approved	[17]
Neu-P11	DMIQDFW	Alzheimer disease	8A20	Phase 2	[18]
FKB01MD	DM2O7NM	N. A.	N. A.	Phase 2	[19]
NXN-188	DMMBAIH	Migraine	8A80	Phase 2	[12]
TGBA01AD	DMJ2FTU	Mood disorder	6A60-6E23	Phase 2	[20]

Drug(s) Targeting 5-HT 5A receptor (HTR5A)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
(+/-)-nantenine	DM0L3GE	Discovery agent	N.A.	Investigative	[21]
SEROTONIN	DMOFCRY	Discovery agent	N.A.	Investigative	[22]
5-CT	DM260KD	Discovery agent	N.A.	Investigative	[23]
TFMPP	DMAC8TP	Discovery agent	N.A.	Investigative	[24]
5,6-dichloro-3,4-dihydroquinazolin-2-amine	DMN1S35	Discovery agent	N.A.	Investigative	[25]
MPDT	DMYX31S	Discovery agent	N.A.	Investigative	[26]
5-chloro-3,4-dihydroquinazolin-2-amine	DMKEFJ0	Discovery agent	N.A.	Investigative	[25]
EDMT	DMS3AXK	Discovery agent	N.A.	Investigative	[26]
5-chloro-4-methyl-3,4-dihydroquinazolin-2-amine	DM7FZU2	Discovery agent	N.A.	Investigative	[25]
[3H]5-CT	DMEAHFZ	Discovery agent	N.A.	Investigative	[27]

Drug(s) Targeting 5-HT 2B receptor (HTR2B)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Triflupromazine	DMKFQJP	Nausea	MD90	Approved	[28]
Minaprine	DM0EP7M	Depression	6A70-6A7Z	Approved	[29]
SPN-812	DMTV7XH	Attention deficit hyperactivity disorder	6A05.Z	Phase 4	[30]
Vabicaserin	DM9GZW6	Psychotic disorder	6A20-6A25	Phase 2	[31]
PRX-08066	DMR7H2V	Pulmonary arterial hypertension	BB01.0	Phase 2	[32]
Pyrimidine derivative 29	DMVOYJ8	N. A.	N. A.	Patented	[33]
Pyrimidine derivative 26	DM90WKN	N. A.	N. A.	Patented	[33]
Pyrimidine derivative 23	DM5MLQU	N. A.	N. A.	Patented	[33]
Pyrimidine derivative 25	DM51MFS	N. A.	N. A.	Patented	[33]
Pyrimidine derivative 27	DMIQSDW	N. A.	N. A.	Patented	[33]

Drug(s) Targeting 5-HT 2A receptor (HTR2A)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
ZOTEPINE	DMF3VXA	Anxiety disorder	6B00-6B0Z	Approved	[34]
Iloperidone	DM6AUFY	Schizophrenia	6A20	Approved	[35]
Flibanserin	DM70DTN	Depression	6A70-6A7Z	Approved	[36]
Lurasidone hydrochloride	DMCVPXO	Schizophrenia	6A20	Approved	[37]
Aniracetam	DMOIFW0	Cerebrovascular ischaemia	8B1Z	Approved	[38]
lumateperone tosylate	DMQ8HOJ	Schizophrenia	6A20	Approved	[39]
Sarpogrelate	DMGLP6S	Diabetic complication	5A2Y	Approved	[40]
Pimavanserin	DMR7IVC	Parkinson disease	8A00.0	Approved	[41]
Zicronapine	DMP8ESD	Schizophrenia	6A20	Phase 3	[42]
TRYPTAMINE	DMAFPHB	N. A.	N. A.	Phase 3	[43]

Drug(s) Targeting 5-HT 1F receptor (HTR1F)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Lasmiditan	DMXLVDT	Migraine	8A80	Approved	[44]
LY-334370	DM43O9N	Migraine	8A80	Phase 2	[45]
5-CT	DM260KD	Discovery agent	N.A.	Investigative	[5]
TFMPP	DMAC8TP	Discovery agent	N.A.	Investigative	[46]
1-naphthylpiperazine	DM6BIWK	Discovery agent	N.A.	Investigative	[5]
BRL-15572	DMM61Y2	Discovery agent	N.A.	Investigative	[47]
2-methyl-5-HT	DM1S5CB	N. A.	N. A.	Investigative	[46]
alpha-methyl-5-HT	DMCAYXF	Discovery agent	N.A.	Investigative	[46]
WAY-466	DMMOH51	Discovery agent	N.A.	Investigative	[48]
[125I]LSD	DMP69QG	Discovery agent	N.A.	Investigative	[49]

Drug(s) Targeting 5-HT 2C receptor (HTR2C)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Lorcaserin	DMG6OYJ	Obesity	5B81	Approved	[50]
Tramadol	DMRQD04	Osteoarthritis	FA00-FA05	Approved	[51]
Mirtazapine	DML53ZJ	Depression	6A70-6A7Z	Approved	[52]
Nefazodone	DM4ZS8M	Major depressive disorder	6A70.3	Approved	[53]
Methysergide	DM1EF73	Migraine	8A80	Approved	[54]
Eltoprazine	DMW6C81	Attention deficit hyperactivity disorder	6A05.Z	Phase 3	[11]
M100907	DM7ZFBA	Sleep-wake disorder	7A00-7B2Z	Phase 3	[55]
SR46349B	DM1ODMR	Primary insomnia	7A00	Phase 3	[56]
Vabicaserin	DM9GZW6	Psychotic disorder	6A20-6A25	Phase 2	[31]
Nuplazid	DMOJA5G	Alzheimer disease	8A20	Phase 2	[57]

Drug(s) Targeting 5-HT 1E receptor (HTR1E)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
5-CT	DM260KD	Discovery agent	N.A.	Investigative	[4]
TFMPP	DMAC8TP	Discovery agent	N.A.	Investigative	[4]
1-naphthylpiperazine	DM6BIWK	Discovery agent	N.A.	Investigative	[4]
BRL-15572	DMM61Y2	Discovery agent	N.A.	Investigative	[47]
2-methyl-5-HT	DM1S5CB	N. A.	N. A.	Investigative	[46]
alpha-methyl-5-HT	DMCAYXF	Discovery agent	N.A.	Investigative	[4]
m-chlorophenylpiperazine	DMM1J2D	Discovery agent	N.A.	Investigative	[4]
EDMT	DMS3AXK	Discovery agent	N.A.	Investigative	[26]
9-OH-risperidone	DMGORXQ	Discovery agent	N.A.	Investigative	[58]
[3H]5-HT	DMYJXV7	Discovery agent	N.A.	Investigative	[59]

Drug(s) Targeting 5-HT receptor (5HTR)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Paliperidone	DM7NPJS	Psychotic disorder	6A20-6A25	Approved	[1]
Ramosetron	DMH7GN8	Diarrhea-predominant irritable bowel syndrome	DD91.01	Approved	[8]
Pizotyline	DMV74ZH	Headache	8A80-8A84	Approved	[1]
Tandospirone	DMPHWU6	Anxiety disorder	6B00-6B0Z	Approved	[8]
Nafronyl	DMVMQ1L	Cerebrovascular ischaemia	8B1Z	Approved	[1]
ITI-007	DMUQ1DO	Depression	6A70-6A7Z	Phase 3	[19]
Fenfluramine	DM0762O	Dravet syndrome	8A61.11	Phase 3	[60]
MIN-117	DMSLIW6	Major depressive disorder	6A70.3	Phase 2	[19]
Lu-AA34893	DM2ZUXK	Anxiety disorder	6B00-6B0Z	Phase 2	[61]
SEP--4199	DMA12HB	Bipolar disorder	6A60	Phase 2	[62]

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	[2]
5-HT 1D receptor (HTR1D)	TT6MSOK	5HT1D_HUMAN	Antagonist	[3]
5-HT 1E receptor (HTR1E)	TTCPG9S	5HT1E_HUMAN	Antagonist	[4]
5-HT 1F receptor (HTR1F)	TT0MI3F	5HT1F_HUMAN	Antagonist	[5]
5-HT 2A receptor (HTR2A)	TTJQOD7	5HT2A_HUMAN	Antagonist	[6]
5-HT 2B receptor (HTR2B)	TT0K1SC	5HT2B_HUMAN	Antagonist	[6]
5-HT 2C receptor (HTR2C)	TTWJBZ5	5HT2C_HUMAN	Antagonist	[6]
5-HT 5A receptor (HTR5A)	TTRUFDT	5HT5A_HUMAN	Antagonist	[7]
5-HT receptor (5HTR)	TT85JO3	NOUNIPROTAC	Modulator	[8]

References

• [1] Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
• [2] 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.
• [3] Primary structure and functional characterization of a human 5-HT1D-type serotonin receptor. Mol Pharmacol. 1991 Aug;40(2):143-8.
• [4] Molecular cloning and pharmacological characterization of the guinea pig 5-HT1E receptor. Eur J Pharmacol. 2004 Jan 26;484(2-3):127-39.
• [5] 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.
• [6] 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.
• [7] Cloning and characterisation of the human 5-HT5A serotonin receptor. FEBS Lett. 1994 Dec 5;355(3):242-6.
• [8] Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
• [9] Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
• [10] Triptans in pregnancy. Ther Drug Monit. 2008 Feb;30(1):5-9.
• [11] Clinical pipeline report, company report or official report of Jazz Pharmaceuticals.
• [12] Company report (NeurAxon)
• [13] 5-HT1B and other related serotonergic proteins are altered in APPswe mutation. Neurosci Lett. 2015 May 6;594:137-43.
• [14] Agonistic properties of alniditan, sumatriptan and dihydroergotamine on human 5-HT1B and 5-HT1D receptors expressed in various mammalian cell lines. Br J Pharmacol. 1998 Apr;123(8):1655-65.
• [15] Irritable bowel syndrome: new agents targeting serotonin receptor subtypes. Drugs. 2001;61(3):317-32.
• [16] An introduction to migraine: from ancient treatment to functional pharmacology and antimigraine therapy. Proc West Pharmacol Soc. 2002;45:199-210.
• [17] Efficacy and tolerability of subcutaneous almotriptan for the treatment of acute migraine: a randomized, double-blind, parallel-group, dose-finding study. Clin Ther. 2001 Nov;23(11):1867-75.
• [18] Clinical pipeline report, company report or official report of Neurim Pharmaceuticals.
• [19] Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
• [20] Company report (Fabrekramer)
• [21] Synthetic studies and pharmacological evaluations on the MDMA ('Ecstasy') antagonist nantenine. Bioorg Med Chem Lett. 2010 Jan 15;20(2):628-31.
• [22] Identification of a potent, selective, and orally active leukotriene a4 hydrolase inhibitor with anti-inflammatory activity. J Med Chem. 2008 Jul 24;51(14):4150-69.
• [23] Expression of functional mouse 5-HT5A serotonin receptor in the methylotrophic yeast Pichia pastoris: pharmacological characterization and localization. FEBS Lett. 1995 Dec 27;377(3):451-6.
• [24] Mouse 5-hydroxytryptamine5A and 5-hydroxytryptamine5B receptors define a new family of serotonin receptors: cloning, functional expression, and chromosomal localization. Mol Pharmacol. 1993 Mar;43(3):313-9.
• [25] Cyclic guanidines as dual 5-HT5A/5-HT7 receptor ligands: structure-activity relationship elucidation. Bioorg Med Chem Lett. 2008 Jan 1;18(1):256-61.
• [26] 2-Substituted tryptamines: agents with selectivity for 5-HT(6) serotonin receptors. J Med Chem. 2000 Mar 9;43(5):1011-8.
• [27] Human 5-HT(5) receptors: the 5-HT(5A) receptor is functional but the 5-HT(5B) receptor was lost during mammalian evolution. Eur J Pharmacol. 2001 Apr 27;418(3):157-67.
• [28] Some properties of 5-hydroxytryptamine receptors in the hindquarters of the rat. Br J Pharmacol. 1979 Sep;67(1):79-85.
• [29] Privileged structures: a useful concept for the rational design of new lead drug candidates. Mini Rev Med Chem. 2007 Nov;7(11):1108-19.
• [30] New Insights into the Mechanism of Action of Viloxazine: Serotonin and Norepinephrine Modulating Properties. J Exp Pharmacol. 2020 Aug 25;12:285-300.
• [31] Prediction of Efficacy of Vabicaserin, a 5-HT2C Agonist, for the Treatment of Schizophrenia Using a Quantitative Systems Pharmacology Model.CPT Pharmacometrics Syst Pharmacol.2014 Apr 23;3:e111.
• [32] Emerging treatments for pulmonary arterial hypertension. Expert Opin Emerg Drugs. 2006 Nov;11(4):609-19.
• [33] Novel serotonin receptor 2 (5-HT2R) agonists and antagonists: a patent review (2004-2014).Expert Opin Ther Pat. 2016;26(1):89-106.
• [34] Current and novel approaches to the drug treatment of schizophrenia. J Med Chem. 2001 Feb 15;44(4):477-501.
• [35] Hughes B: 2009 FDA drug approvals. Nat Rev Drug Discov. 2010 Feb;9(2):89-92.
• [36] Radium 223 dichloride for prostate cancer treatment. Drug Des Devel Ther. 2017 Sep 6;11:2643-2651.
• [37] Mullard A: 2010 FDA drug approvals. Nat Rev Drug Discov. 2011 Feb;10(2):82-5.
• [38] Anxiolytic effects of aniracetam in three different mouse models of anxiety and the underlying mechanism. Eur J Pharmacol. 2001 May 18;420(1):33-43.
• [39] Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health Human Services. 2019
• [40] Beneficial effects of sarpogrelate hydrochloride, a 5-HT2A receptor antagonist, supplemented with pioglitazone on diabetic model mice. Endocr Res. 2009;34(1-2):18-30.
• [41] Pimavanserin, a selective serotonin (5-HT)2A-inverse agonist, enhances the efficacy and safety of risperidone, 2mg/day, but does not enhance efficacy of haloperidol, 2mg/day: comparison with reference dose risperidone, 6mg/day.Schizophr Res.2012 Nov;141(2-3):144-52.
• [42] Clinical pipeline report, company report or official report of Lundbeck.
• [43] Central serotonin receptors as targets for drug research. J Med Chem. 1987 Jan;30(1):1-12.
• [44] Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health Human Services. 2019
• [45] Selective seratonin 1F (5-HT(1F)) receptor agonist LY334370 for acute migraine: a randomised controlled trial. Lancet. 2001 Oct 13;358(9289):1230-4.
• [46] Cloning of another human serotonin receptor (5-HT1F): a fifth 5-HT1 receptor subtype coupled to the inhibition of adenylate cyclase. Proc Natl Acad Sci U S A. 1993 Jan 15;90(2):408-12.
• [47] SB-216641 and BRL-15572--compounds to pharmacologically discriminate h5-HT1B and h5-HT1D receptors. Naunyn Schmiedebergs Arch Pharmacol. 1997 Sep;356(3):312-20.
• [48] Discovery of 5-arylsulfonamido-3-(pyrrolidin-2-ylmethyl)-1H-indole derivatives as potent, selective 5-HT6 receptor agonists and antagonists. J Med Chem. 2005 Jan 27;48(2):353-6.
• [49] Isolation of a mouse "5HT1E-like" serotonin receptor expressed predominantly in hippocampus. J Biol Chem. 1992 Oct 5;267(28):19761-4.
• [50] Anti-obesity drugs. Expert Opin Pharmacother. 2008 Jun;9(8):1339-50.
• [51] The inhibitory effects of tramadol on 5-hydroxytryptamine type 2C receptors expressed in Xenopus oocytes. Anesth Analg. 2004 May;98(5):1401-6, table of contents.
• [52] Inverse agonist and neutral antagonist actions of antidepressants at recombinant and native 5-hydroxytryptamine2C receptors: differential modulatio... Mol Pharmacol. 2008 Mar;73(3):748-57.
• [53] Serotonin 5-HT2C receptors as a target for the treatment of depressive and anxious states: focus on novel therapeutic strategies. Therapie. 2005 Sep-Oct;60(5):441-60.
• [54] Spinal serotonin receptor activation modulates the exercise ventilatory response with increased dead space in goats. Respir Physiol Neurobiol. 2008 May 31;161(3):230-8.
• [55] Non-basic ligands for aminergic GPCRs: the discovery and development diaryl sulfones as selective, orally bioavailable 5-HT2A receptor antagonists ... Bioorg Med Chem Lett. 2010 Jun 15;20(12):3708-12.
• [56] SR46349-B, a 5-HT(2A/2C) receptor antagonist, potentiates haloperidol-induced dopamine release in rat medial prefrontal cortex and nucleus accumbens. Neuropsychopharmacology. 2002 Sep;27(3):430-41.
• [57] The neuropharmacology of sleep paralysis hallucinations: serotonin 2A activation and a novel therapeutic drug. Psychopharmacology (Berl). 2018 Nov;235(11):3083-3091.
• [58] Risperidone compared with new and reference antipsychotic drugs: in vitro and in vivo receptor binding. Psychopharmacology (Berl). 1996 Mar;124(1-2):57-73.
• [59] Molecular cloning of a serotonin receptor from human brain (5HT1E): a fifth 5HT1-like subtype. Proc Natl Acad Sci U S A. 1992 Jun 15;89(12):5517-21.
• [60] Pharmacotherapy for obesity. Drugs. 2005;65(10):1391-418.
• [61] Encyclopedia of Psychopharmacology. Ian Stolerman. 2010. Page(105).
• [62] ClinicalTrials.gov (NCT03543410) A Clinical Study to Test the Effectiveness of an Investigational Drug to Treat People That Have Major Depressive Episodes When They Have Bipolar 1 Depression. U.S. National Institutes of Health.