Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C21H41N5O11 |
Molecular Weight | 539.5771 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 17 / 17 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12C[C@@H](N)[C@@H](O[C@]3([H])[C@@H](N)C[C@@H](N)[C@H](O)[C@H]3O)O[C@]1([H])[C@H](O)[C@H](NC)[C@@H](O[C@@]4([H])O[C@H](CO)[C@@H](N)[C@H](O)[C@H]4O)O2
InChI
InChIKey=XZNUGFQTQHRASN-XQENGBIVSA-N
InChI=1S/C21H41N5O11/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/h5-21,26-32H,2-4,22-25H2,1H3/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 |
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Target ID: 16S rRNA, bacterial |
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Target ID: CHEMBL2095182 Sources: http://adisinsight.springer.com/drugs/800014041 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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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. |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Evaluation of subtherapeutic use of the antibiotics apramycin and carbadox on the prevalence of antimicrobial-resistant Salmonella infection in swine. | 2001 Dec |
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StoPK-1, a serine/threonine protein kinase from the glycopeptide antibiotic producer Streptomyces toyocaensis NRRL 15009, affects oxidative stress response. | 2002 Apr |
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Salmonella enterica serotype Typhimurium DT104 isolated from humans, United States, 1985, 1990, and 1995. | 2002 Apr |
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Biosynthesis of the dideoxysugar component of jadomycin B: genes in the jad cluster of Streptomyces venezuelae ISP5230 for L-digitoxose assembly and transfer to the angucycline aglycone. | 2002 Apr |
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'Streptomyces nanchangensis', a producer of the insecticidal polyether antibiotic nanchangmycin and the antiparasitic macrolide meilingmycin, contains multiple polyketide gene clusters. | 2002 Feb |
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[Establishment of gene replacement/disruption system through homologous recombination in Amycolatopsis mediterranei U32]. | 2002 Jul |
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Phage HK022-based integrative vectors for the insertion of genes in the chromosome of multiply marked Escherichia coli strains. | 2002 Jul 16 |
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[Fermentative hydrolysate of mycelial waste of aminoglycoside antibiotics production as component of culture media used in biosynthesis of tobramycin]. | 2003 |
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Prioritisation of veterinary medicines in the UK environment. | 2003 May 15 |
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Effects of mushroom and herb polysaccharides, as alternatives for an antibiotic, on the cecal microbial ecosystem in broiler chickens. | 2004 Feb |
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Use of a novel allele of the Escherichia coli aacC4 aminoglycoside resistance gene as a genetic marker in mycobacteria. | 2004 May 15 |
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Pharmacokinetics of gentamicin and apramycin in turkeys roosters and hens in the context of pharmacokinetic-pharmacodynamic relationships. | 2004 Oct |
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Crystallographic studies of Homo sapiens ribosomal decoding A site complexed with aminoglycosides. | 2005 |
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Pretreatment of apramycin wastewater by catalytic wet air oxidation. | 2005 |
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Cloning and preliminary characterization of lh3 gene encoding a putative acetyltransferase from a rifamycin SV-producing strain Amycolatopsis mediterranei. | 2005 Aug |
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Effects of antibiotic use in sows on resistance of E. coli and Salmonella enterica Typhimurium in their offspring. | 2005 Fall |
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armA and aminoglycoside resistance in Escherichia coli. | 2005 Jun |
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Effect of oregano essential oil on chicken lactobacilli and E. coli. | 2006 |
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Glycine origin of the methyl substituent on C7'-N of octodiose for the biosynthesis of apramycin. | 2006 Aug |
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Correlation between apramycin and gentamicin use in pigs and an increasing reservoir of gentamicin-resistant Escherichia coli. | 2006 Jul |
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Antimicrobial resistance phenotypes of ETEC isolates from piglets with diarrhea in North Vietnam. | 2006 Oct |
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[The implementation of the broth microdilution method to determine bacterial susceptibility to antimicrobial agents]. | 2007 Jan-Feb |
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Apramycin recognition by the human ribosomal decoding site. | 2007 May-Jun |
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An integrative expression vector for Actinosynnema pretiosum. | 2007 Oct 24 |
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Marker removal from actinomycetes genome using Flp recombinase. | 2008 Aug 1 |
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Transfer of antimicrobial resistance plasmids from Klebsiella pneumoniae to Escherichia coli in the mouse intestine. | 2008 Nov |
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Reducing the activity and secretion of microbial antioxidants enhances the immunogenicity of BCG. | 2009 |
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Characterization and disruption of exonuclease genes from Streptomyces aureofaciens B96 and S. coelicolor A3(2). | 2009 |
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Pharmacokinetics of tobramycin in ducks and sex-related differences. | 2009 Mar |
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Salmonella Indiana as a cause of abortion in ewes: Genetic diversity and resistance patterns. | 2009 Mar 2 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28341099
Apramycin demonstrated an MIC50/MIC90 of 8/32ug/ml for A. baumannii and 16/32ug/ml for P. aeruginosa.
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CFR |
21 CFR 558.59
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21 CFR 556.52
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QJ51GB90
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QJ01GB90
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NCI_THESAURUS |
C258
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QA07AA92
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APRAMYCIN
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)