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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H13FN2O5
Molecular Weight 259.2216
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLEVUDINE F-18

SMILES

CC1=CN([C@H]2O[C@@H](CO)[C@H](O)[C@H]2[18F])C(=O)NC1=O

InChI

InChIKey=GBBJCSTXCAQSSJ-HMQZJZAASA-N
InChI=1S/C10H13FN2O5/c1-4-2-13(10(17)12-8(4)16)9-6(11)7(15)5(3-14)18-9/h2,5-7,9,14-15H,3H2,1H3,(H,12,16,17)/t5-,6+,7-,9-/m0/s1/i11-1

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/15586282

Clevudine F18 is a radioconjugate comprised of the synthetic pyrimidine analog clevudine (1-(2'-deoxy-2'-fluoro-beta-D-arabinofuranosyl)thymine, d-FMAU) labeled with the radioisotope fluorine F18. Upon administration, fluorine F18 clevudine is distributed and taken up by cells based on the rate of the cell’s DNA synthesis. The amount is then measured using positron emission tomography (PET). The compound is investigated as an imaging agent in prostate, breast cancers, and other malignant neoplasms.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Synthesis of 2'-deoxy-2'-[18F]fluoro-beta-D-arabinofuranosyl nucleosides, [18F]FAU, [18F]FMAU, [18F]FBAU and [18F]FIAU, as potential PET agents for imaging cellular proliferation. Synthesis of [18F]labelled FAU, FMAU, FBAU, FIAU.
2003 Apr
Direct comparison of radiolabeled probes FMAU, FHBG, and FHPG as PET imaging agents for HSV1-tk expression in a human breast cancer model.
2004 Apr
Imaging DNA synthesis with [18F]FMAU and positron emission tomography in patients with cancer.
2005 Jan

Sample Use Guides

A dose of 355-385 MBq of [18F]FMAU was intravenously infused into patients over 60s.
Route of Administration: Intravenous
Breast cancer cells were transduced with herpes simplex virus 1 thymidine kinase. Logarithmically growing cells were incubated with about 111 –148 KBq (3 - 4 uCi) of [18F]FMAU. Following incubation and removal of media, the cells were washed with phosphate-buffered saline (PBS, 3x10 mL) and treated with 0.3N perchloric acid. The acidic mixtures were cooled to 4°C for 10 min, centrifuged for 1 min at 14,000 rpm and the supernatant was separated. The cell pellets were washed twice with PCA (1 mL), centrifuged, and the acid soluble fractions, washings, and cell pellets were treated with complete counting scintillation cocktail. Radioactivity was counted in a liquid scintillation counter.
Name Type Language
CLEVUDINE F-18
Common Name English
CLEVUDINE FLUORINE F-18
Common Name English
2,4(1H,3H)-PYRIMIDINEDIONE, 1-(2-DEOXY-2-(FLUORO-18F)-.BETA.-L-ARABINOFURANOSYL)-5-METHYL-
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID60145502
Created by admin on Sat Dec 16 05:40:26 GMT 2023 , Edited by admin on Sat Dec 16 05:40:26 GMT 2023
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FDA UNII
O24SW9A8X6
Created by admin on Sat Dec 16 05:40:26 GMT 2023 , Edited by admin on Sat Dec 16 05:40:26 GMT 2023
PRIMARY
CAS
1027764-69-7
Created by admin on Sat Dec 16 05:40:26 GMT 2023 , Edited by admin on Sat Dec 16 05:40:26 GMT 2023
PRIMARY
PUBCHEM
25024028
Created by admin on Sat Dec 16 05:40:26 GMT 2023 , Edited by admin on Sat Dec 16 05:40:26 GMT 2023
PRIMARY