U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C8H10FN3O5
Molecular Weight 247.1805
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUOROAZOMYCIN ARABINOSIDE

SMILES

O[C@H]1[C@H](O)[C@H](O[C@@H]1CF)N2C=CN=C2[N+]([O-])=O

InChI

InChIKey=LPZSRGRDVVGMMX-JWXFUTCRSA-N
InChI=1S/C8H10FN3O5/c9-3-4-5(13)6(14)7(17-4)11-2-1-10-8(11)12(15)16/h1-2,4-7,13-14H,3H2/t4-,5-,6+,7+/m1/s1

HIDE SMILES / InChI

Molecular Formula C8H10FN3O5
Molecular Weight 247.1805
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

1‐α‐D‐(5‐Fluoro‐5‐deoxyarabinofuranosyl)‐2‐nitroimidazole (fluoroazomycin arabinoside, FAZA) is a putative PET imaging agent when labelled with 18F. Fluoroazomycin arabinoside is essential in the generation of fluorine F 18-fluoroazomycin arabinoside (18F-FAZA), which is a radiofluorinated 2-nitroimidazole derivative with hypoxia (low oxygen)-specific tracer activity. 18F-FAZA is reduced under hypoxic conditions, forming highly reactive intermediates. In its reduced form, 18F-FAZA covalently binds to macromolecules, thereby accumulating in hypoxic cells (e.g. malignant tumors) and allowing radioisotopic imaging of these particular cells with positron emission tomography (PET).

Approval Year

Patents

Patents

Substance Class Chemical
Created
by admin
on Mon Mar 31 22:03:47 GMT 2025
Edited
by admin
on Mon Mar 31 22:03:47 GMT 2025
Record UNII
1QR3UU6P48
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FAZA
Preferred Name English
FLUOROAZOMYCIN ARABINOSIDE
Common Name English
1H-IMIDAZOLE, 1-(5-DEOXY-5-FLUORO-.ALPHA.-D-ARABINOFURANOSYL)-2-NITRO-
Systematic Name English
Code System Code Type Description
CAS
220793-03-3
Created by admin on Mon Mar 31 22:03:47 GMT 2025 , Edited by admin on Mon Mar 31 22:03:47 GMT 2025
PRIMARY
FDA UNII
1QR3UU6P48
Created by admin on Mon Mar 31 22:03:47 GMT 2025 , Edited by admin on Mon Mar 31 22:03:47 GMT 2025
PRIMARY
PUBCHEM
10083297
Created by admin on Mon Mar 31 22:03:47 GMT 2025 , Edited by admin on Mon Mar 31 22:03:47 GMT 2025
PRIMARY