| Identification | Back Directory | [Name]
Isepamicine | [CAS]
58152-03-7 | [Synonyms]
hapa-b
sch21420
isepamicin
ISEPAMICINE
hapa-gentamycinb
ISEPAMICIN SULPHATE
Isepamicine USP/EP/BP
(s)-y-1-oxopropyl)-2-deoxy
Isepamicin Sulfate Impurity Ⅲ:Isepamicine
thyl-3-(methylamino)-beta-l-arabinopyranosyl-(1-6))-n(sup1)-(3-amino-2-hydrox
4-O-(6-Amino-6-deoxy-α-D-glucopyranosyl)-6-O-[4-C-methyl-3-(methylamino)-3-deoxy-β-L-arabinopyranosyl]-N1-[(S)-3-amino-2-hydroxypropionyl]-2-deoxy-D-streptamine
4-O-(6-Amino-6-deoxy-α-D-glucopyranosyl)-6-O-[3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl]-N1-[(S)-3-amino-2-hydroxypropanoyl]-2-deoxy-D-streptamine
4-O-(6-Amino-6-deoxy-α-D-glucopyranosyl)-6-O-[3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl]-N1-[(S)-3-amino-2-hydroxy-1-oxopropyl]-2-deoxy-D-streptamine
D-Streptamine, O-6-amino-6-deoxy-a-D-glucopyranosyl-(14)-O-[3-deoxy-4-C-methyl-3-(methylamino)-b-L-arabinopyranosyl-(16)]-N1-(3-amino-2-hydroxy-1-oxopropyl)-2-deoxy-, (S)-
D-Streptamine, O-6-amino-6-deoxy-α-D-glucopyranosyl-(1→4)-O-[3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl-(1→6)]-N1-[(2S)-3-amino-2-hydroxy-1-oxopropyl]-2-deoxy-
(S)-O-6-Amino-6-deoxy-α-D-glucopyranosyl-(1→4)-O-[3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyrano-syl-(1→6)]-N^<1>^-(3-amino-2-hydroxy-1-oxopropyl)-2-deoxy-D-streptamine
D-Streptamine, O-6-amino-6-deoxy-a-D-glucopyranosyl-(14)-O-[3-deoxy-4-C-methyl-3-(methylamino)-b-L-arabinopyranosyl-(16)]-N1-[(2S)-3-amino-2-hydroxy-1-oxopropyl]-2-deoxy- (9CI)
(S)-O-6-amino-6-deoxy-alpha-D-glucopyranosyl-(1->4)-O-[3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1->6)]-1,3-diamino-N1-(3-aminolactoyl)-1,2,3-trideoxy-D-scyllo-inositol
(2S)-3-Amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-2-[(3R,4R,5R)-3,5-dihydroxy-5-methyl-4-methylaminooxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxypropanamide | [EINECS(EC#)]
261-143-4 | [Molecular Formula]
C22H43N5O12 | [MDL Number]
MFCD00864928 | [MOL File]
58152-03-7.mol | [Molecular Weight]
569.6 |
| Chemical Properties | Back Directory | [Boiling point ]
633.08°C (rough estimate) | [density ]
1.3531 (rough estimate) | [refractive index ]
1.7500 (estimate) | [pka]
11.01±0.35(Predicted) |
| Hazard Information | Back Directory | [Description]
Isepamicin is a aminoglycoside antibiotic indicated for use in the treatment of urinary and
respiratory tract infections. Although it is less potent than most other aminoglycosides, it
is also less nephrotoxic. The broad-spectrum activity of isepamicin generally parallels that
of amikacin in vitro. | [Chemical Properties]
Isepamicin Sulfate: C22H43N5O12?xH2SO4 (x≤2). [67814-76-0]. [α]{D}^26+110.9° (C=1, hydrated in water). Acute toxicity LD50 for male and female mice, male and female rats (mg/kg): 3312, 3320, 3451, 3392 for subcutaneous injection; 234, 236, 489, 476 for intravenous injection; all >5000 for oral administration. | [Originator]
Schering Plough (USA) | [Uses]
Antibacterial (aminoglyco side). | [Brand name]
Isepacin; Exacin | [Antimicrobial activity]
Hydroxyamino propionyl gentamicin B. A semisynthetic
derivative of gentamicin B, modified to render it more resistant
to microbial inactivation.
In-vitro activity is comparable to or slightly greater than
amikacin against Staph. aureus and most enterobacteria; it is
much more active against Ser. marcescens, Enterobacter spp.
and Klebsiebella pneumoniae. It is also active in vitro against
the Mycobacterium avium complex and Nocardia asteroides. It
is less susceptible than amikacin or gentamicin to inactivation
by β-lactam antibiotics. It retains activity against some strains
resistant to most other aminoglycosides.
Pharmacokinetics in neonatal, pediatric, adult, elderly and
renally impaired patients are similar to those of other aminoglycosides.
In adult volunteers the plasma half-life was 2.1 h.
Clearance is reduced in neonates and the elderly. A 7.5 mg/kg
once-daily dosage is recommended for children less than 16
days old. No dosage adjustment is required for the elderly unless
renal function is impaired. Clearance is proportional to creatinine
clearance in patients with chronic renal impairment, and it
is eliminated by hemodialysis.
It has been used in respiratory tract infections, urinary
tract infections and intra-abdominal infections, in adults and
children. It appears to be as effective and well tolerated as
amikacin. It is available in Japan. |
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