CAS 119-04-0

D-Streptamine, O-2,6-diamino-2,6-dideoxy-β-L-idopyranosyl-(1→3)-O-β-D-ribofuranosyl-(1→5)-O-[2,6-diamino-2,6-dideoxy-α-D-glucopyranosyl-(1→4)]-2-deoxy-

Description:

D-Streptamine is an aminoglycoside antibiotic that plays a significant role in the treatment of various bacterial infections. It is characterized by its complex glycosidic structure, which includes multiple amino and deoxy sugar components, contributing to its biological activity. The compound features a unique arrangement of sugar moieties, specifically a β-L-idopyranosyl and a β-D-ribofuranosyl unit, linked through glycosidic bonds. D-Streptamine exhibits a high affinity for bacterial ribosomes, inhibiting protein synthesis, which is crucial for bacterial growth and replication. Its mechanism of action primarily involves binding to the 30S ribosomal subunit, leading to misreading of mRNA and ultimately resulting in the production of nonfunctional proteins. This antibiotic is particularly effective against Gram-negative bacteria and is often used in combination with other antibiotics to enhance therapeutic efficacy. However, its use is limited by potential nephrotoxicity and ototoxicity, necessitating careful monitoring during treatment. Overall, D-Streptamine remains an important compound in the field of antimicrobial therapy.

Formula: C₂₃H₄₆N₆O₁₃

InChI: InChI=1/C23H46N6O13/c24-2-7-13(32)15(34)10(28)21(37-7)40-18-6(27)1-5(26)12(31)20(18)42-23-17(36)19(9(4-30)39-23)41-22-11(29)16(35)14(33)8(3-25)38-22/h5-23,30-36H,1-4,24-29H2/t5-,6+,7-,8+,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+/m1/s1

InChI key: InChIKey=PGBHMTALBVVCIT-VCIWKGPPSA-N

SMILES: O([C@H]1[C@H](O[C@H]2[C@H](O)[C@H](O[C@H]3O[C@@H](CN)[C@@H](O)[C@H](O)[C@H]3N)[C@@H](CO)O2)[C@@H](O)[C@H](N)C[C@@H]1N)[C@H]4O[C@H](CN)[C@@H](O)[C@H](O)[C@H]4N

Synonyms:

• <span class="text-smallcaps">D</smallcap>-Streptamine, O-2,6-diamino-2,6-dideoxy-α-<smallcap>D</smallcap>-glucopyranosyl-(1→4)-O-[O-2,6-diamino-2,6-dideoxy-β-<smallcap>L</smallcap>-idopyranosyl-(1→3)-β-<smallcap>D</span>-ribofuranosyl-(1→5)]-2-deoxy-
• <span class="text-smallcaps">D</smallcap>-Streptamine, O-2,6-diamino-2,6-dideoxy-β-<smallcap>L</smallcap>-idopyranosyl-(1→3)-O-β-<smallcap>D</smallcap>-ribofuranosyl-(1→5)-O-[2,6-diamino-2,6-dideoxy-α-<smallcap>D</span>-glucopyranosyl-(1→4)]-2-deoxy-
• Actilin
• Actiline
• Antibiotic 10676
• Antibiotique EF 185
• D-Streptamine, O-2,6-diamino-2,6-dideoxy-α-D-glucopyranosyl-(1→4)-O-[O-2,6-diamino-2,6-dideoxy-β-L-idopyranosyl-(1→3)-β-D-ribofuranosyl-(1→5)]-2-deoxy-
• Dekamycin III
• Enterfram
• Fradiomycin B
• Framicetina
• Framidal
• Framycetin
• Framycetine
• Framycin
• Framygen
• Francetin
• Fraquinol
• Leo Red Dry Cow
• Neomycin B
• O-2,6-Diamino-2,6-dideoxy-β-<span class="text-smallcaps">L</smallcap>-idopyranosyl-(1→3)-O-β-<smallcap>D</smallcap>-ribofuranosyl-(1→5)-O-[2,6-diamino-2,6-dideoxy-α-<smallcap>D</smallcap>-glucopyranosyl-(1→4)]-2-deoxy-<smallcap>D</span>-streptamine
• Neomycin solution
• D-Streptamine, O-2,6-diamino-2,6-dideoxy-β-L-idopyranosyl-(1→3)-O-β-D-ribofuranosyl-(1→5)-O-[2,6-diamino-2,6-dideoxy-α-D-glucopyranosyl-(1→4)]-2-deoxy-
• O-2,6-Diamino-2,6-dideoxy-β-L-idopyranosyl-(1→3)-O-β-D-ribofuranosyl-(1→5)-O-[2,6-diamino-2,6-dideoxy-α-D-glucopyranosyl-(1→4)]-2-deoxy-D-streptamine
• FRADIOMYCIN B; NEOMYCIN B
• (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-[(2S,3R,4S,5R)-4-[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxy-tetrahydropyran-2-yl]oxy-3-hydroxy-5-methylol-tetrahydrofuran-2-yl]oxy-3-hydroxy-cyclohexoxy]tetrahydropyran-3,4-diol
• antibiotique
• NEOMYCIN B USP/EP/BP
• soframycine
• D-Streptamine, O-2,6-diamino-2,6-dideoxy-.beta.-L-idopyranosyl-(1?3)-O-.beta.-D-ribofuranosyl-(1?5)-O-2,6-diamino-2,6-dideoxy-.alpha.-D-glucopyranosyl-(1?4)-2-deoxy-
• (2R,3S,4R,5R,6R)-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-2-[(2S,3R,4S,5R)-4-[(2R,3R,4R,5S,6S)-6-(aminomethyl)-3-azanyl-4,5-dihydroxy-oxan-2-yl]oxy-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-bis(azanyl)-3-hydroxy-cyclohexyl]oxy-5-azanyl-oxane-3,4-diol
• neomycine standard solution
• 4-O-(2,6-Diamino-2,6-dideoxy-α-D-glucopyranosyl)-5-O-[3-O-(2,6-diamino-2,6-dideoxy-β-L-idopyranosyl)-β-D-ribofuranosyl]-2-deoxy-D-streptamine
• (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-[(2S,3R,4S,5R)-4-[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxycyclohexyl]oxyoxane-3,4-diol
• soframycin
• Neomycin B Hexaacetate

Neomycin B (Framycetin)

CAS: 119-04-0

Formula: C₂₃H₄₆N₆O₁₃

Molecular weight: 614.65

Ref: 4Z-N-080022

Framycetin

CAS: 119-04-0

Framycetin is an aminoglycoside antibiotic and it also inhibits hammerhead ribozyme (Ki: 13.5 μM).

Formula: C₂₃H₄₆N₆O₁₃

Purity: 98%

Color and Shape: Amorphous Solid

Molecular weight: 614.64

Ref: TM-T15348

Neomycin B

Controlled Product

CAS: 119-04-0

Stability Hygroscopic
Applications Neomycin C is an aminoglycoside antibiotic found in many topical medications. Neomycin has been used as a preventive measure for hepatic encephalopathy and hypercholesterolemia.
References Umezawa, S., et al.: Bull. Chem. Soc. Jpm., 53, 3259 (1980); The Journal of antibiotics, NO. 2. 189 (1977);

Formula: C₂₃H₄₆N₆O₁₃

Color and Shape: Neat

Molecular weight: 614.64

Ref: TR-N389983

Neomycin B Hexaacetate

Controlled Product

CAS: 119-04-0

Formula: C₂₃H₄₆N₆O₁₃

Color and Shape: Neat

Molecular weight: 614.64

Ref: TR-N389990

Neomycin B

CAS: 119-04-0

Neomycin B is an aminoglycoside antibiotic, which is derived from the bacterium *Streptomyces fradiae*. It exerts its antibacterial effects by binding to the 30S subunit of bacterial ribosomes, leading to the inhibition of protein synthesis. This binding disrupts the translation process, thereby preventing the growth and proliferation of bacteria. Neomycin B is effective against a wide range of Gram-negative and some Gram-positive bacteria, making it a valuable tool in both medical and research settings.

Formula: C₂₃H₄₆N₆O₁₃

Purity: Min. 95%

Molecular weight: 614.64 g/mol

Ref: 3D-FN175622

Framycetin sulphate

CAS: 119-04-0, 28002-70-2, 4146-30-9

Framycetin sulphate is a broad-spectrum antibiotic that is used to treat microbial infections. It has been shown to be effective against many gram-positive and gram-negative bacteria, including methicillin resistant Staphylococcus aureus. Framycetin sulphate prevents bacterial growth by inhibiting protein synthesis through binding to the 30S ribosomal subunit. This binding inhibits the incorporation of amino acids into proteins, thereby preventing the production of new proteins required for cell division and growth. Framycetin sulphate also has preservative properties, which may be due to its ability to chelate metal ions such as copper and iron. Framycetin sulphate can be administered orally or topically in vivo model studies. The drug was not found to have any significant toxic effects on the liver or kidneys in vivo model studies at concentrations up to 40%.

Formula: C₂₃H₅₂N₆O₂₅S₃

Purity: Min. 95%

Molecular weight: 908.88 g/mol

Ref: 3D-FF150536