PSMA-11 (HBED-CC-PSMA or Psma-hbed-CC) can be used to prepare 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
Physicochemical Properties
| Molecular Formula | C44H62N6O17 |
| Molecular Weight | 947.005 |
| Exact Mass | 946.417 |
| Elemental Analysis | C, 55.81; H, 6.60; N, 8.87; O, 28.72 |
| CAS # | 1366302-52-4 |
| Related CAS # | 2412149-32-5 (TFA);1366302-52-4;PSMA-11 HCl; |
| PubChem CID | 60143283 |
| Appearance | White to off-white solid powder |
| Density | 1.4±0.1 g/cm3 |
| Boiling Point | 1275.1±65.0 °C at 760 mmHg |
| Flash Point | 725.0±34.3 °C |
| Vapour Pressure | 0.0±0.3 mmHg at 25°C |
| Index of Refraction | 1.602 |
| LogP | 0.2 |
| Hydrogen Bond Donor Count | 12 |
| Hydrogen Bond Acceptor Count | 19 |
| Rotatable Bond Count | 35 |
| Heavy Atom Count | 67 |
| Complexity | 1620 |
| Defined Atom Stereocenter Count | 2 |
| SMILES | OC1C=CC(CCC(NCCCCCC(NCCCC[C@@H](C(=O)O)NC(N[C@H](C(=O)O)CCC(=O)O)=O)=O)=O)=CC=1CN(CC(=O)O)CCN(CC(=O)O)CC1C(=CC=C(CCC(=O)O)C=1)O |
| 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 |
| 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 |
| Synonyms | Psma-hbed-CC PSMA-11 PSMA11 PSMA 11 HBED-CC-PSMA. |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| References | : Meißner S, Janssen JC, Prasad V, Brenner W, Diederichs G, Hamm B, Hofheinz F, Makowski MR. Potential of asphericity as a novel diagnostic parameter in the evaluation of patients with (68)Ga-PSMA-HBED-CC PET-positive prostate cancer lesions. EJNMMI Res. 2017 Oct 23;7(1):85. doi: 10.1186/s13550-017-0333-9. PubMed PMID: 29058157; PubMed Central PMCID: PMC5651532. |
| Additional Infomation |
Gozetotide is an unlabeled radiotracer composed of the human prostate specific membrane antigen (PSMA)-targeting ligand and linked to the acyclic radiometal chelator N,N'-bis [2-hydroxy-5-(carboxyethyl)benzyl] ethylenediamine-N,N'-diacetic acid (HBED-CC), that may potentially be used to prevent or reduce salivary gland toxicities of PSMA-targeted radionuclides. Upon administration of gozetotide into the salivary gland, gozetotide may selectively decrease salivary uptake of systemically administered PSMA-targeted radionuclides. This may reduce the salivary gland toxicities of these agents including salivary gland hypofunction and xerostomia. Drug Indication This medicinal product is for diagnostic use only. Locametz, after radiolabelling with gallium 68, is indicated for the detection of prostate specific membrane antigen (PSMA) positive lesions with positron emission tomography (PET) in adults with prostate cancer (PCa) in the following clinical settings: Primary staging of patients with high risk PCa prior to primary curative therapy,Suspected PCa recurrence in patients with increasing levels of serum prostate specific antigen (PSA) after primary curative therapy,Identification of patients with PSMA positive progressive metastatic castration resistant prostate cancer (mCRPC) for whom PSMA targeted therapy is indicated (see section 4. 4). |
Solubility Data
| Solubility (In Vitro) | DMSO : ~100 mg/mL (~105.60 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (2.64 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (2.64 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (2.64 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.0560 mL | 5.2798 mL | 10.5596 mL | |
| 5 mM | 0.2112 mL | 1.0560 mL | 2.1119 mL | |
| 10 mM | 0.1056 mL | 0.5280 mL | 1.0560 mL |