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

* 204318-14-9 N

3D model (JSmol)

* Interactive image

ChemSpider |

* 139675 N

PubChem CID

* 158782

UNII |

* U194AS08HZ Y

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

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

Tracking categories (test):

* SizeSet

EdotreotideClinical data

Trade names| SomaKit TOC
Identifiers
DrugBank|

* DB15494

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.

## Contents

* 1 Yttrium-90
* 2 Lutetium-177
* 3 See also
* 4 References
* 5 External links

## 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

## References

1. ↑ "SomaKit TOC 40 micrograms kit for radiopharmaceutical preparation - Summary of Product Characteristics (SmPC)". 2 July 2021. https://www.medicines.org.uk/emc/product/12722/smpc.
2. ↑ "SomaKit TOC EPAR". 17 September 2018. https://www.ema.europa.eu/en/medicines/human/EPAR/somakit-toc.
3. ↑ Martindale, The Extra Pharmacopoeia, 30th ed, p1161.
4. ↑ S, O'Dorisio (17 June 2016) (in en). Radiolabeled Octreotide in Treating Children With Advanced or Refractory Solid Tumors. US National Library of Medicine. https://www.clinicaltrials.gov/ct2/show/NCT00049023. Retrieved 7 November 2020.
5. ↑ "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. October 2010. doi:10.2967/jnumed.110.075226. PMID 20847174.
6. ↑ "90Y-edotreotide for metastatic carcinoid refractory to octreotide". Journal of Clinical Oncology 28 (10): 1652–9. April 2010. doi:10.1200/JCO.2009.22.8585. PMID 20194865.
7. ↑ "The therapeutic n.c.a. 177Lu-Edotreotide (Solucin)" (in en). ITM Isotopen Technologien München AG. https://itm-radiopharma.com/index.php?id=96.
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).". https://www.clinicaltrialsregister.eu/ctr-search/trial/2016-001897-13/GB.
9. ↑ "EU/03/14/1269". 17 September 2018. https://www.ema.europa.eu/en/medicines/human/orphan-designations/eu03141269.

## External links

* "Edotreotide". Drug Information Portal. U.S. National Library of Medicine. https://druginfo.nlm.nih.gov/drugportal/name/edotreotide.

* v
* t
* e

GH/IGF-1 axis signaling modulators

(somatotropin)|

* Agonists: Albusomatropin
* Bovine somatotropin
* Efpegsomatropin
* Eftansomatropin alfa
* Growth hormone
* Human placental lactogen
* Placental growth hormone (growth hormone variant)
* Somagrebove
* Somapacitan
* Somatosalm
* Somatotropin
* Somatropin pegol
* Somatrem
* Sometribove
* Somatrogon (MOD-4023; hGH-CTP)
* Somavaratan
* Somavubove
* Somidobove

* Antagonists: G120K-hGH
* Pegvisomant

* Antisense oligonucleotides: Atesidorsen

* Binding proteins: GHBP

GHIH
(somatostatin)|

* Agonists: BIM-23052
* CH-275
* Cortistatin-14
* Depreotide
* Edotreotide
* Ilatreotide
* L-803,087
* L-817,818
* Lanreotide
* NNC 26-9100
* Octreotate
* Octreotide
* Pasireotide
* Pentetreotide
* RC-160
* Seglitide
* Somatostatin (GHIH)
* Somatostatin (1-28)
* SRIF-14
* SRIF-28
* TT-232
* Vapreotide
* Veldoreotide

* Antagonists: BIM-23056
* Cyclosomatostatin
* CYN-154806
* Satoreotide

GHRH
(somatocrinin)|

* Agonists: Peptide: ALRN-5281
* CJC-1295
* Dumorelin
* GHRH
* Modified GRF (1-29)
* Rismorelin
* Sermorelin
* Somatorelin
* Tesamorelin

* Antagonists: MZ-5-156

GHS
(ghrelin)|

* Agonists: Peptide: Alexamorelin
* Cortistatin-14
* EP-51216
* Examorelin (hexarelin)
* Ghrelin
* GHRP-1
* GHRP-3
* GHRP-4
* GHRP-5
* GHRP-6
* Ipamorelin
* Lenomorelin
* Livoletide
* LY-444711
* Pralmorelin (GHRP-2)
* Relamorelin
* Tabimorelin
* Ulimorelin; Non-peptide: Adenosine
* Anamorelin
* Capromorelin
* CP-464709
* Ibutamoren (MK-677)
* L-692,585
* Macimorelin
* SM-130686; Unsorted: LY-426410
* LY-444711

* Antagonists: A-778193
* Cortistatin-8
* (D-Lys³)-GHRP-6
* JMV2959
* YIL-781

IGF-1
(somatomedin)|

* See here instead.

* See also: Receptor/signaling modulators • Signaling peptide/protein receptor modulators

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Edotreotide&oldid=224246"
*[CID]: Compound ID
*[EU]: European Union
*[UK]: United Kingdom
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[GH]: Growth hormone
*[IGF-1]: Insulin-like growth factor 1
*[GHBP]: Growth hormone-binding protein
*[GHIH]: Growth hormone-inhibiting hormone
*[GHRH]: Growth hormone releasing hormone
*[GHS]: Growth hormone secretagogue