APRAMYCIN

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

Structure Search

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

HIDE SMILES / InChI

Description
Sources: https://www.drugbank.ca/drugs/DB04626 | http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500010684.pdf | http://www.fao.org/fileadmin/user_upload/vetdrug/docs/12-2012-apramycin.pdf

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
16S rRNA, bacterial 5 Target ID: 16S rRNA, bacterial Sources: https://www.drugbank.ca/drugs/DB04626 \| https://www.ncbi.nlm.nih.gov/pubmed/17705310 \| https://www.ncbi.nlm.nih.gov/pubmed/1915283 \| https://www.google.ru/url?sa=t&rct=j&q=&esrc=s&source=web&cd=4&ved=0ahUKEwjS4smOucPXAhVkP5oKHWc1CKEQFghIMAM&url=https%3A%2F%2Fwww.applichem.com%2Fen%2Fshop%2Fproduct-detail%2Fas%2Fapramycinsulfat-ibiochemicai%2F%3Fgetspecpdf%3D1&usg=AOvVaw3yrw8A5mIqtHCtFSy_31vi	Inhibitor 8297
Tubulin 69 Target ID: CHEMBL2095182 Sources: http://adisinsight.springer.com/drugs/800014041	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Gastrointestinal infections 6 Sources: http://www.fao.org/fileadmin/user_upload/vetdrug/docs/12-2012-apramycin.pdf http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500010684.pdf	Curative		Approved 8429	Apravet Approved Use For 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.
Cancer 592 Sources: http://adisinsight.springer.com/drugs/800014041	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Evaluation of subtherapeutic use of the antibiotics apramycin and carbadox on the prevalence of antimicrobial-resistant Salmonella infection in swine.	2001 Dec	11770640
StoPK-1, a serine/threonine protein kinase from the glycopeptide antibiotic producer Streptomyces toyocaensis NRRL 15009, affects oxidative stress response.	2002 Apr	11972780
Salmonella enterica serotype Typhimurium DT104 isolated from humans, United States, 1985, 1990, and 1995.	2002 Apr	11971772
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	11932454
'Streptomyces nanchangensis', a producer of the insecticidal polyether antibiotic nanchangmycin and the antiparasitic macrolide meilingmycin, contains multiple polyketide gene clusters.	2002 Feb	11832500
[Establishment of gene replacement/disruption system through homologous recombination in Amycolatopsis mediterranei U32].	2002 Jul	12385238
Phage HK022-based integrative vectors for the insertion of genes in the chromosome of multiply marked Escherichia coli strains.	2002 Jul 16	12127487
[Fermentative hydrolysate of mycelial waste of aminoglycoside antibiotics production as component of culture media used in biosynthesis of tobramycin].	2003	15004972
Prioritisation of veterinary medicines in the UK environment.	2003 May 15	12691714
Effects of mushroom and herb polysaccharides, as alternatives for an antibiotic, on the cecal microbial ecosystem in broiler chickens.	2004 Feb	14979567
Use of a novel allele of the Escherichia coli aacC4 aminoglycoside resistance gene as a genetic marker in mycobacteria.	2004 May 15	15135536
Pharmacokinetics of gentamicin and apramycin in turkeys roosters and hens in the context of pharmacokinetic-pharmacodynamic relationships.	2004 Oct	15500579
Crystallographic studies of Homo sapiens ribosomal decoding A site complexed with aminoglycosides.	2005	17150729
Pretreatment of apramycin wastewater by catalytic wet air oxidation.	2005	16158592
Cloning and preliminary characterization of lh3 gene encoding a putative acetyltransferase from a rifamycin SV-producing strain Amycolatopsis mediterranei.	2005 Aug	16132864
Effects of antibiotic use in sows on resistance of E. coli and Salmonella enterica Typhimurium in their offspring.	2005 Fall	16156702
armA and aminoglycoside resistance in Escherichia coli.	2005 Jun	15963296
Effect of oregano essential oil on chicken lactobacilli and E. coli.	2006	17007424
Glycine origin of the methyl substituent on C7'-N of octodiose for the biosynthesis of apramycin.	2006 Aug	16989282
Correlation between apramycin and gentamicin use in pigs and an increasing reservoir of gentamicin-resistant Escherichia coli.	2006 Jul	16709594
Antimicrobial resistance phenotypes of ETEC isolates from piglets with diarrhea in North Vietnam.	2006 Oct	17135566
[The implementation of the broth microdilution method to determine bacterial susceptibility to antimicrobial agents].	2007 Jan-Feb	17290942
Apramycin recognition by the human ribosomal decoding site.	2007 May-Jun	17258916
An integrative expression vector for Actinosynnema pretiosum.	2007 Oct 24	17956638
Marker removal from actinomycetes genome using Flp recombinase.	2008 Aug 1	18550297
Transfer of antimicrobial resistance plasmids from Klebsiella pneumoniae to Escherichia coli in the mouse intestine.	2008 Nov	18703526
Reducing the activity and secretion of microbial antioxidants enhances the immunogenicity of BCG.	2009	19436730
Characterization and disruption of exonuclease genes from Streptomyces aureofaciens B96 and S. coelicolor A3(2).	2009	19418245
Pharmacokinetics of tobramycin in ducks and sex-related differences.	2009 Mar	18006340
Salmonella Indiana as a cause of abortion in ewes: Genetic diversity and resistance patterns.	2009 Mar 2	18823722

Patents

Sample Use Guides

In Vivo Use Guide

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

Apramycin demonstrated an MIC50/MIC90 of 8/32ug/ml for A. baumannii and 16/32ug/ml for P. aeruginosa.

Name

Type

Language

APRAMYCIN

Official Name

English

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

Common Name

English

NSC-758938

Code

English

APRAMYCIN [MART.]

Common Name

English

APRAMYCIN [USAN]

Common Name

English

EBL-1003

Code

English

APRAMYCIN [MI]

Common Name

English

NEBRAMYCIN FACTOR 2

Common Name

English

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-

Common Name

English

EL-857

Code

English

NEBRAMYCIN II

Common Name

English

apramycin [INN]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 558.59