Page last updated: 2024-12-05

alpha-fluoro-beta-alanine

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

Description

alpha-fluoro-beta-alanine: metabolite of HCFU & 5-fluorouracil; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID13351
CHEMBL ID3544571
CHEBI ID80626
SCHEMBL ID637248
MeSH IDM0101008

Synonyms (37)

Synonym
3-amino-2-fluoropropionic acid
3821-81-6
alpha-fluoro-beta-alanine
inchi=1/c3h6fno2/c4-2(1-5)3(6)7/h2h,1,5h2,(h,6,7
3-amino-2-fluoropropanoic acid
FT-0668601
AKOS005255703
a-fluoro-b-alanine
a-fluoro-beta-alanine
2-fluoro-beta-alanine
dl-2-fluoro-3-alanine
A824062
unii-1461s5575q
einecs 223-318-3
1461s5575q ,
SCHEMBL637248
CHEBI:80626 ,
(rs)-3-amino-2-fluoropropionic acid
.alpha.-fluoro-.beta.-alanine
fluoro-.beta.-alanine
2-fluoro-.beta.-alanine
propanoic acid, 3-amino-2-fluoro-
2-fluoro-beta-alanine #
CHEMBL3544571
3-amino-2-fluoropropionic acid, 95%
mfcd00041324
BBL103051
STL556860
Q27149674
CS-W011291
MS-20544
DTXSID00959160
?-fluoro-?-alanine
3-amino-2-fluoropropanoicacid
alpha -fluoro- beta -alanine
EN300-220566
dl-2-fluoro-beta-alanine

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" In terms of survival time in relation to the cumulative dose and molecular weight, FBAL was more toxic than FA."( Experimental neurotoxicity of 5-fluorouracil and its derivatives is due to poisoning by the monofluorinated organic metabolites, monofluoroacetic acid and alpha-fluoro-beta-alanine.
Kuroiwa, T; Matsuo, T; Okeda, R; Shibutani, M; Shimokawa, R; Tajima, T, 1990
)
0.48
" Uracil plus tegafur was shown to be less toxic than the drug alone in all the species, and uracil was found to decrease the toxicity of tegafur."( Effect of coadministration of uracil on the toxicity of tegafur.
Haruno, A; Kunimune, Y; Morita, K; Unemi, N; Yamamoto, J; Yamashita, K; Yoshimura, Y, 1984
)
0.27
" Neurotoxic signs such as hyperesthesia and/or excitement, as well as convulsions, were observed in both FBAL x HCl and FA x Na groups; these toxic signs were also found in the UFT group."( Neurotoxic effects of alpha-fluoro-beta-alanine (FBAL) and fluoroacetic acid (FA) on dogs.
Ariyoshi, T; Yada, H; Yamashita, K, 2004
)
0.64
" In general, the most toxic compound was 5-FU."( Ecotoxicity and genotoxicity assessment of cytotoxic antineoplastic drugs and their metabolites.
Blaha, L; Dott, W; Kovalova, L; Zounkova, R, 2010
)
0.36

Pharmacokinetics

ExcerptReferenceRelevance
"Clinical pharmacokinetic studies in our laboratory demonstrated that 2-fluoro-beta-alanine (FBAL), the major catabolite of fluorouracil (FUra), has a prolonged elimination with an approximately 150-fold longer half-life than that of the unchanged drug in humans [Heggie et al."( Pharmacokinetics and tissue distribution of 2-fluoro-beta-alanine in rats. Potential relevance to toxicity pattern of 5-fluorouracil.
Barnes, S; Diasio, SB; Liu, TP; Soong, SJ; Zhang, RW,
)
0.13
" The ratio of FBAL to 5-FU in Cmax and AUC after dosing of UFT was the lowest among these four test compounds."( [Comparison of pharmacokinetics of 5-FU and alpha-fluoro-beta-alanine, a metabolite of 5-FU, in plasma after administration of UFT, tegafur, 5-FU or doxifluridine to rats].
Hirakawa, Y; Kawaguchi, Y; Kuwata, K; Matsushima, E; Nagayama, S, 2000
)
0.57
" Systemic exposure based on plasma concentrations of capecitabine and its metabolites was determined using individual parameter estimates derived from a population pharmacokinetic model constructed for this purpose in NONMEM."( Population pharmacokinetics and concentration-effect relationships of capecitabine metabolites in colorectal cancer patients.
Blesch, KS; Burger, HU; Gieschke, R; Reigner, B; Steimer, JL, 2003
)
0.32
" The primary pharmacokinetic parameter was AUC(0-infinity ) of 5'-deoxy-5-fluorouridine (5'-DFUR) on day 14."( Pharmacokinetics of capecitabine (Xeloda) in Japanese and Caucasian patients with breast cancer.
Bridgewater, J; Grange, S; Kimura, M; Kuranami, M; Lucraft, H; McAleer, J; Monkhouse, J; Poole, C; Reigner, B; Saeki, T; Sasaki, Y; Schüller, J; Watanabe, T; Weidekamm, E; Yorulmaz, C, 2003
)
0.32
" Therefore, the previously identified increased toxicity and shorter survival in patients with a low SMM, could not be explained by changes in pharmacokinetic characteristics of capecitabine and metabolites."( Worse capecitabine treatment outcome in patients with a low skeletal muscle mass is not explained by altered pharmacokinetics.
Beijnen, JH; Dorlo, TPC; Huitema, ADR; Jacobs, BAW; Kurk, SA; May, AM; Molenaar-Kuijsten, L; Steeghs, N, 2021
)
0.62

Dosage Studied

The study looked at the effects of alpha-fluoro-beta-alanine (FBAL) and fluoroacetic acid (FA) on the formation of vacuolar changes in the dog cerebrum. At the end of perfusion, 90 to 95% of the substrate remained unmetabolized in the medium.

ExcerptRelevanceReference
" At the end of perfusion alpha-fluoro-beta-alanine comprised 90 to 95% of FUDR-derived total radioactivity in the tissue even at initially 2400 microM FUDR, although at this FUDR dosage 20% of the substrate remained unmetabolized in the medium."( Nonlinear elimination kinetics of 5-fluoro-2'-deoxyuridine in isolated perfused rat liver and isolated hepatocytes.
Foth, H; Kahl, GF; Kunellis, EM; Müseler, T, 1990
)
0.58
" The findings indicate that a method is available to rationally address the design of dosing schedules in concurrent therapy regimens."( Alterations of intratumoral pharmacokinetics of 5-fluorouracil in head and neck carcinoma during simultaneous radiochemotherapy.
Bachert, P; Becker, M; Dietz, A; Knopp, MV; Rudat, V; Schlemmer, HP; van Kaick, G; Vanselow, B; Wannenmacher, M; Weidauer, H; Wollensack, P; Zuna, I, 1999
)
0.3
" The ratio of FBAL to 5-FU in Cmax and AUC after dosing of UFT was the lowest among these four test compounds."( [Comparison of pharmacokinetics of 5-FU and alpha-fluoro-beta-alanine, a metabolite of 5-FU, in plasma after administration of UFT, tegafur, 5-FU or doxifluridine to rats].
Hirakawa, Y; Kawaguchi, Y; Kuwata, K; Matsushima, E; Nagayama, S, 2000
)
0.57
" The present results have no clinical implications for the use of capecitabine and argue against the value of therapeutic drug monitoring for dosage adjustment."( Population pharmacokinetics and concentration-effect relationships of capecitabine metabolites in colorectal cancer patients.
Blesch, KS; Burger, HU; Gieschke, R; Reigner, B; Steimer, JL, 2003
)
0.32
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
organooxygen compoundAn organochalcogen compound containing at least one carbon-oxygen bond.
organonitrogen compoundAny heteroorganic entity containing at least one carbon-nitrogen bond.
[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]

Pathways (1)

PathwayProteinsCompounds
Fluoropyrimidine activity015

Bioassays (1)

Assay IDTitleYearJournalArticle
AID1654628Drug metabolism in perfused Wistar rat liver assessed as FAC formation at 16.6 mg/kg measured after 3 hrs by 19F NMR analysis2020Journal of medicinal chemistry, 06-25, Volume: 63, Issue:12
Metabolic and Pharmaceutical Aspects of Fluorinated Compounds.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (68)

TimeframeStudies, This Drug (%)All Drugs %
pre-199011 (16.18)18.7374
1990's27 (39.71)18.2507
2000's16 (23.53)29.6817
2010's10 (14.71)24.3611
2020's4 (5.88)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.33

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index10.33 (24.57)
Research Supply Index4.34 (2.92)
Research Growth Index4.67 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.33)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials4 (5.56%)5.53%
Reviews0 (0.00%)6.00%
Case Studies3 (4.17%)4.05%
Observational0 (0.00%)0.25%
Other65 (90.28%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]