Compound ID | 3095

Update compound information

Aminodeoxybutirosin

Synonym(s): 5"-Amino-5"-deoxybutirosin  |  Aminodeoxybutyrosin

Class: Aminoglycoside

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Protein synthesis inhibitor. Resistant to bacterial enzymatic phosphorylation at the 5' position
Target Pathogen: Active against Staphylococcus aureus (multidrug-resistant strains including methicillin-resistant strains), Klebsiella pneumoniae, Serratia marcescens, Enterobacter aerogenes, Pseudomonas aeruginosa, Escherichia coli, and Salmonella sp.
Description: Semisynthetic compound based on butirosin; protects mice from Gram-negative and -positive infections; more toxic than butirosin when administered via subcutaneous or intravenous route in mice
Institute where first reported: Chemistry Department Research and Development Division Parke, Davis and Company
Year first mentioned: 1973
Development status: Experimental
Chemical structure(s):
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Molecular weight: 554.59
Iso. SMILES: C1C(C(C(C(C1NC(=O)C(CCN)O)O)OC2C(C(C(O2)CN)O)O)OC3C(C(C(C(O3)CN)O)O)N)N
InChI Key: IBLOPEHFKHWIOR-UHFFFAOYSA-N
Can. SMILES: C(CN)C(C(=O)NC1CC(C(C(C1O)OC2C(C(C(CN)O2)O)O)OC3C(C(C(C(CN)O3)O)O)N)N)O
InChI: InChI=1S/C21H42N6O11/c22-2-1-8(28)19(34)27-7-3-6(25)17(37-20-11(26)15(32)13(30)9(4-23)35-20)18(12(7)29)38-21-16(33)14(31)10(5-24)36-21/h6-18,20-21,28-33H,1-5,22-26H2,(H,27,34)
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/206425
Citations:
  • https://www.jstage.jst.go.jp/article/antibiotics1968/28/7/28_7_530/_article/-char/en
  • https://journals.asm.org/doi/10.1128/aac.10.3.543?url_ver=Z39.88-2003&rfr_id=ori%3Arid%3Acrossref.org&rfr_dat=cr_pub++0pubmed
  • https://www.jstage.jst.go.jp/article/antibiotics1968/26/12/26_12_790/_article/-char/en

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