Page last updated: 2024-11-04

p-fluorophenylalanine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

p-Fluorophenylalanine (p-FPA) is a synthetic analog of the amino acid phenylalanine. It is an inhibitor of phenylalanine hydroxylase (PAH), the enzyme responsible for the conversion of phenylalanine to tyrosine. p-FPA is used as a tool to study the role of phenylalanine in various biological processes. It is also used in the treatment of phenylketonuria (PKU), a genetic disorder characterized by a deficiency in PAH. p-FPA is synthesized by reacting phenylalanine with fluorine gas. It is a white crystalline solid that is soluble in water. The effects of p-FPA include inhibition of PAH activity, leading to the accumulation of phenylalanine in the body. This accumulation can lead to various neurological problems in individuals with PKU. p-FPA is important because it provides a way to study the role of phenylalanine in various biological processes. It is also used in the treatment of PKU. p-FPA is studied to better understand the role of phenylalanine in the body and to develop better treatments for PKU. '

p-Fluorophenylalanine: 3-(p-Fluorophenyl)-alanine. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

4-fluorophenylalanine : A phenylalanine derivative in which the hydrogen at position 4 on the benzene ring is replaced by a fluoro group. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID4654
CHEMBL ID3185250
CHEBI ID84060
SCHEMBL ID44070
MeSH IDM0015727

Synonyms (105)

Synonym
DIVK1C_000957
KBIO1_000957
nsc-71433
nsc71433
4-fluoro-dl-.beta.-phenylalanine
dl-phenylalanine, 4-fluoro-
dl-p-fluorophenylalanine
SPECTRUM_001970
IDI1_000957
alnasid
phenylalanine, 4-fluoro-
d,l-fluorophenylalanine
nsc 71433
4-fluoro-dl-para-phenylalanine
alanine, 3-(p-fluorophenyl)-
dl-3-(4-fluorophenyl)alanine
einecs 200-113-7
einecs 200-459-9
d,l-p-fluorophenylalanine
ccris 4819
p-fluorophenylalanine
51-65-0
p-fluoro-dl-phenylalanine
SPECTRUM5_000766
BSPBIO_003356
KBIOSS_002534
KBIO2_007662
KBIO3_002858
KBIO2_002526
KBIO2_005094
KBIOGR_001806
SPECTRUM4_001253
NINDS_000957
SPBIO_000744
SPECTRUM2_000902
SPECTRUM3_001878
4-fluoro-dl-phenylalanine
4-fluorophenylalanine
NCGC00015435-02
STK410968
dl-p-phenylalanine
AKOS000196918
HMS502P19
2-amino-3-(4-fluorophenyl)propionic acid
h-dl-phe(4-f)-oh
F0106
2-amino-3-(4-fluorophenyl)propanoic acid
hsdb 7748
unii-42t8578m1e
42t8578m1e ,
tox21_202890
dtxsid3025332 ,
dtxcid805332
NCGC00260436-01
cas-51-65-0
dl-4-fluorophenylalanine
60-17-3
CCG-39903
FT-0613670
FT-0613669
FT-0600672
AM20060835
AB00239
AB02498
3-(p-fluorophenyl)alanine, dl-
4-fluorophenylalanine, (+/-)-
p-fluorophenylalanine [hsdb]
alanine, 3-(p-fluorophenyl)-, dl-
p-fluorophenylalanine, dl-
4-fluorophenylalanine, dl-
phenylalanine, 4-fluoro-, dl-
AB00052275-04
dl-fluorophenylalanine
CHEBI:84060 ,
AKOS016050376
SCHEMBL44070
SY009526
SY030990
mfcd00063064
4-fluorophenylalanine #
dl-.beta.-p-fluorophenylalanine
dl-(4-fluorophenyl)alanine
2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidineperchloratesalt
W-105874
l-4-fluorophe
CHEMBL3185250
mfcd00002600
AC-9899
l-3-(4-fluorophenyl)alanine
Z57969728
2-amino-3-(4-fluorophenyl)propanoicacid
SY044822
Q27105098
AS-13556
BCP11609
BRD-A12490356-001-03-0
h-p-fluoro-dl-phe-oh
7-amino-3-vinyl-3-cephem-4-carboxylicaciddiphenylmethylestermonohydrochloride
NCGC00015435-04
CS-W017056
EN300-61659
HY-W016340
h-d-phe(p-f)-oh
(r)-2-amino-3-(4-fluoro-phenyl)-propionic acid
h-p-fluoro-d-phe-oh

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" One of the peptides, L-propyl-m-sarcolysyl-L-p-fluorophenylalanine (PSF), is highly toxic to melanoma cells."( Cytotoxicity and DNA cross-linking induced by peptide conjugated m-L-sarcolysin in human melanoma cells.
Hansson, J; Lewensohn, R; Ringborg, U,
)
0.39

Dosage Studied

ExcerptRelevanceReference
" Although these data indicate that enzyme potential was regulated by gene dosage and that the structural gene for each enzyme was continuously available for transcription during the cell-cycle it was not possible by using inhibitors of RNA synthesis, to demonstrate concurrent transcription during enzyme induction."( Induction potential for glyoxylate cycle enzymes during the cell cycle of Euglena gracilis.
Merrett, MJ; Woodward, J, 1975
)
0.25
" The experimental results indicated that the survival rate curve of strain A9 took a typical "exponential shape" with lethal dosage of EMS being 1%."( Breeding and characterization of amino acid-analogue-resistant mutants of Arthrospira platensis.
Cao, Y; Chen, X; Sun, L; Tang, X; Xia, R, 2014
)
0.4
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (4)

ClassDescription
phenylalanine derivativeAn amino acid derivative resulting from reaction of alanine at the amino group or the carboxy group, or from the replacement of any hydrogen of phenylalanine by a heteroatom. The definition normally excludes peptides containing phenylalanine residues.
non-proteinogenic alpha-amino acidAny alpha-amino acid which is not a member of the group of 23 proteinogenic amino acids.
monofluorobenzenesAny member of the class of fluorobenzenes containing a mono- or poly-substituted benzene ring carrying a single fluorine substitutent.
fluoroamino acidAn organofluorine compound that consists of an amino acid substituted by a fluoro group.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (4)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
aryl hydrocarbon receptorHomo sapiens (human)Potency2.10030.000723.06741,258.9301AID743085
v-jun sarcoma virus 17 oncogene homolog (avian)Homo sapiens (human)Potency2.05960.057821.109761.2679AID1159526; AID1159528
thyroid hormone receptor beta isoform 2Rattus norvegicus (Norway rat)Potency3.73490.000323.4451159.6830AID743065; AID743067
heat shock protein beta-1Homo sapiens (human)Potency1.33690.042027.378961.6448AID743210
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (1)

Assay IDTitleYearJournalArticle
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (184)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990131 (71.20)18.7374
1990's21 (11.41)18.2507
2000's19 (10.33)29.6817
2010's10 (5.43)24.3611
2020's3 (1.63)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 16.65

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index16.65 (24.57)
Research Supply Index5.28 (2.92)
Research Growth Index4.30 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (16.65)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews5 (2.55%)6.00%
Case Studies3 (1.53%)4.05%
Observational0 (0.00%)0.25%
Other188 (95.92%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]