Compound ID | 3096

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Butirosin

Synonym(s): Butyrosin

Class: Aminoglycoside

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: Active against Staphylococcus aureus, Streptococcus pyogenes, Enterobacter aerogenes, Klebsiella pneumoniae, Pseudomonas aeruginosa, Shigella sonnei, Escherichia coli, and Mycobacterium tuberculosis; protein synthesis inhibitor (binds to 30S ribosomal subunit)
Description: Natural product from Bacillus circulans; butirosin resistant strains are cross-resistant to gentamicin (susceptible to colistin); colistin resistant strains not cross-resistant to butirosin; effective against Gram-negative and staphylococcal infection in mice when administered parenterally
Institute where first reported: Parke, Davis & Company, Detroit, Michigan, USA
Year first mentioned: 1972
Highest developmental phase: Preliminary human studies (1975)
Development status: Experimental
Chemical structure(s):
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Molecular weight: 555.58
Iso. SMILES: C1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1NC(=O)[C@@H](CCN)O)O)O[C@@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CN)O)O)N)N
InChI Key: XEQLFNPSYWZPOW-NUOYRARPSA-N
Can. SMILES: C(CN)[C@H](C(=O)N[C@@H]1C[C@@H]([C@H]([C@@H]([C@H]1O)O[C@@H]2[C@@H]([C@@H]([C@@H](CO)O2)O)O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@@H](CN)O3)O)O)N)N)O
InChI: InChI=1S/C21H41N5O12/c22-2-1-8(28)19(34)26-7-3-6(24)17(37-20-11(25)15(32)13(30)9(4-23)35-20)18(12(7)29)38-21-16(33)14(31)10(5-27)36-21/h6-18,20-21,27-33H,1-5,22-25H2,(H,26,34)/t6-,7+,8+,9+,10+,11+,12-,13+,14+,15+,16+,17+,18+,20+,21+/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/72393
Citations:
  • https://journals.asm.org/doi/10.1128/aac.2.2.84
  • https://link.springer.com/chapter/10.1007/978-1-4684-7653-8_63
  • https://journals.asm.org/doi/10.1128/aac.2.2.89?url_ver=Z39.88-2003&rfr_id=ori%3Arid%3Acrossref.org&rfr_dat=cr_pub++0pubmed

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