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Chemistry

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Also known as: Dotatoc lu-177, (177ludota)-toc, Lutetium lu 177-edotreotide, Lutetium lu-177-edotreotide, Rgo812q0c8, Lutetium lu-177 dota-tyr3-octreotide
Molecular Formula
C65H89LuN14O18S2
Molecular Weight
1595.6  g/mol
InChI Key
XOPYQJXRGHFPOH-NZMVMCJSSA-K
FDA UNII
RGO812Q0C8

Lutetium-177-edotreotide
Lutetium Lu 177-Edotreotide is a radioconjugate consisting of the somatostatin analogue edotreotide labeled with lutetium Lu 177 with potential antineoplastic activities. Lutetium Lu 177-edotreotide binds to somatostatin receptors (SSTRs), with high affinity to type 2 SSTR, present on the cell membranes of many types of neuroendocrine tumor cells. Upon binding and internalization, this radioconjugate specifically delivers a cytotoxic dose of beta radiation to SSTR-positive cells. Edotreotide is produced by substituting tyrosine for phenylalanine at the 3 position of the somatostatin analogue octreotide (Tyr3-octreotide or TOC) and chelated by the bifunctional, macrocyclic chelating agent dodecanetetraacetic acid (DOTA).
1 2D Structure

Lutetium-177-edotreotide

2 Identification
2.1 Computed Descriptors
2.1.1 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(carboxylatomethyl)-1,4,7,10-tetrazacyclododec-1-yl]acetate;lutetium-177(3+)
2.1.2 InChI
InChI=1S/C65H92N14O18S2.Lu/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);/q;+3/p-3/t39-,40-,47+,48-,49+,50-,51-,52+,53+,58+;/m1./s1/i;1+2
2.1.3 InChI Key
XOPYQJXRGHFPOH-NZMVMCJSSA-K
2.1.4 Canonical 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.[Lu+3]
2.1.5 Isomeric 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)CC2=CNC3=CC=CC=C32)CC4=CC=C(C=C4)O)NC(=O)[C@@H](CC5=CC=CC=C5)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.[177Lu+3]
2.2 Other Identifiers
2.2.1 UNII
RGO812Q0C8
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (177)lu-dotatoc

2. (177ludota)-toc

2.3.2 Depositor-Supplied Synonyms

1. Dotatoc Lu-177

2. (177ludota)-toc

3. Lutetium Lu 177-edotreotide

4. Lutetium Lu-177-edotreotide

5. Rgo812q0c8

6. Lutetium Lu-177 Dota-tyr3-octreotide

7. 321835-55-6

8. Lutetium Lu177 Edotreotide

9. Unii-rgo812q0c8

10. Lutetium Lu177 Edotreotide [usan]

11. Who 12604

12. Lutetium (177lu) Edotreotide [who-dd]

2.4 Create Date
2013-06-10
3 Chemical and Physical Properties
Molecular Weight 1595.6 g/mol
Molecular Formula C65H89LuN14O18S2
Hydrogen Bond Donor Count14
Hydrogen Bond Acceptor Count25
Rotatable Bond Count23
Exact Mass1594.53583 g/mol
Monoisotopic Mass1594.53583 g/mol
Topological Polar Surface Area540 Ų
Heavy Atom Count100
Formal Charge0
Complexity2600
Isotope Atom Count1
Defined Atom Stereocenter Count10
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Radiopharmaceuticals

Compounds that are used in medicine as sources of radiation for radiotherapy and for diagnostic purposes. They have numerous uses in research and industry. (Martindale, The Extra Pharmacopoeia, 30th ed, p1161) (See all compounds classified as Radiopharmaceuticals.)


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