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

Structure Search

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

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

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208054s000lbl.pdf | https://clinicaltrials.gov/ct2/show/NCT03349463 | https://www.ncbi.nlm.nih.gov/pubmed/25453047 | https://www.ncbi.nlm.nih.gov/pubmed/23647854

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 Target ID: Q15758\|\|\|Q96RL9 Gene ID: 6510.0 Gene Symbol: SLC1A5 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/23647854	Substrate 661

Conditions

Condition	Modality	Highest Phase	Product
Prostate cancer 186 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208054s000lbl.pdf	Diagnostic	Approved 8583	AXUMIN Approved Use Axumin is indicated for positron emission tomography (PET) in men with suspected prostate cancer recurrence based on elevated blood prostate specific antigen (PSA) levels following prior treatment. Launch Date 2016
Ovarian epithelial cancer 2 Sources: https://clinicaltrials.gov/ct2/show/NCT03349463	Diagnostic	Approved 8583	AXUMIN Approved Use Unknown
Endometrial cancer 44 Sources: https://clinicaltrials.gov/ct2/show/NCT03349463	Diagnostic	Approved 8583	AXUMIN Approved Use Unknown
Cervical cancer 40 Sources: https://clinicaltrials.gov/ct2/show/NCT03349463	Diagnostic	Approved 8583	AXUMIN Approved Use Unknown

PubMed

Title	Date	PubMed
[(14)C]Fluciclovine (alias anti-[(14)C]FACBC) uptake and ASCT2 expression in castration-resistant prostate cancer cells.	2015-11	26278491
Anti-1-amino-3-18F-fluorocyclobutane-1-carboxylic acid: physiologic uptake patterns, incidental findings, and variants that may simulate disease.	2014-12	25453047
Kinetic analyses of trans-1-amino-3-[18F]fluorocyclobutanecarboxylic acid transport in Xenopus laevis oocytes expressing human ASCT2 and SNAT2.	2013-07	23647854

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:59:47 GMT 2025` Edited by `admin` on `Mon Mar 31 18:59:47 GMT 2025`
Record UNII	38R1Q0L1ZE
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

FLUCICLOVINE (18F)

Preferred Name

English

FLUCICLOVINE F-18

Common Name

English

AXUMIN

Common Name

English

fluciclovine (¹?F) [INN]

Common Name

English

FACBC F-18

Common Name

English

FLUCICLOVINE F 18

Official Name

English

FLUCICLOVINE (18F) [MI]

Common Name

English

Fluciclovine (18f) [WHO-DD]

Common Name

English

(18F)GE-148

Common Name

English

GE-148

Code

English

(18F)FACBC

Common Name

English

GE-148 F-18

Code

English

NMK36

Code

English

FLUCICLOVINE F18

Common Name

English

FLUCICLOVINE F 18 [USAN]

Common Name

English

FACBC

Code

English

NMK-36

Code

English

(1R,3R)-1-AMINO-3(18F)FLUOROCYCLOBUTANE-1-CARBOXYLIC ACID

Common Name

English

FLUCICLOVINE F-18 [ORANGE BOOK]

Common Name

English

CYCLOBUTANECARBOXYLIC ACID, 1-AMINO-3-(FLUORO-18F)-, TRANS-

Systematic Name

English

GE-148 (18F)

Code

English

ANTI-1-AMINO-3-(18F)FLUOROCYCLOBUTANE-1-CARBOXYLIC ACID

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

465814

Created by admin on Mon Mar 31 18:59:47 GMT 2025 , Edited by admin on Mon Mar 31 18:59:47 GMT 2025

EU-Orphan Drug

EU/3/15/1472

Created by admin on Mon Mar 31 18:59:47 GMT 2025 , Edited by admin on Mon Mar 31 18:59:47 GMT 2025

NCI_THESAURUS

C390

Created by admin on Mon Mar 31 18:59:47 GMT 2025 , Edited by admin on Mon Mar 31 18:59:47 GMT 2025

FDA ORPHAN DRUG

929022

Created by admin on Mon Mar 31 18:59:48 GMT 2025 , Edited by admin on Mon Mar 31 18:59:48 GMT 2025

WHO-ATC

V09IX12

Created by admin on Mon Mar 31 18:59:47 GMT 2025 , Edited by admin on Mon Mar 31 18:59:47 GMT 2025

NCI_THESAURUS

C2124

Created by admin on Mon Mar 31 18:59:47 GMT 2025 , Edited by admin on Mon Mar 31 18:59:47 GMT 2025

NDF-RT

N0000177914

Created by admin on Mon Mar 31 18:59:47 GMT 2025 , Edited by admin on Mon Mar 31 18:59:47 GMT 2025

Code System Code Type Description

USAN

DE-44

Created by admin on Mon Mar 31 18:59:48 GMT 2025 , Edited by admin on Mon Mar 31 18:59:48 GMT 2025

PRIMARY

MERCK INDEX

m12012

Created by admin on Mon Mar 31 18:59:48 GMT 2025 , Edited by admin on Mon Mar 31 18:59:48 GMT 2025

PRIMARY

SMS_ID

100000165748

Created by admin on Mon Mar 31 18:59:48 GMT 2025 , Edited by admin on Mon Mar 31 18:59:48 GMT 2025

PRIMARY

PUBCHEM

450601

Created by admin on Mon Mar 31 18:59:47 GMT 2025 , Edited by admin on Mon Mar 31 18:59:47 GMT 2025

PRIMARY

EVMPD

SUB179608

Created by admin on Mon Mar 31 18:59:47 GMT 2025 , Edited by admin on Mon Mar 31 18:59:47 GMT 2025

PRIMARY

ChEMBL

CHEMBL3707268

Created by admin on Mon Mar 31 18:59:47 GMT 2025 , Edited by admin on Mon Mar 31 18:59:47 GMT 2025

PRIMARY

CHEBI

134703

Created by admin on Mon Mar 31 18:59:48 GMT 2025 , Edited by admin on Mon Mar 31 18:59:48 GMT 2025

PRIMARY

WIKIPEDIA

Fluciclovine (18F)

Created by admin on Mon Mar 31 18:59:48 GMT 2025 , Edited by admin on Mon Mar 31 18:59:48 GMT 2025

PRIMARY

NDF-RT

N0000175869

Created by admin on Mon Mar 31 18:59:47 GMT 2025 , Edited by admin on Mon Mar 31 18:59:47 GMT 2025

PRIMARY

Positron Emitting Activity [MoA]

CAS

222727-39-1

Created by admin on Mon Mar 31 18:59:47 GMT 2025 , Edited by admin on Mon Mar 31 18:59:47 GMT 2025

PRIMARY

NCI_THESAURUS

C74002

Created by admin on Mon Mar 31 18:59:47 GMT 2025 , Edited by admin on Mon Mar 31 18:59:47 GMT 2025

PRIMARY

DAILYMED

38R1Q0L1ZE

Created by admin on Mon Mar 31 18:59:48 GMT 2025 , Edited by admin on Mon Mar 31 18:59:48 GMT 2025

PRIMARY

EPA CompTox

DTXSID601027796

Created by admin on Mon Mar 31 18:59:48 GMT 2025 , Edited by admin on Mon Mar 31 18:59:48 GMT 2025

PRIMARY

INN

9243

Created by admin on Mon Mar 31 18:59:47 GMT 2025 , Edited by admin on Mon Mar 31 18:59:47 GMT 2025

PRIMARY

MESH

C117460

Created by admin on Mon Mar 31 18:59:47 GMT 2025 , Edited by admin on Mon Mar 31 18:59:47 GMT 2025

PRIMARY

DRUG BANK

DB13146

Created by admin on Mon Mar 31 18:59:48 GMT 2025 , Edited by admin on Mon Mar 31 18:59:48 GMT 2025

PRIMARY

DRUG CENTRAL

5153

Created by admin on Mon Mar 31 18:59:48 GMT 2025 , Edited by admin on Mon Mar 31 18:59:48 GMT 2025

PRIMARY

RXCUI

1796118

Created by admin on Mon Mar 31 18:59:47 GMT 2025 , Edited by admin on Mon Mar 31 18:59:47 GMT 2025

PRIMARY

FDA UNII

38R1Q0L1ZE

Created by admin on Mon Mar 31 18:59:47 GMT 2025 , Edited by admin on Mon Mar 31 18:59:47 GMT 2025

PRIMARY

Related Record Type Details


					YKG0YF688X

FLUCICLOVINE

NON-LABELED -> LABELED

Amount:


					9PO6C880ZJ

NEUTRAL AMINO ACID TRANSPORTER B(0)

TARGET -> SUBSTRATE

Comments:

lEADS TO ACCUMULATION IN TUMOR CELLS IN RELATION TO NORMAL CELLS

Amount:

Related Record Type Details


					38R1Q0L1ZE

FLUCICLOVINE F-18

ACTIVE MOIETY

Amount:

Details

SMILES

InChI

DescriptionSources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208054s000lbl.pdf | https://clinicaltrials.gov/ct2/show/NCT03349463 | https://www.ncbi.nlm.nih.gov/pubmed/25453047 | https://www.ncbi.nlm.nih.gov/pubmed/23647854

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Approved Use

Approved Use

Approved Use

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208054s000lbl.pdf | https://clinicaltrials.gov/ct2/show/NCT03349463 | https://www.ncbi.nlm.nih.gov/pubmed/25453047 | https://www.ncbi.nlm.nih.gov/pubmed/23647854