PSMA-11 free base
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MedKoo CAT#: 556010

CAS#: 1366302-52-4 (free base)

Description: PSMA-11, also known as DKFZ-​PSMA-​11, HBED-CC-PSMA or Psma-hbed-CC, is a ligand to make gallium Ga 68-labeled PSMA-11, which has potential use as a tracer for PSMA-expressing tumors during positron emission tomography (PET). Upon intravenous administration of gallium Ga 68-labeled PSMA-11, the Glu-urea-Lys(Ahx) moiety targets and binds to PSMA-expressing tumor cells. Upon internalization, PSMA-expressing tumor cells can be detected during PET imaging. PSMA, a tumor-associated antigen and type II transmembrane protein, is expressed on the membrane of prostatic epithelial cells and overexpressed on prostate tumor cells


Chemical Structure

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PSMA-11 free base
CAS# 1366302-52-4 (free base)

Theoretical Analysis

MedKoo Cat#: 556010
Name: PSMA-11 free base
CAS#: 1366302-52-4 (free base)
Chemical Formula: C44H62N6O17
Exact Mass: 946.4171
Molecular Weight: 947.005
Elemental Analysis: C, 55.81; H, 6.60; N, 8.87; O, 28.72

Price and Availability

Size Price Availability Quantity
1.0mg USD 275.0 Ready to ship
5.0mg USD 1150.0 Ready to ship
10.0mg USD 1950.0 Ready to ship
25.0mg USD 3650.0 Ready to ship
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Related CAS #: 2412149-32-5 (TFA)   1366302-52-4 (free base)    

Synonym: DKFZ-​PSMA-​11; Psma-hbed-CC; PSMA-11; PSMA11; PSMA 11; HBED-CC-PSMA; PSMA-11 TFA; Psma-hbed-CC

IUPAC/Chemical Name: (3S,7S)-22-(3-(((2-((5-(2-Carboxyethyl)-2-hydroxybenzyl)(carboxymethyl)amino)ethyl)(carboxymethyl)amino)methyl)-4-hydroxyphenyl)-5,13,20-trioxo-4,6,12,19-tetraazadocosane-1,3,7-tricarboxylic acid

InChi Key: QJUIUFGOTBRHKP-LQJZCPKCSA-N

InChi Code: InChI=1S/C44H62N6O17/c51-34-13-8-28(22-30(34)24-49(26-40(59)60)20-21-50(27-41(61)62)25-31-23-29(9-14-35(31)52)11-16-38(55)56)10-15-37(54)46-18-4-1-2-7-36(53)45-19-5-3-6-32(42(63)64)47-44(67)48-33(43(65)66)12-17-39(57)58/h8-9,13-14,22-23,32-33,51-52H,1-7,10-12,15-21,24-27H2,(H,45,53)(H,46,54)(H,55,56)(H,57,58)(H,59,60)(H,61,62)(H,63,64)(H,65,66)(H2,47,48,67)/t32-,33-/m0/s1

SMILES Code: O=C(O)CC[C@H](NC(N[C@@H](CCCCNC(CCCCCNC(CCC1=CC=C(O)C(CN(CC(O)=O)CCN(CC2=CC(CCC(O)=O)=CC=C2O)CC(O)=O)=C1)=O)=O)C(O)=O)=O)C(O)=O

Appearance: Solid powder

Purity: >97% (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

Biological target: Ga 68 PSMA-11 binds to prostate-specific membrane antigen (PSMA). It binds to cells that express PSMA, including malignant prostate cancer cells, which usually overexpress PSMA. Gallium-68 (Ga 68) is a β+ emitting radionuclide that allows positron emission tomography (PET).
In vitro activity: The procedure was completely automated and provided a high radiochemical yield. It can be performed several times a day, facilitating the clinical demand of this radiopharmaceutical. Reference: Reverchon J, Khayi F, Roger M, Moreau A, Kryza D. Optimization of the radiosynthesis of [68Ga]Ga-PSMA-11 using a Trasis MiniAiO synthesizer: do we need to heat and purify? Nucl Med Commun. 2020 Sep;41(9):977-985. doi: 10.1097/MNM.0000000000001233. PMID: 32796487.
In vivo activity: A total of 635 men were enrolled with a median age of 69 years (range, 44-95 years). On a per-patient basis, PPV was 0.84 (95% CI, 0.75-0.90) by histopathologic validation (primary endpoint, n = 87) and 0.92 (95% CI, 0.88-0.95) by the composite reference standard (n = 217). 68Ga-PSMA-11 PET localized recurrent prostate cancer in 475 of 635 (75%) patients; detection rates significantly increased with prostate-specific antigen (PSA): 38% for <0.5 ng/mL (n = 136), 57% for 0.5 to <1.0 ng/mL (n = 79), 84% for 1.0 to <2.0 ng/mL (n = 89), 86% for 2.0 to <5.0 ng/mL (n = 158), and 97% for ≥5.0 ng/mL (n = 173, P < .001). Interreader reproducibility was substantial (Fleiss κ, 0.65-0.78). There were no serious adverse events associated with 68Ga-PSMA-11 administration. PET-directed focal therapy alone led to a PSA drop of 50% or more in 31 of 39 (80%) patients.Using blinded reads and independent lesion validation, high PPV for 68Ga-PSMA-11 PET, detection rate and interreader agreement for localization of recurrent prostate cancer. Reference: Fendler WP, Calais J, Eiber M, Flavell RR, Mishoe A, Feng FY, Nguyen HG, Reiter RE, Rettig MB, Okamoto S, Emmett L, Zacho HD, Ilhan H, Wetter A, Rischpler C, Schoder H, Burger IA, Gartmann J, Smith R, Small EJ, Slavik R, Carroll PR, Herrmann K, Czernin J, Hope TA. Assessment of 68Ga-PSMA-11 PET Accuracy in Localizing Recurrent Prostate Cancer: A Prospective Single-Arm Clinical Trial. JAMA Oncol. 2019 Jun 1;5(6):856-863. doi: 10.1001/jamaoncol.2019.0096. PMID: 30920593; PMCID: PMC6567829.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
To be determined 100.0 105.6

Preparing Stock Solutions

The following data is based on the product molecular weight 947.005 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: Reverchon J, Khayi F, Roger M, Moreau A, Kryza D. Optimization of the radiosynthesis of [68Ga]Ga-PSMA-11 using a Trasis MiniAiO synthesizer: do we need to heat and purify? Nucl Med Commun. 2020 Sep;41(9):977-985. doi: 10.1097/MNM.0000000000001233. PMID: 32796487.
In vitro protocol: Reverchon J, Khayi F, Roger M, Moreau A, Kryza D. Optimization of the radiosynthesis of [68Ga]Ga-PSMA-11 using a Trasis MiniAiO synthesizer: do we need to heat and purify? Nucl Med Commun. 2020 Sep;41(9):977-985. doi: 10.1097/MNM.0000000000001233. PMID: 32796487.
In vivo protocol: Fendler WP, Calais J, Eiber M, Flavell RR, Mishoe A, Feng FY, Nguyen HG, Reiter RE, Rettig MB, Okamoto S, Emmett L, Zacho HD, Ilhan H, Wetter A, Rischpler C, Schoder H, Burger IA, Gartmann J, Smith R, Small EJ, Slavik R, Carroll PR, Herrmann K, Czernin J, Hope TA. Assessment of 68Ga-PSMA-11 PET Accuracy in Localizing Recurrent Prostate Cancer: A Prospective Single-Arm Clinical Trial. JAMA Oncol. 2019 Jun 1;5(6):856-863. doi: 10.1001/jamaoncol.2019.0096. PMID: 30920593; PMCID: PMC6567829.

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1: Iudicello A, Boschi S, Ghedini P, Lohr F, Panareo S. Optimization of Precursor Preparation in PSMA-11 Radiolabeling to Obtain a Highly Reproducible Radiochemical Yield. Pharmaceuticals (Basel). 2022 Mar 11;15(3):343. doi: 10.3390/ph15030343. PMID: 35337140; PMCID: PMC8953397.

2: Hoffmann MA, von Eyben FE, Fischer N, Rosar F, Müller-Hübenthal J, Buchholz HG, Wieler HJ, Schreckenberger M. Comparison of [18F]PSMA-1007 with [68Ga]Ga-PSMA-11 PET/CT in Restaging of Prostate Cancer Patients with PSA Relapse. Cancers (Basel). 2022 Mar 14;14(6):1479. doi: 10.3390/cancers14061479. PMID: 35326629; PMCID: PMC8946234.

3: Tseng JR, Chang SH, Wu YY, Fan KH, Yu KJ, Yang LY, Hsiao IT, Liu FY, Pang ST. Impact of Three-Month Androgen Deprivation Therapy on [68Ga]Ga-PSMA-11 PET/CT Indices in Men with Advanced Prostate Cancer-Results from a Pilot Prospective Study. Cancers (Basel). 2022 Mar 4;14(5):1329. doi: 10.3390/cancers14051329. PMID: 35267637; PMCID: PMC8909781.

4: Rodnick ME, Sollert C, Stark D, Clark M, Katsifis A, Hockley BG, Parr DC, Frigell J, Henderson BD, Bruton L, Preshlock S, Abghari-Gerst M, Piert MR, Fulham MJ, Eberl S, Gagnon K, Scott PJH. Synthesis of 68Ga- radiopharmaceuticals using both generator-derived and cyclotron-produced 68Ga as exemplified by [68Ga]Ga-PSMA-11 for prostate cancer PET imaging. Nat Protoc. 2022 Mar 4. doi: 10.1038/s41596-021-00662-7. Epub ahead of print. PMID: 35246649.

5: Morawitz J, Kirchner J, Hertelendy J, Loberg C, Schimmöller L, Dabir M, Häberle L, Mamlins E, Antke C, Arsov C, Antoch G, Sawicki LM. Is there a diagnostic benefit of late-phase abdomino-pelvic PET/CT after urination as part of whole-body 68 Ga-PSMA-11 PET/CT for restaging patients with biochemical recurrence of prostate cancer after radical prostatectomy? EJNMMI Res. 2022 Mar 4;12(1):12. doi: 10.1186/s13550-022-00885-z. PMID: 35244791; PMCID: PMC8897520.

6: Rosar F, Bartholomä M, Maus S, Privé BM, Khreish F, Franssen GM, Derks YHW, Nagarajah J, Ezziddin S. 89Zr-PSMA-617 PET/CT May Reveal Local Recurrence of Prostate Cancer Unidentified by 68Ga-PSMA-11 PET/CT. Clin Nucl Med. 2022 Feb 28. doi: 10.1097/RLU.0000000000004108. Epub ahead of print. PMID: 35234197.

7: Ceci F, Rovera G, Iorio GC, Guarneri A, Chiofalo V, Passera R, Oderda M, Dall'Armellina S, Liberini V, Grimaldi S, Bellò M, Gontero P, Ricardi U, Deandreis D. Event-free survival after 68 Ga-PSMA-11 PET/CT in recurrent hormone-sensitive prostate cancer (HSPC) patients eligible for salvage therapy. Eur J Nucl Med Mol Imaging. 2022 Feb 26. doi: 10.1007/s00259-022-05741-9. Epub ahead of print. PMID: 35217883.

8: Fütterer JJ, Nagarajah J. Research Highlight: 68Ga-PSMA-11 PET Imaging for Pelvic Nodal Metastasis in Prostate Cancer. Korean J Radiol. 2022 Mar;23(3):293-294. doi: 10.3348/kjr.2021.0938. PMID: 35213092; PMCID: PMC8876656.

9: Diego RPS, Baptista GR, Filho RVAO, de Albuquerque ETB, de Castro JDV, Dos Santos KM, de Lucena Santos JÂ, da Silveira Oliveira GF, de Lucena Santos PÂ. Application of 68Ga-PSMA-11 PET/CT in the Diagnosis of Prostate Cancer Clinical Relapse. Curr Radiopharm. 2022 Feb 23. doi: 10.2174/1874471015666220223100750. Epub ahead of print. PMID: 35209836.

10: Cegla P, Wojewódzka M, Gorczewska I, Chalewska W, Łapińska G, Ochman P, Sackiewicz A, Dedecjus M. Identification of the Optimal Cut-Off Value of PSA for Assessing Severity of Disease in [68Ga]Ga-PSMA-11 PET/CT Study in Prostate Cancer Patients after Radical Prostatectomy. Diagnostics (Basel). 2022 Jan 29;12(2):349. doi: 10.3390/diagnostics12020349. PMID: 35204440; PMCID: PMC8871181.

11: Chandekar KR, Sood A, Kumar R, Singh H, Singh SK. 68Ga-PSMA-11 uptake in tracheal mucus plug - a potential pitfall. Nucl Med Mol Imaging. 2022 Feb;56(1):63-66. doi: 10.1007/s13139-021-00729-z. Epub 2022 Jan 31. PMID: 35186161; PMCID: PMC8828821.

12: Gauthé M, Sargos P, Benziane Ouaritini N, Barret E, Beauval JB, Brureau L, Créhange G, Dariane C, Fiard G, Fromont G, Mathieu R, Renard-Penna R, Roubaud G, Ruffion A, Rouprêt M, Ploussard G; Cancerology Committee of the French Association of Urology. Restaging of Patients with Persistently Elevated Prostate-specific Antigen After Radical Prostatectomy Using [68Ga]-PSMA-11 Positron Emission Tomography/Computed Tomography: Impact on Disease Management. Eur Urol. 2022 Apr;81(4):e87-e89. doi: 10.1016/j.eururo.2022.01.012. Epub 2022 Feb 4. PMID: 35125228.

13: Sarikaya I. Letter to the Editor: 68Ga-PSMA-11 for renal cortical PET imaging. Clin Transl Imaging. 2022 Jan 25:1-2. doi: 10.1007/s40336-021-00475-4. Epub ahead of print. PMID: 35096684; PMCID: PMC8786448.

14: Li JF, Qin LP, Wu QY, Guo XH, Yang JZ, Wan QC, Cheng MH, Xie LJ. The value of 68 Ga-PSMA-11 positron emission tomography/computerized tomography in evaluating the lacrimal and salivary glands function. Clin Rheumatol. 2022 Jan 28. doi: 10.1007/s10067-021-06038-2. Epub ahead of print. PMID: 35089469.

15: Prive BM, Peters S, Uijen MJM, Janssen MJR, van Gemert WAM, Kreissl MC, Ezziddin S, Konijnenberg MW, Nagarajah J. Letter to the Editor RE: Tumor sink effect in 68Ga-PSMA-11 PET: Myth or Reality? J Nucl Med. 2022 Jan 13:jnumed.122.263802. doi: 10.2967/jnumed.122.263802. Epub ahead of print. PMID: 35027370.

16: Zhao Q, Yang B, Dong A, Zuo C. 18F-PSMA-11 PET/MRI in Prostate Adenocarcinoma With Mucinous Features. Clin Nucl Med. 2022 Jan 11. doi: 10.1097/RLU.0000000000003995. Epub ahead of print. PMID: 35020651.

17: Xu G, Lu Y. 68Ga-PSMA-11 PET Identified Tumor Recurrence in Prostatectomy Bed With Rising PSA of 0.9 ng/mL but Negative on MRI and 18F-Fluciclovine PET Scan. Clin Nucl Med. 2022 Apr 1;47(4):378-379. doi: 10.1097/RLU.0000000000003994. PMID: 35020642.

18: Pitalua-Cortes Q, García-Perez FO, Vargas-Ahumada J, Gonzalez-Rueda S, Gomez-Argumosa E, Ignacio-Alvarez E, Soldevilla-Gallardo I, Torres-Agredo L. Head-to-Head Comparison of 68Ga-PSMA-11 and 131I in the Follow-Up of Well-Differentiated Metastatic Thyroid Cancer: A New Potential Theragnostic Agent. Front Endocrinol (Lausanne). 2021 Dec 22;12:794759. doi: 10.3389/fendo.2021.794759. PMID: 35002972; PMCID: PMC8727771.

19: Nuo Y, Li A, Yang L, Xue H, Wang F, Wang L. Efficacy of 68Ga- PSMA-11 PET/CT with biparametric MRI in diagnosing prostate cancer and predicting risk stratification: a comparative study. Quant Imaging Med Surg. 2022 Jan;12(1):53-65. doi: 10.21037/qims-21-80. PMID: 34993060; PMCID: PMC8666784.

20: Vlachostergios PJ, Niaz MJ, Thomas C, Christos PJ, Osborne JR, Margolis DJA, Khani F, Bander NH, Scherr DS, Tagawa ST. Pilot study of the diagnostic utility of 89 Zr-df-IAB2M and 68 Ga-PSMA-11 PET imaging and multiparametric MRI in localized prostate cancer. Prostate. 2022 Mar;82(4):483-492. doi: 10.1002/pros.24294. Epub 2022 Jan 5. PMID: 34985786.