{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 458457286 | ImageFile = Edotreotide.svg | ImageClass = skin-invert-image | ImageName = | ImageSize = 250px | IUPACName = 2-[4-[2-<nowiki>[[</nowiki>(2''R'')-1-<nowiki>[[</nowiki>(4''R'',7''S'',10''S'',13''R'',16''S'',19''R'')-10-(4-aminobutyl)-4-<nowiki>[[</nowiki>(2''R'',3''R'')-1,3-dihydroxybutan-2-yl]carbamoyl]-7-[(1''R'')-1-hydroxyethyl]-16-[(4-hydroxyphenyl)methyl]-13-(1''H''-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 | OtherNames = SomaKit TOC | Section1 = {{Chembox Identifiers | CASNo = 204318-14-9 | CASNo_Ref = {{cascite|changed|??}} | ChEMBL = 408350 | DrugBank = DB15494 | RTECS = | UNII_Ref = {{fdacite|correct|FDA}} | UNII = U194AS08HZ | PubChem = 158782 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 139675 | 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 | 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 | InChIKey = RZHKDBRREKOZEW-AAXZNHDCBX | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = RZHKDBRREKOZEW-AAXZNHDCSA-N
}} | Section2 = {{Chembox Properties | C=65 | H=92 | N=14 | O=18 | S=2 | Appearance = | Density = | Solubility = | MeltingPt = | BoilingPt = | pKa = | pKb = | Viscosity = }} | Section3 = {{Chembox Pharmacology | Licence_EU=yes | ATCvet = | ATCCode_prefix = | ATCCode_suffix = | ATC_Supplemental = | AdminRoutes = | Bioavail = | Excretion = | HalfLife = | Metabolism = | Legal_status = | Legal_AU = | Legal_AU_comment = | Legal_CA = | Legal_CA_comment = | Legal_NZ = | Legal_NZ_comment = | Legal_US = | Legal_US_comment = | Legal_UK = POM | Legal_UK_comment = <ref>{{cite web | title=SomaKit TOC 40 micrograms kit for radiopharmaceutical preparation - Summary of Product Characteristics (SmPC) | website=(emc) | date=2 July 2021 | url=https://www.medicines.org.uk/emc/product/12722/smpc | access-date=9 July 2021}}</ref> | Legal_EU = Rx-only | Legal_EU_comment = <ref>{{cite web | title=SomaKit TOC EPAR | website=European Medicines Agency (EMA) | date=17 September 2018 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/somakit-toc | access-date=20 October 2020}}</ref> | Legal_UN = | Legal_UN_comment = | Pregnancy_category = | Pregnancy_AU = | Pregnancy_AU_comment = | ProteinBound = | Dependence_liability = }} | Section7 = {{Chembox Hazards | ExternalMSDS = | MainHazards = | FlashPt = }} }}
'''Edotreotide''' (USAN, also known as (DOTA<sup>0</sup>-Phe<sup>1</sup>-Tyr<sup>3</sup>) 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.<ref>Martindale, The Extra Pharmacopoeia, 30th ed, p1161.</ref> When used therapeutically it is an example of peptide receptor radionuclide therapy.
==Yttrium-90==
A phase I clinical trial of yttrium-90 labelled edotreotide concluded in 2011,<ref>{{cite journal |title=Radiolabeled Octreotide in Treating Children With Advanced or Refractory Solid Tumors |url=https://www.clinicaltrials.gov/ct2/show/NCT00049023 |website=ClinicalTrials.gov |date=17 June 2016 |publisher=US National Library of Medicine |access-date=7 November 2020 |language=en|last1=S |first1=O'Dorisio }}</ref> 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.<ref>{{cite journal | vauthors = Menda Y, O'Dorisio MS, Kao S, Khanna G, Michael S, Connolly M, Babich J, O'Dorisio T, Bushnell D, Madsen M | display-authors = 6 | title = Phase I trial of 90Y-DOTATOC therapy in children and young adults with refractory solid tumors that express somatostatin receptors | journal = Journal of Nuclear Medicine | volume = 51 | issue = 10 | pages = 1524–31 | date = October 2010 | pmid = 20847174 | pmc = 3753801 | doi = 10.2967/jnumed.110.075226 }}</ref>
A phase II trial for the use of <sup>90</sup>Y DOTA-TOC for patients with metastatic carcinoid, where octreotide treatment was no longer effective, also reported results in 2010.<ref>{{cite journal | vauthors = Bushnell DL, O'Dorisio TM, O'Dorisio MS, Menda Y, Hicks RJ, Van Cutsem E, Baulieu JL, Borson-Chazot F, Anthony L, Benson AB, Oberg K, Grossman AB, Connolly M, Bouterfa H, Li Y, Kacena KA, LaFrance N, Pauwels SA | display-authors = 6 | title = 90Y-edotreotide for metastatic carcinoid refractory to octreotide | journal = Journal of Clinical Oncology | volume = 28 | issue = 10 | pages = 1652–9 | date = April 2010 | pmid = 20194865 | pmc = 4872330 | doi = 10.1200/JCO.2009.22.8585 }}</ref>
:[[File:Yttrium-90 edotreotide.svg|thumb|left|upright=1.6|Yttrium-90 labeled edotreotide]]{{clear left}}
==Lutetium-177==
Lutetium-177 labelled edotreotide (<sup>177</sup>Lu-DOTA-TOC), with the trade name Solucin, is the subject of a phase 3 clinical trial for treatment of GEP-NETs.<ref>{{cite web |title=The therapeutic n.c.a. 177Lu-Edotreotide (Solucin) |url=https://itm-radiopharma.com/index.php?id=96 |publisher=ITM Isotopen Technologien München AG |access-date=7 November 2020 |language=en}}</ref><ref>{{cite web |title=A prospective, randomised, Controlled, Open-label, Multicentre phase III study to evaluate efficacy and safety of Peptide Receptor Radionuclide Therapy (PRRT) with Lutetium 177-Edotreotide compared to targeted molecular therapy with Everolimus in patients with inoperable, progressive, somatostatin receptor-positive (SSTR+), neuroendocrine tumours of gastroenteric or pancreatic origin (GEP-NET). |url=https://www.clinicaltrialsregister.eu/ctr-search/trial/2016-001897-13/GB |website=EU Clinical Trials Register |access-date=7 November 2020}}</ref> It was granted orphan drug designation by the European Medicines Agency in 2014.<ref>{{cite web |title=EU/03/14/1269 |url=https://www.ema.europa.eu/en/medicines/human/orphan-designations/eu03141269 |website=European Medicines Agency |date=17 September 2018 |access-date=7 November 2020}}</ref>
== See also == * DOTA-TATE, a similar compound
== References == {{reflist}}
{{GH/IGF-1 axis signaling modulators}} {{Portal bar | Medicine}}
Category:Nuclear medicine procedures Category:Radiopharmaceuticals Category:Somatostatin inhibitors Category:Macrocycles Category:Cyclic peptides X Category:DOTA (chelator) derivatives