Cephalothin Sodium

HCID 23675321

Basic information

CAS
58-71-9
Standard SMILES
CC(=O)OCC1=C(C(=O)[O-])N2C(=O)[C@@H](NC(=O)Cc3cccs3)[C@H]2SC1.[Na+]
InChIKey
VUFGUVLLDPOSBC-XRZFDKQNSA-M
Molecular formula
C16H15N2NaO6S2
Average molar mass
418.4 g/mol
Monoisotopic mass
418.02692248

Overview

Cephalothin sodium is an organic sodium salt. It contains a cefalotin.

Names & identifiers

Preferred name
Cephalothin Sodium
IUPAC
sodium (6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
English name
Cephalothin sodium
Molecular formula
C16H16N2O6S2.Na
Molecular weight
419.43

Names & synonyms

CEPHALOTHIN SODIUM58-71-9cefalotin sodiumCephalothin sodium saltSodium cephalothinSeffinSodium cefalotinSodium cephalotinCefalotina sodicaCeporacinCepoveninLospoven
Show more names
CEPHALOTHIN ACID38253CoaxinKeflinAveron 1Cemastin
MicrotinSynclotinToricelocinKeflin In Plastic ContainerC22G6EYP8B7-(Thiophene-2-acetamido)cephalosporanic acid sodium saltCEPHALOTHIN SODIUM W/ DEXTROSE IN PLASTIC CONTAINERNSC-756667

Database identifiers

CAS
58-71-9
PubChem CID
23675321
DTXSID
DTXSID30891362
ChEMBL
CHEMBL1632
ChEBI
CHEBI:3542
UNII
C22G6EYP8B
EC Number
200-394-6

Properties

Computed structural properties

Topological polar surface area
169 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
8
Rotatable bonds
7
Heavy atoms
27

Experimental & physicochemical properties

Human Drugs · 2 items

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Collision Cross Section183.1 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
240 °C · 240°C
alpha
135 ° · D +135° (c = 1.0 in water)
storage temp.
2 · Inert atmosphere,2-8°C
solubility
2 O: · H2O: 50 mg/mL, clear, faintly yellow
form
Solid
color
White to Off-White

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H317 (100%): 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 58 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Status: Active Update: 22-03-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/23180

5-Thia-1-azabicyclo4.2.0oct-2-ene-2-carboxylic acid, 3-(acetyloxy)methyl-8-oxo-7-(2-thienylacetyl)amino-, monosodium salt, (6R,7R)-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-8-oxo-7-[(2-thienylacetyl)amino]-, monosodium salt, (6R-trans)-: Environment tier I assessment
Hazard Classes and CategoriesSkin Sens. 1 (100%)

Safety data

PPE
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
wgk
2
rtecs
XI0388300
hs_code
29419000
Toxicity
LD50 in mice, rats (mg/kg): >20000, >10000 orally; 5670, 7716 i.p. (Kuramoto)
risk_code
42/43

Chemistry & industry

Pharmacology

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

DescriptionCefalothin is a β-lactam cephalosporin antibiotic. It inhibits the growth of various Gram-positive and Gram-negative bacteria, including several strains of S. pyogenes, S. aureus, C. tetani, N. gonorrhoeae, Salmonella, and Shigella (MICs = 0.1-0.2, 0.312-0.625, 0.078, 1.25, 1.56-6.25, and 3.12-12.5 μg/ml, respectively). Cefalothin binds to E. coli penicillin-binding proteins (PBPs; IC50s = S. pyogenes, D. pneumoniae, and S. aureus. Formulations containing cefalothin were previously used in the prophylaxis and treatment of bacterial infections.

UsesCephalothin sodium salt is used to study the mechanism of liposome encapsulated antibiotics1, strategies for co-opting β-lactamases of Gram-negative bacteria for treatment of antibiotics2, and for immunology studies in relation to antibiotics.3 It is used to study the effect of expression, binding and inhibition of penicillin-binding proteins especially PBP6 on bacterial cell wall mucopeptide synthesis.

UsesAntibacterial;Bacterial transpeptidase inhibitor

UsesCephalothin is a first-generation cephalosporin antibiotic used to study the mechanism of liposome encapsulated antibiotics,strategies for co-opting β-lactamases of Gram-negative bacteria for treatment of antibiotics,and for immunology studies in relation to antibiotics.It is used to study the effect of expression, binding and inhibition of penicillin-binding proteins especially PBP6 on bacterial cell wall mucopeptide synthesis.

General DescriptionCephalothin, along with cephaloridine, was the first of the synthetic cephalosporin C class antibiotics to be introduced clinically. It was synthesized from 7-amino-cephalosporanic acid by Lilly Research Laboratories in 1962. Cephalothin shows strong activity against gram-positive and gram-negative bacteria and Leptospira, including benzylpenicillin-resistant strains. It has been used intravenously and intramuscularly to treat a variety of infections caused by Staphylococcus, Streptococcus, Escherichia coli, and Neisseria. The drug is metabolized in vivo, and the metabolite, deacetylcephalothin, is almost inactive.

Suppliers101 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]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]

Additional notes

DefinitionChEBI: Cephalothin sodium is an organic sodium salt. It contains a cefalotin.

Related reactions

27 records

Compound notes

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