Carumonam

HCID 6540466CAS 87638-04-8

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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

AMA 1080CARUMONAMRo 17-2301CarlliIIonalnCARUMONAM USP/EP/BPRo-17-2301:A-masulinAntibiotic Ro 17-2301(2S)-2α-(Carbamoyloxymethyl)-3α-[[(Z)-(2-amino-4-thiazolyl)[(carboxymethoxy)imino]acetyl]amino]-4-oxoazetidine-1-sulfonic acid[[[(Z)-2-[[(2S)-2α-[[(Aminocarbonyl)oxy]methyl]-4-oxo-1-sulfoazetidin-3α-yl]amino]-1-(2-aminothiazol-4-yl)-2-oxoethylidene]amino]oxy]acetic acid[[[(Z)-2-[[(2S,3S)-2-[[(Aminocarbonyl)oxy]methyl]-4-oxo-1-sulfoazetidin-3-yl]amino]-1-(2-amino-4-thiazolyl)-2-oxoethylidene]amino]oxy]acetic acid

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 · 2 items

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

Suppliers16 total

北京华美互利生物化工010-56205725 · [email protected]
陕西缔都医药化工有限公司+86-29-87569262 +86-15003564040 · [email protected]
上海孚一生物科技有限公司+86 (21) 61124340
湖北源梦生物科技有限公司027-68897569 18120462897 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]

Additional notes

DefinitionChEBI: An N-sulfonated monobactam antibiotic.

Related reactions

2 records

Linked notes

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