CAS 738-72-7

Streptimidone

Description:

Streptimidone is an antibiotic compound that belongs to the class of aminoglycosides, primarily used in the treatment of bacterial infections. It is derived from the fermentation of certain Streptomyces species. The chemical structure of streptimidone features a complex arrangement of amino and sugar moieties, which contribute to its biological activity. This compound exhibits broad-spectrum antibacterial properties, particularly effective against Gram-positive bacteria. Its mechanism of action involves inhibiting protein synthesis by binding to the bacterial ribosome, thereby disrupting the translation process. Streptimidone is known for its potential side effects, which may include nephrotoxicity and ototoxicity, necessitating careful monitoring during therapeutic use. Additionally, resistance to streptimidone can develop, which poses challenges in clinical settings. As with many antibiotics, it is crucial to use streptimidone judiciously to minimize the risk of resistance development and to ensure its continued efficacy in treating infections.

Formula: C₁₆H₂₃NO₄

InChI: InChI=1S/C16H23NO4/c1-4-10(2)5-11(3)14(19)9-13(18)6-12-7-15(20)17-16(21)8-12/h4-5,11-13,18H,1,6-9H2,2-3H3,(H,17,20,21)/b10-5+/t11-,13+/m0/s1

InChI key: InChIKey=ZRYKVDWGQVQRPG-RUMBLXRPSA-N

SMILES: C([C@H](CC([C@H](/C=C(/C=C)\C)C)=O)O)C1CC(=O)NC(=O)C1

Synonyms:

• Glutarimide, 3-(2-hydroxy-5,7-dimethyl-4-oxo-6,8-nonadienyl)-
• 4-[(2R,5S,6E)-2-Hydroxy-5,7-dimethyl-4-oxo-6,8-nonadien-1-yl]-2,6-piperidinedione
• 2,6-Piperidinedione, 4-[(2R,5S,6E)-2-hydroxy-5,7-dimethyl-4-oxo-6,8-nonadienyl]-
• 2,6-Piperidinedione, 4-(2-hydroxy-5,7-dimethyl-4-oxo-6,8-nonadienyl)-, [R-[R*,S*-(E)]]-
• 2,6-Piperidinedione, 4-[(2R,5S,6E)-2-hydroxy-5,7-dimethyl-4-oxo-6,8-nonadien-1-yl]-

Streptimidone

CAS: 738-72-7

Streptimidone, a metabolite produced by Streptomyces, exhibits various biological activities, including inhibiting protein synthesis at 50 µg/ml in cell-free assays and reducing tumor growth in rat xenograft models of H.S. No. 1 human sarcoma and H.Ep. No. 3 human epidermoid carcinoma at daily doses of 12.5 and 25 mg/kg.

Formula: C₁₆H₂₃NO₄

Color and Shape: Solid

Molecular weight: 293.36

Ref: TM-TN7532