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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H10FNO4
Molecular Weight 214.1809
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUORODOPA F-18

SMILES

N[C@@H](CC1=CC(O)=C(O)C=C1[18F])C(O)=O

InChI

InChIKey=PAXWQORCRCBOCU-RPDRGXCHSA-N
InChI=1S/C9H10FNO4/c10-5-3-8(13)7(12)2-4(5)1-6(11)9(14)15/h2-3,6,12-13H,1,11H2,(H,14,15)/t6-/m0/s1/i10-1

HIDE SMILES / InChI

Molecular Formula C9H10FNO4
Molecular Weight 214.1809
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Fluorodopa F-18 is the amino acid analog fluorodopa (FDOPA) labeled with fluorine F 18, a positron-emitting isotope. It is diagnostic PET agent, which has been used for decades in imaging the loss of dopaminergic neurons in Parkinson's disease, and more recently to detect, stage and restage neuroendocrine tumours and to search for recurrence of viable glioma tissue. Fluorodopa F-18 is able to cross the blood-brain barrier and is taken up by brain tumor cells. As uptake is higher in tumor cells, tumors may then be imaged using positron emission tomography (PET). Assessing tumor uptake of FDOPA may be beneficial for diagnosis, localization and in determining further treatment. The clinical usefulness of Fluorodopa F-18 has been evaluated and recognised in France and subsequently in several EU countries. Fluorodopa F-18 was registered in France in 2006. 6-fluoro-(18F)-L-3,4-dihydroxyphenylalanine (FDOPA) is a large, neutral amino acid that is transported into presynaptic neurons, where it is converted by the enzyme aromatic aminoacid decarboxylase [AAAD]) into fluorodopamine-(18F), which subsequently enters cathecholamine-storage vesicles. 6-fluoro(18F)-L-dopa crosses the blood-brain barrier; therefore, when injected into the blood stream, it reaches the dopaminergic cells in the brain and is used by the brain as a precursor for dopamine. This makes it possible to monitor intracerebral synthesis and uptake of dopamine by means of the positron-emitting 6-fluoro(18F)-L-3,4-dihydroxyphenylalanine (FDOPA), in conjunction with externally-placed devices suited for detection of annihilation photons, which progressively led to the most recent positron emission tomography (PET) units. Iasodopa, the commercial preparation of FDOPA that obtained a marketing authorisation in France in November 2006 (which is currently recognised by several other EU countries), is a solution for injection. The activity available at time of administration ranges from 0.1 GBq to 0.8 GBq per vial. The half-life of the radionuclide is 109.8 min with emission of positron radiation (Emax: 0.633 MeV) followed by photon annihilation radiations of 0.511 MeV.

CNS Activity

Approval Year

PubMed

PubMed

TitleDatePubMed
Clinical correlates of [18F]fluorodopa uptake in five grafted parkinsonian patients.
1995 Oct
Effect of dopamine loss and the metabolite 3-O-methyl-[18F]fluoro-dopa on the relation between the 18F-fluorodopa tissue input uptake rate constant Kocc and the [18F]fluorodopa plasma input uptake rate constant Ki.
2003 Mar
[Fluorine-18 in radiopharmacy].
2008 Jan
Automated production at the curie level of no-carrier-added 6-[(18)F]fluoro-L-dopa and 2-[(18)F]fluoro-L-tyrosine on a FASTlab synthesizer.
2015 Jun 15

Sample Use Guides

In Vivo Use Guide
Usual adult administered activity [Brain imaging] Intravenous infusion, 74 to 370 megabecquerels (2 to 10 millicuries), with a specific activity of 20 to 40 megabecquerels (740 to 1480 millicuries) per micromole
Route of Administration: Intravenous
Substance Class Chemical
Created
by admin
on Mon Oct 21 23:55:38 UTC 2019
Edited
by admin
on Mon Oct 21 23:55:38 UTC 2019
Record UNII
2C598205QX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FLUORODOPA F-18
Common Name English
6-FLUORO-(18F)-L-3,4-DIHYDROXYPHENYLALANINE
Common Name English
FLUORODOPA F 18 [USAN]
Common Name English
L-3,4-DIHYDROXY-6-(18F)FLUOROPHENYLALANINE
Common Name English
18F-FLUORO-DIHYDROXYPHENYLALANINE
Common Name English
18F-L-FLUORO-DOPA
Common Name English
FLUORODOPA (18F)
INN   WHO-DD  
INN  
Official Name English
FLUORODOPA F 18 [USP]
Common Name English
L-6-(18F)FLUORO-DOPA
Common Name English
FLUORODOPA (18F) [INN]
Common Name English
18F-DOPA
Common Name English
(18F)-6-FLUORO-L,3,4, DIHYDROXYPHENYLALANINE
Systematic Name English
L-TYROSINE, 2-(FLUORO-18F)-5-HYDROXY-
Common Name English
FLUORODOPA F 18
USAN   USP  
USAN  
Official Name English
FLUORODOPA (18F) [WHO-DD]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 543716
Created by admin on Mon Oct 21 23:55:38 UTC 2019 , Edited by admin on Mon Oct 21 23:55:38 UTC 2019
FDA ORPHAN DRUG 621017
Created by admin on Mon Oct 21 23:55:38 UTC 2019 , Edited by admin on Mon Oct 21 23:55:38 UTC 2019
WHO-VATC QV09IX05
Created by admin on Mon Oct 21 23:55:38 UTC 2019 , Edited by admin on Mon Oct 21 23:55:38 UTC 2019
NCI_THESAURUS C2124
Created by admin on Mon Oct 21 23:55:38 UTC 2019 , Edited by admin on Mon Oct 21 23:55:38 UTC 2019
WHO-ATC V09IX05
Created by admin on Mon Oct 21 23:55:38 UTC 2019 , Edited by admin on Mon Oct 21 23:55:38 UTC 2019
FDA ORPHAN DRUG 567816
Created by admin on Mon Oct 21 23:55:38 UTC 2019 , Edited by admin on Mon Oct 21 23:55:38 UTC 2019
Code System Code Type Description
ChEMBL
CHEMBL2110687
Created by admin on Mon Oct 21 23:55:38 UTC 2019 , Edited by admin on Mon Oct 21 23:55:38 UTC 2019
PRIMARY
NCI_THESAURUS
C95766
Created by admin on Mon Oct 21 23:55:38 UTC 2019 , Edited by admin on Mon Oct 21 23:55:38 UTC 2019
PRIMARY
PUBCHEM
56494
Created by admin on Mon Oct 21 23:55:38 UTC 2019 , Edited by admin on Mon Oct 21 23:55:38 UTC 2019
PRIMARY
MESH
C043437
Created by admin on Mon Oct 21 23:55:38 UTC 2019 , Edited by admin on Mon Oct 21 23:55:38 UTC 2019
PRIMARY
WIKIPEDIA
FLUORODOPA
Created by admin on Mon Oct 21 23:55:38 UTC 2019 , Edited by admin on Mon Oct 21 23:55:38 UTC 2019
PRIMARY
EPA CompTox
92812-82-3
Created by admin on Mon Oct 21 23:55:38 UTC 2019 , Edited by admin on Mon Oct 21 23:55:38 UTC 2019
PRIMARY
CAS
92812-82-3
Created by admin on Mon Oct 21 23:55:38 UTC 2019 , Edited by admin on Mon Oct 21 23:55:38 UTC 2019
PRIMARY
EVMPD
SUB07719MIG
Created by admin on Mon Oct 21 23:55:38 UTC 2019 , Edited by admin on Mon Oct 21 23:55:38 UTC 2019
PRIMARY
INN
6692
Created by admin on Mon Oct 21 23:55:38 UTC 2019 , Edited by admin on Mon Oct 21 23:55:38 UTC 2019
PRIMARY
Related Record Type Details
ACTIVE MOIETY