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Copper Cu-64 Dotatate

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ACTIVE PHARMA INGREDIENTS

1 API Suppliers, 1 USDMF, 2 NDC API

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1 USDMF
2 NDC API

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1 FDF Dossiers, 1 FDA Orange Book

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1 FDA Orange Book

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3 US Patents, 2 US Exclusivities

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3 US Patents
2 US Exclusivities

Synopsis

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Chemistry

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Also known as: Copper cu 64 dotatate, Copper 64-dota-tate, Copper cu-64 dotatate, N3858377kc, 1426155-87-4, Copper (64cu) oxodotreotide

Molecular Formula

C₆₅H₈₈CuN₁₄O₁₉S₂

Molecular Weight

1497.5 g/mol

InChI Key

IJRLLVFQGCCPPI-NVGRTJHCSA-L

Copper Cu 64 Dotatate is a radioconjugate consisting of the somatostatin analog tyrosine-3-octreotate (Tyr3-octreotate or TATE) labeled, via the macrocyclic chelating agent 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetra-acetic acid (DOTA), with the positron emission tomography (PET) tracer copper Cu 64, which may be used to image somatostatin receptor (SSTR)-expressing neuroendocrine tumors (NETs) upon PET. Upon administration of copper Cu 64 Dotatate, the TATE moiety targets and binds to SSTRs, with a much higher affinity for type 2 SSTR, present on the cell membranes of many types of NETs. This allows for visualization of SSTR-positive tumor cells upon PET. SSTR subtypes have been shown to be present in large numbers on NETs and their metastases, while most other normal tissues express low levels of SSTR subtypes.

1 2D Structure

Copper Cu-64 Dotatate

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-[[(1S,2R)-1-carboxy-2-hydroxypropyl]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]-10-(carboxylatomethyl)-7-(carboxymethyl)-1,4,7,10-tetrazacyclododec-1-yl]acetate;copper-64(2+)

2.1.2 InChI

InChI=1S/C65H90N14O19S2.Cu/c1-38(80)56-64(96)73-51(63(95)75-57(39(2)81)65(97)98)37-100-99-36-50(72-59(91)47(28-40-10-4-3-5-11-40)68-52(83)32-76-20-22-77(33-53(84)85)24-26-79(35-55(88)89)27-25-78(23-21-76)34-54(86)87)62(94)70-48(29-41-15-17-43(82)18-16-41)60(92)71-49(30-42-31-67-45-13-7-6-12-44(42)45)61(93)69-46(58(90)74-56)14-8-9-19-66;/h3-7,10-13,15-18,31,38-39,46-51,56-57,67,80-82H,8-9,14,19-30,32-37,66H2,1-2H3,(H,68,83)(H,69,93)(H,70,94)(H,71,92)(H,72,91)(H,73,96)(H,74,90)(H,75,95)(H,84,85)(H,86,87)(H,88,89)(H,97,98);/q;+2/p-2/t38-,39-,46+,47-,48+,49-,50+,51+,56+,57+;/m1./s1/i;1+0

2.1.3 InChI Key

IJRLLVFQGCCPPI-NVGRTJHCSA-L

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(C(C)O)C(=O)O)O.[Cu+2]

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]([C@@H](C)O)C(=O)O)O.[64Cu+2]

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Copper Cu-64 Dotatate

2. Copper Oxodotreotide Cu-64

3. Dotatate

2.2.2 Depositor-Supplied Synonyms

1. Copper Cu 64 Dotatate

2. Copper 64-dota-tate

3. Copper Cu-64 Dotatate

4. N3858377kc

5. 1426155-87-4

6. Copper (64cu) Oxodotreotide

7. Unii-n3858377kc

8. Dtxsid901336538

9. Cuprate(2-)-64cu, (n-(2-(4,10-bis((carboxy-kappao)methyl)-7-(carboxymethyl)-1,4,7,10-tetraazacyclododec-1-yl-kappan1,kappan4,kappan7,kappan10)acetyl)-d-phenylalanyl-l-cysteinyl-l-tyrosyl-d-tryptophyl-l-lysyl-l-threonyl-l-cysteinyl-l-threoni

2.3 Create Date

2017-03-16

3 Chemical and Physical Properties

Molecular Formula	C₆₅H₈₈CuN₁₄O₁₉S₂
Molecular Weight	1497.5 g/mol
Hydrogen Bond Donor Count	15
Hydrogen Bond Acceptor Count	26
Rotatable Bond Count	24
Exact Mass	1496.508923 g/mol
Monoisotopic Mass	1496.508923 g/mol
Topological Polar Surface Area	554 Å²
Heavy Atom Count	101
Formal Charge	0
Complexity	2730
Isotope Atom Count	1
Defined Atom Stereocenter Count	10
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Indication

Copper Cu 64 Dotatate is a radiopharmaceutical used with positron emission tomography(PET) to locate somatostatin receptor-positive neuroendocrine tumors.

5 Pharmacology and Biochemistry

5.1 FDA Pharmacological Classification

5.1.1 Pharmacological Classes

Radioactive Diagnostic Agent [EPC]; Positron Emitting Activity [MoA]

5.2 Absorption, Distribution and Excretion

Absorption

Radioactivity can be identified in the kidney, liver, adrenal glands, spleen, and pituitary glands 1-3 hours after copper Cu 64 dotatate is administered.

Route of Elimination

16% - 40% of the original radioactivity was detected in urine 6 hours after the intravenous administration of a single dose.

5.3 Biological Half-Life

The half-life of Copper Cu 64 is 12.7 hours.

5.4 Mechanism of Action

The main target of the positron-emitting Copper Cu 64 dotatate is somatostatin receptor type 2 (SSTR2). SSTR2 is frequently overexpressed in malignant neuroendocrine cells; therefore, accumulation of the radionuclide at the site permits PET imaging to occur.

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