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
Show more names
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
- Formal charge
- 0
- Complexity
- 686
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
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
- Water Solubility
- 158 mg/L · 158 mg/L
- Merck
- 13 · 13,1994
- BRN
- 4120706 · 4120706
- Stability
- Hygroscopic
- InChI
- InChI=1/C16H16N2O6S2.Na/c1-8(19)24-6-9-7-26-15-12(14(21)18(15)13(9)16(22)23)17-11(20)5-10-3-2-4-25-10;/h2-4,12,15H,5-7H2,1H3,(H,17,20)(H,22,23);/t12-,15-;/s3
- InChIKey
- XXDPRVHYESWPEX-JQWYMVCGNA-N
- SMILES
- C(C1=C(CS[C@]2([H])[C@@H](C(N21)=O)NC(=O)CC1SC=CC=1)COC(=O)C)(=O)O.[Na] |&1:5,7,r|
- CAS DataBase Reference
- 58 · 58-71-9(CAS DataBase Reference)
- FDA UNII
- 22 G6EYP8B · C22G6EYP8B
- UNSPSC Code
- 51282506 · 51282506
- NACRES
- 85 · NA.85
- Symbol(GHS)
- 8 · GHS08
- Signal word
- Danger
- Hazard statements
- 317 · H317-H334
- Precautionary statements
- 261 · P261-P280-P284-P304+P340-P342+P311
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- Hazard Codes
- Xn,Xi
- Risk Statements
- 42 · 42/43
- Safety Statements
- 22 · 22-36/37
- WGK Germany
- 2 · 2
- RTECS
- 388300 · XI0388300
- HS Code
- 29419000 · 29419000
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 1 Skin · Resp. Sens. 1Skin Sens. 1
- Toxicity
- 50 in · LD50 in mice, rats (mg/kg): >20000, >10000 orally; 5670, 7716 i.p. (Kuramoto)
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
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
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
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
- Signal word
- Danger
- Symbol(GHS)
- GHS08
- hazard_code
- Xn,Xi
- safety_code
- 22-36/37
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H317-H334
- REACH Registrations
- Active
- Hazard Classifications
- Resp. Sens. 1Skin Sens. 1
- Precautionary statements
- P261-P280-P284-P304+P340-P342+P311
Chemistry & industry
Pharmacology
Applications
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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers101 total
Additional notes
DefinitionChEBI: Cephalothin sodium is an organic sodium salt. It contains a cefalotin.
Related reactions
Compound notes
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