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
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
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
Pharmacology
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
Edotreotide
Clinical data
Trade namesSomaKit TOC
Identifiers
DrugBank

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

References
  1. "SomaKit TOC 40 micrograms kit for radiopharmaceutical preparation - Summary of Product Characteristics (SmPC)". (emc). 2 July 2021. Retrieved 9 July 2021.
  2. "SomaKit TOC EPAR". European Medicines Agency (EMA). Retrieved 20 October 2020.
  3. Martindale, The Extra Pharmacopoeia, 30th ed, p1161.
  4. S, O'Dorisio (17 June 2016). "Radiolabeled Octreotide in Treating Children With Advanced or Refractory Solid Tumors". ClinicalTrials.gov. US National Library of Medicine. Retrieved 7 November 2020.
  5. Menda Y, O'Dorisio MS, Kao S, Khanna G, Michael S, Connolly M, et al. (October 2010). "Phase I trial of 90Y-DOTATOC therapy in children and young adults with refractory solid tumors that express somatostatin receptors". Journal of Nuclear Medicine. 51 (10): 1524–31. doi:10.2967/jnumed.110.075226. PMC 3753801. PMID 20847174.
  6. Bushnell DL, O'Dorisio TM, O'Dorisio MS, Menda Y, Hicks RJ, Van Cutsem E, et al. (April 2010). "90Y-edotreotide for metastatic carcinoid refractory to octreotide". Journal of Clinical Oncology. 28 (10): 1652–9. doi:10.1200/JCO.2009.22.8585. PMC 4872330. PMID 20194865.
  7. "The therapeutic n.c.a. 177Lu-Edotreotide (Solucin)". ITM Isotopen Technologien München AG. Retrieved 7 November 2020.
  8. "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)". EU Clinical Trials Register. Retrieved 7 November 2020.
  9. "EU/03/14/1269". European Medicines Agency. Retrieved 7 November 2020.
  • "Edotreotide". Drug Information Portal. U.S. National Library of Medicine.


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