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
Evaluation of subtherapeutic use of the antibiotics apramycin and carbadox on the prevalence of antimicrobial-resistant Salmonella infection in swine.	2001 Dec	11770640
'Streptomyces nanchangensis', a producer of the insecticidal polyether antibiotic nanchangmycin and the antiparasitic macrolide meilingmycin, contains multiple polyketide gene clusters.	2002 Feb	11832500
Characterization of antimicrobial resistance among Escherichia coli O111 isolates of animal and human origin.	2002 Summer	12118519
In vitro activity of eight oral cephalosporins against Borrelia burgdorferi.	2003 Apr	12672576
Isolation of Escherichia coli O157:H7 from intact colon fecal samples of swine.	2003 Mar	12643837
Identification and functional analysis of dTDP-glucose-4,6-dehydratase gene and its linked gene cluster in an aminoglycoside antibiotics producer of Streptomyces tenebrarius H6.	2004 Aug	15297914
High frequency transfer and horizontal spread of apramycin resistance in calf faecal Escherichia coli.	2004 Aug	15231771
Antibiotic resistance among enterotoxigenic Escherichia coli from piglets and calves with diarrhea.	2004 Jul	15317393
Multidrug-resistant strains of Salmonella enterica Typhimurium, United States, 1997-1998.	2004 May	15200811
Two relA/spoT homologous genes are involved in the morphological and physiological differentiation of Streptomyces clavuligerus.	2004 May	15133110
[The use of aminoglycosides, colistin and beta-lactam antibiotics as animal feed drugs for pigs in Schleswig-Holstein].	2004 Sep-Oct	15495930
Antimicrobial resistance and serotype prevalence of Salmonella isolated from dairy cattle in the southwestern United States.	2004 Spring	15140394
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
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
Salmonella Derby clonal spread from pork.	2005 May	15890121
Antibiotic resistance from wastewater oxidation ponds.	2005 Nov-Dec	16381146
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
[The implementation of the broth microdilution method to determine bacterial susceptibility to antimicrobial agents].	2007 Jan-Feb	17290942
Fluorescent HIV-1 Dimerization Initiation Site: design, properties, and use for ligand discovery.	2007 Mar 21	17319662
Apramycin recognition by the human ribosomal decoding site.	2007 May-Jun	17258916
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
Unveiling novel RecO distant orthologues involved in homologous recombination.	2008 Aug 1	18670631
Biosynthesis of 3'-deoxy-carbamoylkanamycin C in a Streptomyces tenebrarius mutant strain by tacB gene disruption.	2008 Feb	18408324
[Disruption of zwf2 gene to improve oxytetraclyline biosynthesis in Streptomyces rimosus M4018].	2008 Jan	18338571
Evaluation of a survey approach to estimating the prevalence of cattle carrying antimicrobial-resistant Escherichia coli.	2008 Mar	17448712
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
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
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