Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H41N5O11.H2O4S |
| Molecular Weight | 637.656 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 17 / 17 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OS(O)(=O)=O.CN[C@H]1[C@@H](O)[C@H]2O[C@H](O[C@@H]3[C@@H](N)C[C@@H](N)[C@H](O)[C@H]3O)[C@H](N)C[C@@H]2O[C@@H]1O[C@H]4O[C@H](CO)[C@@H](N)[C@H](O)[C@H]4O
InChI
InChIKey=WGLYHYWDYPSNPF-RQFIXDHTSA-N
InChI=1S/C21H41N5O11.H2O4S/c1-26-11-14(30)18-8(33-20(11)37-21-16(32)13(29)10(25)9(4-27)34-21)3-7(24)19(36-18)35-17-6(23)2-5(22)12(28)15(17)31;1-5(2,3)4/h5-21,26-32H,2-4,22-25H2,1H3;(H2,1,2,3,4)/t5-,6+,7-,8+,9-,10-,11+,12+,13+,14-,15-,16-,17-,18+,19+,20-,21-;/m1./s1
Apramycin is a broad-spectrum aminocyclitol antibiotic produced by a strain of Streptomyces tenebrarius. It has a bactericidal action against many gram-negative bacteria. Apramycin is a structurally unique antibiotic that contains a bicyclic sugar moiety and a monosubstituted deoxystreptamine. It is not approved for use in humans. Apramycin is registered for use in more than twenty countries in cattle, pigs and chickens. The drug exerts its antibacterial effect by inhibiting
protein synthesis at the level of peptidyl translocation. It is mostly used for treating gastrointestinal
infections. Apramycin is available in soluble powder and feed premix formulations.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2095182 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | Apravet Approved UseFor treatment of gastrointestinal tract infections caused by susceptible to apramycin microorganisms: Colibacillosis and Salmonellosis in calves; Bacterial enteritis in pigs; Colibacillosis in lambs; septicaemia caused by E. coli in poultry; infections of the gastrointestinal tract caused by susceptible micro-organisms in rabbits. |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Characterization of the enzyme aac(3)-Id in a clinical isolate of Salmonella enterica serovar Haifa causing traveler's diarrhea. | 2009-10 |
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| Salmonella Indiana as a cause of abortion in ewes: Genetic diversity and resistance patterns. | 2009-03-02 |
|
| Pharmacokinetics of tobramycin in ducks and sex-related differences. | 2009-03 |
|
| Structural features and oxidative stress towards plasmid DNA of apramycin copper complex. | 2009-02-21 |
|
| Effects of in-feed egg yolk antibodies on Salmonella shedding, bacterial antibiotic resistance, and health of pigs. | 2009-02 |
|
| Role of sgcR3 in positive regulation of enediyne antibiotic C-1027 production of Streptomyces globisporus C-1027. | 2009-01-22 |
|
| Reducing the activity and secretion of microbial antioxidants enhances the immunogenicity of BCG. | 2009 |
|
| Characterization and disruption of exonuclease genes from Streptomyces aureofaciens B96 and S. coelicolor A3(2). | 2009 |
|
| The SmpB-tmRNA tagging system plays important roles in Streptomyces coelicolor growth and development. | 2009 |
|
| Effects of treatment with antimicrobial agents on the human colonic microflora. | 2008-12 |
|
| Intermediate filament-like proteins in bacteria and a cytoskeletal function in Streptomyces. | 2008-11 |
|
| Transfer of antimicrobial resistance plasmids from Klebsiella pneumoniae to Escherichia coli in the mouse intestine. | 2008-11 |
|
| [Effect on production of avermectins of spore pigment biosynthesis in Streptomyces avermitilis NRRL8165]. | 2008-10 |
|
| Unveiling novel RecO distant orthologues involved in homologous recombination. | 2008-08-01 |
|
| Marker removal from actinomycetes genome using Flp recombinase. | 2008-08-01 |
|
| A multicopy suppressor screening approach as a means to identify antibiotic resistance determinant candidates in Yersinia pestis. | 2008-07-21 |
|
| A new post-PKS modification process in the carbamoyltransferase gene inactivation strain of Streptomyces hygroscopicus 17997. | 2008-06 |
|
| [Simultaneous determination of aminoglycoside antibiotics in milk by liquid chromatography with tandem mass spectrometry]. | 2008-06 |
|
| Cloning and characterization of an rRNA methyltransferase from Sorangium cellulosum. | 2008-05-23 |
|
| Antimicrobial resistance of Salmonella enterica isolates from apparently healthy and clinically ill finishing pigs in Spain. | 2008-05 |
|
| Functional expression of the Cre recombinase in actinomycetes. | 2008-04 |
|
| Evaluation of a survey approach to estimating the prevalence of cattle carrying antimicrobial-resistant Escherichia coli. | 2008-03 |
|
| [Genome labeling of the streptomyces strain HS007]. | 2008-02 |
|
| Biosynthesis of 3'-deoxy-carbamoylkanamycin C in a Streptomyces tenebrarius mutant strain by tacB gene disruption. | 2008-02 |
|
| Comparison of the pharmacokinetics of five aminoglycoside and aminocyclitol antibiotics using allometric analysis in mammal and bird species. | 2008-02 |
|
| Genome-wide transcriptome analysis reveals that a pleiotropic antibiotic regulator, AfsS, modulates nutritional stress response in Streptomyces coelicolor A3(2). | 2008-01-29 |
|
| [Disruption of zwf2 gene to improve oxytetraclyline biosynthesis in Streptomyces rimosus M4018]. | 2008-01 |
|
| A reservoir of drug-resistant pathogenic bacteria in asymptomatic hosts. | 2008 |
|
| Associations of antimicrobial uses with antimicrobial resistance of fecal Escherichia coli from pigs on 47 farrow-to-finish farms in Ontario and British Columbia. | 2008 |
|
| Molecular epidemiology and antimicrobial resistance of Salmonella typhimurium DTI04 on Ontario swine farms. | 2008 |
|
| An integrative expression vector for Actinosynnema pretiosum. | 2007-10-24 |
|
| Survey of the prevalence of Salmonella species on commercial laying farms in the United Kingdom. | 2007-10-06 |
|
| Differential selectivity of natural and synthetic aminoglycosides towards the eukaryotic and prokaryotic decoding A sites. | 2007-09-24 |
|
| Determination of apramycin in animal feeds by solid-phase extraction and liquid chromatography with precolumn derivatization and fluorescence detection. | 2007-09-01 |
|
| A comprehensive library of mutations of Epstein Barr virus. | 2007-09 |
|
| TatBC, TatB, and TatC form structurally autonomous units within the twin arginine protein transport system of Escherichia coli. | 2007-08-21 |
|
| New pleiotropic effects of eliminating a rare tRNA from Streptomyces coelicolor, revealed by combined proteomic and transcriptomic analysis of liquid cultures. | 2007-08-02 |
|
| Transcriptional regulation of multi-drug tolerance and antibiotic-induced responses by the histone-like protein Lsr2 in M. tuberculosis. | 2007-06 |
|
| Fluorescent HIV-1 Dimerization Initiation Site: design, properties, and use for ligand discovery. | 2007-03-21 |
|
| Tandem repeat analysis for surveillance of human Salmonella Typhimurium infections. | 2007-03 |
|
| [The implementation of the broth microdilution method to determine bacterial susceptibility to antimicrobial agents]. | 2007-02-13 |
|
| Targeted Gene Disruption of the Cyclo (L-Phe, L-Pro) Biosynthetic Pathway in Streptomyces sp. US24 Strain. | 2007 |
|
| Apramycin recognition by the human ribosomal decoding site. | 2006-10-31 |
|
| Antimicrobial resistance phenotypes of ETEC isolates from piglets with diarrhea in North Vietnam. | 2006-10 |
|
| Enhancement of bacterial competitive fitness by apramycin resistance plasmids from non-pathogenic Escherichia coli. | 2006-09-22 |
|
| Glycine origin of the methyl substituent on C7'-N of octodiose for the biosynthesis of apramycin. | 2006-08 |
|
| Correlation between apramycin and gentamicin use in pigs and an increasing reservoir of gentamicin-resistant Escherichia coli. | 2006-07 |
|
| Effects of supplementation of beta-glucans on growth performance, nutrient digestibility, and immunity in weanling pigs. | 2006-06 |
|
| Effect of oregano essential oil on chicken lactobacilli and E. coli. | 2006 |
|
| Crystallographic studies of Homo sapiens ribosomal decoding A site complexed with aminoglycosides. | 2005 |
Sample Use Guides
In calves, apramycin is intended to be administered at a dose of 20 to 40 mg/kg bw/day in drinking
water, milk replacer or feed for 5 days. In pigs, it is intended to be administered at a dose of 7.5 to
12.5 mg/kg bw/day in drinking water or as premix incorporated in feed at a dose of 4 to
8 mg/kg bw/day (80–200mg/kg feed) for less than 28 days. In poultry, it is intended to be administered
at a dose of 20 to 80 mg/kg bw/day (250 to 500 mg/L) in drinking water for 5–7 days or as premix
incorporated in feed at a dose of 2 to 5 mg/kg feed for 5 days. In rabbits, it is intended to be
administered at a dose of 10 to 15 mg/kg bw/day (50 to 100 mg/L) in drinking water for 5 to 8 days or
as premix incorporated in feed at a dose of 5 to 10 mg/kg bw/day (50–100 mg/kg feed) for less than
21 days.
Route of Administration:
Oral
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CFR |
21 CFR 520.110
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NCI_THESAURUS |
C258
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65710-07-8
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8UYL6NAZ3Q
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300000029151
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3081544
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265-890-7
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C011666
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C79973
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DBSALT001615
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ACTIVE MOIETY
SUBSTANCE RECORD
