Ceftazidime pentahydrateProduct ingredient for Ceftazidime

Name
Ceftazidime pentahydrate
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

Accession Number
DBSALT001024
Structure
Synonyms
Not Available
UNII
9M416Z9QNR
CAS Number
78439-06-2
Weight
Average: 636.65
Monoisotopic: 636.151962842
Chemical Formula
C22H32N6O12S2
InChI Key
NMVPEQXCMGEDNH-TZVUEUGBSA-N
InChI
InChI=1S/C22H22N6O7S2.5H2O/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);5*1H2/b26-13-;;;;;/t14-,18-;;;;;/m1...../s1
IUPAC Name
1-{[(6R,7R)-2-carboxy-7-{[(2Z)-2-[(1-carboxylato-1-methylethoxy)imino]-1-hydroxy-2-(2-imino-2,3-dihydro-1,3-thiazol-4-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium pentahydrate
SMILES
O.O.O.O.O.[H][C@]12SCC(C[N+]3=CC=CC=C3)=C(N1C(=O)[C@@]2([H])N=C(O)C(=N/OC(C)(C)C([O-])=O)\C1=CSC(=N)N1)C(O)=O
KEGG Drug
D00921
ChemSpider
5020249
ChEBI
3509
ChEMBL
CHEMBL3186392
Predicted Properties
PropertyValueSource
Water Solubility0.028 mg/mLALOGPS
logP-0.71ALOGPS
logP-2.5Chemaxon
logS-4.3ALOGPS
pKa (Strongest Acidic)2.82Chemaxon
pKa (Strongest Basic)0.72Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count11Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area191.68 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity157.19 m3·mol-1Chemaxon
Polarizability53.03 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon