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Basic information
- Standard SMILES
NC(=O)OC[C@@H]1[C@H](NC(=O)/C(=N\OCC(=O)O)c2csc(N)n2)C(=O)N1S(=O)(=O)O- InChIKey
UIMOJFJSJSIGLV-JNHMLNOCSA-N- Molecular formula
- C12H14N6O10S2
- Average molar mass
- 466.41 g/mol
- Monoisotopic mass
- 466.02128265
Names & identifiers
- Preferred name
- Carumonam
- IUPAC
- ({(Z)-[1-(2-Amino-1,3-thiazol-4-yl)-2-({(2S,3S)-2-[(carbamoyloxy)methyl]-4-oxo-1-sulfoazetidin-3-yl}amino)-2-oxoethylidene]amino}oxy)acetic acid
- English name
- CARUMONAM
- Molecular formula
- C12H14N6O10S2
- Molecular weight
- 466.4
Names & synonyms
Database identifiers
- CAS
87638-04-8- PubChem CID
- 6540466
- DTXSID
DTXSID3048312- ChEMBL
CHEMBL1614658- ChEBI
CHEBI:55486- UNII
- 486890PI06
- Nikkaji
- J23.309I
Properties
Physicochemical properties
- alpha
- 26 · D26 -45° (c = 1 in DMSO)
- Density
- 2.13 · 2.13±0.1 g/cm3(Predicted)
- pka
- -0.43 · -0.43±0.60(Predicted)
- FDA UNII
- 486890 PI06 · 486890PI06
- ATC code
- 1 DF02 · J01DF02
Chemistry & industry
Applications
DescriptionCanunonam is an injectable antibiotic, the second monobactam ever developed (the first being Squibb’s aztreonam). It is highly active against Gram negative bacteria, particularly pseudomom, and is reportedly effective in the treatment of pneumonia, cystitis, peritonitis and secondary infections.
UsesCARUMONAM is monocyclic β-lactam antibiotics. Their antibacterial spectrum is similar to amantadine, exhibiting high antibacterial activity against Gram-negative bacteria. While their activity against Pseudomonas aeruginosa is slightly weaker than amantadine and ceftazidime, it is better than other antibiotics. They are highly effective against Klebsiella pneumoniae and are also effective against bacteria resistant to gentamicin and third- and fourth-generation cephalosporins. They are very stable against various bacterial inulinases and chromosomal or plasmid-mediated β-lactamases. They are used for sepsis, chronic respiratory infections, cholangitis, peritonitis, chronic bronchitis, and cystitis caused by susceptible bacteria.
Upstream & downstream products
Upstream raw materials
Suppliers16 total
Additional notes
DefinitionChEBI: An N-sulfonated monobactam antibiotic.
Related reactions
Linked notes
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