58152-03-7 Usage
Description
Isepamicin is an aminoglycoside antibiotic that is primarily used for the treatment of urinary and respiratory tract infections. It is known for its broad-spectrum activity, which is similar to that of amikacin in vitro. Although it is less potent than most other aminoglycosides, it has the advantage of being less nephrotoxic, making it a safer option for patients with compromised kidney function.
Uses
Used in Pharmaceutical Industry:
Isepamicin is used as an antibacterial agent for the treatment of urinary and respiratory tract infections. Its broad-spectrum activity and lower nephrotoxicity make it a preferred choice for patients with kidney-related concerns.
As an aminoglycoside antibiotic, isepamicin is effective against a wide range of bacteria, including both Gram-negative and Gram-positive organisms. It works by binding to the 30S ribosomal subunit in bacterial cells, inhibiting protein synthesis and ultimately leading to bacterial cell death. This makes it a valuable tool in the fight against bacterial infections, particularly in cases where other antibiotics may be less effective or contraindicated due to potential kidney toxicity.
Originator
Schering Plough (USA)
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.
Check Digit Verification of cas no
The CAS Registry Mumber 58152-03-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,8,1,5 and 2 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 58152-03:
(7*5)+(6*8)+(5*1)+(4*5)+(3*2)+(2*0)+(1*3)=117
117 % 10 = 7
So 58152-03-7 is a valid CAS Registry Number.
InChI:InChI=1/C22H43N5O12/c1-22(35)6-36-20(15(33)18(22)26-2)39-17-8(27-19(34)9(28)4-23)3-7(25)16(14(17)32)38-21-13(31)12(30)11(29)10(5-24)37-21/h7-18,20-21,26,28-33,35H,3-6,23-25H2,1-2H3,(H,27,34)/t7-,8+,9?,10+,11+,12-,13+,14-,15+,16+,17-,18+,20+,21+,22-/m0/s1
58152-03-7Relevant articles and documents
Synthesis method of isepamicin
-
, (2022/03/27)
The invention discloses a synthesis method of isepamicin, which comprises the following steps: taking gentamicin B as a raw material, reacting with a metal chelating agent and (Boc) 2O to obtain an intermediate P1, esterifying the intermediate P1 and Boc-(S)-isoserine to obtain an intermediate P2, and carrying out acidolysis deprotection on the intermediate P2 to obtain isepamicin. Both the intermediate P1 and the intermediate P2 are refined in a recrystallization mode, purification through an ion exchange column chromatography separation method in the prior art is replaced, the synthesis method is easy to operate, short in period, little in waste liquid and easy for industrial production, the prepared isepamicin is high in purity, and the synthesis route of the isepamicin is as follows: the synthesis route of the isepamicin is shown in the specification.
A semisynthesis of isepamicin by fragmentation method
Moon, Man Sik,Jun, Sook Jin,Lee, So Ha,Cheong, Chan Seong,Kim, Kwan Soo,Lee, Byung Suk
, p. 607 - 609 (2007/10/03)
Garamine derivative, key intermediate, was obtained from acid cleavage of sisomicin derivative. Its subsequent product was glycosylated with 6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-d-glucopyranosyl chloride using silver triflate as a promoter to give isepamicin.