Compound: sisomicin
SMILES: O1C(=CC[C@H]([C@H]1O[C@H]2[C@H](O)[C@@H](O[C@H]3OC[C@@](O)(C)[C@@H]([C@H]3O)NC)[C@H](N)C[C@@H]2N)N)CN
InChIKey: URWAJWIAIPFPJE-YFMIWBNJSA-N
Synonyms: sisomicin, Rickamicin, 32385-11-8, Sisomycin, Sissomicin, Antibiotic 66-40, Sisomicina, Sisomicine, Antibiotic 6640, Sisomicinum, Sch 13475, Dehydrogentamicin Cla, X55XSL74YQ, Sch13475, CHEBI:9169, (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, D-Streptamine, O-3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-6)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1-4))-2-deoxy-, 4,5 Dehydrogentamicin, Sizomycin, (1S,2S,3R,4S,6R)-4,6-diamino-3-[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yloxy]-2-hydroxycyclohexyl 3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranoside, 4,5-Dehydrogentamicin, DTXSID0023583, (1S,2S,3R,4S,6R)-4,6-diamino-3-((2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yloxy)-2-hydroxycyclohexyl 3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranoside, (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, (2R,3R,4R,5R)-2-((1S,2S,3R,4S,6R)-4,6-diamino-3-((3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy-5-methyl-4-(methylamino)oxane-3,5-diol, (2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[[3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol, RefChem:886367, J01GB08, DTXCID301508648, (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, 251-018-2, Sch-13475, C19H37N5O7, Sisomin, (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)tetrahydro-2H-pyran-3,5-diol, Sisomicine [INN-French], Sisomicinum [INN-Latin], Salvamina, Sisomicina [INN-Spanish], Siseptin sulfate, (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, (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-hydroxy-cyclohexoxy]-5-methyl-4-(methylamino)tetrahydropyran-3,5-diol, O-2,6-Diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1-4)-O-(3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-6))-2-deoxy-D-streptamine, EINECS 251-018-2, UNII-X55XSL74YQ, BRN 1357913, Sisomicin [USAN:INN:BAN], sisomicin-sulfate, (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)tetrahydro-2H-pyran-3,5-diol, SiS, SISOMICIN [INN], SISOMICIN [MI], Sisomicin (USAN/INN), SISOMICIN [USAN], SISOMICIN [WHO-DD], SCHEMBL49395, O-2,6-Diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1-4)-O-(3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-6)-2-deoxy-D-streptamine, O-3-Deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-4)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1-6))-2-deoxy-L-streptamine, CHEMBL221886, orb1705491, GTPL10858, HY-B1222A, MSK7716, (2S-CIS)-4-O-(3-AMINO-6-(AMINOMETHYL)-3,4-DIHYDRO-2H-PYRAN-2-YL)-2-DEOXY-6-O-(3-DEOXY-4-C-METHYL-3-(METHYLAMINO)-.BETA.-L-ARABINOPYRANOSYL)-D-STREPTAMINE, MFCD00865123, MSK7716-100W, AKOS015895179, MSK7716-1000W, AS27839, DB12604, Sisomicin Solution in Water, 100ug/mL, (2S-cis)-4-O-(3-Amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl)-2-deoxy-6-O-(3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl)-D-streptamine, DA-67611, Sisomicin Solution in Water, 1000ug/mL, SY488279, CS-0013807, NS00011534, C00494, D02544, G78298, GENTAMICIN SULFATE IMPURITY A [EP IMPURITY], NETILMICIN SULFATE IMPURITY A [EP IMPURITY], Q3962119, Gentamicin Sulfate EP Impurity A; Netilmicin Sulfate EP Impurity A; Sisomicin, 2-DEOXY-4-O-(3-DEOXY-4-C-METHYL-3-(METHYLAMINO)-.BETA.-L-ARABINOPYRANOSYL)-6-O-(2,6-DIAMINO-2,3,4,6-TETRADEOXY-.ALPHA.-D-GLYCERO-HEX-4-ENOPYRANOSYL)-L-STREPTAMINE, O-3-DEOXY-4-C-METHYL-3-(METHYLAMINO)-.BETA-L-ARABINOPYRANOSYL-(1->4)-O-(2,6-DIAMINO-2,3,4,6-TETRADEOXY-.ALPHA.-D-GLYCERO-HEX-4-ENOPYRANOSYL-(1->6))-2-DEOXY-L-STREPTAMINE
Theoretical properties:
molecular_formula: C19H37N5O7
molecular_weight: 447.5 g/mol
exact_mass: 447.26929854 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 8
hydrogen_bond_acceptor_count: 12
rotatable_bond_count: 6
heavy_atom_count: 31
topological_polar_surface_area: 214 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Sisomycin is an amino cyclitol glycoside, an aminoglycoside antibiotic, a beta-L-arabinoside and a monosaccharide derivative.
chembl: SISOMICIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: Sisomicin (bactoCeaze, ensamycin, and initially antibiotic 6640 and rickamicin), is an aminoglycoside antibiotic, isolated from the fermentation broth of Micromonospora inositola. It is a newer broad-spectrum aminoglycoside most structurally related to gentamicin.
Sisomicin is the most predictably active aminoglycoside against Gram-positive bacteria. Like most other aminoglycosides, sisomicin is bactericidal for sensitive clinical isolates. The minimum bactericidal concentrations (MBC) have been found to be equivalent or very close to the minimum inhibitory concentrations (MIC). Like other aminoglycosides, most clinical isolates of Pseudomonas aeruginosa remain susceptible to sisomicin. Resistance to sisomicin may be enzymatically or non-enzymatically mediated. Sisomicin is inactivated by the same enzymes as gentamicin, but it is active against many organisms that resist gentamicin by non-enzymatic mechanisms.
Some studies show that sisomicin has been effective in the treatment of infections that either had failed to respond to other drugs or were due to microorganisms resistant in vitro to other aminoglycosides.