Page last updated: 2024-11-05

aminopenicillanic acid

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

Description

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

6-aminopenicillanic acid : A penicillanic acid compound having a (6R)-amino substituent. The active nucleus common to all penicillins, it may be substituted at the 6-amino position to form the semisynthetic penicillins, resulting in a variety of antibacterial and pharmacologic characteristics. [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 CID11082
CHEMBL ID1236749
CHEBI ID16705
SCHEMBL ID66332
MeSH IDM0045472

Synonyms (95)

Synonym
ec 208-993-4
unii-qr0c4r7xvn
qr0c4r7xvn ,
CHEMBL1236749 ,
aminopenicillanic acid
6beta-aminopenicillanic acid
CHEBI:16705 ,
6-aminopenicillamine acid
6-amino-2,2-dimethylpenam-3alpha-carboxylic acid
(+)-6-aminopenicillanic acid
(2s,5r,6r)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
penin
phenacyl 6-aminopenicillinate
nsc-50071
6-aps
penicin
[2s-(2alpha,5alpha,6beta)]-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(2s,5r,6r)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptan-2-carbonsaeure
4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-, (2s,5r,6r)-
ai3-52557
6-AMINOPENICILLANATE ,
6-aminopenicillanic acid
551-16-6
6-apa
C02954
SR-01000640154-1 ,
(+)-6-aminopenicillanic acid, 96%
nsc 50071
4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-, (2s,5r,6r)-
einecs 208-993-4
NCGC00160198-01
AC-11282
A0800
x1e ,
BMSE000312
4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-, (2s,6r)-
rel-(2r,6s)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
09070_fluka
(2s)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
tox21_111749
cas-551-16-6
dtxcid5026097
dtxsid7046097 ,
A830497
CCG-50809
bdbm50420257
EPITOPE ID:117703
S12351
AKOS015907713
S5035
flucloxacillin magnesium octahydrate impurity c [ep impurity]
cloxacillin sodium impurity c [ep impurity]
benzylpenicillin sodium impurity a [ep impurity]
phenoxymethylpenicillin (benzathine) tetrahydrate impurity c [ep impurity]
ampicillin trihydrate impurity a [ep impurity]
sulbactam sodium impurity b [ep impurity]
dicloxacillin sodium impurity c [ep impurity]
6-aminopenicillanic acid [mi]
phenoxymethylpenicillin impurity c [ep impurity]
piperacillin sodium impurity h [ep]
6-amino-penicillanic acid
oxacillin sodium monohydrate impurity a [ep impurity]
(2s,5r,6r)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
ampicillin impurity a [ep impurity]
benzylpenicillin potassium impurity a [ep impurity]
flucloxacillin sodium monohydrate impurity c [ep impurity]
amoxicillin sodium impurity a [ep impurity]
phenoxymethylpenicillin potassium impurity c [ep impurity]
amoxicillin trihydrate impurity a [ep impurity]
SCHEMBL66332
KS-5277
6-aminopenicillinic acid (6-apa)
6-aminopenicillanicacid
amino penicillanic acid
6beta-amino-2,2-dimethylpenam-3alpha-carboxylic acid
(3s, 5r, 6r)-6-amino-2,2-dimethylpenam-3-carboxylic acid
6-aminopenici llanic acid
NGHVIOIJCVXTGV-ALEPSDHESA-N
(3s,5r,6r)-6-amino-2,2-dimethylpenam-3-carboxylic acid
W-105586
STR03060
(2s,5r,6r)-(+)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
mfcd00005176
(+)-6-aminopenicillanic acid, analytical standard
EN300-114057
flucloxacillin impurity c, european pharmacopoeia (ep) reference standard
(2s,5r,6r)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (6-aminopenicillanic acid)
Q2823234
BCP13375
CS-W014265
6-aminopenicillanic-acid
HY-W013549
(2s,5r,6r)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid
6-apa (2s,5r,6r)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid penicin penin
Z1269203097

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51

Dosage Studied

ExcerptRelevanceReference
"Two multivariate chemometric models, namely, partial least-squares regression (PLSR) and linear support vector regression (SVR), are presented for the analysis of amoxicillin trihydrate and dicloxacillin sodium in the presence of their common impurity (6-aminopenicillanic acid) in raw materials and in pharmaceutical dosage form via handling UV spectral data and making a modest comparison between the two models, highlighting the advantages and limitations of each."( Partial Least-Squares and Linear Support Vector Regression Chemometric Methods for Simultaneous Determination of Amoxicillin Trihydrate and Dicloxacillin Sodium in the Presence of Their Common Impurity.
Abdelaleem, EA; Hussein, EA; Naguib, IA; Zaazaa, HE, 2016
)
0.61
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
allergenA chemical compound, or part thereof, which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.
[role 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]

Drug Classes (2)

ClassDescription
amino acid zwitterionThe zwitterionic form of an amino acid having a negatively charged carboxyl group and a positively charged amino group.
penicillanic acids
[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 (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Solute carrier family 15 member 1Homo sapiens (human)Ki30,000.00000.18003.39339.8000AID681115
Solute carrier family 15 member 2Rattus norvegicus (Norway rat)Ki19,000.00003.00006.47788.5000AID681114
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (6)

Processvia Protein(s)Taxonomy
monoatomic ion transportSolute carrier family 15 member 1Homo sapiens (human)
protein transportSolute carrier family 15 member 1Homo sapiens (human)
peptide transportSolute carrier family 15 member 1Homo sapiens (human)
dipeptide import across plasma membraneSolute carrier family 15 member 1Homo sapiens (human)
tripeptide import across plasma membraneSolute carrier family 15 member 1Homo sapiens (human)
proton transmembrane transportSolute carrier family 15 member 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
proton-dependent oligopeptide secondary active transmembrane transporter activitySolute carrier family 15 member 1Homo sapiens (human)
peptide:proton symporter activitySolute carrier family 15 member 1Homo sapiens (human)
tripeptide transmembrane transporter activitySolute carrier family 15 member 1Homo sapiens (human)
dipeptide transmembrane transporter activitySolute carrier family 15 member 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
plasma membraneSolute carrier family 15 member 1Homo sapiens (human)
brush borderSolute carrier family 15 member 1Homo sapiens (human)
membraneSolute carrier family 15 member 1Homo sapiens (human)
apical plasma membraneSolute carrier family 15 member 1Homo sapiens (human)
plasma membraneSolute carrier family 15 member 1Homo sapiens (human)
apical plasma membraneSolute carrier family 15 member 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (24)

Assay IDTitleYearJournalArticle
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.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
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.
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.
AID1209734Inhibition of mouse OAT1 expressed in CHO cells assessed as inhibition of fluorescein uptake at 500 uM over 20 mins relative to untreated-control2013Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 41, Issue:4
Organic anion transporter 3 interacts selectively with lipophilic β-lactam antibiotics.
AID1377969Antibacterial activity against Proteus mirabilis ATCC 12453 measured after overnight incubation by two-fold serial dilution method2017European journal of medicinal chemistry, Sep-29, Volume: 138Antibiofilm potential of 16-oxo-cleroda-3, 13(14) E-diene-15 oic acid and its five new γ-amino γ-lactone derivatives against methicillin resistant Staphylococcus aureus and Streptococcus mutans.
AID1594610Drug reactivity against serine in PBS buffer by NMR assay2019Bioorganic & medicinal chemistry, 05-15, Volume: 27, Issue:10
Characterising covalent warhead reactivity.
AID1377974Antibiofilm activity against Klebsiella pneumoniae ATCC 13882 measured after overnight incubation by crystal violet-staining based assay2017European journal of medicinal chemistry, Sep-29, Volume: 138Antibiofilm potential of 16-oxo-cleroda-3, 13(14) E-diene-15 oic acid and its five new γ-amino γ-lactone derivatives against methicillin resistant Staphylococcus aureus and Streptococcus mutans.
AID681114TP_TRANSPORTER: inhibition of Gly-Sar uptake (pH6.0) in SKPT cells2005European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V, Jan, Volume: 59, Issue:1
Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1.
AID1377968Antibiofilm activity against Streptococcus mutans ATCC 25175 measured after overnight incubation by crystal violet-staining based assay2017European journal of medicinal chemistry, Sep-29, Volume: 138Antibiofilm potential of 16-oxo-cleroda-3, 13(14) E-diene-15 oic acid and its five new γ-amino γ-lactone derivatives against methicillin resistant Staphylococcus aureus and Streptococcus mutans.
AID1209733Binding affinity to mouse OAT3 expressed in CHO cells at 10 to 1000 uM measured over 20 mins2013Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 41, Issue:4
Organic anion transporter 3 interacts selectively with lipophilic β-lactam antibiotics.
AID1377975Antibiofilm activity against Proteus mirabilis ATCC 12453 measured after overnight incubation by crystal violet-staining based assay2017European journal of medicinal chemistry, Sep-29, Volume: 138Antibiofilm potential of 16-oxo-cleroda-3, 13(14) E-diene-15 oic acid and its five new γ-amino γ-lactone derivatives against methicillin resistant Staphylococcus aureus and Streptococcus mutans.
AID1594616Irreversible drug reactivity against cysteine in PBS buffer by NMR assay2019Bioorganic & medicinal chemistry, 05-15, Volume: 27, Issue:10
Characterising covalent warhead reactivity.
AID1594615Irreversible drug reactivity against serine in PBS buffer by NMR assay2019Bioorganic & medicinal chemistry, 05-15, Volume: 27, Issue:10
Characterising covalent warhead reactivity.
AID1209735Inhibition of mouse OAT3 expressed in CHO cells assessed as inhibition of fluorescein uptake at 500 uM over 20 mins relative to untreated-control2013Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 41, Issue:4
Organic anion transporter 3 interacts selectively with lipophilic β-lactam antibiotics.
AID1377967Antibacterial activity against Streptococcus mutans ATCC 25175 measured after overnight incubation by two-fold serial dilution method2017European journal of medicinal chemistry, Sep-29, Volume: 138Antibiofilm potential of 16-oxo-cleroda-3, 13(14) E-diene-15 oic acid and its five new γ-amino γ-lactone derivatives against methicillin resistant Staphylococcus aureus and Streptococcus mutans.
AID1377972Antibiofilm activity against methicillin-resistant Staphylococcus aureus ATCC 43300 measured after overnight incubation by crystal violet-staining based assay2017European journal of medicinal chemistry, Sep-29, Volume: 138Antibiofilm potential of 16-oxo-cleroda-3, 13(14) E-diene-15 oic acid and its five new γ-amino γ-lactone derivatives against methicillin resistant Staphylococcus aureus and Streptococcus mutans.
AID1377973Antibacterial activity against Klebsiella pneumoniae ATCC 13882 measured after overnight incubation by two-fold serial dilution method2017European journal of medicinal chemistry, Sep-29, Volume: 138Antibiofilm potential of 16-oxo-cleroda-3, 13(14) E-diene-15 oic acid and its five new γ-amino γ-lactone derivatives against methicillin resistant Staphylococcus aureus and Streptococcus mutans.
AID1209736Inhibition of human OAT3 expressed in CHO cells assessed as inhibition of fluorescein uptake at 500 uM over 20 mins relative to untreated-control2013Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 41, Issue:4
Organic anion transporter 3 interacts selectively with lipophilic β-lactam antibiotics.
AID781325pKa (acid-base dissociation constant) as determined by Liao ref: J Chem Info Model 20092014Pharmaceutical research, Apr, Volume: 31, Issue:4
Comparison of the accuracy of experimental and predicted pKa values of basic and acidic compounds.
AID1377970Antibacterial activity against methicillin-resistant Staphylococcus aureus ATCC 43300 measured after overnight incubation by two-fold serial dilution method2017European journal of medicinal chemistry, Sep-29, Volume: 138Antibiofilm potential of 16-oxo-cleroda-3, 13(14) E-diene-15 oic acid and its five new γ-amino γ-lactone derivatives against methicillin resistant Staphylococcus aureus and Streptococcus mutans.
AID681115TP_TRANSPORTER: inhibition of Gly-Sar uptake (pH6.0) in Caco-2 cells2005European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V, Jan, Volume: 59, Issue:1
Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1.
AID1594609Drug reactivity against cysteine in PBS buffer by NMR assay2019Bioorganic & medicinal chemistry, 05-15, Volume: 27, Issue:10
Characterising covalent warhead reactivity.
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 (190)

TimeframeStudies, This Drug (%)All Drugs %
pre-199075 (39.47)18.7374
1990's26 (13.68)18.2507
2000's46 (24.21)29.6817
2010's39 (20.53)24.3611
2020's4 (2.11)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 49.28

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

MetricThis Compound (vs All)
Research Demand Index49.28 (24.57)
Research Supply Index5.34 (2.92)
Research Growth Index4.46 (4.65)
Search Engine Demand Index77.56 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (49.28)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews7 (3.37%)6.00%
Case Studies6 (2.88%)4.05%
Observational0 (0.00%)0.25%
Other195 (93.75%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]