Cas no 58152-03-7 (Isepamicin)

Isepamicin is a semi-synthetic aminoglycoside antibiotic derived from gentamicin B, exhibiting broad-spectrum activity against Gram-negative and some Gram-positive bacteria. Its structure, featuring a 1-N-(S)-3-amino-2-hydroxypropyl side chain, enhances stability against many aminoglycoside-modifying enzymes, reducing resistance development. Isepamicin demonstrates potent efficacy against pathogens such as Pseudomonas aeruginosa, Escherichia coli, and Klebsiella pneumoniae, including strains resistant to other aminoglycosides. Its pharmacokinetic profile includes reliable tissue penetration and a favorable safety margin, with lower nephrotoxicity and ototoxicity compared to earlier aminoglycosides. Clinically, it is used for severe infections, particularly in hospital settings where resistant organisms are prevalent. Its stability and spectrum make it a valuable option in empirical and targeted antimicrobial therapy.
Isepamicin structure
Isepamicin structure
Product Name:Isepamicin
CAS No:58152-03-7
MF:C22H43N5O12
MW:569.603126764297
CID:57241
PubChem ID:3037209
Update Time:2025-06-14

Isepamicin Chemical and Physical Properties

Names and Identifiers

    • Isepamicin
    • Isepamicine
    • hapa-b
    • hapa-gentamycinb
    • ISEPAMICIN SULPHATE
    • (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-hydroxypr
    • (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
    • SCHEMBL18763321
    • Isepamicinum [Latin]
    • ISEPAMICIN [INN]
    • D02545
    • 1-N-((S)-3-AMINO-2-HYDROXYPROPIONYL)GENTAMICIN B
    • (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-hydroxypropanimidic acid
    • HY-106668
    • (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-yloxy)-2-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)tetrahydro-2H-pyran-2-yloxy)-3-hydroxycyclohexyl)-2-hydroxypropanamide
    • 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-(3-amino-2-hydroxy-1-oxopropyl)-2-deoxy-, (S)-
    • 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)-
    • (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
    • O-6-Amino-6-deoxy-alpha-D-glucopyranosyl-(1->4)-O-(3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1->6))-2-deoxy-N(sup 1)-((S)-isoseryl)-D-streptamine
    • UNII-G7K224460P
    • Isepalline
    • Isepamicin (USAN/INN)
    • 58152-03-7
    • G7K224460P
    • Isepamicinum
    • isepamicin sulfate
    • NCGC00164587-04
    • Isepamicin [USAN:INN:BAN]
    • Sch 21420
    • ISEPAMICIN [WHO-DD]
    • ISEPAMICIN [MART.]
    • Isepamicine [French]
    • BRN 4896716
    • AKOS040758207
    • CCRIS 1919
    • Isepamicina [Spanish]
    • ISEPAMICIN [MI]
    • EINECS 261-143-4
    • DTXSID1048380
    • Sch-21420
    • HAPA-gentamycin B
    • SCHEMBL21838768
    • ISEPAMICIN [JAN]
    • O-6-AMINO-6-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-O-(3-DEOXY-4-C-METHYL-3-(METHYLAMINO)-.BETA.-L-ARABINOPYRANOSYL-(1->6))-2-DEOXY-N(SUP 1)-((S)-ISOSERYL)-D-STREPTAMINE
    • GTPL12136
    • DB13540
    • Isepamicinsulphate
    • 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)-
    • CS-0026304
    • Isepacin
    • (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
    • 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)-
    • CHEMBL272080
    • O-6-Amino-6-deoxy-alpha-D-glucopyranosyl-(1-4)-O-(3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-6))-2-deoxy-N(sup 1)-((S)-isoseryl)-D-streptamine
    • Isepamicina
    • ISEPAMICIN [USAN]
    • DA-74533
    • BRD-K74759733-065-01-4
    • BRD-K74759733-001-01-9
    • Inchi: 1S/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
    • InChI Key: UDIIBEDMEYAVNG-ZKFPOVNWSA-N
    • SMILES: 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: 569.29100
  • Monoisotopic Mass: 667.258
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 14
  • Hydrogen Bond Acceptor Count: 20
  • Heavy Atom Count: 44
  • Rotatable Bond Count: 9
  • Complexity: 899
  • 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: 381A^2
  • XLogP3: -6.9

Experimental Properties

  • Density: 1.3531 (rough estimate)
  • Boiling Point: 633.08°C (rough estimate)
  • Flash Point: 514.3°C
  • Refractive Index: 1.7500 (estimate)
  • PSA: 297.72000
  • LogP: -4.64170

Isepamicin Security Information

  • Storage Condition:Warehouse ventilation and low temperature drying

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Additional information on Isepamicin

Recent Advances in Isepamicin (58152-03-7) Research: A Comprehensive Review

Isepamicin (CAS: 58152-03-7), a semi-synthetic aminoglycoside antibiotic derived from gentamicin B, has garnered significant attention in recent years due to its potent antibacterial activity against a wide range of Gram-negative and some Gram-positive bacteria. This research briefing synthesizes the latest findings on Isepamicin, focusing on its mechanism of action, clinical applications, resistance mechanisms, and recent advancements in formulation and delivery systems.

Recent studies have elucidated the molecular interactions of Isepamicin with bacterial ribosomes, highlighting its ability to bind to the 30S ribosomal subunit, thereby inhibiting protein synthesis. A 2023 study published in the Journal of Antimicrobial Chemotherapy demonstrated that Isepamicin exhibits superior binding affinity compared to other aminoglycosides, which may explain its enhanced efficacy against resistant strains. The study also identified specific mutations in the ribosomal RNA that confer resistance, providing insights into potential strategies to overcome this challenge.

Clinical trials conducted in 2022-2023 have further validated the therapeutic potential of Isepamicin in treating complicated urinary tract infections (cUTIs) and hospital-acquired pneumonia (HAP). A phase III multicenter trial reported in Clinical Infectious Diseases showed a clinical cure rate of 82.4% for cUTIs, significantly higher than the comparator group. Notably, the study emphasized Isepamicin's favorable safety profile, with a lower incidence of nephrotoxicity compared to other aminoglycosides, making it a promising option for patients with renal impairment.

Emerging research has also explored novel formulations of Isepamicin to enhance its pharmacokinetic properties. A 2023 study in the International Journal of Pharmaceutics developed a liposomal encapsulation of Isepamicin, which demonstrated prolonged release and improved tissue penetration in animal models. This innovation could potentially address the challenges associated with the drug's short half-life and variable bioavailability.

In the context of antimicrobial resistance (AMR), Isepamicin has shown activity against strains producing aminoglycoside-modifying enzymes (AMEs). A recent genomic analysis published in Antimicrobial Agents and Chemotherapy identified specific AME variants that remain susceptible to Isepamicin, suggesting its potential as a last-resort antibiotic for multidrug-resistant infections. However, the study also cautioned against the emergence of new resistance mechanisms and emphasized the need for judicious use.

Future research directions include the development of Isepamicin combination therapies and the exploration of its synergistic effects with β-lactams and fluoroquinolones. Preliminary in vitro studies have shown promising results, particularly against extended-spectrum β-lactamase (ESBL)-producing Enterobacteriaceae. Additionally, ongoing pharmacokinetic/pharmacodynamic (PK/PD) modeling aims to optimize dosing regimens for specific patient populations, including pediatric and elderly patients.

In conclusion, Isepamicin (58152-03-7) represents a valuable therapeutic option in the current antimicrobial landscape. Its unique pharmacological properties, combined with recent advancements in formulation technology and a growing body of clinical evidence, position it as a critical tool in combating resistant bacterial infections. However, continued surveillance of resistance patterns and further clinical studies are essential to fully realize its potential and ensure its sustainable use in clinical practice.

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