Compounds > 4-fluorotryptophan
Page last updated: 2024-11-07

4-fluorotryptophan

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

Description

4-fluorotryptophan is a synthetic analogue of tryptophan. It is a fluorinated amino acid that has been studied as a potential therapeutic agent for a variety of diseases. 4-fluorotryptophan has been shown to inhibit the growth of cancer cells and to have antidepressant effects. It has also been studied as a potential treatment for Huntington's disease and other neurodegenerative disorders. The synthesis of 4-fluorotryptophan typically involves the fluorination of tryptophan using a variety of reagents, such as N-fluorobenzenesulfonimide or Selectfluor. The compound is then purified and characterized using standard techniques. 4-fluorotryptophan is studied because it has unique pharmacological properties that make it a promising candidate for the development of new drugs. For example, 4-fluorotryptophan is a potent inhibitor of the enzyme indoleamine 2,3-dioxygenase (IDO), which is involved in the degradation of tryptophan. Inhibition of IDO has been shown to have a number of therapeutic effects, including anti-inflammatory, anti-tumor, and antidepressant effects. In addition, 4-fluorotryptophan is a substrate for the enzyme tryptophan hydroxylase, which is involved in the synthesis of serotonin. This suggests that 4-fluorotryptophan may be able to modulate serotonin levels in the brain, which could have therapeutic implications for a variety of diseases.'

4-fluorotryptophan: RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID101198
CHEMBL ID4078473
SCHEMBL ID1727642
SCHEMBL ID18029333
MeSH IDM0117964

Synonyms (27)

Synonym
4-fluoro-d,l-tryptophan
nsc529108
nsc-529108
25631-17-8
4-fluoro-dl-tryptophan, crystalline
F-6800
4-fluoro-dl-tryptophan
4-fluorotryptophan
25631-05-4
2-amino-3-(4-fluoro-1h-indol-3-yl)propanoic acid
A817932
tryptophan, 4-fluoro-
nsc 529108
FT-0618531
AKOS022929311
SCHEMBL1727642
SCHEMBL18029333
mfcd00039689
DTXSID30275961
h-trp(4-f)-oh
FS-6606
A50405
2-amino-3-(4-fluoro-1h-indol-3-yl)propanoicacid
CHEMBL4078473
EN300-369983
CS-0186533
PD042105
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (19)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (21.05)18.7374
1990's7 (36.84)18.2507
2000's4 (21.05)29.6817
2010's3 (15.79)24.3611
2020's1 (5.26)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 16.79

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 Index16.79 (24.57)
Research Supply Index3.00 (2.92)
Research Growth Index4.61 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (16.79)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other19 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
5-hydroxytryptophan
5-Hydroxytryptophan: The immediate precursor in the biosynthesis of SEROTONIN from tryptophan. It is used as an antiepileptic and antidepressant.. 5-hydroxytryptophan : A tryptophan derivative that is tryptophan substituted by a hydroxy group at position 5.		1.9910hydroxytryptophanhuman metabolite;
neurotransmitter
3,3-dimethylallyl pyrophosphate
3,3-dimethylallyl pyrophosphate: isomeric with isopentenyl pyrophosphate. prenyl diphosphate : A prenol phosphate that is a phosphoantigen comprising the O-pyrophosphate of prenol.		2.0710prenol phosphateepitope;
Escherichia coli metabolite;
mouse metabolite;
phosphoantigen
indole
[no description available]		2.0710indole;
polycyclic heteroarene		Escherichia coli metabolite
guanidine
Guanidine: A strong organic base existing primarily as guanidium ions at physiological pH. It is found in the urine as a normal product of protein metabolism. It is also used in laboratory research as a protein denaturant. (From Martindale, the Extra Pharmacopoeia, 30th ed and Merck Index, 12th ed) It is also used in the treatment of myasthenia and as a fluorescent probe in HPLC.. guanidine : An aminocarboxamidine, the parent compound of the guanidines.		1.9810carboxamidine;
guanidines;
one-carbon compound
p-fluorophenylalanine
p-Fluorophenylalanine: 3-(p-Fluorophenyl)-alanine.. 4-fluorophenylalanine : A phenylalanine derivative in which the hydrogen at position 4 on the benzene ring is replaced by a fluoro group.		2.4120fluoroamino acid;
monofluorobenzenes;
non-proteinogenic alpha-amino acid;
phenylalanine derivative
adenosine monophosphate
Adenosine Monophosphate: Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position.		1.9710adenosine 5'-phosphate;
purine ribonucleoside 5'-monophosphate		adenosine A1 receptor agonist;
cofactor;
EC 3.1.3.1 (alkaline phosphatase) inhibitor;
EC 3.1.3.11 (fructose-bisphosphatase) inhibitor;
fundamental metabolite;
micronutrient;
nutraceutical
phenylalanine
Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.		1.9810amino acid zwitterion;
erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid;
phenylalanine;
proteinogenic amino acid		algal metabolite;
EC 3.1.3.1 (alkaline phosphatase) inhibitor;
Escherichia coli metabolite;
human xenobiotic metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
valine
Valine: A branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway.. valine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isopropyl group.. L-valine : The L-enantiomer of valine.		2.6930L-alpha-amino acid zwitterion;
L-alpha-amino acid;
proteinogenic amino acid;
pyruvate family amino acid;
valine		algal metabolite;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
tryptophan
Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.		4.3190erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid zwitterion;
L-alpha-amino acid;
proteinogenic amino acid;
tryptophan zwitterion;
tryptophan		antidepressant;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
arginine
Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group.		2.0110arginine;
glutamine family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		biomarker;
Escherichia coli metabolite;
micronutrient;
mouse metabolite;
nutraceutical
2-fluorophenylalanine
2-fluorophenylalanine: p-fluorophenylalanine is a minor descriptor; RN given refers to cpd with unspecified isomeric designation. 2-fluoro-DL-phenylalanine : A racemate comprising equimolar amounts of 2-fluoro-L-phenylalanine and 2-fluoro-D-phenylalanine.. 2-fluorophenylalanine : A phenylalanine derivative in which the hydrogen at position 2 on the benzene ring is replaced by a fluoro group.		1.9810monofluorobenzenes;
non-proteinogenic alpha-amino acid;
phenylalanine derivative
5-fluorotryptophan
5-fluorotryptophan: RN given refers to cpd with unspecified isomeric designation. 5-fluorotryptophan : A non-proteinogenic alpha-amino acid that is tryptophan in which the hydrogen at position 5 on the indole ring is replaced by a fluoro group.		2.940non-proteinogenic alpha-amino acid;
organofluorine compound;
tryptophan derivative
3-fluorophenylalanine
3-fluorophenylalanine: p-fluorophenylalanine is a minor descriptor; RN given refers cpd with unspecified isomeric designation		1.9810
fluorine
Fluorine: A nonmetallic, diatomic gas that is a trace element and member of the halogen family. It is used in dentistry as fluoride (FLUORIDES) to prevent dental caries.		2.3920diatomic fluorine;
gas molecular entity		NMR chemical shift reference compound
1,5-i-aedans
1,5-I-AEDANS: fluorescent probes which are sulfhydryl reagents; combine reactivity of iodoacetamide toward sulfhydryl groups with spectral properties of naphthalenesulfonic acids; structure. 5-{[2-(iodoacetamido)ethyl]amino}naphthalene-1-sulfonic acid : An aminonaphthalenesulfonic acid fluorophore with a structure consisting of ethylenediamine substituted on the nitrogens with iodoacetyl and 5-sulfonyl-1-naphthyl groups.		1.9910aminonaphthalenesulfonic acidfluorescent probe
6-fluorotryptophan
6-fluorotryptophan: an inhibitor of serotonin synthesis; RN given refers to parent cpd without isomeric designation		3.2660indolyl carboxylic acid
cysteine
Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.		2.4620cysteiniumfundamental metabolite
7-azatryptophan
7-azatryptophan: RN given refers to cpd without isomeric designation; structure		1.9910
anticodon
Anticodon: The sequential set of three nucleotides in TRANSFER RNA that interacts with its complement in MESSENGER RNA, the CODON, during translation in the ribosome.		2.0110
muramidase
Muramidase: A basic enzyme that is present in saliva, tears, egg white, and many animal fluids. It functions as an antibacterial agent. The enzyme catalyzes the hydrolysis of 1,4-beta-linkages between N-acetylmuramic acid and N-acetyl-D-glucosamine residues in peptidoglycan and between N-acetyl-D-glucosamine residues in chitodextrin. EC 3.2.1.17.		1.9810
ConditionIndicatedRelationship StrengthStudiesTrials
Breast Cancer
[description not available]		02.0410
Breast Neoplasms
Tumors or cancer of the human BREAST.		02.0410