Ceftazidime

CAT: 0804-HY-B0593-04Size: 5 gDry Ice: NoHazardous: No

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Description

Ceftazidime (GR20263), an antibiotic, has a broad spectrum activity against Gram-positive and Gram-negative aerobic bacteria. Ceftazidime is also active against Enterobacteriaceae (including β-lactamase-positive strains) and is resistant to hydrolysis by most β-lactamases[1].

CAS Number

72558-82-8

Product Name Alternative

GR20263

UNSPSC

12352005

Hazard Statement

H317, H319, H334

Target

Antibiotic; Bacterial; Beta-lactamase

Type

Reference compound

Related Pathways

Anti-infection

Applications

COVID-19-immunoregulation

Field of Research

Infection; Cancer

Assay Protocol

https://www.medchemexpress.com/Ceftazidime.html

Purity

99.86

Solubility

DMSO : 50 mg/mL (ultrasonic; warming; heat to 80°C) |H2O : 100 mg/mL (ultrasonic)

Smiles

O=C1[C@@H](NC(/C(C2=CSC(N)=N2)=N\OC(C)(C(O)=O)C)=O)[C@@]3([H])SCC(C[N+]4=CC=CC=C4)=C(C([O-])=O)N13

Molecular Formula

C22H22N6O7S2

Molecular Weight

546.58

Precautions

H317, H319, H334

References & Citations

[1]Richards DM, et al. Ceftazidime. A review of its antibacterial activity, pharmacokinetic properties and therapeutic use. Drugs. 1985 Feb;29 (2) :105-61.|[2]Esmat Kamali, et al. In vitro activities of cellulase and ceftazidime, alone and in combination against Pseudomonas aeruginosa biofilms. BMC Microbiol. 2021 Dec 16;21 (1) :347. |[3]Qiuxia Lin, et al. Avibactam potentiated the activity of both ceftazidime and aztreonam against S. maltophilia clinical isolates in vitro. BMC Microbiol. 2021 Feb 22;21 (1) :60. |[4]Shawn H MacVane, et al. Unexpected in vivo activity of ceftazidime alone and in combination with avibactam against New Delhi metallo-β-lactamase-producing Enterobacteriaceae in a murine thigh infection model. Antimicrob Agents Chemother. 2014 Nov;58 (11) :7007-9.

Shipping Conditions

Room Temperature

Storage Conditions

4°C (Powder, protect from light)

Scientific Category

Reference compound1

Clinical Information

Launched

Isoform

β-lactam

Chemical Information

Ceftazidime

Ceftazidime is a third-generation cephalosporin antibiotic bearing pyridinium-1-ylmethyl and {[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-{[(2-carboxypropan-2-yl)oxy]imino}acetamido groups at positions 3 and 7, respectively, of the cephem skeleton. It has a role as an antibacterial drug, an EC 2.4.1.129 (peptidoglycan glycosyltransferase) inhibitor and a drug allergen. It is a cephalosporin and an oxime O-ether. It is a conjugate acid of a ceftazidime(1-).

CAS Number	72558-82-8
PubChem CID	5481173
IUPAC Name	(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
Molecular Formula	C22H22N6O7S2
Molecular Weight	546.6
XLogP	0.4
Topological Polar Surface Area	245
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	8
Heavy Atom Count	37
Formal Charge	0
Complexity	1020

SMILES

CC(C)(C(=O)O)O/N=C(/C1=CSC(=N1)N)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C[N+]4=CC=CC=C4)C(=O)[O-]

InChI

InChI=1S/C22H22N6O7S2/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)/b26-13-/t14-,18-/m1/s1

InChIKey

ORFOPKXBNMVMKC-DWVKKRMSSA-N

Chemical Structure

2D Structure

CAS: 72558-82-8

CID: 5481173

Formula: C22H22N6O7S2

MW: 546.6

Interactive 3D Structure

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View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	546.6
XLogP3	0.4
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	8
Exact Mass	546.09913941
Monoisotopic Mass	546.09913941
Topological Polar Surface Area	245 Å²
Heavy Atom Count	37
Formal Charge	0
Complexity	1020
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
Compound Is Canonicalized	Yes

Alternative Products

Catalog	Name
C39SD1050	Ceftazidime

Ceftazidime

Chemical Information

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