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Sisomicin

CAS No.:
32385-11-8
Catalog Number:
AG00C0C4
Molecular Formula:
C19H37N5O7
Molecular Weight:
447.5264
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
50mg
≥98%
1 week
United States
$91
- +
100mg
≥98%
1 week
United States
$119
- +
500mg
≥98%
1 week
United States
$318
- +
1g
≥98%
1 week
United States
$404
- +
Product Description
Catalog Number:
AG00C0C4
Chemical Name:
Sisomicin
CAS Number:
32385-11-8
Molecular Formula:
C19H37N5O7
Molecular Weight:
447.5264
MDL Number:
MFCD00059734
IUPAC Name:
(2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol
InChI:
InChI=1S/C19H37N5O7/c1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17/h3,9-18,24-27H,4-7,20-23H2,1-2H3/t9-,10+,11-,12+,13-,14-,15+,16-,17-,18-,19+/m1/s1
InChI Key:
URWAJWIAIPFPJE-YFMIWBNJSA-N
SMILES:
NCC1=CC[C@H]([C@H](O1)O[C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@H]1OC[C@]([C@@H]([C@H]1O)NC)(C)O)N)N
EC Number:
251-018-2
UNII:
X55XSL74YQ
Properties
Complexity:
643  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
11  
Defined Bond Stereocenter Count:
0
Exact Mass:
447.269g/mol
Formal Charge:
0
Heavy Atom Count:
31  
Hydrogen Bond Acceptor Count:
12  
Hydrogen Bond Donor Count:
8  
Isotope Atom Count:
0
Molecular Weight:
447.533g/mol
Monoisotopic Mass:
447.269g/mol
Rotatable Bond Count:
6  
Topological Polar Surface Area:
214A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-5.1  
Literature
Title Journal
Simultaneous determination of 15 aminoglycoside(s) residues in animal derived foods by automated solid-phase extraction and liquid chromatography-tandem mass spectrometry. Food chemistry 20121115
Activity of plazomicin (ACHN-490) against MDR clinical isolates of Klebsiella pneumoniae, Escherichia coli, and Enterobacter spp. from Athens, Greece. Journal of chemotherapy (Florence, Italy) 20120801
A high pH based reversed-phase high performance liquid chromatographic method for the analysis of aminoglycoside plazomicin and its impurities. Journal of pharmaceutical and biomedical analysis 20120701
Comparison of the next-generation aminoglycoside plazomicin to gentamicin, tobramycin and amikacin. Expert review of anti-infective therapy 20120401
EPR studies of free radicals decay and survival in gamma irradiated aminoglycoside antibiotics: sisomicin, tobramycin and paromomycin. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20120214
Complete genome sequence, lifestyle, and multi-drug resistance of the human pathogen Corynebacterium resistens DSM 45100 isolated from blood samples of a leukemia patient. BMC genomics 20120101
Impact of metal ions on netilmicin-melanin interaction. Acta poloniae pharmaceutica 20120101
Hybrid aminoglycoside antibiotics via Tsuji palladium-catalyzed allylic deoxygenation. Organic letters 20111216
Activity of ACHN-490 against meticillin-resistant Staphylococcus aureus (MRSA) isolates from patients in US hospitals. International journal of antimicrobial agents 20111001
Discovery of selective bioactive small molecules by targeting an RNA dynamic ensemble. Nature chemical biology 20110626
Antimicrobial activity of a novel aminoglycoside, ACHN-490, against Acinetobacter baumannii and Pseudomonas aeruginosa from New York City. The Journal of antimicrobial chemotherapy 20110201
Activity of aminoglycosides, including ACHN-490, against carbapenem-resistant Enterobacteriaceae isolates. The Journal of antimicrobial chemotherapy 20110101
Lack of the delta subunit of RNA polymerase increases virulence related traits of Streptococcus mutans. PloS one 20110101
Comparative genomics study of multi-drug-resistance mechanisms in the antibiotic-resistant Streptococcus suis R61 strain. PloS one 20110101
Acquired antibiotic resistance genes: an overview. Frontiers in microbiology 20110101
Activity of a novel aminoglycoside, ACHN-490, against clinical isolates of Escherichia coli and Klebsiella pneumoniae from New York City. The Journal of antimicrobial chemotherapy 20101001
Combating evolution with intelligent design: the neoglycoside ACHN-490. Current opinion in microbiology 20101001
Thermodynamics and kinetics of association of antibiotics with the aminoglycoside acetyltransferase (3)-IIIb, a resistance-causing enzyme. Biochemistry 20100518
Biomimetic synthesis and structural refinement of the macrocyclic dimer aminoglycoside 66-40C--the remarkably selective self-condensation of a putative aldehyde intermediate in the submerged culture medium producing sisomicin. Chemical communications (Cambridge, England) 20100328
Determination of aminoglycoside and macrolide antibiotics in meat by pressurized liquid extraction and LC-ESI-MS. Journal of separation science 20100301
Immunoassays for the rapid detection of gentamicin and micronomicin in swine muscle. Journal of AOAC International 20100101
Inactivation of the Ecs ABC transporter of Staphylococcus aureus attenuates virulence by altering composition and function of bacterial wall. PloS one 20100101
Identification of gentamicin impurities by liquid chromatography tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis 20091205
Development of a non-derivatization high-performance liquid chromatography method with resonance Rayleigh scattering detection for the detection of sisomicin in rat serum. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20091201
Characterization of the enzyme aac(3)-Id in a clinical isolate of Salmonella enterica serovar Haifa causing traveler's diarrhea. Enfermedades infecciosas y microbiologia clinica 20091001
Genetic analysis of antimicrobial resistance in Escherichia coli isolated from diarrheic neonatal calves. Veterinary microbiology 20090512
[Antibiotics given subcutaneously to elderly]. Presse medicale (Paris, France : 1983) 20090301
Molecular cloning and sequence analysis of the sisomicin biosynthetic gene cluster from Micromonospora inyoensis. Biotechnology letters 20090301
Synthesis and comparative antibacterial activity of verdamicin C2 and C2a. A new oxidation of primary allylic azides in dihydro[2H]pyrans. Organic letters 20090115
Characterization and identification of a novel marine Streptomyces sp. produced antibacterial substance. Marine biotechnology (New York, N.Y.) 20090101
Contact sensitization in venous eczema: preliminary results of patch testing with Indian standard series and topical medicaments. Indian journal of dermatology, venereology and leprology 20090101
Deep recurrent infection of the hip after tumoral resection in an 18-years old male--a case report. Journal of medicine and life 20081115
Evaluation of the stability of gentamicin in different antibiotic carriers using a validated MEKC method. Journal of pharmaceutical and biomedical analysis 20081104
Characterization of impurities in sisomicin and netilmicin by liquid chromatography/mass spectrometry. Rapid communications in mass spectrometry : RCM 20081101
Improved liquid chromatographic method with pulsed electrochemical detection for the analysis of gentamicin. Journal of chromatography. A 20080502
Micellar electrokinetic chromatography of aminoglycosides. Methods in molecular biology (Clifton, N.J.) 20080101
Inhibition of poly(A) polymerase by aminoglycosides. Biochimie 20071001
Evaluation of combined deactivators-supplemented agar medium (CDSAM) for recovery of dermatophytes from patients with tinea pedis. Medical mycology 20070601
16S rRNA methylase-producing, gram-negative pathogens, Japan. Emerging infectious diseases 20070401
Aminoglycoside resistance in members of the Staphylococcus sciuri group. Microbial drug resistance (Larchmont, N.Y.) 20070101
Inhibition of the catalytic activity of trans-acting antigenomic delta ribozyme by selected antibiotics and their Cu2+ complexes. Biochemical and biophysical research communications 20061103
Prevalence of methicillin-resistant Staphylococcus aureus (MRSA) in community-acquired primary pyoderma. Indian journal of dermatology, venereology and leprology 20060101
[Study on cloning of sisomicin-resistant gene (sisR) from Micromonospora inyoensis]. Sheng wu gong cheng xue bao = Chinese journal of biotechnology 20050101
ATP, histidine or magnesium ions can protect DNA against sisomicin-induced damage, following stray Cu(II) binding. Archives of biochemistry and biophysics 20041101
[Electrospray ion trap mass spectrometry of eight aminoglycoside antibiotics]. Yao xue xue bao = Acta pharmaceutica Sinica 20041001
Acid-base versus structural properties of an aminoglycoside antibiotic--sisomicin: NMR and potentiometric approach. Bioorganic & medicinal chemistry 20040801
Effectiveness of short-term antibiotic prophylaxis on postoperative recovery course after pulmonary lobectomies. Journal of the Chinese Medical Association : JCMA 20040601
Voltage-dependent inhibition of rat skeletal muscle sodium channels by aminoglycoside antibiotics. Pflugers Archiv : European journal of physiology 20040501
Distribution and characterization of Campylobacter spp. from Russian poultry. Journal of food protection 20040201
Determination of tobramycin in serum using liquid chromatography-tandem mass spectrometry and comparison with a fluorescence polarisation assay. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20030905
A new micellar electrokinetic capillary chromatography method for separation of the components of the aminoglycoside antibiotics. Electrophoresis 20030901
Role of the acetyltransferase AAC(6')-Iz modifying enzyme in aminoglycoside resistance in Stenotrophomonas maltophilia. The Journal of antimicrobial chemotherapy 20030401
Inhibition of bacterial IF2 binding to fMet-tRNA((fMet)) by aminoglycosides. Bioorganic & medicinal chemistry letters 20030324
Novel antibiotic-resistance markers in pGK12-derived vectors for Borrelia burgdorferi. Gene 20030116
[Evaluation of outcomes of combined specific prophylaxis with the antibiotic resistant immunogenic plague pathogen strain and emergency prophylaxis with aminoglycosides in the experimental plague model in white mice]. Antibiotiki i khimioterapiia = Antibiotics and chemoterapy [sic] 20030101
Transferable plasmid mediating resistance to multiple antimicrobial agents in Klebsiella pneumoniae isolates in Greece. Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases 20020901
[Analysis of the response factors of different aminoglycoside antibiotics detected by evaporative light-scattering detector]. Yao xue xue bao = Acta pharmaceutica Sinica 20020301
A comparative clinical study of sisomicin cream versus mupirocin ointment in pyodermas. Indian journal of dermatology, venereology and leprology 20020101
Electrophoretically mediated microanalysis of gentamicin with in-capillary derivatization and UV detection. Electrophoresis 20010801
[Microbiological research for the Hungarian pharmaceutical industry]. Acta pharmaceutica Hungarica 20010101
Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production. Cell 19930924
[Comparative ototoxicity of aminoglycoside antibiotics in a guinea pig model (author's transl)]. La Nouvelle presse medicale 19781129
Hypocalcemia with hypoparathyroidism and renal tubular dysfunction associated with aminoglycoside therapy. Cancer 19770401
Properties