(6R,7R)-7-[(2R)-2-amino-2-(cyclohexa-1,4-dien-1-yl)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 1167
• Molecular Formular: C16H19N3O4S
• Molecular Mass: 349.40476
• Monoisotopic Mass: 349.1096271
• SMILES: S1[C@H]2N(C(=O)[C@H]2NC(=O)[C@H](N)C2=CCC=CC2)C(=C(C1)C)C(=O)O
• Canonical SMILES: O=C([C@@H](C1=CCC=CC1)N)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)C
• InChI: InChI=1S/C16H19N3O4S/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9/h2-3,6,10-11,15H,4-5,7,17H2,1H3,(H,18,20)(H,22,23)/t10-,11-,15-/m1/s1
• InChIKey: RDLPVSKMFDYCOR-UEKVPHQBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2R)-2-amino-2-(cyclohexa-1,4-dien-1-yl)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: cefradine
• Synonyms: Cefradin; Cephradine; Cephradine; Cefradine; Sefril; Cefradine; CEPHRADINE

Database IDs

• CAS Number: 38821-53-3
• EC Number: 254-137-8
• MDL Number: MFCD00865048
• PubChem SID: 160964630; 24278342; 46505082
• PubChem CID: 38103

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.4648793
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.4420826
• LogD (pH = 7.4): -2.6352267
• Log P: -2.4468315
• Molar Refractivity: 91.9956 cm^3
• Polarizability: 34.87967 Å^3
• Polar Surface Area: 112.73 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.7
• LOG S: -2.65
• Solubility (Water): 7.78e-01 g/l

PROPERTIES

Physical Property

• Solubility: 21.3 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
• Melting Point: 140-142°C

Safety Information

• Storage Condition: 2-8°C, Desiccate, Protect from light
• RTECS: XI0336000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 36/37/38-42/43
• Safety Statements: 22-26-36/37-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H317-H319-H334-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338-P342 + P311
• Storage Temperature: 2-8°C

DETAILS

DrugBank - DB01333

• Drug Groups: approved
• Description: A semi-synthetic cephalosporin antibiotic. [PubChem]
• Elimination: Over 90 percent of the drug is excreted unchanged in the urine within six hours.
• References: Neiss ES: Cephradine--a summary of preclinical studies and clinical pharmacology. J Ir Med Assoc. 1973 Mar 24;Suppl:1-12. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - C8395

Application
Cefradin is a semi-synthetic cephalosporin antibiotic that is used to study the effect of expression, binding, and inhibition of PBP3 and other penicillin-binding proteins (PBPs) on bacterial cell wall mucopeptide synthesis.
Cefradin is used to study the effect of expression, binding, and inhibition of PBP3 and other penicillin-binding proteins (PBPs) on bacterial cell wall mucopeptide synthesis.
Biochem/physiol Actions
Cefradin inhibits the last stage of bacterial cell wall synthesis by binding to certain penicillin-binding proteins (PBPs), such as PBP3, which results in cell lysis. Cell lysis is mediated by bacterial cell wall autolytic enzymes. Cefradin may interfere with autolysin inhibitors.

REFERENCES

• Neiss ES: Cephradine--a summary of preclinical studies and clinical pharmacology. J Ir Med Assoc. 1973 Mar 24;Suppl:1-12. Pubmed