PSMA617 TFA
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MedKoo CAT#: 206934

CAS#: PSMA617 TFA

Description: PSMA-617, also know as vipivotide tetraxetan. It is a ligand used to make 177Lu-PSMA-617, which is a radioactive molecule to fight cancer. PSMA617 possesses a small peptide, which was designed to target prostate-specific membrane antigen (PSMA). PSMA617 demonstrates high radiolytic stability for at least 72 h. PSMA617 has high inhibition potency (equilibrium dissociation constant Ki=2.34±2.94 nM on LNCaP; Ki=0.37±0.21 nM enzymatically determined). 177 Lu-PSMA-617 offers a potential additional life-prolonging treatment option for men with mCRPC.


Chemical Structure

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PSMA617 TFA
CAS# PSMA617 TFA

Theoretical Analysis

MedKoo Cat#: 206934
Name: PSMA617 TFA
CAS#: PSMA617 TFA
Chemical Formula: C57H75F12N9O24
Exact Mass: 0.00
Molecular Weight: 1,498.250
Elemental Analysis: C, 45.70; H, 5.05; F, 15.22; N, 8.41; O, 25.63

Price and Availability

Size Price Availability Quantity
1mg USD 250 Ready to ship
2mg USD 350 Ready to ship
5mg USD 750 Ready to ship
10mg USD 1150 Ready to ship
25mg USD 2250 Ready to Ship
50mg USD 3950 Ready to Ship
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Related CAS #: 1702967-37-0 (free base)   PSMA617 TFA,  

Synonym: PSMA-617; PSMA617; PSMA 617; PSMA617 TFA; PSMA617 triflouroacetic acid salt; vipivotide tetraxetan; DKFZ-PSMa-617;

IUPAC/Chemical Name: (((S)-1-carboxy-5-((S)-3-(naphthalen-2-yl)-2-((1r,4S)-4-((2-(4,7,10-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetamido)methyl)cyclohexane-1-carboxamido)propanamido)pentyl)carbamoyl)-L-glutamic acid tetra(trifluoroacetic acid)

InChi Key: QYDURPMZUHFQEZ-YDPXIYKZSA-N

InChi Code: InChI=1S/C49H71N9O16.4C2HF3O2/c59-40(28-55-17-19-56(29-42(62)63)21-23-58(31-44(66)67)24-22-57(20-18-55)30-43(64)65)51-27-32-8-12-35(13-9-32)45(68)52-39(26-33-10-11-34-5-1-2-6-36(34)25-33)46(69)50-16-4-3-7-37(47(70)71)53-49(74)54-38(48(72)73)14-15-41(60)61;4*3-2(4,5)1(6)7/h1-2,5-6,10-11,25,32,35,37-39H,3-4,7-9,12-24,26-31H2,(H,50,69)(H,51,59)(H,52,68)(H,60,61)(H,62,63)(H,64,65)(H,66,67)(H,70,71)(H,72,73)(H2,53,54,74);4*(H,6,7)/t32-,35-,37-,38-,39-;;;;/m0..../s1

SMILES Code: O=C(O)CC[C@@H](C(O)=O)NC(N[C@H](C(O)=O)CCCCNC([C@@H](NC([C@H]1CC[C@H](CNC(CN2CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC2)=O)CC1)=O)CC3=CC=C4C=CC=CC4=C3)=O)=O.O=C(O)C(F)(F)F.O=C(O)C(F)(F)F.O=C(O)C(F)(F)F.O=C(O)C(F)(F)F

Appearance: White to off-white solid powder

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: Soluble in water and ethanol.

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

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:

Biological target: Vipivotide tetraxetan (PSMA-617) is a high potent prostate-specific membrane antigen (PSMA) inhibitor.
In vitro activity: N/A
In vivo activity: To investigate treatment response as a function of disease burden, mice were treated with 40 kBq of 225Ac-PSMA-617 at either one- (early treatment cohort) or three- weeks (late treatment cohort) post intracardiac injection with C4-2 cells. This activity was chosen as it is well tolerated and efficacious in a subcutaneous mouse model (unpublished data). Early and late treatment resulted in a significant survival benefit (27 vs. 13 weeks; p<0.001). Disease remained stable in the early and late treatment groups for 8 and 3 weeks, respectively (Figure Figure22). One mouse from each group was excluded from analysis as no disease was evident on BLI. Reference: Theranostics. 2020; 10(6): 2612–2620. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7052903/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Water 150.0 100.13
DMSO 125.0 83.43

Preparing Stock Solutions

The following data is based on the product molecular weight 1,498.25 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
Formulation protocol: 1. Ruigrok EAM, van Vliet N, Dalm SU, de Blois E, van Gent DC, Haeck J, de Ridder C, Stuurman D, Konijnenberg MW, van Weerden WM, de Jong M, Nonnekens J. Extensive preclinical evaluation of lutetium-177-labeled PSMA-specific tracers for prostate cancer radionuclide therapy. Eur J Nucl Med Mol Imaging. 2021 May;48(5):1339-1350. doi: 10.1007/s00259-020-05057-6. Epub 2020 Oct 23. PMID: 33094433; PMCID: PMC8113296. 2. Cui C, Hanyu M, Hatori A, Zhang Y, Xie L, Ohya T, Fukada M, Suzuki H, Nagatsu K, Jiang C, Luo R, Shao G, Zhang M, Wang F. Synthesis and evaluation of [64Cu]PSMA-617 targeted for prostate-specific membrane antigen in prostate cancer. Am J Nucl Med Mol Imaging. 2017 Apr 15;7(2):40-52. PMID: 28533936; PMCID: PMC5435610. 3. Stuparu AD, Meyer CAL, Evans-Axelsson SL, Lückerath K, Wei LH, Kim W, Poddar S, Mona CE, Dahlbom M, Girgis MD, Radu CG, Czernin J, Slavik R. Targeted alpha therapy in a systemic mouse model of prostate cancer - a feasibility study. Theranostics. 2020 Feb 3;10(6):2612-2620. doi: 10.7150/thno.42228. PMID: 32194823; PMCID: PMC7052903. 4. Umbricht CA, Köster U, Bernhardt P, Gracheva N, Johnston K, Schibli R, van der Meulen NP, Müller C. Alpha-PET for Prostate Cancer: Preclinical investigation using 149Tb-PSMA-617. Sci Rep. 2019 Nov 28;9(1):17800. doi: 10.1038/s41598-019-54150-w. PMID: 31780798; PMCID: PMC6882876.
In vitro protocol: 1. Ruigrok EAM, van Vliet N, Dalm SU, de Blois E, van Gent DC, Haeck J, de Ridder C, Stuurman D, Konijnenberg MW, van Weerden WM, de Jong M, Nonnekens J. Extensive preclinical evaluation of lutetium-177-labeled PSMA-specific tracers for prostate cancer radionuclide therapy. Eur J Nucl Med Mol Imaging. 2021 May;48(5):1339-1350. doi: 10.1007/s00259-020-05057-6. Epub 2020 Oct 23. PMID: 33094433; PMCID: PMC8113296. 2. Cui C, Hanyu M, Hatori A, Zhang Y, Xie L, Ohya T, Fukada M, Suzuki H, Nagatsu K, Jiang C, Luo R, Shao G, Zhang M, Wang F. Synthesis and evaluation of [64Cu]PSMA-617 targeted for prostate-specific membrane antigen in prostate cancer. Am J Nucl Med Mol Imaging. 2017 Apr 15;7(2):40-52. PMID: 28533936; PMCID: PMC5435610.
In vivo protocol: 1. Stuparu AD, Meyer CAL, Evans-Axelsson SL, Lückerath K, Wei LH, Kim W, Poddar S, Mona CE, Dahlbom M, Girgis MD, Radu CG, Czernin J, Slavik R. Targeted alpha therapy in a systemic mouse model of prostate cancer - a feasibility study. Theranostics. 2020 Feb 3;10(6):2612-2620. doi: 10.7150/thno.42228. PMID: 32194823; PMCID: PMC7052903. 2. Umbricht CA, Köster U, Bernhardt P, Gracheva N, Johnston K, Schibli R, van der Meulen NP, Müller C. Alpha-PET for Prostate Cancer: Preclinical investigation using 149Tb-PSMA-617. Sci Rep. 2019 Nov 28;9(1):17800. doi: 10.1038/s41598-019-54150-w. PMID: 31780798; PMCID: PMC6882876.

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1: Rathke H, Holland-Letz T, Mier W, Flechsig P, Mavriopoulou E, Röhrich M, Kopka K, Hohenfellner M, Giesel FL, Haberkorn UA, Kratochwil C. Response prediction of (177)Lu-PSMA-617 RLT using PSA, Chromogranin A, and LDH. J Nucl Med. 2019 Oct 25. pii: jnumed.119.231431. doi: 10.2967/jnumed.119.231431. [Epub ahead of print] PubMed PMID: 31653712.

2: Morgenroth A, Tinkir E, Vogg ATJ, Sankaranarayanan RA, Baazaoui F, Mottaghy FM. Targeting of prostate-specific membrane antigen for radio-ligand therapy of triple-negative breast cancer. Breast Cancer Res. 2019 Oct 22;21(1):116. doi: 10.1186/s13058-019-1205-1. PubMed PMID: 31640747; PubMed Central PMCID: PMC6805467.

3: Hofman MS, Emmett L, Violet J, Y Zhang A, Lawrence NJ, Stockler M, Francis RJ, Iravani A, Williams S, Azad A, Martin A, McJannett M; ANZUP TheraP team, Davis ID. TheraP: a randomized phase 2 trial of (177) Lu-PSMA-617 theranostic treatment vs cabazitaxel in progressive metastatic castration-resistant prostate cancer (Clinical Trial Protocol ANZUP 1603). BJU Int. 2019 Oct 22. doi: 10.1111/bju.14876. [Epub ahead of print] PubMed PMID: 31638341.

4: Seifert R, Kessel K, Boegemann M, Koehler M, Roll W, Stegger L, Weckesser M, Rahbar K. Additional local therapy of liver metastases in mCRPC patients receiving systemic PSMA targeted therapy. J Nucl Med. 2019 Oct 10. pii: jnumed.119.233429. doi: 10.2967/jnumed.119.233429. [Epub ahead of print] PubMed PMID: 31601703.

5: Kratochwil C, Giesel FL, Heussel CP, Kazdal D, Endris V, Nientiedt C, Bruchertseifer F, Kippenberger M, Rathke H, Leichsenring J, Hohenfellner M, Morgenstern A, Haberkorn U, Duensing S, Stenzinger A. Patients resistant against PSMA-targeting alpha-radiation therapy often harbor mutations in DNA-repair associated genes. J Nucl Med. 2019 Oct 10. pii: jnumed.119.234559. doi: 10.2967/jnumed.119.234559. [Epub ahead of print] PubMed PMID: 31601699.

6: Suman S, Parghane RV, Joshi A, Prabhash K, Bakshi G, Talole S, Banerjee S, Basu S. Therapeutic efficacy, Prognostic variables and Clinical Outcome of (177)Lu-PSMA-617 PRLT in Progressive mCRPC following multiple lines of treatment: prognostic implications of high FDG uptake on dual tracer PET-CT vis-à-vis Gleason Score in such cohort. Br J Radiol. 2019 Oct 10:20190380. doi: 10.1259/bjr.20190380. [Epub ahead of print] PubMed PMID: 31600089.

7: Iravani A, Violet J, Azad A, Hofman MS. Lutetium-177 prostate-specific membrane antigen (PSMA) theranostics: practical nuances and intricacies. Prostate Cancer Prostatic Dis. 2019 Oct 8. doi: 10.1038/s41391-019-0174-x. [Epub ahead of print] Review. PubMed PMID: 31595044.

8: Dos Santos JC, Beijer B, Bauder-Wüst U, Schäfer M, Leotta K, Eder M, Benešová M, Kleist C, Giesel F, Kratochwil C, Kopka K, Haberkorn U, Mier W. Development of Novel PSMA Ligands for Imaging and Therapy with Copper Isotopes. J Nucl Med. 2019 Sep 20. pii: jnumed.119.229054. doi: 10.2967/jnumed.119.229054. [Epub ahead of print] PubMed PMID: 31541034.

9: Kurth J, Krause BJ, Schwarzenböck SM, Bergner C, Hakenberg OW, Heuschkel M. First-in-human dosimetry of gastrin-releasing peptide receptor antagonist [(177)Lu]Lu-RM2: a radiopharmaceutical for the treatment of metastatic castration-resistant prostate cancer. Eur J Nucl Med Mol Imaging. 2019 Sep 3. doi: 10.1007/s00259-019-04504-3. [Epub ahead of print] PubMed PMID: 31482426.

10: Müller C, De Prado Leal M, Dominietto MD, Umbricht CA, Safai S, Perrin RL, Egloff M, Bernhardt P, van der Meulen NP, Weber DC, Schibli R, Lomax AJ. Combination of Proton Therapy and Radionuclide Therapy in Mice: Preclinical Pilot Study at the Paul Scherrer Institute. Pharmaceutics. 2019 Sep 2;11(9). pii: E450. doi: 10.3390/pharmaceutics11090450. PubMed PMID: 31480730.

11: Gosewisch A, Ilhan H, Tattenberg S, Mairani A, Parodi K, Brosch J, Kaiser L, Gildehaus FJ, Todica A, Ziegler S, Bartenstein P, Böning G. 3D Monte Carlo bone marrow dosimetry for Lu-177-PSMA therapy with guidance of non-invasive 3D localization of active bone marrow via Tc-99m-anti-granulocyte antibody SPECT/CT. EJNMMI Res. 2019 Aug 14;9(1):76. doi: 10.1186/s13550-019-0548-z. PubMed PMID: 31414241; PubMed Central PMCID: PMC6694348.

12: Thang SP, Violet J, Sandhu S, Iravani A, Akhurst T, Kong G, Ravi Kumar A, Murphy DG, Williams SG, Hicks RJ, Hofman MS. Poor Outcomes for Patients with Metastatic Castration-resistant Prostate Cancer with Low Prostate-specific Membrane Antigen (PSMA) Expression Deemed Ineligible for (177)Lu-labelled PSMA Radioligand Therapy. Eur Urol Oncol. 2018 Dec 13. pii: S2588-9311(18)30205-0. doi: 10.1016/j.euo.2018.11.007. [Epub ahead of print] PubMed PMID: 31412006.

13: Kessel K, Seifert R, Schäfers M, Weckesser M, Schlack K, Boegemann M, Rahbar K. Second line chemotherapy and visceral metastases are associated with poor survival in patients with mCRPC receiving (177)Lu-PSMA-617. Theranostics. 2019 Jul 9;9(17):4841-4848. doi: 10.7150/thno.35759. eCollection 2019. PubMed PMID: 31410185; PubMed Central PMCID: PMC6691377.

14: Banerjee SR, Kumar V, Lisok A, Chen J, Minn I, Brummet M, Boinapally S, Cole M, Ngen E, Wharram B, Brayton C, Hobbs RF, Pomper MG. (177)Lu-labeled low-molecular-weight agents for PSMA-targeted radiopharmaceutical therapy. Eur J Nucl Med Mol Imaging. 2019 Nov;46(12):2545-2557. doi: 10.1007/s00259-019-04434-0. Epub 2019 Aug 10. PubMed PMID: 31399803.

15: Paller CJ, Piana D, Eshleman JR, Riel S, Denmeade SR, Isaacsson Velho P, Rowe SP, Pomper MG, Antonarakis ES, Luo J, Eisenberger MA. A pilot study of prostate-specific membrane antigen (PSMA) dynamics in men undergoing treatment for advanced prostate cancer. Prostate. 2019 Oct;79(14):1597-1603. doi: 10.1002/pros.23883. Epub 2019 Jul 30. PubMed PMID: 31361358.

16: Müller C, Singh A, Umbricht CA, Kulkarni HR, Johnston K, Benešová M, Senftleben S, Müller D, Vermeulen C, Schibli R, Köster U, van der Meulen NP, Baum RP. Preclinical investigations and first-in-human application of (152)Tb-PSMA-617 for PET/CT imaging of prostate cancer. EJNMMI Res. 2019 Jul 25;9(1):68. doi: 10.1186/s13550-019-0538-1. PubMed PMID: 31346796; PubMed Central PMCID: PMC6658632.

17: Ucar B. Synthesis and characterization of natural lanthanum labelled DOTA-Peptides for simulating radioactive Ac-225 labeling. Appl Radiat Isot. 2019 Nov;153:108816. doi: 10.1016/j.apradiso.2019.108816. Epub 2019 Jul 19. PubMed PMID: 31344650.

18: Abouzayed A, Yim CB, Mitran B, Rinne SS, Tolmachev V, Larhed M, Rosenström U, Orlova A. Synthesis and Preclinical Evaluation of Radio-Iodinated GRPR/PSMA Bispecific Heterodimers for the Theranostics Application in Prostate Cancer. Pharmaceutics. 2019 Jul 23;11(7). pii: E358. doi: 10.3390/pharmaceutics11070358. PubMed PMID: 31340483; PubMed Central PMCID: PMC6680768.

19: Subramaniam RM. Section Editor's Notebook: Prostate Cancer Theranosis in Clinical Practice and in Clinical Trials-(68)Ga-Prostate-Specific Member Antigen (PSMA)-11 PET/CT and (177)Lu-PSMA-617 Therapy. AJR Am J Roentgenol. 2019 Aug;213(2):241-242. doi: 10.2214/AJR.19.21391. PubMed PMID: 31328993.

20: Ray Banerjee S, Minn IL, Kumar V, Josefsson A, Lisok A, Brummet M, Chen J, Kiess A, Baidoo K, Brayton C, Mease RC, Brechbiel M, Sgouros G, Hobbs RF, Pomper MG. Preclinical evaluation of (203/212)Pb-labeled low-molecular-weight compounds for targeted radiopharmaceutical therapy of prostate cancer. J Nucl Med. 2019 Jun 28. pii: jnumed.119.229393. doi: 10.2967/jnumed.119.229393. [Epub ahead of print] PubMed PMID: 31253744.

This product was cited in below papers.
1. Kalidindi TM, Lee SG, Jou K, Chakraborty G, Skafida M, Tagawa ST, Bander NH, Schoder H, Bodei L, Pandit-Taskar N, Lewis JS, Larson SM, Osborne JR, Pillarsetty NVK. A simple strategy to reduce the salivary gland and kidney uptake of PSMA-targeting small molecule radiopharmaceuticals. Eur J Nucl Med Mol Imaging. 2021 Jan 25. doi: 10.1007/s00259-020-05150-w. Epub ahead of print. PMID: 33495926.