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Details

Stereochemistry EPIMERIC
Molecular Formula C6H10FO7P
Molecular Weight 243.1144
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BAY-1075553 F-18

SMILES

C([C@]([H])(CP(=O)(O)O)C(=O)O)C([H])(C(=O)O)F

InChI

InChIKey=SJIJEWUUIKDXIM-KMRZSKAOSA-N
InChI=1S/C6H10FO7P/c7-4(6(10)11)1-3(5(8)9)2-15(12,13)14/h3-4H,1-2H2,(H,8,9)(H,10,11)(H2,12,13,14)/t3-,4?/m1/s1/i7-1

HIDE SMILES / InChI

Molecular Formula C6H10FO7P
Molecular Weight 243.1144
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 1 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Substance Class Chemical
Created
by admin
on Fri Jun 25 20:40:05 UTC 2021
Edited
by admin
on Fri Jun 25 20:40:05 UTC 2021
Record UNII
7Y9R4VZJ3P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BAY-1075553 F-18
Code English
(18F)BAY-1075553
Code English
BAY 1075553
Code English
PENTANEDIOIC ACID, 2-(FLUORO-18F)-4-(PHOSPHONOMETHYL)-, (2SR,4S)-
Systematic Name English
(2SR,4S)-2-(FLUORANYL-18F)-4-(PHOSPHONOMETHYL)PENTANEDIOIC ACID
Systematic Name English
Code System Code Type Description
FDA UNII
7Y9R4VZJ3P
Created by admin on Fri Jun 25 20:40:05 UTC 2021 , Edited by admin on Fri Jun 25 20:40:05 UTC 2021
PRIMARY
PUBCHEM
71559387
Created by admin on Fri Jun 25 20:40:05 UTC 2021 , Edited by admin on Fri Jun 25 20:40:05 UTC 2021
PRIMARY
CAS
1312438-66-6
Created by admin on Fri Jun 25 20:40:05 UTC 2021 , Edited by admin on Fri Jun 25 20:40:05 UTC 2021
PRIMARY
Related Record Type Details
TARGET->RADIOLIGAND
Related Record Type Details
ACTIVE MOIETY
RESULTS: There were no relevant changes in laboratory values or physical examination. Urinary bladder wall received the largest dose equivalent 0.12 mSv/MBq. The whole-body mean effective dose was 0.015 mSv/MBq. There was a significant correlation between detected prostatic lesions by the two imaging modalities (Kappa=0.356, P<0.001) and no significant difference in sensitivity (P=0.16) and specificity (P=0.41). The sensitivity and specificity of PET imaging using BAY1075553 for lymph node (LN) staging was 42.9 % and 100 %, while it was 81.2 % and 50 % using FCH. The two modalities were closely correlated regarding detection of LNs and bone metastases, although BAY1075553 failed to detect a bone marrow metastasis. Degenerative bone lesions often displayed intense uptake of BAY1075553. CONCLUSIONS: BAY1075553 PET-CT produced no adverse effects, was well tolerated, and detected primary and metastatic prostate cancer. FCH PET-CT results were superior, however, with respect to detecting LN and bone marrow metastases.
ACTIVE MOIETY
Purpose Prostate-specific membrane antigen (PSMA) is a transmembrane protein overexpressed in prostate cancer and is therefore being explored as a biomarker for diagnosing and staging of the disease. Here we report preclinical data on BAY 1075553 (a 9:1 mixture of (2S,4S)- and (2R,4S)-2-(18F) fluoro-4-phosphonomethyl-pentanedioic acid), a novel 18Flabelled smallmolecule inhibitor of PSMA enzymatic activity, which can be efficiently synthesized from a direct radiolabelling precursor.