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Details

Stereochemistry ACHIRAL
Molecular Formula C5H8FNO2
Molecular Weight 132.1237
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUCICLOVINE F-18

SMILES

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

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q15758|||Q96RL9
Gene ID: 6510.0
Gene Symbol: SLC1A5
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
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

1.46422078E12
Diagnostic
AXUMIN

Approved Use

Unknown
Diagnostic
AXUMIN

Approved Use

Unknown
Diagnostic
AXUMIN

Approved Use

Unknown
PubMed

PubMed

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

Patents

Sample Use Guides

The recommended dose is 370 MBq (10 mCi) administered as an intravenous bolus injection.
Route of Administration: Intravenous
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.
Name Type Language
FLUCICLOVINE F-18
DASH  
Common Name English
FLUCICLOVINE (18F) [WHO-DD]
Common Name English
AXUMIN
Common Name English
FLUCICLOVINE (18F) [INN]
Common Name English
FACBC F-18
Common Name English
FLUCICLOVINE F 18
USAN  
USAN  
Official Name English
FLUCICLOVINE (18F) [MI]
Common Name English
FLUCICLOVINE (18F)
INN   WHO-DD  
INN  
Official 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 Sat Jun 26 07:07:47 UTC 2021 , Edited by admin on Sat Jun 26 07:07:47 UTC 2021
EU-Orphan Drug EU/3/15/1472
Created by admin on Sat Jun 26 07:07:47 UTC 2021 , Edited by admin on Sat Jun 26 07:07:47 UTC 2021
NCI_THESAURUS C390
Created by admin on Sat Jun 26 07:07:47 UTC 2021 , Edited by admin on Sat Jun 26 07:07:47 UTC 2021
WHO-ATC V09IX12
Created by admin on Sat Jun 26 07:07:47 UTC 2021 , Edited by admin on Sat Jun 26 07:07:47 UTC 2021
NCI_THESAURUS C2124
Created by admin on Sat Jun 26 07:07:47 UTC 2021 , Edited by admin on Sat Jun 26 07:07:47 UTC 2021
NDF-RT N0000177914
Created by admin on Sat Jun 26 07:07:47 UTC 2021 , Edited by admin on Sat Jun 26 07:07:47 UTC 2021
Code System Code Type Description
MERCK INDEX
M12012
Created by admin on Sat Jun 26 07:07:47 UTC 2021 , Edited by admin on Sat Jun 26 07:07:47 UTC 2021
PRIMARY
PUBCHEM
450601
Created by admin on Sat Jun 26 07:07:47 UTC 2021 , Edited by admin on Sat Jun 26 07:07:47 UTC 2021
PRIMARY
EVMPD
SUB179608
Created by admin on Sat Jun 26 07:07:47 UTC 2021 , Edited by admin on Sat Jun 26 07:07:47 UTC 2021
PRIMARY
ChEMBL
CHEMBL3707268
Created by admin on Sat Jun 26 07:07:47 UTC 2021 , Edited by admin on Sat Jun 26 07:07:47 UTC 2021
PRIMARY
NDF-RT
N0000175869
Created by admin on Sat Jun 26 07:07:47 UTC 2021 , Edited by admin on Sat Jun 26 07:07:47 UTC 2021
PRIMARY Positron Emitting Activity [MoA]
CAS
222727-39-1
Created by admin on Sat Jun 26 07:07:47 UTC 2021 , Edited by admin on Sat Jun 26 07:07:47 UTC 2021
PRIMARY
NCI_THESAURUS
C74002
Created by admin on Sat Jun 26 07:07:47 UTC 2021 , Edited by admin on Sat Jun 26 07:07:47 UTC 2021
PRIMARY
INN
9243
Created by admin on Sat Jun 26 07:07:47 UTC 2021 , Edited by admin on Sat Jun 26 07:07:47 UTC 2021
PRIMARY
MESH
C117460
Created by admin on Sat Jun 26 07:07:47 UTC 2021 , Edited by admin on Sat Jun 26 07:07:47 UTC 2021
PRIMARY
DRUG BANK
DB13146
Created by admin on Sat Jun 26 07:07:47 UTC 2021 , Edited by admin on Sat Jun 26 07:07:47 UTC 2021
PRIMARY
DRUG CENTRAL
5153
Created by admin on Sat Jun 26 07:07:47 UTC 2021 , Edited by admin on Sat Jun 26 07:07:47 UTC 2021
PRIMARY
RXCUI
1796118
Created by admin on Sat Jun 26 07:07:47 UTC 2021 , Edited by admin on Sat Jun 26 07:07:47 UTC 2021
PRIMARY
FDA UNII
38R1Q0L1ZE
Created by admin on Sat Jun 26 07:07:47 UTC 2021 , Edited by admin on Sat Jun 26 07:07:47 UTC 2021
PRIMARY