APRAMYCIN SULFATE

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

Structure Search

SMILES

OS(O)(=O)=O.[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=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

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
Isolation of Escherichia coli O157:H7 from intact colon fecal samples of swine.	2003 Mar	12643837
Prioritisation of veterinary medicines in the UK environment.	2003 May 15	12691714
Characterization of antimicrobial resistant Salmonella Kinshasa from dairy calves in Texas.	2004	14746546
High frequency transfer and horizontal spread of apramycin resistance in calf faecal Escherichia coli.	2004 Aug	15231771
Combating drug-resistant bacteria: small molecule mimics of plasmid incompatibility as antiplasmid compounds.	2004 Dec 1	15563166
Acquisition and epidemiology of antibiotic-resistant Escherichia coli in a cohort of newborn calves.	2004 May	15056641
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
Enhancement of bacterial competitive fitness by apramycin resistance plasmids from non-pathogenic Escherichia coli.	2006 Sep 22	17148431
TatBC, TatB, and TatC form structurally autonomous units within the twin arginine protein transport system of Escherichia coli.	2007 Aug 21	17686475
Transcriptional regulation of multi-drug tolerance and antibiotic-induced responses by the histone-like protein Lsr2 in M. tuberculosis.	2007 Jun	17590082
Apramycin recognition by the human ribosomal decoding site.	2007 May-Jun	17258916
Survey of the prevalence of Salmonella species on commercial laying farms in the United Kingdom.	2007 Oct 6	17921438
A comprehensive library of mutations of Epstein Barr virus.	2007 Sep	17698655
Differential selectivity of natural and synthetic aminoglycosides towards the eukaryotic and prokaryotic decoding A sites.	2007 Sep 24	17705310
A reservoir of drug-resistant pathogenic bacteria in asymptomatic hosts.	2008	19015729
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	18505211
Molecular epidemiology and antimicrobial resistance of Salmonella typhimurium DTI04 on Ontario swine farms.	2008	18505209
Functional expression of the Cre recombinase in actinomycetes.	2008 Apr	18299828
Unveiling novel RecO distant orthologues involved in homologous recombination.	2008 Aug 1	18670631
Marker removal from actinomycetes genome using Flp recombinase.	2008 Aug 1	18550297
Effects of treatment with antimicrobial agents on the human colonic microflora.	2008 Dec	19337440
[Genome labeling of the streptomyces strain HS007].	2008 Feb	18437992
Biosynthesis of 3'-deoxy-carbamoylkanamycin C in a Streptomyces tenebrarius mutant strain by tacB gene disruption.	2008 Feb	18408324
Comparison of the pharmacokinetics of five aminoglycoside and aminocyclitol antibiotics using allometric analysis in mammal and bird species.	2008 Feb	17888470
[Disruption of zwf2 gene to improve oxytetraclyline biosynthesis in Streptomyces rimosus M4018].	2008 Jan	18338571
Genome-wide transcriptome analysis reveals that a pleiotropic antibiotic regulator, AfsS, modulates nutritional stress response in Streptomyces coelicolor A3(2).	2008 Jan 29	18230178
A multicopy suppressor screening approach as a means to identify antibiotic resistance determinant candidates in Yersinia pestis.	2008 Jul 21	18644132
A new post-PKS modification process in the carbamoyltransferase gene inactivation strain of Streptomyces hygroscopicus 17997.	2008 Jun	18667782
[Simultaneous determination of aminoglycoside antibiotics in milk by liquid chromatography with tandem mass spectrometry].	2008 Jun	18633203
Antimicrobial resistance of Salmonella enterica isolates from apparently healthy and clinically ill finishing pigs in Spain.	2008 May	18387141
Cloning and characterization of an rRNA methyltransferase from Sorangium cellulosum.	2008 May 23	18355448
Intermediate filament-like proteins in bacteria and a cytoskeletal function in Streptomyces.	2008 Nov	18976278
Transfer of antimicrobial resistance plasmids from Klebsiella pneumoniae to Escherichia coli in the mouse intestine.	2008 Nov	18703526
[Effect on production of avermectins of spore pigment biosynthesis in Streptomyces avermitilis NRRL8165].	2008 Oct	19149180
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
The SmpB-tmRNA tagging system plays important roles in Streptomyces coelicolor growth and development.	2009	19212432
Effects of in-feed egg yolk antibodies on Salmonella shedding, bacterial antibiotic resistance, and health of pigs.	2009 Feb	19350971
Structural features and oxidative stress towards plasmid DNA of apramycin copper complex.	2009 Feb 21	19322482
Role of sgcR3 in positive regulation of enediyne antibiotic C-1027 production of Streptomyces globisporus C-1027.	2009 Jan 22	19159491
Salmonella Indiana as a cause of abortion in ewes: Genetic diversity and resistance patterns.	2009 Mar 2	18823722
Characterization of the enzyme aac(3)-Id in a clinical isolate of Salmonella enterica serovar Haifa causing traveler's diarrhea.	2009 Oct	19403206

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 SULFATE

Common Name

English

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-OCTODIALDO-1,5:8,4-DIPYRANOSYL-(1-4)-2-DEOXY-, SULFATE

Common Name

English

APRAMYCIN SULPHATE

Common Name

English

APRAMYCIN SULFATE [GREEN BOOK]

Common Name

English

(+)-APRAMYCIN SULFATE

Common Name

English

APRAMYCIN SULFATE [MART.]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 520.110