(6R,7R)-7-[(2R)-2-amino-2-phenylacetamido]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 72713
• Molecular Formular: C15H14ClN3O4S
• Molecular Mass: 367.80736
• Monoisotopic Mass: 367.03935462
• SMILES: [C@@H]12N(C(=C(CS1)Cl)C(=O)O)C(=O)[C@H]2NC(=O)[C@@H](c1ccccc1)N
• Canonical SMILES: N[C@H](c1ccccc1)C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)Cl
• InChI: InChI=1S/C15H14ClN3O4S/c16-8-6-24-14-10(13(21)19(14)11(8)15(22)23)18-12(20)9(17)7-4-2-1-3-5-7/h1-5,9-10,14H,6,17H2,(H,18,20)(H,22,23)/t9-,10-,14-/m1/s1
• InChIKey: QYIYFLOTGYLRGG-GPCCPHFNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2R)-2-amino-2-phenylacetamido]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: cefaclorum; cefaclor
• Synonyms: Cefaclor; Ceclor; Distaclor; Keflor; Raniclor; Cefaclor (Ceclor); Panoral; 3-Chloro-7-d-(2-phenylglycinamido)-3-cephem-4-carboxylic acid; CEFACLOR

Database IDs

• CAS Number: 53994-73-3
• EC Number: 258-909-5
• MDL Number: MFCD00151471
• Beilstein Number: 8176092
• PubChem SID: 162037634; 24278331
• PubChem CID: 51039

CALCULATED PROPERTIES

• Acid pKa: 3.3266125
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.3051183
• LogD (pH = 7.4): -2.5596933
• Log P: -2.3070648
• Molar Refractivity: 89.5618 cm^3
• Polarizability: 34.69509 Å^3
• Polar Surface Area: 112.73 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 1 M HCl: soluble50 mg/mL, clear to very faintly turbid, yellow; DMSO

Safety Information

• Storage Condition: -20°C; Room Temperature (15-30°C)
• RTECS: XI0363000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 42/43
• Safety Statements: 22-36/37-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H317-H334
• GHS Precautionary statements: P261-P280-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

• Purity: ~98%; ≥99.0% (TLC)
• Salt Data: Free Base
• Impurities: ≤6% water
• Empirical Formula (Hill Notation): C15H14ClN3O4S

DETAILS

MP Biomedicals - 02198943

Purity: ~98%

Selleck Chemicals - S1499

Research Area: Infection
Biological Activity:
Cefaclor belongs to the family of antibiotics known as the cephalosporins (cefalosporins). The cephalosporins are broad-spectrum antibiotics that are used for the treatment of septicaemia, pneumonia, meningitis, biliary-tract infections, peritonitis, and urinary-tract infections. The pharmacology of the cephalosporins is similar to that of the penicillins, excretion being principally renal. Cephalosporins penetrate the cerebrospinal fluid poorly unless the meninges are inflamed; cefotaxime is a more suitable cephalosporin than cefaclor for infections of the central nervous system, e.g. meningitis. Cefaclor is active against many bacteria, including both Gram-negative and Gram-positive organisms. [1]

Sigma Aldrich - C6895

Application
Cefaclor is used to study the mechanism of human renal transporters such as hOAT1, hPEPT1, and hPEPT2. Used to study the effects of inhibition of penicillin-binding proteins on bacterial cell wall mucopeptide synthesis.
Cefaclor is used to study urinary tract, intra-abdominal, and Haemophilus influenzae infections 1. It is used to study the mechanism of human renal organic anion and peptide transporters such as hOAT1, hPEPT1, and hPEPT2 and to study the effects of inhibition of penicillin-binding proteins on bacterial cell wall mucopeptide synthesis .
Biochem/physiol Actions
Cefaclor is active against Gram-negative and Gram-positive bacteria. Excretion of cefaclor is primarily renal. Cefaclor binds to penicillin-binding proteins thereby inhibiting cell wall synthesis 1.

REFERENCES

• http://en.wikipedia.org/wiki/Cefaclor