Bicyclomycin

Bicyclomycin
Clinical data
Trade namesbicozamycin
ATC code
  • None
Identifiers
  • (1S,6R)-6-Hydroxy-5-methylene-1-[(1'S,2'S)-1,2,3-trihydroxy-2-methylpropyl]-2-oxa-7,9-diazabicyclo[4.2.2]decane-8,10-dione
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
Chemical and physical data
FormulaC12H18N2O7
Molar mass302.283 g·mol−1
3D model (JSmol)
  • C[C@](CO)([C@@H]([C@@]12C(=O)N[C@@](C(=C)CCO1)(C(=O)N2)O)O)O
  • InChI=1S/C12H18N2O7/c1-6-3-4-21-12(7(16)10(2,19)5-15)9(18)13-11(6,20)8(17)14-12/h7,15-16,19-20H,1,3-5H2,2H3,(H,13,18)(H,14,17)/t7-,10-,11+,12-/m0/s1
  • Key:WOUDXEYYJPOSNE-VKZDFBPFSA-N

Bicyclomycin (Bicozamycin) is a broad spectrum antibiotic active against Gram-negative bacteria and the Gram-positive bacterium, Micrococcus luteus that was isolated[1][2] from Streptomyces sapporonesis and Streptomyces aizumenses in 1972. It belongs to a class of naturally occurring 2,5-diketopiperazines,[3] that are among the most numerous of all the naturally occurring peptide antibiotics. This clinically useful antibiotic is rapidly absorbed in humans when given intramuscularly, has low toxicity and has been used to treat diarrhea in humans and bacterial diarrhea in calves and pigs.[4]

  1. ^ Miyoshi T, Miyairi N, Aoki H, Kosaka M, Sakai H (October 1972). "Bicyclomycin, a new antibiotic. I. Taxonomy, isolation and characterization". The Journal of Antibiotics. 25 (10): 569–575. doi:10.7164/antibiotics.25.569. PMID 4648311.
  2. ^ Miyamura S, Ogasawara N, Otsuka H, Niwayama S, Tanaka H (October 1972). "Antibiotic no. 5879, a new water-soluble antibiotic against gram-negative bacteria". The Journal of Antibiotics. 25 (10): 610–612. doi:10.7164/antibiotics.25.610. PMID 4648315.
  3. ^ Borthwick AD (July 2012). "2,5-Diketopiperazines: synthesis, reactions, medicinal chemistry, and bioactive natural products". Chemical Reviews. 112 (7): 3641–3716. doi:10.1021/cr200398y. PMID 22575049.
  4. ^ Kohn H, Widger W (September 2005). "The molecular basis for the mode of action of bicyclomycin". Current Drug Targets. Infectious Disorders. 5 (3): 273–295. doi:10.2174/1568005054880136. PMID 16181146.