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Details

Stereochemistry ABSOLUTE
Molecular Formula C8H10FN3O5
Molecular Weight 246.183
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUOROAZOMYCIN ARABINOSIDE F-18

SMILES

O[C@H]1[C@H](O)[C@H](O[C@@H]1C[18F])N2C=CN=C2[N+]([O-])=O

InChI

InChIKey=LPZSRGRDVVGMMX-FJBGPTLJSA-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/i9-1

HIDE SMILES / InChI

Molecular Formula C8H10FN3O5
Molecular Weight 246.183
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Fluoroazomycin Arabinoside F-18 (18F-FAZA) 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). (18)F-FAZA shows superior biokinetics and is, thus, a promising PET tracer for the visualization of tumor hypoxia. Clinical evaluation of 18F-FAZA is currently ongoing, and early results have been reported for head and neck, lung, prostate, and rectal cancers.

Approval Year

PubMed

PubMed

TitleDatePubMed
Hypoxia-specific tumor imaging with 18F-fluoroazomycin arabinoside.
2005 Jan
PET imaging of tumor hypoxia using 18F-fluoroazomycin arabinoside in stage III-IV non-small cell lung cancer patients.
2013 Aug
Head and neck tumor hypoxia imaging by 18F-fluoroazomycin-arabinoside (18F-FAZA)-PET: a review.
2014 Jan
Prognostic value of (18) F-fluoroazomycin arabinoside PET/CT in patients with advanced non-small-cell lung cancer.
2015 Nov

Sample Use Guides

Tongue cancer: Fluoroazomycin Arabinoside F-18 (18F-FAZA) will be administered via intravenous injection at a dose of 5.2 MBq/kg with a minimum dose of 200 Megabecquerel (MBq) (5.4 Millicurie (mCi)) and a maximum dose of 600 MBq (16.2 mCi) prior to positron emission tomography (PET) imaging. A single dose of oral pimonidazole capsules at a dose of 0.5 g/m2, will be taken by participants 16-20 hours prior to tumor resection surgery.
Route of Administration: Intravenous
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:05:06 UTC 2023
Edited
by admin
on Sat Dec 16 08:05:06 UTC 2023
Record UNII
UG7I3Y42PV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FLUOROAZOMYCIN ARABINOSIDE F-18
Common Name English
(18F)-FAZA
Common Name English
18F-FAZA
Common Name English
FAZA F-18
Common Name English
1H-IMIDAZOLE, 1-(5-DEOXY-5-(FLUORO-18F)-.ALPHA.-D-ARABINOFURANOSYL)-2-NITRO-
Systematic Name English
(18F)FLUOROAZOMYCIN ARABINOSIDE
Common Name English
Code System Code Type Description
NCI_THESAURUS
C62520
Created by admin on Sat Dec 16 08:05:06 UTC 2023 , Edited by admin on Sat Dec 16 08:05:06 UTC 2023
PRIMARY
FDA UNII
UG7I3Y42PV
Created by admin on Sat Dec 16 08:05:06 UTC 2023 , Edited by admin on Sat Dec 16 08:05:06 UTC 2023
PRIMARY
DRUG BANK
DB15134
Created by admin on Sat Dec 16 08:05:06 UTC 2023 , Edited by admin on Sat Dec 16 08:05:06 UTC 2023
PRIMARY
PUBCHEM
2826728
Created by admin on Sat Dec 16 08:05:06 UTC 2023 , Edited by admin on Sat Dec 16 08:05:06 UTC 2023
PRIMARY
CAS
864084-85-5
Created by admin on Sat Dec 16 08:05:06 UTC 2023 , Edited by admin on Sat Dec 16 08:05:06 UTC 2023
PRIMARY
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ACTIVE MOIETY