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

General Information of Drug (ID: DMSEIUP)

• Drug Name: 2-iodo-melatonin Drug Info
• Synonyms: 2-Iodomelatonin; 93515-00-5; n-[2-(2-iodo-5-methoxy-1h-indol-3-yl)ethyl]acetamide; CHEMBL289233; N-(2-(2-Iodo-5-methoxy-1H-indol-3-yl)ethyl)acetamide; acetamide,n-[2-(2-iodo-5-methoxy-1h-indol-3-yl)ethyl]-; Acetamide, N-(2-(2-iodo-5-methoxy-1H-indol-3-yl)ethyl)-, (3beta)-; Acetamide, N-(2-(2-iodo-5-methoxy-1H-indol-3-yl)ethyl)-; SR-01000075935; 2-I-MLT; Melatonin,2-Iodo; ML2; Tocris-0737; Lopac-I-1899; AC1L3GZ8; AC1Q5P6Z; Lopac0_000610; SCHEMBL163451; GTPL1343; BDBM29611; CTK8F4316; DTXSID30239462; 2-iodomelatonin; IODOMELATONIN

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1] , [2]

• Cross-matching ID:
  PubChem CID: 115348
  ChEBI ID: CHEBI:109558
  CAS Number: CAS 93515-00-5
  TTD Drug ID: DMSEIUP

Molecule-Related Drug Atlas

Drug(s) Targeting Melatonin receptor type 1B (MTNR1B)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Ramelteon	DM7IW9J	Insomnia	7A00-7A0Z	Approved	[5]
Tasimelteon	DMLOQ1V	Insomnia	7A00-7A0Z	Approved	[6]
VLB-01	DMQGV5P	Epilepsy	8A60-8A68	Phase 3	[7]
N-(2,3,4,9-Tetrahydro-1H-carbazol-3-yl)-acetamide	DMWC70I	Discovery agent	N.A.	Investigative	[8]
5-methoxycarbonylamino-N-acetyltryptamine	DMCZSP3	Discovery agent	N.A.	Investigative	[9]
N-(3-(2-ethoxy-5-methoxyphenyl)propyl)acetamide	DMLWGPC	Discovery agent	N.A.	Investigative	[10]
Beta-methylmelatonin	DMKH32S	Discovery agent	N.A.	Investigative	[11]
UCM-454	DMSVJFG	Discovery agent	N.A.	Investigative	[12]
N-(3-(4-hydroxy-3-methoxyphenyl)propyl)acetamide	DMILWPS	Discovery agent	N.A.	Investigative	[10]
N-(3-(5-methoxy-2-propoxyphenyl)propyl)acetamide	DMHM0WI	Discovery agent	N.A.	Investigative	[10]

Drug(s) Targeting Quinone reductase 2 (NQO2)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Melatonin	DMKWFBT	Insomnia	7A00-7A0Z	Approved	[13]
NSC-645809	DMPJQZG	Breast cancer	2C60-2C65	Phase 2	[14]
Prolarix	DMZIQ8G	Solid tumour/cancer	2A00-2F9Z	Phase 2	[15]
CB1954	DMVP4YK	Solid tumour/cancer	2A00-2F9Z	Discontinued in Phase 2	[16]
Flavin-Adenine Dinucleotide	DM5S4GK	Discovery agent	N.A.	Investigative	[16]
3,4,5-Trimethoxy-4'-amino-trans-stilbene	DMDBOJ5	Discovery agent	N.A.	Investigative	[17]
NSC-645808	DMMBAR3	Discovery agent	N.A.	Investigative	[14]
Decynium 22	DMWCTZ7	Discovery agent	N.A.	Investigative	[18]
NSC-106080	DMR6P9S	Discovery agent	N.A.	Investigative	[18]
NSC-99528	DMXZAIG	Discovery agent	N.A.	Investigative	[18]

Drug(s) Targeting Melatonin receptor type 1A (MTNR1A)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Melatonin	DMKWFBT	Insomnia	7A00-7A0Z	Approved	[19]
Ramelteon	DM7IW9J	Insomnia	7A00-7A0Z	Approved	[5]
Tasimelteon	DMLOQ1V	Insomnia	7A00-7A0Z	Approved	[6]
Neu-P11	DMIQDFW	Alzheimer disease	8A20	Phase 2	[20]
LY-156735	DM5IX9M	Anxiety disorder	6B00-6B0Z	Phase 2	[21]
Agomelatine	DMXYA5K	Major depressive disorder	6A70.3	Withdrawn from market	[22]
Luzindole	DMXRJQV	Sleep-wake disorder	7A00-7B2Z	Terminated	[23]
S-20928	DMQDWMJ	Sleep-wake disorder	7A00-7B2Z	Terminated	[24]
GR-133347	DMNRJA0	Anxiety disorder	6B00-6B0Z	Terminated	[25]
GR-131663	DMKAGLV	Anxiety disorder	6B00-6B0Z	Terminated	[26]

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Melatonin receptor type 1A (MTNR1A)	TT0WAIE	MTR1A_HUMAN	Agonist	[3] , [2]
Melatonin receptor type 1B (MTNR1B)	TT32JK8	MTR1B_HUMAN	Inhibitor	[2]
Quinone reductase 2 (NQO2)	TTJLP0R	NQO2_HUMAN	Inhibitor	[4]

References

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• [2] Synthesis of nitroindole derivatives with high affinity and selectivity for melatoninergic binding sites MT(3). J Med Chem. 2002 Apr 25;45(9):1853-9.
• [3] Characterization of a retinal melatonin receptor. J Pharmacol Exp Ther. 1985 Aug;234(2):395-401.
• [4] Synthesis of casimiroin and optimization of its quinone reductase 2 and aromatase inhibitory activities. J Med Chem. 2009 Apr 9;52(7):1873-84.
• [5] MT1 and MT2 melatonin receptors: ligands, models, oligomers, and therapeutic potential. J Med Chem. 2014 Apr 24;57(8):3161-85.
• [6] URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7393).
• [7] Interpreting expression profiles of cancers by genome-wide survey of breadth of expression in normal tissues. Genomics 2005 Aug;86(2):127-41.
• [8] Mapping the melatonin receptor. 2. synthesis and biological activity of indole derived melatonin analogues with restricted conformations of the C-3 amidoethane side chain, Bioorg. Med. Chem. Lett. 4(13):1559-1564 (1994).
• [9] Design and synthesis of benzofuranic derivatives as new ligands at the melatonin-binding site MT3. Bioorg Med Chem. 2008 May 1;16(9):4954-62.
• [10] Synthesis of substituted N-[3-(3-methoxyphenyl)propyl] amides as highly potent MT(2)-selective melatonin ligands. Bioorg Med Chem Lett. 2010 Apr 15;20(8):2582-5.
• [11] Mapping the melatonin receptor. 7. Subtype selective ligands based on beta-substituted N-acyl-5-methoxytryptamines and beta-substituted N-acyl-5-me... J Med Chem. 2006 Jun 15;49(12):3509-19.
• [12] 2-[(2,3-dihydro-1H-indol-1-yl)methyl]melatonin analogues: a novel class of MT2-selective melatonin receptor antagonists. J Med Chem. 2009 Feb 12;52(3):826-33.
• [13] The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.
• [14] Imidazoacridin-6-ones as novel inhibitors of the quinone oxidoreductase NQO2. Bioorg Med Chem Lett. 2010 May 1;20(9):2832-6.
• [15] CenterWatch. Drugs in Clinical Trials Database. CenterWatch. 2008.
• [16] How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
• [17] Design, synthesis, and biological evaluation of resveratrol analogues as aromatase and quinone reductase 2 inhibitors for chemoprevention of cancer. Bioorg Med Chem. 2010 Jul 15;18(14):5352-66.
• [18] In silico identification and biochemical evaluation of novel inhibitors of NRH:quinone oxidoreductase 2 (NQO2). Bioorg Med Chem Lett. 2010 Dec 15;20(24):7331-6.
• [19] The human MT1 melatonin receptor stimulates cAMP production in the human neuroblastoma cell line SH-SY5Y cells via a calcium-calmodulin signal transduction pathway. J Neuroendocrinol. 2005 Mar;17(3):170-8.
• [20] URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 288).
• [21] Melatonin and sleep in aging population. Exp Gerontol. 2005 Dec;40(12):911-25.
• [22] Melatonin receptor agonists: SAR and applications to the treatment of sleep-wake disorders. Curr Top Med Chem. 2008;8(11):954-68.
• [23] Luzindole (N-0774): a novel melatonin receptor antagonist. J Pharmacol Exp Ther. 1988 Sep;246(3):902-10.
• [24] Effects of two melatonin analogues, S-20098 and S-20928, on melatonin receptors in the pars tuberalis of the rat. J Pineal Res. 1998 Oct;25(3):172-6.
• [25] US patent application no. 5,151,446, Substituted 2-amidotetralins as melatonin agonists and antagonists.
• [26] Novel non-indolic melatonin receptor agonists differentially entrain endogenous melatonin rhythm and increase its amplitude. Eur J Pharmacol. 1999 Oct 15;382(3):157-66.