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edotreotide

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| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 458457286

| ImageFile = Edotreotide.svg

| ImageName =

| ImageSize = 250px

| IUPACName = 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

| OtherNames = SomaKit TOC

| Section1 = {{Chembox Identifiers

| CASNo = 204318-14-9

| CASNo_Ref = {{cascite|changed|??}}

| ChEMBL = 408350

| DrugBank = DB15494

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| 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

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| Section3 = {{Chembox Pharmacology

| Licence_EU=yes

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| Legal_UK = POM

| Legal_UK_comment = {{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}}

| Legal_EU = Rx-only

| Legal_EU_comment = {{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}}

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| Section7 = {{Chembox Hazards

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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.Martindale, The Extra Pharmacopoeia, 30th ed, p1161. 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,{{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 }} 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.{{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 }}

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.{{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 }}

:File:Yttrium-90 edotreotide.svg labeled edotreotide]]{{clear left}}

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.{{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}}{{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}} It was granted orphan drug designation by the European Medicines Agency in 2014.{{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}}

See also

References

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Category:Nuclear medicine procedures

Category:Radiopharmaceuticals

Category:Somatostatin inhibitors

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Category:Cyclic peptides

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Category:DOTA (chelator) derivatives