CAS 32385-11-8

Sisomicin

Description:

Sisomicin is an aminoglycoside antibiotic that is primarily used to treat infections caused by Gram-negative bacteria. It is derived from the fermentation of the bacterium Micromonospora purpurea. Sisomicin exhibits a broad spectrum of antibacterial activity, particularly effective against various strains of Pseudomonas and Enterobacter species. The mechanism of action involves binding to the 30S ribosomal subunit, leading to the inhibition of protein synthesis, which ultimately results in bacterial cell death. Sisomicin is typically administered via injection due to its poor oral bioavailability. Its pharmacokinetics include renal excretion, necessitating dosage adjustments in patients with impaired kidney function. While generally well-tolerated, potential side effects may include nephrotoxicity and ototoxicity, common concerns associated with aminoglycosides. Sisomicin's chemical structure features multiple amino groups, contributing to its solubility and interaction with bacterial ribosomes. As with all antibiotics, appropriate susceptibility testing is recommended to ensure effectiveness against specific pathogens.

Formula: C₁₉H₃₇N₅O₇·H₂O₄S

InChI: InChI=1/C19H37N5O7.H2O4S/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;1-5(2,3)4/h3,9-18,24-27H,4-7,20-23H2,1-2H3;(H2,1,2,3,4)/t9-,10+,11-,12+,13?,14-,15+,16-,17-,18-,19+;/m1./s1

InChI key: InChIKey=URWAJWIAIPFPJE-YFMIWBNJSA-N

SMILES: O([C@@H]1[C@@H](O)[C@H](O[C@H]2OC(CN)=CC[C@H]2N)[C@@H](N)C[C@H]1N)[C@@H]3[C@H](O)[C@@H](NC)[C@@](C)(O)CO3

Synonyms:

• <span class="text-smallcaps">D</smallcap>-Streptamine, O-3-deoxy-4-C-methyl-3-(methylamino)-β-<smallcap>L</smallcap>-arabinopyranosyl-(1→6)-O-[2,6-diamino-2,3,4,6-tetradeoxy-α-<smallcap>D</span>-glycero-hex-4-enopyranosyl-(1→4)]-2-deoxy-
• Antibiotic 66-40
• Antibiotic 6640
• BactoCeaze
• Ensamycin
• O-3-Deoxy-4-C-methyl-3-(methylamino)-β-<span class="text-smallcaps">L</smallcap>-arabinopyranosyl-(1→6)-O-[2,6-diamino-2,3,4,6-tetradeoxy-α-<smallcap>D</smallcap>-glycero-hex-4-enopyranosyl-(1→4)]-2-deoxy-<smallcap>D</span>-streptamine
• Rickamicin
• Sch 13475
• Siseptin
• Sisomicin
• Sisomicina
• Sisomicine
• Dehydrogentamicin Cla
• 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-
• (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 3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranoside
• (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 (2xi)-3-deoxy-4-C-methyl-3-(methylamino)-beta-L-erythro-pentopyranoside sulfate (salt)
• (1S,2S,3R,4S,6R)-4,6-diamino-3-{[3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy}-2-hydroxycyclohexyl 3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranoside
• Sisomicin base
• 4,6-diamino-3-{[3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy}-2-hydroxycyclohexyl 3-deoxy-4-C-methyl-3-(methylamino)pentopyranoside
• 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
• 6-O-(4-C-Methyl-3-methylamino-3-deoxy-β-L-arabinopyranosyl)-4-O-(2,6-diamino-2,3,4,6-tetradeoxy-α-D-glycero-4-hexenopyranosyl)-2-deoxy-D-streptamine
• O-3-Deoxy-4-C-methyl-3-(methylamino)--L-arabinopyranosyl-(1-6)-O-[2,6-diamino-2,3,4,6-tetradeoxy-a-D-glycero-hex-4-enopyranosyl-(1-4)]-2-deoxy- D-Streptamine
• Sisomicin (C1a oxidation peak)
• Sisomicin base (intermediates)
• SISOMYCIN
• O-3-deoxy-4C-methyl-3-(methylamino)--L-arabinopiranozyl-(1-6)-O[2,6-diamino-2,3,4,6-tetradeooxy-a-D-glycerohexy-4-enopiranozyl-(1-4)]-2-deoxy-D-streptamycin

Sisomicin

CAS: 32385-11-8

Formula: C₁₉H₃₇N₅O₇

Purity: 97%

Color and Shape: Solid

Molecular weight: 447.5264

Ref: IN-DA00C0C4

Sisomicin

CAS: 32385-11-8

Sisomicin is a broad-spectrum aminoglycoside antibiotic isolated from Micromonospora inyoensis. It is highly active against staphylococci.

Formula: C₁₉H₃₇N₅O₇

Purity: 98%

Color and Shape: Solid

Molecular weight: 447.53

Ref: TM-T20675

Sisomicin (Netilmicin EP Impurity A)

CAS: 32385-11-8

Formula: C₁₉H₃₇N₅O₇

Color and Shape: White To Off-White Solid

Molecular weight: 447.53

Ref: 4Z-S-080002

Sisomicin

CAS: 32385-11-8

Molecular weight: 447.53

Ref: 7W-GA4392

Sisomicin

Controlled Product

CAS: 32385-11-8

Applications Sisomicin is an Antibacterial. Gentamicin-like aminoglycoside antibiotic; has broad spectrum antibiotic activity.
References Weinstein, M.J., et al.: J. Antibiot., 23, 551 (1970), Sculier, J.P., et al.: J. Antimicrob. Chemother., 9, 63 (1982), Noone, P., et al.: Drugs, 27, 548 (1984),

Formula: C₁₉H₃₇N₅O₇

Color and Shape: Neat

Molecular weight: 447.53

Ref: TR-S488500

Sisomicin

CAS: 32385-11-8

Sisomicin is an aminoglycoside antibiotic with action on bacterial protein synthesis inhibition and is used for treating severe bacterial infections resistant to other aminoglycosides.

Formula: C₁₉H₃₇N₅O₇

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 447.53 g/mol

Ref: 3D-AS27839

Netilmicin EP Impurity A

CAS: 32385-11-8

Formula: C₁₉H₃₇N₅O₇

Molecular weight: 447.53

Ref: ST-EA-CP-N94001

Sisomicin Sulfate

CAS: 32385-11-8, 53179-09-2

Formula: C₁₉H₃₇N₅O₇H₂SO₄

Purity: >98.0%(HPLC)

Color and Shape: White to Almost white powder to crystal

Molecular weight: 692.71

Ref: 3B-I1049