apramycin : An aminoglycoside that is 2-deoxystreptamine that is substituted on the oxygen at position 4 by an (8R)-2-amino-8-O-(4-amino-4-deoxy-alpha-D-glucopyranosyl)-2,3,7-trideoxy-7-(methylamino)-D-glycero-alpha-D-allo-octodialdo-1,5:8,4-dipyranos-1-yl) group. [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]
ID Source | ID |
---|---|
PubMed CID | 3081545 |
CHEMBL ID | 1230961 |
CHEBI ID | 2790 |
SCHEMBL ID | 18388 |
MeSH ID | M0058148 |
Synonym |
---|
AB01275497-01 |
CHEMBL1230961 |
chebi:2790 , |
d-streptamine, o-4-amino-4-deoxy-alpha-d-glucopyranosyl-(1-8)-o-(8r)-2-amino-2,3,7-trideoxy-7-(methylamino)-d-glycero-alpha-d-allo-octadialdo-1,5:8,4-dipyranosyl-(1-4)-2-deoxy- |
cas-37321-09-8 |
NCGC00016836-01 |
apramycin |
37321-09-8 |
C01555 |
nebramycin ii |
DB04626 |
4-o-(3alpha-amino-6alpha-((4-amino-4-deoxy-alpha-d-glucopyranosyl)oxy)-2,3,4,5abeta,6,7,8,8aalpha-octahydro-8beta-hydroxy-7beta-(methylamino)pyrano(3,2-b)pyran-2alpha-yl)-2-deoxy-d-streptamine |
4-o-((8r)-2-amino-8-o-(4-amino-4-deoxy-alpha-d-glucopyranosyl)-2,3,7-trideoxy-7-(methylamino)-d-glycero-alpha-d-allo-octodialdo-1,5:8,4-dipyranos-1-yl)-2-deoxy-d-streptamine |
D02322 |
apramycin (usan/inn) |
AM2 , |
einecs 253-460-1 |
apramycinum [inn-latin] |
nebramycin factor 2 |
d-streptamine, 4-o-((8r)-2-amino-8-o-(4-amino-4-deoxy-alpha-d-glucopyranosyl)-2,3,7-trideoxy-7-(methylamino)-d-glycero-alpha-d-allo-octodialdo-1,5:8,4-dipyranos-1-yl)-2-deoxy- |
apramicina [inn-spanish] |
apralan |
apramycine [inn-french] |
ambylan |
el-857/820 |
el 857 |
HMS2090I15 |
(2r,3r,4s,5s,6s)-2-[[(2r,3s,4r,4ar,6s,7r,8as)-7-amino-6-[(1r,2r,3s,4r,6s)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy-4-hydroxy-3-(methylamino)-2,3,4,4a,6,7,8,8a-octahydropyrano[3,2-b]pyran-2-yl]oxy]-5-amino-6-(hydroxymethyl)oxane-3,4-diol |
apramycinum |
(2r,3s,4r,4ar,6s,7r,8as)-7-amino-6-{[(1r,2r,3s,4r,6s)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy}-4-hydroxy-3-(methylamino)octahydropyrano[3,2-b]pyran-2-yl 4-amino-4-deoxy-alpha-d-glucopyranoside |
apramycine |
apramicina |
tox21_110639 |
dtxcid3025465 |
dtxsid5045465 , |
d-streptamine, o-4-amino-4-deoxy-alpha-d-glucopyranosyl-(1.fwdarw.8)-o-(8r)-2-amino-2,3,7-trideoxy-7-(methylamino)-d-glycero-alpha-d-allo-octodialdo-1,5:8,4-dipyranosyl-(1.fwdarw.4)-2-deoxy- |
apramycin [usan:inn:ban] |
388k3tr36z , |
unii-388k3tr36z |
el-857 |
nsc 758938 |
ebl-1003 |
apramycin [usan] |
apramycin [mart.] |
apramycin [mi] |
4-o-((8r)-2-amino-8-o-(4-amino-4-deoxy-.alpha.-d-glucopyranosyl)-2,3,7-trideoxy-7-(methylamino)-d-glycero-.alpha.-d-allo-octodialdo-1,5:8,4-dipyranos-1-yl)-2-deoxy-d-streptamine |
apramycin [inn] |
d-streptamine, 4-o-((8r)-2-amino-8-o-(4-amino-4-deoxy-.alpha.-d-glucopyranosyl)-2,3,7-trideoxy-7-(methylamino)-d-glycero-.alpha.-d-allo-octodialdo-1,5:8,4-dipyranos-1-yl)-2-deoxy- |
HY-17558 |
SCHEMBL18388 |
apramycin, antibiotic for culture media use only |
W-106548 |
(2r,3r,4s,5s,6s)-5-amino-2-(((2r,3s,4r,4ar,6s,7r,8as)-7-amino-6-(((1r,2r,3s,4r,6s)-4,6-diamino-2,3-dihydroxycyclohexyl)oxy)-4-hydroxy-3-(methylamino)octahydropyrano[3,2-b]pyran-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2h-pyran-3,4-diol |
(2r,3r,4s,5s,6s)-5-amino-2-((2r,3s,4r,4ar,6s,7r)-7-amino-6-((1r,2r,3s,4r,6s)-4,6-diamino-2,3-dihydroxycyclohexyloxy)-4-hydroxy-3-(methylamino)octahydropyrano[3,2-b]pyran-2-yloxy)-6-(hydroxymethyl)tetrahydro-2h-pyran-3,4-diol |
(2r,3r,4s,5s,6s)-5-amino-2-{[(2r,3s,4r,4ar,6s,7r,8as)-7-amino-6-{[(1r,2r,3s,4r,6s)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy}-4-hydroxy-3-(methylamino)octahydropyrano[3,2-b]pyran-2-yl]oxy}-6-(hydroxymethyl)tetrahydro-2h-pyran-3,4-diol (non-preferred name) |
apramycin (nebramycin ii) |
AKOS032944905 |
Q418940 |
gtpl10760 |
el857 |
A936645 |
Apramycin is an aminoglycoside antibiotic with broad-spectrum in vitro activity against MDR Gram-negative pathogens and Staphylococcus aureus. It is a structurally unique member of the 2-deoxystreptamine class.
Excerpt | Reference | Relevance |
---|---|---|
"Apramycin has broad-spectrum, rapidly bactericidal activity against N. " | ( Evaluation of apramycin against spectinomycin-resistant and -susceptible strains of Neisseria gonorrhoeae. Berg, G; Kang, AD; Kirby, JE; Riedel, S; Smith, KP; Vijayakumar, D, 2019) | 2.32 |
Apramycin treatment (0.5g/l in the drinking water) of 3-to 5-week-old Leghorn chicks for 24 or 48 hours resulted in a reduction, to an undetectable level, in the number of coliforms in the digestive tract for at least the first 24 h.
Excerpt | Reference | Relevance |
---|---|---|
" In concentrations of up to 300 mg/l the preparation did not produce an essential effect on the clinico-laboratory indices, and did not lead to toxic alterations of the viscera." | ( [Subchronic toxicity of apramycin in pigs]. Diakov, L; Lashev, L; Pashov, D, 1987) | 0.58 |
"5-Å resolution, our results provide a conceptual framework for further development of less toxic aminoglycosides by hypothesis-driven chemical synthesis." | ( Dissociation of antibacterial activity and aminoglycoside ototoxicity in the 4-monosubstituted 2-deoxystreptamine apramycin. Akbergenov, R; Böttger, EC; Dubbaka, SR; Duscha, S; Lang, K; Matt, T; Meyer, M; Ng, CL; Perez-Fernandez, D; Ramakrishnan, V; Schacht, J; Sha, SH; Shcherbakov, D; Vasella, A; Xie, J, 2012) | 0.59 |
Excerpt | Reference | Relevance |
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"Comparative studies on some selected pharmacokinetic parameters for kanamycin in sheep, goats, rabbits, chickens and pigeons, and for apramycin in sheep, rabbits, chickens and pigeons were carried out after intravenous administration of the two drugs at a dose of 10 mg/kg." | ( Interspecies differences in the pharmacokinetics of kanamycin and apramycin. Lashev, LD; Marinkov, TN; Pashov, DA, 1992) | 0.72 |
"To perform a population pharmacokinetic (PPK) analysis and predict an efficacious dose based on data from a first-in-human Phase I trial." | ( Population pharmacokinetics of apramycin from first-in-human plasma and urine data to support prediction of efficacious dose. Chirkova, A; Friberg, LE; Hobbie, SN; Lindberg, J; Palma Villar, R; Rosenborg, S; Zhao, C, 2022) | 1.01 |
A new compound granular premix of amoxicillin (20% w/w dry mass) andapramycin was developed. Its pharmacokinetics and relative bioavailability were determined in pigs following oral administration following a cross-over study design.
Excerpt | Reference | Relevance |
---|---|---|
"Apramycin was administered to chickens orally, intramuscularly and intravenously to determine blood concentration, kinetic behaviour, bioavailability and tissue residues." | ( Kinetic disposition, systemic bioavailability and tissue distribution of apramycin in broiler chickens. Afifi, NA; Ramadan, A, ) | 1.81 |
"A new compound granular premix of amoxicillin (20% w/w dry mass)/apramycin (5% w/w dry mass) was developed, and its pharmacokinetics and relative bioavailability were determined in pigs following oral administration following a cross-over study design." | ( Pharmacokinetics and relative bioavailability of an oral amoxicillin-apramycin combination in pigs. Dai, C; Tang, S; Velkov, T; Xiao, X; Yang, X; Zhao, T, 2017) | 0.93 |
"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 |
apramycin influence on minimum inhibitory concentrations (MIC) of intestinal Escherichia coli in young broiler chickens. oral administration of the antibiotic at a dosage equivalent to a prophylactic course of treatment for 10 d.
Excerpt | Relevance | Reference |
---|---|---|
" This investigation was carried out in terms of a dose-response study." | ( Effects of mushroom and herb polysaccharides, as alternatives for an antibiotic, on the cecal microbial ecosystem in broiler chickens. Guo, FC; Kwakkel, RP; Li, HS; Li, WK; Li, XP; Luo, JY; Verstegen, MW; Williams, BA, 2004) | 0.32 |
" For bacterial infections, the choice of dosing regimen is typically relying on preclinical pharmacokinetic (PK) and pharmacodynamic (PD) data, because the bacterial load and disease severity, and consequently the PK/PD relationship, cannot be quantified well on clinical data, given the low-information end points used." | ( Pivotal Role of Translation in Anti-Infective Development. Friberg, LE, 2021) | 0.62 |
Role | Description |
---|---|
antimicrobial agent | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. |
antibacterial drug | A drug used to treat or prevent bacterial infections. |
[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] |
Class | Description |
---|---|
2-deoxystreptamine derivative | Any derivative of 2-deoxystreptamine. |
organic heterobicyclic compound | |
aminoglycoside | |
[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] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
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. |
AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
AID1328385 | Antibacterial activity against Staphylococcus aureus after 24 hrs by MTT based microdilution assay | 2016 | Journal of natural products, 09-23, Volume: 79, Issue:9 | Total Synthesis of (±)-Isoperbergins and Correction of the Chemical Structure of Perbergin. |
AID1264892 | Antimicrobial activity against Mycobacterium smegmatis ATCC 14468 for 17 to 48 hrs by MTT assay | 2015 | Journal of natural products, Nov-25, Volume: 78, Issue:11 | Identification of Elaiophylin Skeletal Variants from the Indonesian Streptomyces sp. ICBB 9297. |
AID1882862 | Antibacterial activity against Escherichia coli K12 expressing modified luxABCDE genes assessed as reduction in bacterial growth by measuring reduction in bioluminescence at 40 uM incubated for 16 hrs by microplate reader analysis | 2022 | European journal of medicinal chemistry, Jul-05, Volume: 237 | The role of the maleimide ring system on the structure-activity relationship of showdomycin. |
AID1882861 | Antibacterial activity against Escherichia coli K12 expressing modified luxABCDE genes assessed as reduction in bacterial growth by measuring reduction in optical density at 40 uM incubated for 16 hrs by microplate reader analysis | 2022 | European journal of medicinal chemistry, Jul-05, Volume: 237 | The role of the maleimide ring system on the structure-activity relationship of showdomycin. |
AID1328387 | Antibacterial activity against Escherichia coli after 24 hrs by MTT based microdilution assay | 2016 | Journal of natural products, 09-23, Volume: 79, Issue:9 | Total Synthesis of (±)-Isoperbergins and Correction of the Chemical Structure of Perbergin. |
AID1264895 | Antimicrobial activity against Escherichia coli ATCC 11775 for 17 to 48 hrs by MTT assay | 2015 | Journal of natural products, Nov-25, Volume: 78, Issue:11 | Identification of Elaiophylin Skeletal Variants from the Indonesian Streptomyces sp. ICBB 9297. |
AID1638003 | Antiribosomal activity against humanized bacterial ribosome incorporating human cytoplasmic ribosome Cyt14 assessed as inhibition of luciferase production by cell-free translation assay | 2019 | MedChemComm, Apr-01, Volume: 10, Issue:4 | Synthesis of saccharocin from apramycin and evaluation of its ribosomal selectivity. |
AID1638006 | Selectivity ratio of IC50 for antiribosomal activity against humanized bacterial ribosome incorporating human cytoplasmic ribosome Cyt14 to IC50 for antiribosomal activity against wild type bacterial ribosomes | 2019 | MedChemComm, Apr-01, Volume: 10, Issue:4 | Synthesis of saccharocin from apramycin and evaluation of its ribosomal selectivity. |
AID1638011 | Antibacterial activity against Pseudomonas aeruginosa AG220 | 2019 | MedChemComm, Apr-01, Volume: 10, Issue:4 | Synthesis of saccharocin from apramycin and evaluation of its ribosomal selectivity. |
AID1264891 | Antimicrobial activity against Staphylococcus aureus ATCC 12600 for 17 to 48 hrs by MTT assay | 2015 | Journal of natural products, Nov-25, Volume: 78, Issue:11 | Identification of Elaiophylin Skeletal Variants from the Indonesian Streptomyces sp. ICBB 9297. |
AID1638007 | Antibacterial activity against Escherichia coli AG001 | 2019 | MedChemComm, Apr-01, Volume: 10, Issue:4 | Synthesis of saccharocin from apramycin and evaluation of its ribosomal selectivity. |
AID1638002 | Antiribosomal activity against humanized bacterial ribosome incorporating A1555G mutant of human mitochondrial ribosome assessed as inhibition of luciferase production by cell-free translation assay | 2019 | MedChemComm, Apr-01, Volume: 10, Issue:4 | Synthesis of saccharocin from apramycin and evaluation of its ribosomal selectivity. |
AID1264894 | Antimicrobial activity against Pseudomonas aeruginosa ATCC 9721 for 17 to 48 hrs by MTT assay | 2015 | Journal of natural products, Nov-25, Volume: 78, Issue:11 | Identification of Elaiophylin Skeletal Variants from the Indonesian Streptomyces sp. ICBB 9297. |
AID1328383 | Antibacterial activity against Rhodococcus fascians after 24 hrs by MTT based microdilution assay | 2016 | Journal of natural products, 09-23, Volume: 79, Issue:9 | Total Synthesis of (±)-Isoperbergins and Correction of the Chemical Structure of Perbergin. |
AID1328384 | Antibacterial activity against Mycobacterium smegmatis after 48 hrs by MTT based microdilution assay | 2016 | Journal of natural products, 09-23, Volume: 79, Issue:9 | Total Synthesis of (±)-Isoperbergins and Correction of the Chemical Structure of Perbergin. |
AID1638001 | Antiribosomal activity against humanized bacterial ribosome incorporating complete decoding A site from human mitochondrial ribosome Mit13 assessed as inhibition of luciferase production by cell-free translation assay | 2019 | MedChemComm, Apr-01, Volume: 10, Issue:4 | Synthesis of saccharocin from apramycin and evaluation of its ribosomal selectivity. |
AID1638000 | Antiribosomal activity against wild type bacterial ribosomes assessed as inhibition of luciferase production by cell-free translation assay | 2019 | MedChemComm, Apr-01, Volume: 10, Issue:4 | Synthesis of saccharocin from apramycin and evaluation of its ribosomal selectivity. |
AID1638012 | Antibacterial activity against Methicillin-resistant Staphylococcus aureus AG038 | 2019 | MedChemComm, Apr-01, Volume: 10, Issue:4 | Synthesis of saccharocin from apramycin and evaluation of its ribosomal selectivity. |
AID1638005 | Selectivity ratio of IC50 for antiribosomal activity against humanized bacterial ribosome incorporating A1555G mutant of human mitochondrial ribosome to IC50 for antiribosomal activity against wild type bacterial ribosomes | 2019 | MedChemComm, Apr-01, Volume: 10, Issue:4 | Synthesis of saccharocin from apramycin and evaluation of its ribosomal selectivity. |
AID1264893 | Antimicrobial activity against Bacillus subtilis ATCC 6051 for 17 to 48 hrs by MTT assay | 2015 | Journal of natural products, Nov-25, Volume: 78, Issue:11 | Identification of Elaiophylin Skeletal Variants from the Indonesian Streptomyces sp. ICBB 9297. |
AID1638009 | Antibacterial activity against Enterobacter cloacae AG290 | 2019 | MedChemComm, Apr-01, Volume: 10, Issue:4 | Synthesis of saccharocin from apramycin and evaluation of its ribosomal selectivity. |
AID1638010 | Antibacterial activity against Acinetobacter baumannii AG309 | 2019 | MedChemComm, Apr-01, Volume: 10, Issue:4 | Synthesis of saccharocin from apramycin and evaluation of its ribosomal selectivity. |
AID1638008 | Antibacterial activity against Klebsiella pneumoniae AG215 | 2019 | MedChemComm, Apr-01, Volume: 10, Issue:4 | Synthesis of saccharocin from apramycin and evaluation of its ribosomal selectivity. |
AID1638004 | Selectivity ratio of IC50 for antiribosomal activity against humanized bacterial ribosome incorporating complete decoding A site from human mitochondrial ribosome Mit13 to IC50 for antiribosomal activity against wild type bacterial ribosomes | 2019 | MedChemComm, Apr-01, Volume: 10, Issue:4 | Synthesis of saccharocin from apramycin and evaluation of its ribosomal selectivity. |
AID1328386 | Antibacterial activity against Pseudomonas aeruginosa after 24 hrs by MTT based microdilution assay | 2016 | Journal of natural products, 09-23, Volume: 79, Issue:9 | Total Synthesis of (±)-Isoperbergins and Correction of the Chemical Structure of Perbergin. |
AID1159550 | Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening | 2015 | Nature cell biology, Nov, Volume: 17, Issue:11 | 6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling. |
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 23 (14.20) | 18.7374 |
1990's | 30 (18.52) | 18.2507 |
2000's | 39 (24.07) | 29.6817 |
2010's | 40 (24.69) | 24.3611 |
2020's | 30 (18.52) | 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 strong demand-to-supply ratio for research on this compound.
| This Compound (44.24) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 6 (3.59%) | 5.53% |
Reviews | 3 (1.80%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 158 (94.61%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Trial | Phase | Enrollment | Study Type | Start Date | Status | ||
---|---|---|---|---|---|---|---|
A Phase I, Randomized, Double-blind, Placebo-controlled, Single Ascending Dose Study to Assess the Safety, Tolerability, and Pharmacokinetics of Apramycin Administered Intravenously in Healthy Adults. [NCT04105205] | Phase 1 | 40 participants (Actual) | Interventional | 2019-09-25 | Completed | ||
A Phase I, Open-label Study to Assess Lung Pharmacokinetics and Safety of a Single Dose of Apramycin Administered Intravenously in Healthy Adult Subjects [NCT05590728] | Phase 1 | 20 participants (Anticipated) | Interventional | 2023-06-16 | Recruiting | ||
[information is prepared from clinicaltrials.gov, extracted Sep-2024] |