| Revision as of 13:26, 1 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'UNII', 'CASNo').← Previous edit |
Latest revision as of 22:45, 12 September 2024 edit undoGraeme Bartlett (talk | contribs)Administrators249,716 edits merge infobox sections |
| (48 intermediate revisions by 28 users not shown) |
| Line 1: |
Line 1: |
|
{{chembox |
|
{{chembox |
|
|
| Verifiedfields = changed |
| ⚫ |
| ImageFile = DOTATOC.png |
|
|
|
| Watchedfields = changed |
| ⚫ |
| ImageName = |
|
|
|
| verifiedrevid = 458457286 |
|
⚫ |
| ImageFile = Edotreotide.svg |
|
⚫ |
| ImageName = |
|
|
| ImageSize = 250px |
|
| IUPACName = 2-carbamoyl]-7--16--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 |
|
| IUPACName = 2-carbamoyl]-7--16--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 = |
|
| OtherNames = SomaKit TOC |
|
| Section1 = {{Chembox Identifiers |
|
| Section1 = {{Chembox Identifiers |
|
⚫ |
| CASNo = 204318-14-9 |
| ⚫ |
| SMILES = CC(C1C(=O)NC(CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)CCCCN)CC2=CNC3=CC=CC=C32)CC4=CC=C(C=C4)O)NC(=O)C(CC5=CC=CC=C5)NC(=O)CN6CCN(CCN(CCN(CC6)CC(=O)O)CC(=O)O)CC(=O)O)C(=O)NC(CO)C(C)O)O |
|
|
|
| CASNo_Ref = {{cascite|changed|??}} |
| ⚫ |
| CASNo = <!-- blanked - oldvalue: 204318-14-9 --> |
|
|
| CASNo_Ref = |
|
| ChEMBL = 408350 |
|
| RTECS = |
|
| DrugBank = DB15494 |
|
| UNII = U194AS08HZ |
|
| RTECS = |
|
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
|
| UNII = U194AS08HZ |
|
| PubChem = 158782 |
|
| PubChem = 158782 |
|
|
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
| ⚫ |
| 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 |
|
|
|
| ChemSpiderID = 139675 |
| ⚫ |
| InChIKey = RZHKDBRREKOZEW-AAXZNHDCSA-N |
|
|
⚫ |
| SMILES = C(1C(=O)N(CSSC(C(=O)N(C(=O)N(C(=O)N(C(=O)N1)CCCCN)Cc2cc3c2cccc3)Cc4ccc(cc4)O)NC(=O)(Cc5ccccc5)NC(=O)CN6CCN(CCN(CCN(CC6)CC(=O)O)CC(=O)O)CC(=O)O)C(=O)N(CO)(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 |
|
| Section2 = {{Chembox Properties |
|
| C=65 | H=92 | N=14 | O=18 | S=2 |
|
| C=65 | H=92 | N=14 | O=18 | S=2 |
|
| Appearance = |
|
| Appearance = |
|
| Density = |
|
| Density = |
|
| Solubility = |
|
| Solubility = |
|
| MeltingPt = |
|
| MeltingPt = |
|
| BoilingPt = |
|
| BoilingPt = |
|
| pKa = |
|
| pKa = |
|
| pKb = |
|
| pKb = |
|
| Viscosity = |
|
| Viscosity = |
|
}} |
|
}} |
|
| Section3 = {{Chembox Structure |
|
| Section3 = {{Chembox Pharmacology |
|
|
| Licence_EU=yes |
|
| MolShape = |
|
|
| Coordination = |
|
| ATCvet = |
|
|
| ATCCode_prefix = |
|
| CrystalStruct = |
|
|
| Dipole = |
|
| 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=] (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 |
|
| Section7 = {{Chembox Hazards |
|
| ExternalMSDS = |
|
| ExternalMSDS = |
|
| MainHazards = |
|
| MainHazards = |
|
| FlashPt = |
|
| FlashPt = |
|
| RPhrases = |
|
|
| SPhrases = |
|
|
}} |
|
}} |
|
}} |
|
}} |
| ⚫ |
] labelled edotreotide]] |
|
| ⚫ |
'''Edotreotide''' (], codenamed '''SMT487''', also known as (DOTA<sup>0</sup>-Phe<sup>1</sup>-Tyr<sup>3</sup>)octreotide, or '''DOTATOC''') is a substance which, when bound to various ], is used in the treatment and diagnosis of certain types of cancer.<ref>Martindale, The Extra Pharmacopoeia, 30th ed, p1161.</ref> |
|
|
|
|
|
|
⚫ |
'''Edotreotide''' (], also known as (]<sup>0</sup>-]<sup>1</sup>-]<sup>3</sup>) ], '''DOTA-TOC''', '''DOTATOC''') is a substance which, when bound to various ], 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 ]. |
|
It has been the subject of a trial by the ] to determine its effects in young cancer patients (up to 25 years of age) for its ability to locate ] cancer cells without harming normal cells. Specific cancers being included in the trial include ], childhood ]s and ].<ref></ref> |
|
|
|
|
|
|
==See also== |
|
==Yttrium-90== |
| ⚫ |
* ], a similar compound |
|
|
|
|
|
|
|
A ] of ] 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 ], childhood ]s and ].<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> |
| ⚫ |
==References== |
|
|
|
|
|
|
A ] for the use of <sup>90</sup>Y DOTA-TOC for patients with ] ], where ] 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> |
|
|
|
|
⚫ |
:] labeled edotreotide]]{{clear left}} |
|
|
|
|
|
==Lutetium-177== |
|
|
|
|
|
] labelled edotreotide (<sup>177</sup>Lu-DOTA-TOC), with the ] Solucin, is the subject of a ] for treatment of ]s.<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 ] by the ] 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 == |
|
⚫ |
* ], a similar compound |
|
|
|
|
⚫ |
== References == |
|
{{reflist}} |
|
{{reflist}} |
|
* {{pmid|20194865}} |
|
|
|
|
|
|
|
{{GH/IGF-1 axis signaling modulators}} |
| ⚫ |
] |
|
|
|
{{Portal bar | Medicine}} |
|
|
|
|
|
|
] |
|
⚫ |
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
|
|
|
{{antineoplastic-drug-stub}} |
|
|
|
|
|
|
|
{{pharma-stub}} |
|
] |
|