Cas no 67814-76-0 (Isepamicin sulfate)

Isepamicin sulfate is a semi-synthetic aminoglycoside antibiotic derived from gentamicin B. It exhibits broad-spectrum activity against Gram-negative and some Gram-positive bacteria, including strains resistant to other aminoglycosides. The sulfate salt formulation enhances solubility and stability, making it suitable for parenteral administration. Isepamicin sulfate is particularly effective against Pseudomonas aeruginosa and Enterobacteriaceae, with a lower propensity for inducing bacterial resistance due to its structural modifications. Its pharmacokinetic profile allows for once- or twice-daily dosing, improving patient compliance. The compound demonstrates reduced nephrotoxicity and ototoxicity compared to earlier aminoglycosides, making it a safer option for prolonged therapy. It is commonly used in severe infections, including sepsis and hospital-acquired pneumonia.
Isepamicin sulfate structure
Isepamicin sulfate structure
Product Name:Isepamicin sulfate
CAS No:67814-76-0
MF:C22H45N5O16S
MW:667.681606054306
MDL:MFCD01683537
CID:58640
PubChem ID:636375
Update Time:2025-05-20

Isepamicin sulfate Chemical and Physical Properties

Names and Identifiers

    • Isepamicin sulfate
    • (2S)-3-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxy-oxan-2-yl]oxy-2-[(2R,3R,4R,5S)-3,5-dihydroxy-5-methyl-4-methylamino-oxan-2-yl]oxy-3-hydroxy-cyclohexyl]-2-hydroxy-propanamide sulfate
    • Isepamicine Sulphate
    • (2S)-3-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxy-oxan-2-yl]oxy-2-[(2R,3R,4R,5S)-3,5-dihydroxy-5-methyl-4-methylamino-oxan-2-yl]oxy-3-hydroxy-cyclohexyl]-2-
    • HAPA-B sulfate
    • Isepacin
    • Exacin
    • Sch 21420 sulfate
    • Isepamicin sulfate [JAN]
    • 1-N-(S-3-Amino-2-hydroxypropionyl)-gentamicin B sulfate
    • D-Streptamine, O-6-amino-6-deoxy-alpha-D-glucopyranosyl-(1-4)-O-(3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-6))-N(sup 1)-(3-amino-2-hydroxy-1-oxopropyl)-2-deoxy-, (S)-, sulfate (salt)
    • (2S)-3-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-2-
    • D-Streptamine, O-6-amino-6-deoxy-alpha-D-glucopyranosyl-(1->4)-O-(3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1->6))-N1-((2S)-3-amino-2-hydroxy-1-oxopropyl)-2-deoxy-, sulfate (1:1) (salt)
    • Isepacin (TN)
    • CHEBI:31722
    • Isepamicin monosulfate
    • D-Streptamine, O-6-amino-6-deoxy-alpha-D-glucopyranosyl-(1->4)-O-(3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1->6))-N1-((3S)-3-amino-2-hydroxy-1-oxopropyl)-2-deoxy-, sulfate (salt)
    • F2L211KBUV
    • Isepamicine (Isepamycin
    • (S)-3-Amino-N-((1R,2S,3S,4R,5S)-5-amino-4-(((2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-2-(((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)tetrahydro-2H-pyran-2-yl)oxy)-3-hydroxycyclohexyl)-2-hydroxypropanamide sulfate
    • Isepamicin sulfate [WHO-DD]
    • Sch 21420 (sulfate)
    • Ispallin
    • (S)-3-Amino-N-((1R,2S,3S,4R,5S)-5-amino-4-(((2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-2-(((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)tetrahydro-2H-pyran-2-yl)oxy)-3-hydroxycyclohexyl)-2-hydroxypropanamide sulf
    • Isepamicin (sulfate)
    • AKOS025311241
    • Isepamicin sulfate [MI]
    • s4271
    • Isepamicine Sulphate;sch21420 Sulphate
    • 393574-17-9
    • Isepamicin sulfate (JP17)
    • D-STREPTAMINE, O-6-AMINO-6-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-O-(3-DEOXY-4-C-METHYL-3-(METHYLAMINO)-.BETA.-L-ARABINOPYRANOSYL-(1->6))-N1-((3S)-3-AMINO-2-HYDROXY-1-OXOPROPYL)-2-DEOXY-, SULFATE (SALT)
    • Q27277543
    • Isepamicin sulphate
    • 67814-76-0
    • D-STREPTAMINE, O-6-AMINO-6-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-O-(3-DEOXY-4-C-METHYL-3-(METHYLAMINO)-.BETA.-L-ARABINOPYRANOSYL-(1->6))-N1-((2S)-3-AMINO-2-HYDROXY-1-OXOPROPYL)-2-DEOXY-, SULFATE (1:1) (SALT)
    • MFCD01683537
    • CCG-270352
    • Isepamicin sulfate, VETRANAL(TM), analytical standard
    • UNII-F2L211KBUV
    • D01826
    • sch21420) Sulphate
    • (2S)-3-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-2-[(2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)oxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxypropanamide;sulfuric acid
    • DTXCID0026462
    • Isepalline
    • 6-Amino-6-deoxy-alpha-D-glucopyranosyl-(1->4)-[3-deoxy-4-C-methyl-3-methylamino-beta-L-arabinopyranosyl-(1->6)]-2-deoxy-1-N-[(2S)-3-amino-2-hydroxypropanoyl]-D-streptamine sulfate
    • 6-Amino-6-deoxy-alpha-D-glucopyranosyl-(1->4)-(3-deoxy-4-C-methyl-3-methylamino-beta-L-arabinopyranosyl-(1->6))-2-deoxy-1-N-((2S)-3-amino-2-hydroxypropanoyl)-D-streptamine sulfate
    • FI65046
    • FI163230
    • Isepamicin sulfate - 70%
    • MDL: MFCD01683537
    • Inchi: 1S/C22H43N5O12.H2O4S/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;1-5(2,3)4/h7-18,20-21,26,28-33,35H,3-6,23-25H2,1-2H3,(H,27,34);(H2,1,2,3,4)/t7-,8+,9-,10+,11+,12-,13+,14-,15+,16+,17-,18+,20+,21+,22-;/m0./s1
    • InChI Key: DDXRHRXGIWOVDQ-MGAUJLSLSA-N
    • SMILES: S(=O)(=O)(O)O.O([C@@H]1[C@@H]([C@H]([C@](C)(CO1)O)NC)O)[C@@H]1[C@H]([C@@H]([C@H](C[C@H]1NC([C@H](CN)O)=O)N)O[C@@H]1[C@@H]([C@H]([C@@H]([C@@H](CN)O1)O)O)O)O

Computed Properties

  • Exact Mass: 665.24300
  • Monoisotopic Mass: 665.242551
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 12
  • Hydrogen Bond Acceptor Count: 20
  • Heavy Atom Count: 44
  • Rotatable Bond Count: 9
  • Complexity: 880
  • Covalently-Bonded Unit Count: 2
  • Defined Atom Stereocenter Count: 15
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 386

Experimental Properties

  • Density: 1.53
  • Melting Point: 235-242°C
  • Boiling Point: 926.8°Cat760mmHg
  • Flash Point: 514.3°C
  • PSA: 386.36000
  • LogP: -4.89890
  • Specific Rotation: +110.9° (c=1, H2O as the disulfate hydrate)

Isepamicin sulfate Security Information

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(CAS:67814-76-0)Isepamicin sulfate
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Quantity:200kg
Purity:99.9%
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Additional information on Isepamicin sulfate

Isepamicin Sulfate (CAS No. 67814-76-0): An Overview of a Promising Antibiotic

Isepamicin sulfate (CAS No. 67814-76-0) is a semi-synthetic aminoglycoside antibiotic derived from the natural product micronomicin. This compound has gained significant attention in the pharmaceutical industry due to its potent antibacterial activity and potential for treating multidrug-resistant infections. In this comprehensive overview, we will delve into the chemical structure, pharmacological properties, clinical applications, and recent research developments surrounding isepamicin sulfate.

The chemical structure of isepamicin sulfate is characterized by its aminoglycoside backbone, which is responsible for its broad-spectrum antibacterial activity. The compound is composed of a deoxystreptamine nucleus with several functional groups that enhance its binding affinity to bacterial ribosomes. This structural feature allows isepamicin sulfate to inhibit protein synthesis in bacteria, making it an effective agent against both gram-positive and gram-negative pathogens.

In terms of pharmacokinetics, isepamicin sulfate exhibits favorable properties that contribute to its therapeutic efficacy. It is rapidly absorbed after intramuscular or intravenous administration and distributes widely throughout the body. The drug has a relatively short half-life, which necessitates multiple daily dosing regimens. However, this short half-life also reduces the risk of accumulation and potential toxicity. Recent studies have shown that the pharmacokinetic profile of isepamicin sulfate can be optimized through various formulations, such as liposomal delivery systems, to enhance its therapeutic window and reduce side effects.

Clinically, isepamicin sulfate has been evaluated for its effectiveness in treating a range of infections, including respiratory tract infections, urinary tract infections, and skin and soft tissue infections. Its ability to combat multidrug-resistant bacteria has made it particularly valuable in settings where conventional antibiotics are less effective. A recent meta-analysis published in the Journal of Antimicrobial Chemotherapy highlighted the superior efficacy of isepamicin sulfate compared to other aminoglycosides in treating multidrug-resistant gram-negative infections.

The safety profile of isepamicin sulfate has also been extensively studied. While all aminoglycosides carry the risk of nephrotoxicity and ototoxicity, isepamicin sulfate has demonstrated a more favorable safety profile compared to older agents like gentamicin and tobramycin. Clinical trials have shown that the incidence of adverse effects is generally low when isepamicin sulfate is used at recommended doses and for short durations. However, careful monitoring of renal function and auditory function is still recommended during treatment.

In addition to its clinical applications, recent research has explored the potential of isepamicin sulfate in combination therapy with other antibiotics to combat drug-resistant bacteria. A study published in the International Journal of Antimicrobial Agents investigated the synergistic effects of isepamicin sulfatesulfate?(CAS?No.?67814-76-0)?with?beta-lactam?antibiotics?such?as?meropenem.?The?results?demonstrated?that?the?combination?therapy?significantly?enhanced?bactericidal?activity?against?Pseudomonas aeruginosa?and?Klebsiella pneumoniae,?two?notable?multipledrug-resistant pathogens.

Beyond its immediate clinical applications, there is ongoing research into the mechanisms by which isepamicin sulfate exerts its antibacterial effects. A study published in the Journal of Medicinal Chemistry identified specific binding sites on bacterial ribosomes where isepamicin sulfate interacts to inhibit protein synthesis. Understanding these molecular interactions could lead to the development of novel derivatives with enhanced activity and reduced toxicity.

In conclusion, Isepamicin sulfate (CAS No. 67814-76-0) represents a promising antibiotic with significant potential for treating multidrug-resistant infections. Its favorable pharmacokinetic profile, broad-spectrum activity, and improved safety compared to older aminoglycosides make it an attractive option for clinicians. Ongoing research into combination therapy and molecular mechanisms will likely further enhance its therapeutic value in the future.

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