Basic information
- CAS
52152-93-9- Standard SMILES
NC(=O)c1cc[n+](CC2=C(C(=O)[O-])N3C(=O)[C@@H](NC(=O)[C@@H](c4ccccc4)S(=O)(=O)[O-])[C@H]3SC2)cc1.[Na+]- InChIKey
REACMANCWHKJSM-DWBVFMGKSA-M- Molecular formula
- C22H19N4NaO8S2
- Average molar mass
- 554.5 g/mol
- Monoisotopic mass
- 554.05420021
Overview
Cefsulodin sodium is an organic molecular entity.
Names & identifiers
- Preferred name
- Cefsulodin Sodium
- IUPAC
- sodium (6R,7R)-3-[(4-carbamoylpyridin-1-ium-1-yl)methyl]-8-oxo-7-[[(2R)-2-phenyl-2-sulfonatoacetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
- English name
- cefsulodin sodium salt
- Molecular formula
- C22H20N4O8S2.Na
- Molecular weight
- 555.54
Names & synonyms
cefsulodin sodium52152-93-9CEFSULODIN SODIUM SALTSulcephalosporinCefomonilTakesulinTilmaporAbbott-46811Abbott-468 11CGP 7174ESCE 129CGP-7174/E
Show more names
Ulfarsce129ulfaretpyocefalcgp7174emonasporpseudocef
Sodium, CefsulodinCGP-71741E2D087186PYNSC-758163Hydrogen (6R-(6alpha,7beta(R*)))-4-carbamoyl-1-((2-carboxylato-8-oxo-7-(phenylsulphonatoacetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)pyridinium, monosodium saltCefsulodin Monosodium SaltRefChem:574979sodium;(6R,7R)-3-((4-carbamoylpyridin-1-ium-1-yl)methyl)-8-oxo-7-(((2R)-2-phenyl-2-sulfonato-acetyl)amino)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate
Database identifiers
- CAS
52152-93-9- PubChem CID
- 656644
- ChEMBL
CHEMBL1256939、CHEMBL1590946- ChEBI
CHEBI:31380- UNII
- 2D087186PY
Properties
Computed structural properties
- Topological polar surface area
- 227 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 6
- Heavy atoms
- 37
- Formal charge
- 0
- Complexity
- 1,040
Physicochemical properties
- Melting point
- 175 C · 175 C
- storage temp.
- -20 °C · Inert atmosphere,Store in freezer, under -20°C
- solubility
- 2 O: · H2O: 50 mg/mL, clear, light yellow
- form
- powder or crystals
- color
- Off-White to Pale Yellow
- Water Solubility
- Soluble in water.
- Merck
- 13 · 13,1958
- Stability
- Hygroscopic
- InChIKey
- REACMANCWHKJSM-DWBVFMGKSA-M
- SMILES
- N12C([C@@H](NC(=O)[C@H](S([O-])(=O)=O)C3C=CC=CC=3)[C@H]1SCC(C[N+]1=CC=C(C(=O)N)C=C1)=C2C([O-])=O)=O.[Na+] |&1:2,6,17,r|
- FDA UNII
- 2 D087186PY · 2D087186PY
- EPA Substance Registry System
- 4 · Pyridinium, 4-(aminocarbonyl)-1-[[(6R,7R)-2-carboxy-8-oxo-7-[[(2R)-phenylsulfoacetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-, inner salt, monosodium salt (52152-93-9)
- UNSPSC Code
- 51284140 · 51284140
- NACRES
- 85 · NA.85
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H315 (96.2%): Causes skin irritation [Warning Skin corrosion/irritation]
P233, P260, P261, P264, P264+P265, P271, P272, P280, P284, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 53 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Pyridinium, 4-(aminocarbonyl)-1-[[2-carboxy-8-oxo-7-[(phenylsulfoacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-, hydroxide, inner salt, monosodium salt, [6R-[6.alpha.,7.beta.(R*)]]-
PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.
Cefsulodine sodium: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesSkin Irrit. 2 (96.2%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- UU1785000
- hs_code
- 29419059
- Toxicity
- LD50 in mice (mg/kg): >4000 i.p.; >15000 orally (Bryskier)
- risk_code
- 36/37/38-42/43-20/21/22
- Signal word
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Uses & manufacturing
General Manufacturing InformationPyridinium, 4-(aminocarbonyl)-1-[[(6R,7R)-2-carboxy-8-oxo-7-[[(2R)-2-phenyl-2-sulfoacetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-, inner salt, sodium salt (1:1): ACTIVE
Applications
DescriptionCefsulodin was synthesized by Takeda Chemicals Industries in 1974 by introducing the sulfobenzyl group, the same moiety as in sulbenicillin, at the 7 position of the cephem nucleus. Its side chain at the 3 position is similar to that of cephaloridine except for the carbamoyl group. The introduction of these hydrophilic groups increases the activity against Pseudomonas aeruginosa, but it markedly decreases it against gram-positive and other gramnegative bacteria. Therefore cefsulodin is used as a specific antibiotic against infections caused by the opportunistic pathogen P. aeruginosa.
UsesCefsulodin is most commonly used in CIN agar to select for Yersinia microorganisms. The compound displays a mechanism of action like many β lactam antibiotics through inhibition of cell wall synthesis by competitively inhibiting penicillin binding protein (PBP) crosslinking of peptidoglycan resulting in inhibition of the final transpeptidation step. Through the inability for Cefsulodin sodium salt hydrate to inhibit cefsulodin-resistant mutants of Pseudomonas aeruginosa PAO4089 growth displayed that Cefsulodin sodium salt hydrate may compete with PBP3 in addition to PBP1A and PBP1B.
Usesbetaadrenergic blocker
UsesCefsulodin is a third generation cephalosporin (C258750) antibiotic designed specifically for Pseudomonas Aeruginosa.
UsesA β lactam antibiotic.
Preparation methods
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…