Ceftolozane
(6R,7R)-3-[[5-amino-4-(2-aminoethylcarbamoylamino)-1-methylpyrazol-2-ium-2-yl]methyl]-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
Molecular Identity
Ceftolozane
(6R,7R)-3-[[5-amino-4-(2-aminoethylcarbamoylamino)-1-methylpyrazol-2-ium-2-yl]methyl]-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
PubChem CID: 53234134
Ceftolozane is a fifth-generation cephalosporin antibiotic having (5-amino-4-{[(2-aminoethyl)carbamoyl]amino}-1-methyl-1H-pyrazol-2-ium-2-yl)methyl and [(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-{[(2-carboxypropan-2-yl)oxy]imino}acetyl]amino side groups located at positions 3 and 7 respectively; developed for the treatment of infections with gram-negative bacteria that have become resistant to conventional antibiotics. It is a cephalosporin and a member of thiadiazoles.
2D Structure
Properties
C23H30N12O8S2
Molecular Formula
666.70
Molecular Weight
g/mol
666.1751
Exact Mass
Da
-3.2
XLogP
Drug-like (Lipinski: < 5)
356
TPSA
May have limited oral absorption
7
H-Bond Donors
16
H-Bond Acceptors
1280
Complexity
SMILES
Canonical SMILES
SMILES: CC(C)(C(=O)O)ON=C(C1=NSC(=N1)N)C(=O)NC2C3N(C2=O)C(=C(CS3)C[N+]4=CC(=C(N4C)N)NC(=O)NCCN)C(=O)[O-]Isomeric SMILES
SMILES: CC(C)(C(=O)O)O/N=C(/C1=NSC(=N1)N)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C[N+]4=CC(=C(N4C)N)NC(=O)NCCN)C(=O)[O-]Synonyms(20)
CEFTOLOZANE689293-68-3ceftolozanoceftolozanum37A4IES95QCXA-101 FREE BASE(6R,7R)-3-[[3-amino-4-(2-aminoethylcarbamoylamino)-2-methylpyrazol-1-ium-1-yl]methyl]-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateCHEBI:134719DTXSID901031217FR-264205(6R,7R)-3-((3-Amino-4-(2-aminoethylcarbamoylamino)-2-methylpyrazol-1-ium-1-yl)methyl)-7-(((2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl)amino)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate(6R,7R)-3-([3-Amino-4-(2-aminoethylcarbamoylamino)-2-methylpyrazol-1-ium-1-yl]methyl)-7-([(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateRefChem:124268DTXCID301516229FR26 4205
Data from PubChem (NCBI)
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