Compounds > alafosfalin
Page last updated: 2024-09-23

alafosfalin

Description

alafosfalin: RN given refers to parent cpd; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID71957
CHEMBL ID3989665
SCHEMBL ID1582301
MeSH IDM0049017

Synonyms (54)

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

Research Excerpts

Overview

ExcerptReference
"Alafosfalin is a phosphonodipeptide with significant activity as an antibacterial agent and as a potentiator of beta-lactam antibiotics. "( Allen, JG; Lees, LJ, 1980)

Effects

ExcerptReference
"Alafosfalin has an elimination half-life of about 60 min and does not accumulate during chronic administration."( Allen, JG; Lees, LJ, 1980)
"Alafosfalin has an elimination half-life of about 60 min and does not accumulate during chronic administration."( Allen, JG; Lees, LJ, 1980)

Bioassays (22)

Assay IDTitleYearJournalArticle
AID71060In vivo antibacterial activity was measured relative to alafosfalin against Escherichia coli 281007 strain after po administration.1986Journal 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.
AID205390Compound was tested for its antibacterial activity against Serratia marcescens ATCC 14756 strain.1986Journal 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.
AID208019Compound was tested in vitro for its antibacterial activity against Streptococcus faecalis FS5 strain.1986Journal 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.
AID205832Compound was tested in vitro for its antibacterial activity against Staphylococcus aureus 561037 strain.1986Journal 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.
AID95718Compound was tested for its antibacterial activity against Klebsiella aerogenes 331001 strain.1986Journal 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.
AID70592Compound was tested in vitro for its antibacterial activity against Escherichia coli NCIB 8879 strain.1986Journal 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.
AID689982Tmax in Sprague-Dawley rat at 20 mg/kg, sc administered as single dose2011Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17
Remarkable potential of the α-aminophosphonate/phosphinate structural motif in medicinal chemistry.
AID85971Compound was tested in vitro for its antibacterial activity against Haemophilus influenzae NCTC 4560 strain.1986Journal 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.
AID208018Compound was tested for its antibacterial activity against Streptococcus faecalis 58511 strain.1986Journal 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.
AID67538Compound was tested for its antibacterial activity against Enterobacter 250002 strain.1986Journal 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.
AID205671Compound was tested for its antibacterial activity against Staphylococcus aureus NCIB 8625 strain.1986Journal 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.
AID85969Compound was tested for its antibacterial activity against Haemophilus influenzae NCTC 4560 strain.1986Journal 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.
AID200861Compound was tested for its antibacterial activity against Salmonella Typhimurium 538003 strain.1986Journal 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.
AID71061In vivo antibacterial activity was measured relative to alafosfalin against Escherichia coli 281007 strain after sc administration.1986Journal 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.
AID689979Half life in human at 200 mg, im2011Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17
Remarkable potential of the α-aminophosphonate/phosphinate structural motif in medicinal chemistry.
AID689981AUC in Sprague-Dawley rat at 20 mg/kg, sc administered as single dose2011Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17
Remarkable potential of the α-aminophosphonate/phosphinate structural motif in medicinal chemistry.
AID70572Compound was tested for its antibacterial activity against Escherichia coli NCIB 8879 strain.1986Journal 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.
AID689980Half life in Sprague-Dawley rat at 20 mg/kg, sc administered as single dose2011Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17
Remarkable potential of the α-aminophosphonate/phosphinate structural motif in medicinal chemistry.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID504749qHTS profiling for inhibitors of Plasmodium falciparum proliferation2011Science (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]

Research

Studies (31)

TimeframeStudies, This Drug (%)All Drugs %
pre-199021 (67.74)18.7374
1990's0 (0.00)18.2507
2000's2 (6.45)29.6817
2010's6 (19.35)24.3611
2020's2 (6.45)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (3.23%)5.53%
Reviews1 (3.23%)6.00%
Case Studies1 (3.23%)4.05%
Observational0 (0.00%)0.25%
Other28 (90.32%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceDescriptionRelationhip StrengthStudiesTrialsClassesRoles
acetohydroxamic acid[no description available]medium10acetohydroxamic acids;
carbohydroximic acid		algal metabolite;
EC 3.5.1.5 (urease) inhibitor
alendronate[no description available]medium101,1-bis(phosphonic acid);
primary amino compound		bone density conservation agent;
EC 2.5.1.1 (dimethylallyltranstransferase) inhibitor
incadronate[no description available]medium101,1-bis(phosphonic acid)
pamidronate[no description available]medium10phosphonoacetic acid
risedronic acid[no description available]medium10pyridines
fosinoprilat[no description available]medium10L-proline derivative;
phosphinic acids		antihypertensive agent;
EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
zoledronic acid[no description available]medium101,1-bis(phosphonic acid);
imidazoles		bone density conservation agent
fosinopril[no description available]medium10
rxp 407[no description available]medium10
emtricitabine[no description available]medium10monothioacetal;
nucleoside analogue;
organofluorine compound;
pyrimidone		antiviral drug;
HIV-1 reverse transcriptase inhibitor
tenofovir[no description available]medium10nucleoside analogue;
phosphonic acids		antiviral drug;
drug metabolite;
HIV-1 reverse transcriptase inhibitor
alanine[no description available]medium271alanine zwitterion;
alanine;
L-alpha-amino acid;
proteinogenic amino acid;
pyruvate family amino acid		EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor;
fundamental metabolite
abacavir[no description available]medium102,6-diaminopurinesantiviral drug;
drug allergen;
HIV-1 reverse transcriptase inhibitor
dolutegravir[no description available]medium10difluorobenzene;
monocarboxylic acid amide;
organic heterotricyclic compound;
secondary carboxamide		HIV-1 integrase inhibitor
glycylsarcosine[no description available]medium10dipeptide zwitterion;
dipeptide
fosfomycin[no description available]medium20epoxide;
phosphonic acids		antimicrobial agent;
EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor
fosmidomycin[no description available]medium20hydroxamic acid;
phosphonic acids		antimicrobial agent;
bacterial metabolite;
EC 1.1.1.267 (1-deoxy-D-xylulose-5-phosphate reductoisomerase) inhibitor
cephalexin[no description available]medium31beta-lactam antibiotic allergen;
cephalosporin;
semisynthetic derivative		antibacterial drug
cefamandole[no description available]medium10cephalosporin;
semisynthetic derivative		antibacterial drug
carbenicillin[no description available]medium10penicillin allergen;
penicillin		antibacterial drug
amdinocillin[no description available]medium10penicillinantibacterial drug;
antiinfective agent
ampicillin[no description available]medium30beta-lactam antibiotic;
penicillin allergen;
penicillin		antibacterial drug
penicillin g[no description available]medium20penicillin allergen;
penicillin		antibacterial drug;
drug allergen;
epitope
cephalosporin c[no description available]medium10cephalosporinfungal metabolite
beta-lactams[no description available]medium10beta-lactam antibiotic allergen;
beta-lactam
uridine diphosphate[no description available]medium10pyrimidine ribonucleoside 5'-diphosphate;
uridine 5'-phosphate		Escherichia coli metabolite;
mouse metabolite
aminoethylphosphonic acid[no description available]medium10phosphonic acids;
primary amino compound;
zwitterion		human metabolite;
metabolite;
mouse metabolite
1-aminomethylphosphonic acid[no description available]medium10one-carbon compound;
phosphonic acids
organophosphonates[no description available]medium10divalent inorganic anion;
phosphite ion
1-(aminoethyl)phosphonic acid[no description available]medium10phosphonoacetic acid
cycloserine[no description available]medium104-amino-1,2-oxazolidin-3-one;
organonitrogen heterocyclic antibiotic;
organooxygen heterocyclic antibiotic;
zwitterion		antiinfective agent;
antimetabolite;
antitubercular agent;
metabolite;
NMDA receptor agonist
ConditionIndicatedRelationship StrengthStudiesTrials
Bacterial Disease0low20
Bacterial Infection0low20
Bacterial Infections0low20
Bacteriuria0low10
Blood Poisoning0low20
Bloodstream Infection0low20
Cholera0low10
Chronic Esophagitis, Eosinophilic0low10
Deglutition Disorders0low10
Dysphagia0low10
E coli Infections0low20
E. coli Infection0low20
Eosinophilic Esophagitis0low10
Escherichia coli Infections0low20
Esophageal Dysphagia0low10
Esophagitis, Eosinophilic0low10
HIV Coinfection0low10
HIV Infections0low10
HTLV-III Infections0low10
HTLV-III-LAV Infections0low10
Infection, Bacterial0low20
Infections, Bacterial0low20
Infections, E coli0low20
Infections, Escherichia coli0low20
Oropharyngeal Dysphagia0low10
Poisoning, Blood0low20
Pyaemia0low20
Pyemia0low20
Pyohemia0low20
Sensitivity and Specificity0low10
Sepsis0low20
Septicemia0low20
Severe Sepsis0low20
Swallowing Disorders0low10
T-Lymphotropic Virus Type III Infections, Human0low10
Urinary Tract Infections0medium21
Vibrio cholerae Infection0low10

Research Highlights

Long-term Use (1)

ArticleYear
Pharmacokinetics of alafosfalin, alone and in combination with cephalexin, in humans.
Antimicrobial agents and chemotherapy, Volume: 17, Issue: 6		1980
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Pharmacokinetics (1)

ArticleYear
Phosphonopeptides as antibacterial agents: metabolism and pharmacokinetics of alafosfalin in animals and humans.
Antimicrobial agents and chemotherapy, Volume: 16, Issue: 3		1979
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioavailability (3)

ArticleYear
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Molecular pharmacology, Volume: 96, Issue: 5		2019
Pharmacokinetics of alafosfalin, alone and in combination with cephalexin, in humans.
Antimicrobial agents and chemotherapy, Volume: 17, Issue: 6		1980
Phosphonopeptides as antibacterial agents: metabolism and pharmacokinetics of alafosfalin in animals and humans.
Antimicrobial agents and chemotherapy, Volume: 16, Issue: 3		1979
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Dosage (1)

ArticleYear
Phosphonopeptides as antibacterial agents: metabolism and pharmacokinetics of alafosfalin in animals and humans.
Antimicrobial agents and chemotherapy, Volume: 16, Issue: 3		1979
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Interactions (2)

ArticleYear
Pharmacokinetics of alafosfalin, alone and in combination with cephalexin, in humans.
Antimicrobial agents and chemotherapy, Volume: 17, Issue: 6		1980
Antibacterial properties of alafosfalin combined with cephalexin.
Antimicrobial agents and chemotherapy, Volume: 20, Issue: 4		1981
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]