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Merck

219380

Cefotaxime sodium salt

Potent β-lactamase-resistant antibiotic of cephalosporin class. Active against Gram-positive and Gram-negative organisms, including Gram-negative anaerobes. Inhibits cell wall synthesis.

Synonym(s):

7-[2-(2-Amino-4-thiazolyl)glyoxylamido]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 7²-(Z)-(O-methyloxime) Acetate, Na, Cefotaxim sodium salt

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About This Item

Empirical Formula (Hill Notation):
C16H16N5NaO7S2
CAS Number:
64485-93-4
Molecular Weight:
477.45
UNSPSC Code:
12352200
Beilstein/REAXYS Number:
5711411
MDL number:
MFCD00079073

Key Documents

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Product Name

Cefotaxime sodium salt, Potent β-lactamase-resistant antibiotic of cephalosporin class. Active against Gram-positive and Gram-negative organisms, including Gram-negative anaerobes. Inhibits cell wall synthesis.

InChI

1S/C16H17N5O7S2.Na/c1-6(22)28-3-7-4-29-14-10(13(24)21(14)11(7)15(25)26)19-12(23)9(20-27-2)8-5-30-16(17)18-8;/h5,10,14H,3-4H2,1-2H3,(H2,17,18)(H,19,23)(H,25,26);/q;+1/p-1/b20-9-;/t10-,14-;/m1./s1

SMILES string

[Na+].[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\c3csc(N)n3)C([O-])=O

InChI key

AZZMGZXNTDTSME-JUZDKLSSSA-M

assay

≥91% dry basis (HPLC)

form

crystalline solid

optical activity

[α]/D +58 to +64°, c = 1 in H2O

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
desiccated (hygroscopic)
protect from light

color

white

solubility

water: 250 mg/mL

shipped in

ambient

storage temp.

15-25°C

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Biochem/physiol Actions

Cefotaxim inhibits bacterial cell wall synthesis by binding to penicillin-binding proteins (PBPs) which inhibits the final transpeptidation step of peptidoglycan synthesis in bacterial cell walls. As a result, bacteria lyse due to cell wall autolytic enzymes.
Mode of Action: Inhibits bacterial cell wall synthesis.

Disclaimer

Toxicity: Standard Handling (A)

General description

Potent β-lactamase-resistant antibiotic of cephalosporin class. Active against gram-positive and gram-negative organisms, including gram-negative anaerobes. Inhibits cell wall synthesis. Has an optimal pH of 4.5-6.5.

Other Notes

Broad spectrum third generation cephalosporin antibiotic.
Molinari, G., et al. 1991. J. Chemotherap. 3, 6.
Vallee, F., and LeBel, M. 1991. Antimicrob. Agents Chemother. 35, 2057.

Preparation Note

Following reconstitution, aliquot and freeze (-20°C) for long term storage or refrigerate (4°C) for short-term storage. Stock solutions are stable for up to 10 days at 4°C or for up to 13 weeks at -20°C.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H317,H334

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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