58152-03-7

Basic information

• Product Name: Isepamicine
• Synonyms: (s)-y-1-oxopropyl)-2-deoxy;hapa-b;hapa-gentamycinb;isepamicin;sch21420;thyl-3-(methylamino)-beta-l-arabinopyranosyl-(1-6))-n(sup1)-(3-amino-2-hydrox;ISEPAMICIN SULPHATE;(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
• CAS NO: 58152-03-7
• Molecular Formula: C₂₂H₄₃N₅O₁₂
• Molecular Weight: 569.6
• EINECS: 261-143-4
• Mol File: 58152-03-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 633.08°C (rough estimate)
• Flash Point: 514.3°C
• Appearance: /
• Density: 1.3531 (rough estimate)
• Refractive Index: 1.7500 (estimate)
• PKA: 11.01±0.35(Predicted)
• CAS DataBase Reference: Isepamicine(CAS DataBase Reference)
• NIST Chemistry Reference: Isepamicine(58152-03-7)
• EPA Substance Registry System: Isepamicine(58152-03-7)

Safety Data

• Hazardous Substances Data: 58152-03-7(Hazardous Substances Data)

Usage

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.

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.

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

Upstream product

• 74464-85-0 gentamicin B 
• 845258-88-0 C₆₉H₇₈N₆O₁₉ 
• 556059-94-0 C₆₁H₇₂N₆O₁₇ 
• 845258-90-4 1-[(2-benzyloxy-3-N-benzyloxycarbonyl)-L-isoserinyl]-3,3-di-N-benzyloxycarbonylgaramine 
• 42869-68-1 6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosyl chloride 
• 32385-11-8 sisomicin 
• 66567-23-5 3,6'-bis-N-benzyloxycarbonylgentamicin B 
• 66567-35-9 C₄₆H₆₁O₁₈N₅ 

Downstream Products

• 401947-35-1 3,6',3''-tri-N-(t-butoxycarbonyl)-3'''-N-(benzyloxycarbonyl)isepamicin 
• 731002-39-4 6'-N-benzyloxycarbonyl-3,3'',3'''-tri-N-(t-butoxycarbonyl)-isepamicin 
• 401947-25-9 3,3'',3'''-tri-N-(t-butoxycarbonyl)-isepamicin 
• 401947-24-8 3,6',3''-tri-N-(t-butoxycarbonyl)-isepamicin 
• 67987-06-8 6'-N-(t-butoxycarbonyl)-3'''-N-(benzyloxycarbonyl)isepamicin 
• 401947-33-9 6'-N-benzyloxycarbonyl-isepamicin 
• 401947-32-8 6'-N-(t-butoxycarbonyl)-isepamicin 

Relevant articles and documents

Synthesis method of isepamicin

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

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.