Sisomicin

Base Information

• Chemical Name: Sisomicin
• CAS No.: 32385-11-8
• Deprecated CAS: 34406-63-8,37332-59-5,53179-08-1
• Molecular Formula: C19H37N5O7
• Molecular Weight: 447.532
• European Community (EC) Number: 251-018-2
• UNII: X55XSL74YQ
• Nikkaji Number: J342.544D
• Wikipedia: Sisomicin
• Wikidata: Q3962119
• NCI Thesaurus Code: C72569
• Metabolomics Workbench ID: 53436
• ChEMBL ID: CHEMBL221886
• Mol file: 32385-11-8.mol

Synonyms:4,5 Dehydrogentamicin;4,5-Dehydrogentamicin;Antibiotic 6640;Extramycin;Pathomycin;Rickamicin;Sch 13475;Sch-13475;Sch13475;Siseptin;Sisomicin;Sisomicin Sulfate;Sisomicin Sulfate (2:5) Salt;Sisomycin;Sissomicin;Sizomycin

Chemical Property of Sisomicin

Chemical Property:

• Vapor Pressure: 1.79E-30mmHg at 25°C
• Melting Point: 80-93°C
• Refractive Index: 1.7600 (estimate)
• Boiling Point: 676.579 °C at 760 mmHg
• PKA: 13.29±0.70(Predicted)
• Flash Point: 362.982 °C
• PSA: 296.70000
• Density: 1.387 g/cm³
• LogP: -0.23140
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Aqueous Acid (Slightly), DMSO (Slightly), Methanol (Slightly), Water (Slightly,
• XLogP3: -5.1
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 6
• Exact Mass: 447.26929854
• Heavy Atom Count: 31
• Complexity: 643

Purity/Quality:

99% ^*data from raw suppliers

Sisomicin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(COC(C(C1NC)O)OC2C(CC(C(C2O)OC3C(CC=C(O3)CN)N)N)N)O
• Isomeric SMILES: C[C@@]1(CO[C@@H]([C@@H]([C@H]1NC)O)O[C@H]2[C@@H](C[C@@H]([C@H]([C@@H]2O)O[C@@H]3[C@@H](CC=C(O3)CN)N)N)N)O
• Recent ClinicalTrials: Sisomicin Cream Vs Nadifloxacin Cream in Primary Pyodermas (Study P04460)
• Uses: Sisomicin is an Antibacterial. Gentamicin-like aminoglycoside antibiotic; has broad spectrum antibiotic activity. Antibacterial. Gentamicin-like aminoglycoside antibiotic; has broad spectrum antibiotic activity antibacterial, binds to ribosomes
• Therapeutic Function: Antibiotic

Technology Process of Sisomicin

There total 10 articles about Sisomicin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

sisomicin hemipentasulfate → sisomicin (32385-11-8)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 5h; Reagent/catalyst;

Reference yield: 92.0%

Sisomicin sulfate (53179-09-2,53776-71-9,68231-64-1) → sisomicin (32385-11-8)

Guidance literature:

With activated anion exchange resin (amberlite 4200 Cl); In methanol; at 15 - 20 ℃; for 18h; Inert atmosphere;

Reference yield: 10.0%

N-[(1S,2R,3S,4S)-2-[(2S,3R)-3-Acetylamino-6-(acetylamino-methyl)-3,4-dihydro-2H-pyran-2-yloxy]-4-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-methylamino-tetrahydro-pyran-2-yloxy)-5-ethylamino-3-hydroxy-cyclohexyl]-acetamide (66567-31-5) → sisomicin (32385-11-8) + 1-deamino-1-hydroxysisomicin (66065-95-0,66101-45-9) + netilmicin (56391-56-1) + 1-epi-N-ethylsisomicin (67650-39-9)

Guidance literature:

With sodium hydroxide; for 50h; Further byproducts given; Heating;

DOI:10.1039/P19810002168

upstream raw materials:

N-[(1S,2R,3S,4S)-2-[(2S,3R)-3-Acetylamino-6-(acetylamino-methyl)-3,4-dihydro-2H-pyran-2-yloxy]-4-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-methylamino-tetrahydro-pyran-2-yloxy)-5-ethylamino-3-hydroxy-cyclohexyl]-acetamide

N-[(1S,2R,3R,4S)-2-[(2S,3R)-3-Acetylamino-6-(acetylamino-methyl)-3,4-dihydro-2H-pyran-2-yloxy]-5-amino-4-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-methylamino-tetrahydro-pyran-2-yloxy)-3-hydroxy-cyclohexyl]-acetamide

3,2',6'-tri-N-acetyl-1-deamino-1-oxosisomicin

3,2',6'-tri-N-acetylsisomicin

Downstream raw materials:

isepamicin

1-[(2-benzyloxy-3-N-benzyloxycarbonyl)-L-isoserinyl]-3,3-di-N-benzyloxycarbonylgaramine

C₆₁H₇₂N₆O₁₇

C₆₉H₇₈N₆O₁₉

Refernces

• 1、 -. "Preparation method of pradimicin antibiotics". Paragraph 0081-0083; 0125; 0128; 0148; 0151; 0154; 0160. . Retrieved 2019/01/08.
• 2、 -. "ANTIBACTERIAL AMINOGLYCOSIDE ANALOGS". Page/Page column 48. . Retrieved 2009/06/27.