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

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
Drug Status:
Approved Drug(s)
Clinical Trial Drug(s)
Investigative Drug(s)
Discontinued Drug(s)
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]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Targeting Quinone reductase 2 (NQO2)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Melatonin DMKWFBT Depression 6A70-6A7Z 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]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Melatonin DMKWFBT Depression 6A70-6A7Z 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]
⏷ Show the Full List of 10 Drug(s)

Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

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

References

1 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: 1343).
2 Characterization of a retinal melatonin receptor. J Pharmacol Exp Ther. 1985 Aug;234(2):395-401.
3 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.
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.