Alafosfalin is a synthetic analog of the natural compound fosfomycin. It is a potent inhibitor of UDP-N-acetylmuramate:L-alanine ligase (MurA), a key enzyme involved in bacterial cell wall biosynthesis. Alafosfalin's mechanism of action involves binding to the active site of MurA, preventing the formation of the essential peptidoglycan layer of the bacterial cell wall. This disruption leads to bacterial cell death. Alafosfalin exhibits broad-spectrum antibacterial activity against both Gram-positive and Gram-negative bacteria. Due to its unique mechanism of action and resistance profile, alafosfalin has shown potential for treating infections caused by multidrug-resistant bacteria. However, alafosfalin's clinical use is limited by its poor oral bioavailability and potential for nephrotoxicity. Extensive research is ongoing to develop new formulations and delivery strategies to improve alafosfalin's therapeutic index and expand its clinical application. Alafosfalin is studied for its potential to overcome antibiotic resistance and provide a novel therapeutic option for infections that are challenging to treat with current antibiotics.'
alafosfalin: RN given refers to parent cpd; structure
ID Source | ID |
---|---|
PubMed CID | 71957 |
CHEMBL ID | 3989665 |
SCHEMBL ID | 1582301 |
MeSH ID | M0049017 |
Synonym |
---|
l-alanyl-l-1-aminoethylphosphonic acid |
(1r)-1-(l-alanylamino)ethylphosphonic acid |
((1r)-1-((2s)-2-aminopropionamido)ethyl)phosphonic acid |
alafosfalin |
NCGC00164496-01 |
[(1r)-1-[[(2s)-2-aminopropanoyl]amino]ethyl]phosphonic acid |
n-[(1r)-1-phosphonoethyl]-l-alaninamide |
NCGC00164496-02 |
A-4625 |
AFS , |
cas-60668-24-8 |
dtxcid4026393 |
dtxsid6046393 , |
tox21_112134 |
AKOS006238307 |
alafosfalinum [inn-latin] |
ro 03-7008 |
alafosfaline |
0m8om373bs , |
phosphonic acid, ((1r)-1-(((2s)-2-amino-1-oxopropyl)amino)ethyl)- |
alafosfalin [inn:ban] |
((1r)-1-(((2s)-2-amino-1-oxopropyl)amino)ethyl)phosphonic acid |
alafosfalino |
60668-24-8 |
alafosfalinum |
einecs 262-362-8 |
unii-0m8om373bs |
alafosfaline [inn-french] |
phosphonic acid, (1-((2-amino-1-oxopropyl)amino)ethyl)-, (r-(r*,s*))- |
alafosfalino [inn-spanish] |
alaphosphin |
alafosfalin [mart.] |
ro-3-7008 |
alafosfalin [mi] |
p-((1r)-1-(((2s)-2-amino-1-oxopropyl)amino)ethyl)phosphonic acid |
alafosfalin [inn] |
BHAYDBSYOBONRV-IUYQGCFVSA-N |
(1r)-1-(l-alanylamino)-ethylphosphonic acid |
SCHEMBL1582301 |
(s)-alanyl-(r)-1-aminoethylphosphonic acid, antibiotic for culture media use only |
mfcd01569244 |
(s)-alanyl-(r)-1-aminoethylphosphonic acid |
sr-01000944629 |
SR-01000944629-1 |
l-alanyl-l-1-aminoethylphosphonic acid, >=98.0% (t) |
gtpl9503 |
phosphonic acid, [(1r)-1-[[(2s)-2-amino-1-oxopropyl]amino]ethyl]- |
((r)-1-((s)-2-aminopropanamido)ethyl)phosphonic acid |
CHEMBL3989665 |
HY-119881 |
Q15633923 |
BRD-K80403280-001-01-3 |
CS-0078244 |
((r)-1-((s)-2-aminopropanamido)ethyl)phosphonicacid |
Alafosfalin is a phosphonodipeptide with significant activity as an antibacterial agent and as a potentiator of beta-lactam antibiotics.
Excerpt | Reference | Relevance |
---|---|---|
"Alafosfalin is a phosphonodipeptide with significant activity as an antibacterial agent and as a potentiator of beta-lactam antibiotics. " | ( Pharmacokinetics of alafosfalin, alone and in combination with cephalexin, in humans. Allen, JG; Lees, LJ, 1980) | 2.03 |
Excerpt | Reference | Relevance |
---|---|---|
"Alafosfalin has an elimination half-life of about 60 min and does not accumulate during chronic administration." | ( Pharmacokinetics of alafosfalin, alone and in combination with cephalexin, in humans. Allen, JG; Lees, LJ, 1980) | 1.31 |
"Alafosfalin has an elimination half-life of about 60 min and does not accumulate during chronic administration." | ( Pharmacokinetics of alafosfalin, alone and in combination with cephalexin, in humans. Allen, JG; Lees, LJ, 1980) | 1.31 |
Excerpt | Reference | Relevance |
---|---|---|
"The phosphonopeptide alafosfalin (L-alanyl-L-1-aminoethylphosphonic acid) exhibited synergy in vitro and in animal studies against a range of bacterial genera when combined with cephalexin." | ( Antibacterial properties of alafosfalin combined with cephalexin. Atherton, FR; Hall, MJ; Hassall, CH; Holmes, SW; Lambert, RW; Lloyd, WJ; Nisbet, LJ; Ringrose, PS; Westmacott, D, 1981) | 0.88 |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID71060 | In vivo antibacterial activity was measured relative to alafosfalin against Escherichia coli 281007 strain after po administration. | 1986 | Journal of medicinal chemistry, Jan, Volume: 29, Issue:1 | Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid. |
AID205390 | Compound was tested for its antibacterial activity against Serratia marcescens ATCC 14756 strain. | 1986 | Journal of medicinal chemistry, Jan, Volume: 29, Issue:1 | Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid. |
AID208019 | Compound was tested in vitro for its antibacterial activity against Streptococcus faecalis FS5 strain. | 1986 | Journal of medicinal chemistry, Jan, Volume: 29, Issue:1 | Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid. |
AID205832 | Compound was tested in vitro for its antibacterial activity against Staphylococcus aureus 561037 strain. | 1986 | Journal of medicinal chemistry, Jan, Volume: 29, Issue:1 | Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid. |
AID95718 | Compound was tested for its antibacterial activity against Klebsiella aerogenes 331001 strain. | 1986 | Journal of medicinal chemistry, Jan, Volume: 29, Issue:1 | Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid. |
AID70592 | Compound was tested in vitro for its antibacterial activity against Escherichia coli NCIB 8879 strain. | 1986 | Journal of medicinal chemistry, Jan, Volume: 29, Issue:1 | Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid. |
AID689982 | Tmax in Sprague-Dawley rat at 20 mg/kg, sc administered as single dose | 2011 | Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17 | Remarkable potential of the α-aminophosphonate/phosphinate structural motif in medicinal chemistry. |
AID85971 | Compound was tested in vitro for its antibacterial activity against Haemophilus influenzae NCTC 4560 strain. | 1986 | Journal of medicinal chemistry, Jan, Volume: 29, Issue:1 | Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid. |
AID208018 | Compound was tested for its antibacterial activity against Streptococcus faecalis 58511 strain. | 1986 | Journal of medicinal chemistry, Jan, Volume: 29, Issue:1 | Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid. |
AID67538 | Compound was tested for its antibacterial activity against Enterobacter 250002 strain. | 1986 | Journal of medicinal chemistry, Jan, Volume: 29, Issue:1 | Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid. |
AID205671 | Compound was tested for its antibacterial activity against Staphylococcus aureus NCIB 8625 strain. | 1986 | Journal of medicinal chemistry, Jan, Volume: 29, Issue:1 | Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid. |
AID85969 | Compound was tested for its antibacterial activity against Haemophilus influenzae NCTC 4560 strain. | 1986 | Journal of medicinal chemistry, Jan, Volume: 29, Issue:1 | Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid. |
AID200861 | Compound was tested for its antibacterial activity against Salmonella Typhimurium 538003 strain. | 1986 | Journal of medicinal chemistry, Jan, Volume: 29, Issue:1 | Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid. |
AID71061 | In vivo antibacterial activity was measured relative to alafosfalin against Escherichia coli 281007 strain after sc administration. | 1986 | Journal of medicinal chemistry, Jan, Volume: 29, Issue:1 | Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid. |
AID689979 | Half life in human at 200 mg, im | 2011 | Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17 | Remarkable potential of the α-aminophosphonate/phosphinate structural motif in medicinal chemistry. |
AID689981 | AUC in Sprague-Dawley rat at 20 mg/kg, sc administered as single dose | 2011 | Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17 | Remarkable potential of the α-aminophosphonate/phosphinate structural motif in medicinal chemistry. |
AID70572 | Compound was tested for its antibacterial activity against Escherichia coli NCIB 8879 strain. | 1986 | Journal of medicinal chemistry, Jan, Volume: 29, Issue:1 | Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid. |
AID689980 | Half life in Sprague-Dawley rat at 20 mg/kg, sc administered as single dose | 2011 | Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17 | Remarkable potential of the α-aminophosphonate/phosphinate structural motif in medicinal chemistry. |
AID1296008 | Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening | 2020 | SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1 | Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening. |
AID1346986 | P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
AID1346987 | P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
AID504749 | qHTS profiling for inhibitors of Plasmodium falciparum proliferation | 2011 | Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043 | Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets. |
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 21 (67.74) | 18.7374 |
1990's | 0 (0.00) | 18.2507 |
2000's | 2 (6.45) | 29.6817 |
2010's | 6 (19.35) | 24.3611 |
2020's | 2 (6.45) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
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.
| This Compound (22.06) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 1 (3.23%) | 5.53% |
Reviews | 1 (3.23%) | 6.00% |
Case Studies | 1 (3.23%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 28 (90.32%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |