FLUCICLOVINE F-18

Details

Stereochemistry	ACHIRAL
Molecular Formula	C5H8FNO2
Molecular Weight	132.1235
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

N[C@]1(C[C@H]([18F])C1)C(O)=O

InChI

InChIKey=NTEDWGYJNHZKQW-DGMDOPGDSA-N

InChI=1S/C5H8FNO2/c6-3-1-5(7,2-3)4(8)9/h3H,1-2,7H2,(H,8,9)/t3-,5-/i6-1

HIDE SMILES / InChI

Molecular Formula	C5H8FNO2
Molecular Weight	132.1235
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Trans-1-amino-3-[(18)F]fluorocyclobutanecarboxylic acid (also known as Fluciclovine (18F)) was approved under brand name AXUMIN as a radioactive diagnostic agent indicated for positron emission tomography (PET) imaging in men with suspected prostate cancer recurrence. Besides, this radioactive compound is used in patients with cervical, ovarian epithelial or endometrial cancers. Fluciclovine F 18 is a synthetic amino acid transported across mammalian cell membranes by amino acid transporters, such as LAT-1 and ASCT2, which are upregulated in prostate cancer cells, but as was shown, this compound has a higher affinity for ASCT2 in comparison with other transporters.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Neutral amino acid transporter B(0) 1	Substrate 661

Conditions

Condition	Modality	Highest Phase	Product
Prostate cancer 178	Diagnostic	Approved 8,429	AXUMIN
Ovarian epithelial cancer 2	Diagnostic	Approved 8,429	AXUMIN
Endometrial cancer 43	Diagnostic	Approved 8,429	AXUMIN
Cervical cancer 40	Diagnostic	Approved 8,429	AXUMIN

PubMed

Show entries

Title	Date	PubMed
Kinetic analyses of trans-1-amino-3-[18F]fluorocyclobutanecarboxylic acid transport in Xenopus laevis oocytes expressing human ASCT2 and SNAT2.	2013 Jul	23647854
Anti-1-amino-3-18F-fluorocyclobutane-1-carboxylic acid: physiologic uptake patterns, incidental findings, and variants that may simulate disease.	2014 Dec	25453047
[(14)C]Fluciclovine (alias anti-[(14)C]FACBC) uptake and ASCT2 expression in castration-resistant prostate cancer cells.	2015 Nov	26278491

Showing 1 to 3 of 3 entries

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Patents

Sample Use Guides

In Vivo Use Guide

The recommended dose is 370 MBq (10 mCi) administered as an intravenous bolus injection.

Route of Administration: Intravenous

In Vitro Use Guide

Kinetic assays for trans-1-amino-3-fluoro-[1-(14)C]cyclobutanecarboxylic acid ([(14)C]FACBC) were performed in Xenopus laevis oocytes over-expressing either ASCT2 or sodium-coupled neutral amino acid transporter 2 (SNAT2), both of which are highly expressed in prostate cancer cells. ASCT2 and SNAT2 transported [14C]FACBC with Michaelis–Menten kinetics Km values of 96.7 ± 45.2 μM and 196.5 ± 19.7 μM, respectively. LAT1 and LAT2 transported [(14)C]FACBC with Michaelis-Menten Km values of 230.4 ± 184.5 μM and 738.5 ± 87.6 μM, respectively.