Details of the Drug

General Information of Drug (ID: DMQ08AJ)

Drug Name

Edotreotide

Synonyms

Edotreotide; SMT-487; UNII-U194AS08HZ; 204318-14-9; U194AS08HZ; CHEMBL408350; DOTATOC; DOTA-D-PHE-CYS-TYR-D-TRP-LYS-THR-CYS-THR-OL (DISULFIDE BRIDGE: 2-7); SMT 487; Edotreotide [USAN:INN]; DOTA-TOC acetate; AC1L4KLV; SCHEMBL1649285; SCHEMBL19712197; RZHKDBRREKOZEW-AAXZNHDCSA-N; BDBM50165171; N-((4,7,10-Tris(carboxymethyl)-1,4,7,10-tetraazacycoldodec-1-yl)acetyl-D-phenylalanyl-L-cysteinyl-L-tyrosyl-D-tryprophyl-L-lysyl-L-threonyl-N-((1R,2R)-2-hydroxy-1-(hydroxymethyl)propyl)-L-cysteinamide cyclic (2-7)-disulfide

Indication

Disease Entry	ICD 11	Status	REF
Acromegaly	5A60.0	Phase 2	[1], [2]

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 5

Molecular Weight (mw)

1421.6

Topological Polar Surface Area (xlogp)

-7.2

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C65H92N14O18S2
IUPAC Name: 2-[4-[2-[[(2R)-1-[[(4R,7S,10S,13R,16S,19R)-10-(4-aminobutyl)-4-[[(2R,3R)-1,3-dihydroxybutan-2-yl]carbamoyl]-7-[(1R)-1-hydroxyethyl]-16-[(4-hydroxyphenyl)methyl]-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicos-19-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-2-oxoethyl]-7,10-bis(carboxymethyl)-1,4,7,10-tetrazacyclododec-1-yl]acetic acid
Canonical SMILES: C[C@H]([C@H]1C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N1)CCCCN)CC2=CNC3=CC=CC=C32)CC4=CC=C(C=C4)O)NC(=O)[C@@H](CC5=CC=CC=C5)NC(=O)CN6CCN(CCN(CCN(CC6)CC(=O)O)CC(=O)O)CC(=O)O)C(=O)N[C@H](CO)[C@@H](C)O)O
InChI: InChI=1S/C65H92N14O18S2/c1-39(81)51(36-80)72-64(96)53-38-99-98-37-52(73-60(92)48(28-41-10-4-3-5-11-41)68-54(84)32-76-20-22-77(33-55(85)86)24-26-79(35-57(89)90)27-25-78(23-21-76)34-56(87)88)63(95)70-49(29-42-15-17-44(83)18-16-42)61(93)71-50(30-43-31-67-46-13-7-6-12-45(43)46)62(94)69-47(14-8-9-19-66)59(91)75-58(40(2)82)65(97)74-53/h3-7,10-13,15-18,31,39-40,47-53,58,67,80-83H,8-9,14,19-30,32-38,66H2,1-2H3,(H,68,84)(H,69,94)(H,70,95)(H,71,93)(H,72,96)(H,73,92)(H,74,97)(H,75,91)(H,85,86)(H,87,88)(H,89,90)/t39-,40-,47+,48-,49+,50-,51-,52+,53+,58+/m1/s1
InChIKey: RZHKDBRREKOZEW-AAXZNHDCSA-N

Cross-matching ID

PubChem CID: 158782
CAS Number: 204318-14-9
TTD ID: D0J8PI

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Somatostatin receptor (SSTR)	TTOMNR9	NOUNIPROTAC	Modulator	[3]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

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: 5638).
2	ClinicalTrials.gov (NCT00006370) Radiolabeled SMT-487 (Yttrium Y 90-DOTA-tyr3-octreotide) in Treating Patients With Refractory Small Cell Lung Cancer or Metastatic Breast Cancer. U.S. National Institutes of Health.
3	Interpreting expression profiles of cancers by genome-wide survey of breadth of expression in normal tissues. Genomics 2005 Aug;86(2):127-41.
4	Peptide receptor radionuclide therapy with 177Lu-DOTATATE for patients with somatostatin receptor-expressing neuroendocrine tumors: the first US phase 2 experience. Pancreas. 2014 May;43(4):518-25.
5	Lutetium-labelled peptides for therapy of neuroendocrine tumours. Eur J Nucl Med Mol Imaging. 2012 Feb;39 Suppl 1(Suppl 1):S103-12.
6	DG3173 (somatoprim), a unique somatostatin receptor subtypes 2-, 4- and 5-selective analogue, effectively reduces GH secretion in human GH-secreting pituitary adenomas even in Octreotide non-responsive tumours.Eur J Endocrinol.2012 Feb;166(2):223-34.
7	FK960, a novel potential anti-dementia drug, enhances high K(+)-evoked release of somatostatin from rat hippocampal slices. Brain Res. 2001 Feb 16;892(1):111-7.
8	Multimodal Imaging of 2-Cycle PRRT with 177 Lu-DOTA-JR11 and 177 Lu-DOTATOC in an Orthotopic Neuroendocrine Xenograft Tumor Mouse Model. J Nucl Med. 2021 Mar;62(3):393-398.
9	Radiopharmaceutical therapy in cancer: clinical advances and challenges. Nat Rev Drug Discov. 2020 Sep;19(9):589-608.
10	Clinical pipeline report, company report or official report of Orano Med.
11	Antagonist effects of seglitide (MK 678) at somatostatin receptors in guinea-pig isolated right atria.. Br J Pharmacol. 1993 August; 109(4): 898-899.