Sisomicin sulfate (2:5)
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| Category | Antibiotics |
| Catalog number | BBF-03896 |
| CAS | 53179-09-2 |
| Molecular Weight | 1385.44 |
| Molecular Formula | C19H37N5O7.5/2H2O4S |
| Purity | ≥95% |
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Description
Sisomicin Sulfate 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.
Specification
| Related CAS | 32385-11-8 (free base) 53776-71-9 (x-sulfate) 37281-43-9 (Deleted CAS) 70074-95-2 (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-, sulfate (2:5); 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-, sulfate (2:5) (salt); Antibiotic 66-40 sulfate; Baymicin; Extramycin; Mensiso; Sisobiotic; Sisolline; Sisomicin sulfate; Sisomin; Sisomycin sulfate; Sissomicin sulfate |
| Shelf Life | As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly |
| Storage | Store at -20°C |
| 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;sulfuric acid |
| Canonical SMILES | CC1(COC(C(C1NC)O)OC2C(CC(C(C2O)OC3C(CC=C(O3)CN)N)N)N)O.CC1(COC(C(C1NC)O)OC2C(CC(C(C2O)OC3C(CC=C(O3)CN)N)N)N)O.OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O |
| InChI | InChI=1S/2C19H37N5O7.5H2O4S/c2*1-19(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;5*1-5(2,3)4/h2*3,9-18,24-27H,4-7,20-23H2,1-2H3;5*(H2,1,2,3,4)/t2*9-,10+,11-,12+,13-,14-,15+,16-,17-,18-,19+;;;;;/m11../s1 |
| InChI Key | CIKNYWFPGZCHDL-ZHFUJENKSA-N |
| Source | Micromonospora Inyoesis. |
Properties
| Appearance | White to Off-white Solid |
| Application | Anti-Bacterial Agents |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 676.6°C at 760 mmHg |
| Melting Point | >157°C |
| Solubility | Soluble in DMSO |
Reference Reading
1.Penetration of topical chloramphenicol into the anterior chamber.
Papa V1. Clin Experiment Ophthalmol. 2015 Jul;43(5):493-4. doi: 10.1111/ceo.12468. Epub 2014 Dec 12.
2.Determination of equilibrium constant of amino carbamate adduct formation in sisomicin by a high pH based high performance liquid chromatography.
Wlasichuk KB1, Tan L2, Guo Y1, Hildebrandt DJ1, Zhang H1, Karr DE1, Schmidt DE Jr3. J Pharm Biomed Anal. 2015;111:126-30. doi: 10.1016/j.jpba.2015.03.033. Epub 2015 Apr 3.
Amino carbamate adduct formation from the amino group of an aminoglycoside and carbon dioxide has been postulated as a mechanism for reducing nephrotoxicity in the aminoglycoside class compounds. In this study, sisomicin was used as a model compound for amino carbamate analysis. A high pH based reversed-phase high performance liquid chromatography (RP-HPLC) method is used to separate the amino carbamate from sisomicin. The carbamate is stable as the breakdown is inhibited at high pH and any reactive carbon dioxide is removed as the carbonate. The amino carbamate was quantified and the molar fraction of amine as the carbamate of sisomicin was obtained from the HPLC peak areas. The equilibrium constant of carbamate formation, Kc, was determined to be 3.3 × 10(-6) and it was used to predict the fraction of carbamate over the pH range in a typical biological systems. Based on these results, the fraction of amino carbamate at physiological pH values is less than 13%, and the postulated mechanism for nephrotoxicity protection is not valid.
3.Microbiological spectrum and susceptibility pattern of clinical isolates from the neonatal unit in a single medical center.
Nitsch-Osuch A1, Choroszy-Król I2, Kuchar E3, Korzeniewski K4, Życińska K1, Wardyn K1. Adv Clin Exp Med. 2015 Jan-Feb;24(1):15-22. doi: 10.17219/acem/38170.
BACKGROUND: Infections are a frequent and significant cause of morbidity and mortality in neonatal units. The bacterial pathogens and their susceptibility patterns should be monitored in hospital settings. The aim of the study was to describe the distribution of the bacterial agents and their antibiotic resistant and susceptibility patterns in the Special Neonatal Care Unit (SNCU).
4.Frequency distribution of genes encoding aminoglycoside modifying enzymes in uropathogenic E. coli isolated from Iranian hospital.
Soleimani N1, Aganj M, Ali L, Shokoohizadeh L, Sakinc T. BMC Res Notes. 2014 Nov 25;7:842. doi: 10.1186/1756-0500-7-842.
BACKGROUND: Escherichia coli is considered as the most common cause of urinary tract infection (UTI) and acquired multiple resistances to a wide range of antibiotics such as aminoglycosides. Enzymatic alteration of aminoglycosides (AMEs) by aminoglycoside- modifying enzymes is the main mechanism of resistance to these antibiotics in E. coli. The aim of this study was detection and investigation of frequency of genes encoding aminoglycoside modifying enzymes (aac(3)-IIa and ant(2'')-Ia) in UPEC isolated from hospitalized patients in teaching hospital of Tehran, Iran.
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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 ╳
