sodium 4-carbamoyl-1-{[(6R,7R)-2-carboxylato-8-oxo-7-[(2R)-2-phenyl-2-sulfonatoacetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium

• ChemBase ID: 106048
• Molecular Formular: C22H19N4NaO8S2
• Molecular Mass: 554.52803
• Monoisotopic Mass: 554.05419987
• SMILES: [Na+].O=C1N2C(=C(CS[C@@H]2[C@@H]1NC(=O)[C@@H](c1ccccc1)S(=O)(=O)[O-])C[n+]1ccc(C(=O)N)cc1)C(=O)[O-]
• Canonical SMILES: O=C([C@H](S(=O)(=O)[O-])c1ccccc1)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])C[n+]1ccc(cc1)C(=O)N.[Na+]
• InChI: InChI=1S/C22H20N4O8S2.Na/c23-18(27)13-6-8-25(9-7-13)10-14-11-35-21-15(20(29)26(21)16(14)22(30)31)24-19(28)17(36(32,33)34)12-4-2-1-3-5-12;/h1-9,15,17,21H,10-11H2,(H4-,23,24,27,28,30,31,32,33,34);/q;+1/p-1/t15-,17-,21-;/m1./s1
• InChIKey: REACMANCWHKJSM-DWBVFMGKSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 4-carbamoyl-1-{[(6R,7R)-2-carboxylato-8-oxo-7-[(2R)-2-phenyl-2-sulfonatoacetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium
• IUPAC Traditional name: sodium 4-carbamoyl-1-{[(6R,7R)-2-carboxylato-8-oxo-7-[(2R)-2-phenyl-2-sulfonatoacetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium
• Synonyms: Cefsulodin sodium salt hydrate; CEFSULODIN SODIUM SALT

Database IDs

• CAS Number: 52152-93-9
• EC Number: 257-692-4
• MDL Number: MFCD07793338
• PubChem SID: 162092710; 24278340
• PubChem CID: 656644

CALCULATED PROPERTIES

• Acid pKa: -1.0812536
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -7.435669
• LogD (pH = 7.4): -7.4622836
• Log P: -5.785873
• Molar Refractivity: 138.3214 cm^3
• Polarizability: 49.44992 Å^3
• Polar Surface Area: 193.71 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: 2-8°C
• RTECS: UU1785000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38-42/43
• Safety Statements: 22-26-36/37-45
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H317-H319-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

DETAILS

MP Biomedicals - 02198677

Sodium Salt

Sigma Aldrich - C8145

Biochem/physiol Actions
Cefsulodin is a cephalosporin. Cephalosporins disrupt cell wall synthesis by inhibiting PBP crosslinking of peptidoglycan.
Application
Cefsulodin is a third generation cephalosporin antibiotic that has very specific activity against Pseudomonas aeruginosa. Cefuslodin is used in CIN (cefsulodin-Irgasan-novobiocin) agar to select for microorganisms such as E. coli. Cefsulodin is a substrate for rat Oatp1a4. It has been used to study multidrug resistance-associated protein 4 in efflux transport of prostaglandin E2 across the mouse blood-brain barrier1. Cefsulodin is used to study the effect of expression, binding, and inhibition of PBP1 and other penicillin-binding proteins (PBPs) on bacterial cell wall mucopeptide synthesis.
Cefsulodin is used to study the effect of expression, binding, and inhibition of PBP1 and other penicillin-binding proteins (PBPs) on bacterial cell wall mucopeptide synthesis.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information