CHEMBL2103872

Synopsis, Chemistry

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Also known as: Ceftolozane, Cxa-101 free base, Cxa-101, Chembl2103872

Molecular Formula

C₂₃H₃₀N₁₂O₈S₂

Molecular Weight

666.7 g/mol

InChI Key

JHFNIHVVXRKLEF-DCZLAGFPSA-N

Ceftolozane is a semi-synthetic, broad-spectrum, fifth-generation cephalosporin antibiotic with bactericidal activity against certain Gram-negative and Gram-positive bacteria. Upon administration, ceftolozane binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. This interferes with the final transpeptidation step required to form peptidoglycan chain cross-links, which are a key component of and provide strength and rigidity to the bacterial cell wall. This inhibits bacterial cell wall synthesis and reduces cell wall stability, which weakens the bacterial cell wall and causes bacterial cell lysis.

1 2D Structure

CHEMBL2103872

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[(Z)-[2-[[(6R,7R)-3-[[3-amino-4-(2-aminoethylcarbamoylamino)-2-methylpyrazol-1-ium-1-yl]methyl]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-7-yl]amino]-1-(5-amino-1,2,4-thiadiazol-3-yl)-2-oxoethylidene]amino]oxy-2-methylpropanoate

2.1.2 InChI

InChI=1S/C23H30N12O8S2/c1-23(2,20(40)41)43-31-11(15-30-21(26)45-32-15)16(36)29-12-17(37)35-13(19(38)39)9(8-44-18(12)35)6-34-7-10(14(25)33(34)3)28-22(42)27-5-4-24/h7,12,18,25H,4-6,8,24H2,1-3H3,(H7,26,27,28,29,30,32,36,38,39,40,41,42)/b31-11-/t12-,18-/m1/s1

2.1.3 InChI Key

JHFNIHVVXRKLEF-DCZLAGFPSA-N

2.1.4 Canonical 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

2.1.5 Isomeric 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

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Ceftolozane

2. Ceftolozane Sulfate

3. Cxa-101

4. Fr 264205

5. Fr-264205

6. Fr26 4205

7. Fr264205

2.2.2 Depositor-Supplied Synonyms

1. Ceftolozane

2. Cxa-101 Free Base

3. Cxa-101

4. Chembl2103872

2.3 Create Date

2013-05-30

3 Chemical and Physical Properties

Molecular Formula	C₂₃H₃₀N₁₂O₈S₂
Molecular Weight	666.7 g/mol
XLogP3	-3.2
Hydrogen Bond Donor Count	7
Hydrogen Bond Acceptor Count	16
Rotatable Bond Count	11
Exact Mass	666.17509831 g/mol
Monoisotopic Mass	666.17509831 g/mol
Topological Polar Surface Area	356 Å²
Heavy Atom Count	45
Formal Charge	0
Complexity	1280
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1