Sisomicin
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-03456 |
| CAS | 32385-11-8 |
| Molecular Weight | 447.53 |
| Molecular Formula | C19H37N5O7 |
| Purity | ≥98% |
Online Inquiry
Description
It is an aminoglycoside antibiotic produced by the strain of Micromonospora inyoensis NRRL 3292. It has a broad-spectrum antibacterial effects against Gram-positive and Gram-negative bacteria including B. subtilis, S. aureus, E. coli, and P. aeruginosa. It has no cross-resistance to kanamycin, but has cross-resistance to gentamycin. 50 mg/kg of Sisomicin has protective effect on mice infected with Rickettsia spinosa.
Specification
| Related CAS | 53776-71-9 (x-sulfate) 53179-09-2 (Sisomicin sulfate (2:5)) 34406-63-8 (Deleted CAS) 37332-59-5 (Deleted CAS) 53179-08-1 (Deleted CAS) |
| Synonyms | D-Streptamine, O-3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl-(1→6)-O-[2,6-diamino-2,3,4,6-tetradeoxy-α-D-glycero-hex-4-enopyranosyl-(1→4)]-2-deoxy-; Antibiotic 6640; SCH 13475; Rickamicin; Sisomycin; Sissomicin; O-3-Deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl-(1→6)-O-[2,6-diamino-2,3,4,6-tetradeoxy-α-D-glycero-hex-4-enopyranosyl-(1→4)]-2-deoxy-D-streptamine; Antibiotic 66-40; BactoCeaze; Ensamycin; Sch 13475; Siseptin |
| Storage | Store at-20°C under inert atmosphere |
| 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 |
| Canonical SMILES | CC1(COC(C(C1NC)O)OC2C(CC(C(C2O)OC3C(CC=C(O3)CN)N)N)N)O |
| 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 |
Properties
| Appearance | Pale Yellow to Yellow Solid |
| Application | Protein Synthesis Inhibitors |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 676.6±55.0°C at 760 mmHg |
| Melting Point | 185-190°C (dec.) |
| Density | 1.38±0.1 g/cm3 |
| Solubility | Soluble in Aqueous Acid (Slightly), DMSO (Slightly), Methanol (Slightly), Water (Slightly) |
Reference Reading
1. New Antibiotics for Multidrug-Resistant Bacterial Strains: Latest Research Developments and Future Perspectives
Marco Terreni, Massimo Pregnolato, Marina Taccani Molecules . 2021 May 2;26(9):2671. doi: 10.3390/molecules26092671.
The present work aims to examine the worrying problem of antibiotic resistance and the emergence of multidrug-resistant bacterial strains, which have now become really common in hospitals and risk hindering the global control of infectious diseases. After a careful examination of these phenomena and multiple mechanisms that make certain bacteria resistant to specific antibiotics that were originally effective in the treatment of infections caused by the same pathogens, possible strategies to stem antibiotic resistance are analyzed. This paper, therefore, focuses on the most promising new chemical compounds in the current pipeline active against multidrug-resistant organisms that are innovative compared to traditional antibiotics: Firstly, the main antibacterial agents in clinical development (Phase III) from 2017 to 2020 are listed (with special attention on the treatment of infections caused by the pathogensNeisseria gonorrhoeae, including multidrug-resistant isolates, andClostridium difficile), and then the paper moves on to the new agents of pharmacological interest that have been approved during the same period. They include tetracycline derivatives (eravacycline), fourth generation fluoroquinolones (delafloxacin), new combinations between one β-lactam and one β-lactamase inhibitor (meropenem and vaborbactam), siderophore cephalosporins (cefiderocol), new aminoglycosides (plazomicin), and agents in development for treating drug-resistant TB (pretomanid). It concludes with the advantages that can result from the use of these compounds, also mentioning other approaches, still poorly developed, for combating antibiotic resistance: Nanoparticles delivery systems for antibiotics.
2. Micromonospora-produced sisomicin components
E Katz, B K Lee, G H Wagman, R G Condon, M J Weinstein J Antibiot (Tokyo) . 1976 Jul;29(7):677-84. doi: 10.7164/antibiotics.29.677.
A sisomicin fermentation carried out in the presence of (methyl-14C)-L-methionine resulted in a crude mixture, composed of methyl-14C-labeled sisomicin as a major component; and two 4''-C-desmethylsisomicin (66-40B and 66-40D) isomer-like components, an unidentified component and a gentamicin A-like antibiotic as minor components. When (methyl-14C)-L-methionine was added in an early stage of the fermentation (24 hours), incorporation of methyl-14C-label into polar components (e.g., gentamicin A-like antibiotic) preceded that into sisomicin. Chromatographic evidence for the bioconversion of (methyl-14C)-gentamicin A to a radioactive sisomicin-like product (possibly (3''-N-methyl-14C)-sisomicin) was seen, when a Micromonospora blocked mutant was incubated in the presence of the former antibiotic.
3. Analysis of histamine and sisomicin in gentamicin: Search for the causative agents of adverse effects
Ulrike Holzgrabe, Jonas Wohlfart Arch Pharm (Weinheim) . 2021 Dec;354(12):e2100260. doi: 10.1002/ardp.202100260.
In 1998, the aminoglycoside antibiotic gentamicin sulfate caused several cases of deaths in the United States, after the switch from twice- to once-daily application. Endotoxins were discussed as the cause for the adverse effects and sisomicin was identified as the lead impurity; batches containing sisomicin were contaminated with more impurities and were responsible for the fatalities. In 2016, anaphylactic reactions in horses, and later in humans with one fatality, were observed after application of gentamicin sulfate contaminated with histamine. To determine whether histamine was responsible for the 1990s death cases as well, histamine was quantified by means of liquid chromatography-tandem mass spectrometry (LC-MS/MS) in 30 samples of gentamicin sulfate analyzed in previous studies. Furthermore, a relative quantification of sisomicin was performed to check for a correlation between histamine and the lead impurity. A maximum amount of 11.52 ppm histamine was detected, which is below the limit for anaphylactic reactions of 16 ppm, and no correlation of the two impurities was observed. However, the European Medicines Agency recommends a stricter limit with regard to the maximum single dose of gentamicin sulfate to reach a greater gap between the maximum histamine exposition of 4.3 µg and the quantity known to cause hypotension of 7 µg. The low amounts of histamine and the fact that there is no connection with the contamination with sisomicin showed that histamine was not the cause for the death cases in the United States in 1998, and endotoxins remain the most probable explanation.
Recommended Products
| BBF-01693 | Doxorubicin EP Impurity A (Daunorubicin) | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
| BBF-02614 | Nystatin | Inquiry |
| BBF-05862 | Epirubicin | Inquiry |
| BBF-03754 | CASTANOSPERMINE | Inquiry |
| BBF-00764 | Cerebroside C | Inquiry |
Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
