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

General Information of Drug (ID: DMCZSP3)

• Drug Name: 5-methoxycarbonylamino-N-acetyltryptamine Drug Info
• Synonyms: 5-Methoxycarbonylamino-N-acetyltryptamine; GR 135531; 190277-13-5; 5-MCA-NAT; 5MCA-NAT; CHEMBL504585; methyl 3-(2-acetamidoethyl)-1H-indol-5-ylcarbamate; methyl N-[3-(2-acetamidoethyl)-1H-indol-5-yl]carbamate; Methyl {3-[2-(Acetylamino)ethyl]-1h-Indol-5-Yl}carbamate; Methyl [3-[2-(acetylamino)ethyl]-1H-indol-5-yl]carbamate; Tocris-0896; AC1N7T0H; GTPL3393; SCHEMBL4655625; CTK6J2921; CHEBI:93457; DTXSID70401560; MPZVHKLZCUEJFO-UHFFFAOYSA-N; MolPort-003-848-587; HMS3266P16; ZINC2567732; BN0231; BDBM50260394; PDSP2_001790

Indication

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

• Cross-matching ID:
  PubChem CID: 4284525
  ChEBI ID: CHEBI:93457
  CAS Number: CAS 190277-13-5
  TTD Drug ID: DMCZSP3

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	[3]
Tasimelteon	DMLOQ1V	Insomnia	7A00-7A0Z	Approved	[4]
VLB-01	DMQGV5P	Epilepsy	8A60-8A68	Phase 3	[5]
2-iodo-melatonin	DMSEIUP	Discovery agent	N.A.	Investigative	[6]
N-(2,3,4,9-Tetrahydro-1H-carbazol-3-yl)-acetamide	DMWC70I	Discovery agent	N.A.	Investigative	[7]
N-(3-(2-ethoxy-5-methoxyphenyl)propyl)acetamide	DMLWGPC	Discovery agent	N.A.	Investigative	[8]
Beta-methylmelatonin	DMKH32S	Discovery agent	N.A.	Investigative	[9]
UCM-454	DMSVJFG	Discovery agent	N.A.	Investigative	[10]
N-(3-(4-hydroxy-3-methoxyphenyl)propyl)acetamide	DMILWPS	Discovery agent	N.A.	Investigative	[8]
N-(3-(5-methoxy-2-propoxyphenyl)propyl)acetamide	DMHM0WI	Discovery agent	N.A.	Investigative	[8]

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

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Melatonin	DMKWFBT	Depression	6A70-6A7Z	Approved	[11]
Ramelteon	DM7IW9J	Insomnia	7A00-7A0Z	Approved	[3]
Tasimelteon	DMLOQ1V	Insomnia	7A00-7A0Z	Approved	[4]
Neu-P11	DMIQDFW	Alzheimer disease	8A20	Phase 2	[12]
LY-156735	DM5IX9M	Anxiety disorder	6B00-6B0Z	Phase 2	[13]
Agomelatine	DMXYA5K	Major depressive disorder	6A70.3	Withdrawn from market	[14]
Luzindole	DMXRJQV	Sleep-wake disorder	7A00-7B2Z	Terminated	[15]
S-20928	DMQDWMJ	Sleep-wake disorder	7A00-7B2Z	Terminated	[16]
GR-133347	DMNRJA0	Anxiety disorder	6B00-6B0Z	Terminated	[17]
GR-131663	DMKAGLV	Anxiety disorder	6B00-6B0Z	Terminated	[18]

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	Inhibitor	[2]
Melatonin receptor type 1B (MTNR1B)	TT32JK8	MTR1B_HUMAN	Inhibitor	[2]

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: 3393).
• [2] 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.
• [3] MT1 and MT2 melatonin receptors: ligands, models, oligomers, and therapeutic potential. J Med Chem. 2014 Apr 24;57(8):3161-85.
• [4] 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).
• [5] Interpreting expression profiles of cancers by genome-wide survey of breadth of expression in normal tissues. Genomics 2005 Aug;86(2):127-41.
• [6] 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.
• [7] 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).
• [8] 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.
• [9] 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.
• [10] 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.
• [11] 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.
• [12] 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).
• [13] Melatonin and sleep in aging population. Exp Gerontol. 2005 Dec;40(12):911-25.
• [14] Melatonin receptor agonists: SAR and applications to the treatment of sleep-wake disorders. Curr Top Med Chem. 2008;8(11):954-68.
• [15] Luzindole (N-0774): a novel melatonin receptor antagonist. J Pharmacol Exp Ther. 1988 Sep;246(3):902-10.
• [16] 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.
• [17] US patent application no. 5,151,446, Substituted 2-amidotetralins as melatonin agonists and antagonists.
• [18] 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.