Edotreotide

Edotreotide (USAN, also known as (DOTA⁰-Phe¹-Tyr³) octreotide, DOTA-TOC, DOTATOC) is a substance which, when bound to various radionuclides, is used in the treatment and diagnosis of certain types of cancer.^[3] When used therapeutically it is an example of peptide receptor radionuclide therapy.

Edotreotide

Names
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
Other names SomaKit TOC
Identifiers
CAS Number	204318-14-9 N
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL408350
ChemSpider	139675 N
DrugBank	DB15494
PubChem CID	158782
UNII	U194AS08HZ Y
CompTox Dashboard (EPA)	DTXSID701021591
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 N Key: RZHKDBRREKOZEW-AAXZNHDCSA-N N InChI=1/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 Key: RZHKDBRREKOZEW-AAXZNHDCBX
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)Cc2c[nH]c3c2cccc3)Cc4ccc(cc4)O)NC(=O)[C@@H](Cc5ccccc5)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
Properties
Chemical formula	C65H92N14O18S2
Molar mass	1421.65 g·mol−1
Pharmacology
License data	EU EMA: by INN
Legal status	UK: POM (Prescription only)[1] EU: Rx-only[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Yttrium-90

A phase I clinical trial of yttrium-90 labelled edotreotide concluded in 2011,^[4] aiming to investigated effects in young cancer patients (up to 25 years of age). Specific cancers being included in the trial include neuroblastoma, childhood brain tumours and gastrointestinal cancer.^[5]

A phase II trial for the use of ⁹⁰Y DOTA-TOC for patients with metastatic carcinoid, where octreotide treatment was no longer effective, also reported results in 2010.^[6]

Yttrium-90 labeled edotreotide

Lutetium-177

Lutetium-177 labelled edotreotide (¹⁷⁷Lu-DOTA-TOC), with the trade name Solucin, is the subject of a phase 3 clinical trial for treatment of GEP-NETs.^[7][8] It was granted orphan drug designation by the European Medicines Agency in 2014.^[9]

See also

• DOTA-TATE, a similar compound