NAV

Fluorodopa (18F)

Identification

Generic Name
Fluorodopa (18F)
DrugBank Accession Number
DB13848
Background

Fluorodopa F 18 is a fluorinated analog of levodopa used as a diagnostic agent for positron emission tomography (PET) in the evaluation of Parkinsonian syndromes.1 Fluorodopa F 18 PET is used adjunctly with other diagnostic investigations and serves primarily to visualize dopaminergic nerve terminals in the striatum.1

Type
Small Molecule
Groups
Approved, Experimental
Structure
3D
Similar Structures
Weight
Average: 214.183
Monoisotopic: 214.061920473
Chemical Formula
C9H10FNO4
Synonyms
  • 6-Fluoro-(18F)-L-3,4-Dihydroxyphenylalanine
  • Fluorodopa (18F)
  • Fluorodopa F-18
  • L-3,4-Dihydroxy-6-[18F]Fluorophenylalanine
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Pharmacology

Indication

Fluorodopa F 18 is indicated for use with positron emission tomography (PET) to visualize dopaminergic nerve terminals in the striatum for the evaluation of adult patients with suspected Parkinsonian syndromes (PS).1

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Diagnostic agentParkinsonian syndromes•••••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Fluorodopa F 18 is decarboxylated by aromatic amino acid decarboxylase (AADC) in the striatum to fluorodopamine F 18. Fluorodopamine F 18 is then further metabolized by monoamine oxidase (MAO) to yield [18F] 6-fluoro-3,4-dihydroxyphenylacetic acid, then subsequently by COMT to yield [18F]6-fluorohomovanillic acid.1

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Route of elimination

Approximately 80% of the administered radioactivity is eliminated in the urine.1

Half-life

The plasma half-life following intravenous administration is approximately 1-3 hours.1

Clearance

The agent is cleared from blood and tissue within 24 hours following administration.1

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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BenserazideThe bioavailability of Fluorodopa (18F) can be increased when combined with Benserazide.
CarbidopaThe bioavailability of Fluorodopa (18F) can be increased when combined with Carbidopa.
MethyldopaThe bioavailability of Fluorodopa (18F) can be increased when combined with Methyldopa.
Food Interactions
  • Take on an empty stomach. Before fluorodopa F18 administration do not eat or drink anything, except for water, for at least 4 hours.

Products

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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Fluorodopa F18Injection8.33 mCi/1mLIntravenousTHE FEINSTEIN INSTITUTES FOR MEDICAL RESEARCH2019-10-10Not applicableUS flag
Fluorodopa F18Injection40 mCi/1mLIntravenousTHE FEINSTEIN INSTITUTES FOR MEDICAL RESEARCH2019-10-10Not applicableUS flag

Categories

ATC Codes
V09IX05 — Fluorodopa (18f)
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as tyrosine and derivatives. These are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Tyrosine and derivatives
Alternative Parents
Phenylalanine and derivatives / Phenylpropanoic acids / Amphetamines and derivatives / L-alpha-amino acids / P-fluorophenols / M-fluorophenols / Catechols / 1-hydroxy-2-unsubstituted benzenoids / Aralkylamines / Fluorobenzenes
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Substituents
1-hydroxy-2-unsubstituted benzenoid / 3-fluorophenol / 3-halophenol / 3-phenylpropanoic-acid / 4-fluorophenol / 4-halophenol / Alpha-amino acid / Amine / Amino acid / Amphetamine or derivatives
show 27 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
6-fluoro-L-dopa, fluorine-18 radiopharmaceutical (CHEBI:49166)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
2C598205QX
CAS number
92812-82-3
InChI Key
PAXWQORCRCBOCU-RPDRGXCHSA-N
InChI
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
IUPAC Name
(2S)-2-amino-3-[2-(¹⁸F)fluoro-4,5-dihydroxyphenyl]propanoic acid
SMILES
N[C@@H](CC1=CC(O)=C(O)C=C1[18F])C(O)=O

References

General References
  1. FDA Approved Drug Products: Fluorodopa F18 injection for intravenous use [Link]
Human Metabolome Database
HMDB0304885
ChemSpider
50970
RxNav
2571853
ChEBI
49166
ChEMBL
CHEMBL3400972
ZINC
ZINC000100079068
Wikipedia
Fluorodopa

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2RecruitingTreatmentHigh Grade Glioma: Glioblastoma (GBM)1
Not AvailableRecruitingNot AvailableRecurrent Soft Tissue Sarcoma / Resectable Soft Tissue Sarcoma / Soft Tissue Sarcoma1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, solutionParenteral
Injection, solutionParenteral90 MBQ/ML
InjectionIntravenous40 mCi/1mL
InjectionIntravenous8.33 mCi/1mL
Solution, concentrateParenteral0.3 GBq
Injection, solutionParenteral0.3 Gbq
Injection, solutionParenteral222 MBQ/ML
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.39 mg/mLALOGPS
logP-2ALOGPS
logP-1.6Chemaxon
logS-2ALOGPS
pKa (Strongest Acidic)1.32Chemaxon
pKa (Strongest Basic)9.4Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area103.78 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity49.29 m3·mol-1Chemaxon
Polarizability19.09 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-006x-4900000000-077ffd7c889badd08543
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0890000000-c1dc5e870454ef106d7b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0w90-2940000000-9c67c6cc9f13e08184a1
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ufr-0900000000-c6f99c712384c74a88af
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-2900000000-6e12e626a435b95658a9
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-7900000000-f613cb9cfa6dcf5b9d31
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000f-5900000000-8bc3a2554a38b3b76e81
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Enzymes

Details1. Aromatic-L-amino-acid decarboxylase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Pyridoxal phosphate binding
Specific Function
Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name
DDC
Uniprot ID
P20711
Uniprot Name
Aromatic-L-amino-acid decarboxylase
Molecular Weight
53925.815 Da
References
  1. FDA Approved Drug Products: Fluorodopa F18 injection for intravenous use [Link]

Drug created at June 23, 2017 20:49 / Updated at April 20, 2023 07:02