Cefotaxime Sodium

HCID 10695961CAS 64485-93-4
Substructure searchFind similar structures

Basic information

Standard SMILES
CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(COC(C)=O)CS[C@H]12)c1csc(N)n1.[Na+]
InChIKey
AZZMGZXNTDTSME-JUZDKLSSSA-M
Molecular formula
C16H16N5NaO7S2
Average molar mass
477.5 g/mol
Monoisotopic mass
477.03888413

Overview

Cefotaxime sodium is a cephalosporin organic sodium salt having acetoxymethyl and [2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino side-groups. It contains a cefotaxime(1-).

Names & identifiers

Preferred name
Cefotaxime Sodium
IUPAC
sodium (6R,7R)-3-(acetyloxymethyl)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
English name
Cefotaxime sodium
Molecular formula
C16H18N5NaO7S2
Molecular weight
479.46

Names & synonyms

CEFOTAXIME SODIUMCEFOTAXIME SODIUM SALT64485-93-4Sodium cefotaximePretor(+)-Cefotaxime sodium saltHR 756DTXSID4046991RU 24756HR-756258J72S7TZHR756
Show more names
ctxCEFOTAXIME SODIUM STERILECLAFORANCEFOTAXIME NA-SALTCefotaxime free acidCEFOTAXIM SODIUM SALTCefotaxime Sodium (350 mg)Cefotaxime for peak identification
Ru-24756NSC-756666Sodium 7-(2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido)cephalosporanateCHEBI:3498DTXCID201476109Cefotaxime and dextrose 2.4% in plastic containerCefotaxime and dextrose 3.9% in plastic containerCLAFORAN IN DEXTROSE 5% IN PLASTIC CONTAINER

Database identifiers

CAS
64485-93-4
PubChem CID
10695961
DTXSID
DTXSID4046991
ChEMBL
CHEMBL1010
ChEBI
CHEBI:3498
UNII
258J72S7TZ
EC Number
264-915-9

Properties

Computed structural properties

Topological polar surface area
230 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
12
Rotatable bonds
8
Heavy atoms
31

Experimental & physicochemical properties

Solubility68.2 [ug/mL] (The mean of the results at pH 7.4)
Human Drugs · 2 items

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Physicochemical properties

Melting point
162 · 162-163 C
alpha
20 · D20 +55±2° (c = 0.8 in water)
refractive index
61 ° · 61 ° (C=1, H2O)
storage temp.
2 · Keep in dark place,Inert atmosphere,2-8°C
solubility
2 O: · H2O: aqueous solutions of pH 4.3-6.2 are stable up to 3 weeks at 2-8 °C.soluble
form
powder

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H317 (99.2%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P321, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 132 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationCefotaxime sodium: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Sens. 1 (99.2%)

Toxicology

Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Cefotaxime sodium

vLess-DILI-concern

5

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Safety data

wgk
2
rtecs
XI0250000
hs_code
29419000
risk_code
42/43
Signal word
Danger
Symbol(GHS)
GHS08

Chemistry & industry

Pharmacology

FDA Pharmacological Classification · 2 items

CEFOTAXIME INJECTION

Cephalosporin Antibacterial [EPC]; Cephalosporins [CS]

MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Applications · 5 items

DescriptionCefotaxime was synthesized by Hoechst and Roussel-Uclaf in 1977. It was the first derivative of cephalosporin to introduce the methoxyimino and aminothiazole groups at the 7 position of the cephem nucleus. Although it shows unexpectedly low oral absorption, its excellent activity against a wide range of gram-positive and gram-negative organisms, including Serratia, Enterobacter, Citrobacter, and anaerobes, guided research and development of the newer synthetic cephems, the so-called thirdgeneration cephalosporins.

UsesBroad spectrum third generation cephalosporin antibiotic. The name Cefotaxime applies to the isomer having a syn-methoxy imino group

UsesCephalosporin antibacterial

UsesCefotaxime sodium salt acts as a beta-lactamase resistant antibiotic. It is used as an effective antibacterial against gram-negative bacteria, with the notable exception of pseudomonas and penicillin-resistant strains of streptococcus pneumoniae. It is used to treat infections of the bones, joints, skin, respiratory tract and blood stream.

General DescriptionPharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards

Upstream & downstream products

Downstream products

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
北京安司莫森技术有限公司010-82954736 13391601435 · [email protected]

Additional notes

DefinitionChEBI: A cephalosporin organic sodium salt having acetoxymethyl and [2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino side-groups.

Related reactions

6 records
New reaction record

Linked notes

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