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MedKoo Cat#: 125679 | Name: DOTA-TATE
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

DOTA-TATE can be reacted with the radionuclides gallium-68 (T1/2 = 68 min), lutetium-177 (T1/2 = 6.65 d) and copper-64 (T1/2 = 12.7 h) to form radiopharmaceuticals for positron emission tomography (PET) imaging or radionuclide therapy. DOTA-TATE is a compound containing tyrosine3-octreotate, an SSR agonist, and the bifunctional chelator DOTA (tetraxetan). SSRs are found with high density in numerous malignancies, including CNS, breast, lung, and lymphatics.

Chemical Structure

DOTA-TATE
DOTA-TATE
CAS#177943-88-3 (free base)

Theoretical Analysis

MedKoo Cat#: 125679

Name: DOTA-TATE

CAS#: 177943-88-3 (free base)

Chemical Formula: C65H90N14O19S2

Exact Mass: 1434.5900

Molecular Weight: 1435.63

Elemental Analysis: C, 54.38; H, 6.32; N, 13.66; O, 21.17; S, 4.47

Price and Availability

Size Price Availability Quantity
5mg USD 1,650.00 2 Weeks
10mg USD 2,950.00 2 Weeks
100mg USD 6,950.00 2 Weeks
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Related CAS #
177943-89-4 (acetate) 177943-88-3 (free base)
Synonym
Dotatate; DOTA-octreotate; DOTA-TATE; Oxodotreotide
IUPAC/Chemical Name
2,2',2''-(10-(2-(((2R)-1-(((4R,10S,13R,19R)-13-((1H-indol-3-yl)methyl)-10-(4-aminobutyl)-4-(((1S,2S)-1-carboxy-2-hydroxypropyl)carbamoyl)-16-(4-hydroxybenzyl)-7-((R)-1-hydroxyethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-19-yl)amino)-1-oxo-3-phenylpropan-2-yl)amino)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetic acid
InChi Key
QVFLVLMYXXNJDT-DPCFUMSXSA-N
InChi Code
InChI=1S/C65H90N14O19S2/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)/t38-,39+,46+,47-,48?,49-,50+,51+,56?,57+/m1/s1
SMILES Code
C[C@@H](O)C1C(N[C@H](C(N[C@H](C(O)=O)[C@@H](O)C)=O)CSSC[C@H](NC([C@H](NC(CN2CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC2)=O)CC3=CC=CC=C3)=O)C(NC(CC4=CC=C(O)C=C4)C(N[C@H](CC5=CNC6=CC=CC=C65)C(N[C@@H](CCCCN)C(N1)=O)=O)=O)=O)=O
Appearance
To be determined
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
DOTA-TATE can be reacted with the radionuclides gallium-68 (T1/2 = 68 min), lutetium-177 (T1/2 = 6.65 d) and copper-64 (T1/2 = 12.7 h) to form radiopharmaceuticals for positron emission tomography (PET) imaging or radionuclide therapy. 177Lu DOTA-TATE therapy is a form of peptide receptor radionuclide therapy (PRRT) which targets somatostatin receptors (SSR).[3][4] In that form of application it is a form of targeted drug delivery. The role of SSR agonists (i.e. somatostatin and its analogs such as octreotide, somatuline and vapreotide) in neuroendocrine tumours (NETs) is well established, and massive SSR overexpression is present in several NETs. (Tyr3)-octreotate binds the transmembrane receptors of NETs with highest activity for SSR2 and is actively transported into the cell via endocytosis, allowing trapping of the radioactivity and increasing the probability of the desired double-strand DNA breakage (for tumour control). Trapping improves the probability of this kind of effect due to the relatively short range of the beta particles emitted by 177Lu, which have a maximum range in tissue of <2 mm. Bystander effects include cellular damage by free radical formation. 68Ga-NOTA-TATE and 68Ga-DOTA-TATE demonstrated comparable tumour uptake in an AR42J mouse model. An initial clinical study revealed that 68Ga-NOTA-TATE may have reduced background uptake in the major organs such as the liver. Although the subject numbers were limited, further investigation of 68Ga-NOTA-TATE is warranted for detecting SSTR2-positive neuroendocrine tumours.

Preparing Stock Solutions

The following data is based on the product molecular weight 1,435.63 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Sakulpisuti C, Chamroonrat W, Tepmongkol S. Cutaneous Management after Extravasation of High-Concentrated Amino Acid Solution Administered for Renal Protection in PRRT. Tomography. 2022 Feb 3;8(1):356-363. doi: 10.3390/tomography8010029. PMID: 35202194; PMCID: PMC8880062. 2: Prado-Wohlwend S, Del Olmo-García MI, Bello-Arques P, Merino-Torres JF. [177Lu]Lu-DOTA-TATE and [131I]MIBG Phenotypic Imaging- Based Therapy in Metastatic/Inoperable Pheochromocytomas and Paragangliomas: Comparative Results in a Single Center. Front Endocrinol (Lausanne). 2022 Feb 7;13:778322. doi: 10.3389/fendo.2022.778322. PMID: 35197929; PMCID: PMC8859101. 3: Del Olmo-García MI, Prado-Wohlwend S, Bello P, Segura A, Merino-Torres JF. Peptide Receptor Radionuclide Therapy with [177Lu]Lu-DOTA-TATE in Patients with Advanced GEP NENS: Present and Future Directions. Cancers (Basel). 2022 Jan 24;14(3):584. doi: 10.3390/cancers14030584. PMID: 35158852; PMCID: PMC8833790. 4: Mollazadegan K, Skogseid B, Botling J, Akerstrom T, Eriksson B, Welin S, Sundin A, Crona J. Poor outcome after systemic therapy in secondary high-grade pancreatic neuroendocrine tumors. Endocr Connect. 2022 Feb 1:EC-21-0604.R1. doi: 10.1530/EC-21-0604. Epub ahead of print. PMID: 35148276. 5: Khatami A, Sistani G, Sutherland DEK, DeBrabandere S, Reid RH, Laidley DT. Toxicity and Tolerability of 177Lu-DOTA-TATE PRRT with a Modified Administered Activity Protocol in NETs of Variable Origin - A Phase 2 Registry Study. Curr Radiopharm. 2021 Aug 9. doi: 10.2174/1874471014666210810100435. Epub ahead of print. PMID: 35135467. 6: Beil FT, Stürznickel J, Rolvien T, Amling M, Oheim R. Tumorlokalisation und Therapie der onkogenen Osteomalazie [Tumor localization and treatment of tumor- induced osteomalacia]. Z Rheumatol. 2022 Feb 1. German. doi: 10.1007/s00393-022-01160-1. Epub ahead of print. PMID: 35103802. 7: Korsen JA, Kalidindi TM, Khitrov S, Samuels ZV, Chakraborty G, Gutierrez JA, Poirier JT, Rudin CM, Chen Y, Morris MJ, Pillarsetty N, Lewis JS. Molecular imaging of Neuroendocrine Prostate Cancer by targeting Delta-like Ligand 3. J Nucl Med. 2022 Jan 20:jnumed.121.263221. doi: 10.2967/jnumed.121.263221. Epub ahead of print. PMID: 35058323. 8: Gustafsson J, Taprogge J. Theoretical aspects on the use of single-time-point dosimetry for radionuclide therapy. Phys Med Biol. 2022 Jan 19;67(2). doi: 10.1088/1361-6560/ac46e0. PMID: 34965519. 9: Mansi R, Plas P, Vauquelin G, Fani M. Distinct In Vitro Binding Profile of the Somatostatin Receptor Subtype 2 Antagonist [177Lu]Lu-OPS201 Compared to the Agonist [177Lu]Lu-DOTA-TATE. Pharmaceuticals (Basel). 2021 Dec 4;14(12):1265. doi: 10.3390/ph14121265. PMID: 34959665; PMCID: PMC8706879. 10: Spada F, Campana D, Lamberti G, Laudicella R, Dellamano R, Dellamano L, Leeuwenkamp O, Baldari S. [177Lu]Lu-DOTA-TATE versus standard of care in adult patients with gastro-enteropancreatic neuroendocrine tumours (GEP- NETs): a cost-consequence analysis from an Italian hospital perspective. Eur J Nucl Med Mol Imaging. 2021 Dec 24. doi: 10.1007/s00259-021-05656-x. Epub ahead of print. PMID: 34950969. 11: Del Olmo-Garcia MI, Prado-Wohlwend S, Andres A, Soriano JM, Bello P, Merino- Torres JF. Somatostatin and Somatostatin Receptors: From Signaling to Clinical Applications in Neuroendocrine Neoplasms. Biomedicines. 2021 Dec 1;9(12):1810. doi: 10.3390/biomedicines9121810. PMID: 34944626; PMCID: PMC8699000. 12: Prado-Wohlwend S, Bernal-Vergara JC, Utrera-Costero A, Cañón-Sánchez JR, Agudelo-Cifuentes M, Bello-Arques P; Endocrinology Working Group of the SEMNIM. Peptide receptor radionuclide therapy with [177Lu]Lu-DOTA-TATE. Rev Esp Med Nucl Imagen Mol (Engl Ed). 2022 Jan-Feb;41(1):55-65. doi: 10.1016/j.remnie.2021.11.001. Epub 2021 Dec 14. PMID: 34920969. 13: Glover M, Caplin M, Leeuwenkamp OR, Longworth L. Use of [177Lu]Lu-DOTA-TATE in the treatment of gastroenteropancreatic neuroendocrine tumours: Results of a UK cost-effectiveness modelling study. EJC Suppl. 2021 Nov 9;16:14-23. doi: 10.1016/j.ejcsup.2021.06.003. PMID: 34912479; PMCID: PMC8591195. 14: Khan MS, Stamp E, Sammon C, Brabander T, de Herder WW, Pavel ME. Matching- adjusted indirect treatment comparison of [177Lu]Lu-DOTA-TATE, everolimus and sunitinib in advanced, unresectable gastroenteropancreatic neuroendocrine tumours: Relative effectiveness of [177Lu]Lu-DOTA-TATE in gastroenteropancreatic neuroendocrine tumours. EJC Suppl. 2021 Nov 9;16:5-13. doi: 10.1016/j.ejcsup.2021.06.002. PMID: 34912478; PMCID: PMC8591206. 15: Caplin ME. Can the peptide receptor radionuclide therapy [177Lu]Lu-DOTA-TATE provide a net benefit for NET patients? EJC Suppl. 2021 Nov 9;16:1-4. doi: 10.1016/j.ejcsup.2021.06.001. PMID: 34912477; PMCID: PMC8591180. 16: Kamaldeep, Wanage G, Loharkar S, Das T, Basu S, Banerjee S. Estimation of Absorbed Doses of Indigenously Produced "Direct-route" Lutetium-177-Labeled DOTA-TATE PRRT in Normal Organs and Tumor Lesions in Patients of Metastatic Neuroendocrine Tumors: Comparison with No-Carrier-Added [177Lu]Lu- DOTA-TATE and the Trend with Multiple Cycles. Cancer Biother Radiopharm. 2021 Dec 15. doi: 10.1089/cbr.2021.0340. Epub ahead of print. PMID: 34910891. 17: Prigent K, Vigne J. Advances in Radiopharmaceutical Sciences for Vascular Inflammation Imaging: Focus on Clinical Applications. Molecules. 2021 Nov 24;26(23):7111. doi: 10.3390/molecules26237111. PMID: 34885690; PMCID: PMC8659223. 18: Anzola LK, Rivera JN, Ramirez JC, Signore A, Mut F. Molecular Imaging of Vulnerable Coronary Plaque with Radiolabeled Somatostatin Receptors (SSTR). J Clin Med. 2021 Nov 25;10(23):5515. doi: 10.3390/jcm10235515. PMID: 34884218; PMCID: PMC8658082. 19: de Vries-Huizing DMV, Versleijen MWJ, Sinaasappel M, Walraven I, Geluk- Jonker MM, Tesselaar MET, Hendrikx JJMA, de Wit-van der Veen BJ, Stokkel MPM. Haematotoxicity during peptide receptor radionuclide therapy: Baseline parameters differences and effect on patient's therapy course. PLoS One. 2021 Nov 18;16(11):e0260073. doi: 10.1371/journal.pone.0260073. PMID: 34793530; PMCID: PMC8601524. 20: Amoui M, Ahmadi R, Qutbi M, Asli IN. Somatostatin-receptor avidity of pancreatic neuroendocrine tumor thrombus in porto-caval venous systems on 99mTc-Octreotide and posttherapeutic 177Lu-DOTA-TATE scans. World J Nucl Med. 2021 Aug 20;20(3):324-326. doi: 10.4103/wjnm.wjnm_35_21. PMID: 34703406; PMCID: PMC8488892.

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