Ceftazidime sodiumProduct ingredient for Ceftazidime

Name

Ceftazidime sodium

Drug Entry

Ceftazidime

Bacteria possess a cell wall comprising a glycopeptide polymer commonly known as peptidoglycan, which is synthesized and remodelled through the action of a family of enzymes known as "penicillin-binding proteins" (PBPs).¹ β-lactam antibiotics, including cephalosporins, are PBP inhibitors that, through inhibition of essential PBPs, result in impaired cell wall homeostasis, loss of cell integrity, and ultimately bacterial cell death.^1,2,3 Ceftazidime is a third-generation cephalosporin with broad-spectrum antibacterial activity, including against some treatment-resistant bacteria such as Pseudomonas aeruginosa.¹²

Ceftazidime was approved by the FDA on July 19, 1985, and is currently available either alone or in combination with the non-β-lactam β-lactamase inhibitor avibactam to treat a variety of bacterial infections.^12,13

See full entry for Ceftazidime

Accession Number

DBSALT001474

Structure

Similar Structures

Synonyms

Not Available

UNII

CMC30V039K

CAS Number

73547-61-2

Weight

Average: 568.55
Monoisotopic: 568.08108367

Chemical Formula

C₂₂H₂₁N₆NaO₇S₂

InChI Key

JEEWDSDYUSEQML-ROMZVAKDSA-M

InChI

InChI=1S/C22H22N6O7S2.Na/c1-22(2,20(33)34)35-26-13(12-10-37-21(23)24-12)16(29)25-14-17(30)28-15(19(31)32)11(9-36-18(14)28)8-27-6-4-3-5-7-27;/h3-7,10,14,18H,8-9H2,1-2H3,(H4-,23,24,25,29,31,32,33,34);/q;+1/p-1/b26-13-;/t14-,18-;/m1./s1

IUPAC Name

sodium 1-{[(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1-carboxy-1-methylethoxy)imino]acetamido]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium

SMILES

[Na+].CC(C)(O\N=C(/C(=O)N[C@H]1[C@H]2SCC(C[N+]3=CC=CC=C3)=C(N2C1=O)C([O-])=O)C1=CSC(N)=N1)C([O-])=O

External Links

ChemSpider: 23107180
ChEBI: 53675
ChEMBL: CHEMBL1200768
Wikipedia: Ceftazidime

Predicted Properties

Property	Value	Source
Water Solubility	0.00674 mg/mL	ALOGPS
logP	-0.78	ALOGPS
logP	-4.5	Chemaxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	2.77	Chemaxon
pKa (Strongest Basic)	4.26	Chemaxon
Physiological Charge	-1	Chemaxon
Hydrogen Acceptor Count	10	Chemaxon
Hydrogen Donor Count	2	Chemaxon
Polar Surface Area	194.05 Å²	Chemaxon
Rotatable Bond Count	9	Chemaxon
Refractivity	154.72 m³·mol^-1	Chemaxon
Polarizability	50.87 Å³	Chemaxon
Number of Rings	4	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Ceftazidime sodiumProduct ingredient for Ceftazidime

Structure for Ceftazidime sodium (DBSALT001474)