Neomycin

Base Information

• Chemical Name: Neomycin
• CAS No.: 119-04-0
• Deprecated CAS: 11025-81-3,1393-86-8,11013-50-6
• Molecular Formula: C23H46 N6 O13
• Molecular Weight: 614.651
• European Community (EC) Number: 204-292-2,215-766-3
• UNII: 4BOC774388
• DSSTox Substance ID: DTXSID2023359
• Nikkaji Number: J4.458J
• Wikipedia: Neomycin
• Wikidata: Q4492348
• NCI Thesaurus Code: C65770,C66227,C683,C75943
• RXCUI: 7299
• Pharos Ligand ID: 8W1AQSCWNPXB
• Metabolomics Workbench ID: 43243
• ChEMBL ID: CHEMBL184618
• Mol file: 119-04-0.mol

Synonyms:Antibiotic 10676;Framycetin;Framycetin Sulfate;Neomycin B;Neomycin B Sulfate;Soframycin;Sulfate, Framycetin;Sulfate, Neomycin B

Chemical Property of Neomycin

Chemical Property:

• Appearance/Colour: Clear Liquid
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 927.1 °C at 760 mmHg
• PKA: 12.93±0.70(Predicted)
• Flash Point: 514.5 °C
• PSA: 353.11000
• Density: 1.61 g/cm³
• LogP: -4.69350
• Storage Temp.: 2-8°C
• Solubility.: Aqueous Acid (Slightly), Water (Slightly)
• XLogP3: -9
• Hydrogen Bond Donor Count: 13
• Hydrogen Bond Acceptor Count: 19
• Rotatable Bond Count: 9
• Exact Mass: 614.31228554
• Heavy Atom Count: 42
• Complexity: 872

Purity/Quality:

99% ^*data from raw suppliers

Neomycin B ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 42/43-63-36/37/38
• Safety Statements: 26-36/37/39-45-36/37-23

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Pharmaceuticals
• Drug Classes: Aminoglycosides
• Canonical SMILES: C1C(C(C(C(C1N)OC2C(C(C(C(O2)CN)O)O)N)OC3C(C(C(O3)CO)OC4C(C(C(C(O4)CN)O)O)N)O)O)N
• Isomeric SMILES: C1[C@H]([C@@H]([C@H]([C@@H]([C@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CN)O)O)N)O[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O[C@@H]4[C@@H]([C@H]([C@@H]([C@@H](O4)CN)O)O)N)O)O)N
• Recent ClinicalTrials: SURGIcal COmplication and MIcrobiome ChangeS in Colorectal Surgery
• Recent EU Clinical Trials: Phase IV, unicentric, randomized and open study to confirm the decrease of the incidence of the surgical site infection after elective right hemicolectomy with anterographic mechanical preparation associated with oral and intravenous antibiotic therapy versus oral and intravenous antibiotic and versus only intravenous antibiotic
• Uses: Neomycin C is an aminoglycoside antibiotic found in many topical medications. Neomycin has been used as a preventive measure for hepatic encephalopathy and hypercholesterolemia.

Technology Process of Neomycin

There total 4 articles about Neomycin 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: 65.0%

5-O-<3-O-(2,6-diazido-4-O-benzyl-2,6-dideoxy-β-L-idopyranosyl)-β-D-ribofuranosyl>-1,3,2',6'-tetra-N-(benzyloxycarbonyl)neamine → neomycin B (119-04-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In 1,4-dioxane; water; acetic acid; for 26h; Pressure (range begins): 4 ;

DOI:10.1016/0008-6215(88)85087-0

Reference yield:

neomycin C (66-86-4,119-04-0,58617-08-6) → neomycin B (119-04-0)

Guidance literature:

With sodium dithionite; reduced form of S-adenosyl-L-methionine epimerase C₂₄₉A mutant; S-Adenosyl-L-methionine; In aq. buffer; at 20 ℃; for 30h; Reagent/catalyst; Glovebox; Enzymatic reaction;

DOI:10.1021/ja507759f

Reference yield:

neomycin B sulphate (25389-98-4) → neomycin B (119-04-0)

Guidance literature:

With Amberlite-IRA 400 (OH^-);

DOI:10.3390/antibiotics8030109

upstream raw materials:

neomycin C

neomycin B sulphate

Downstream raw materials:

γ-L-Glu-[(S)-4-amino-2-hydroxybutyryl]-neomycin B

neomycin A

4-O-(2,6-di-deoxy-α-D-2,6-di-amine-glucopyranosyl)-2-deoxy-streptamine hydrochloride

1,3,2',6'-tetraazido-3',4'-di-O-acetylneamine

Refernces

• 1、 Zárate, Sandra G.,Bastida, Agatha,Santana, Andrés G.,Revuelta, Julia. "Synthesis of ring II/III fragment of Kanamycin: A new minimum structural motif for aminoglycoside recognition". . . Retrieved 2019/08/20.
• 2、 Umezawa,Harayama,Nishimura. "The total synthesis of neomycin C". . p. 3259 - 3262. Retrieved 2007/10/02.