(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 hydrate

• ChemBase ID: 163867
• Molecular Formular: C15H16ClN3O5S
• Molecular Mass: 385.82264
• Monoisotopic Mass: 385.04991931
• SMILES: [C@H]1(C(=O)N2[C@@H]1SCC(=C2C(=O)O)Cl)NC(=O)[C@@H](c1ccccc1)N.O
• Canonical SMILES: N[C@H](c1ccccc1)C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)Cl.O
• InChI: InChI=1S/C15H14ClN3O4S.H2O/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);1H2/t9-,10-,14-;/m1./s1
• InChIKey: WKJGTOYAEQDNIA-IOOZKYRYSA-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 hydrate
• IUPAC Traditional name: cefaclor hydrate
• Synonyms: (6R,7R)-7-[(2-Amino-2-phenylacetyl)amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Monohydrate; Ceclor; Distaclor; Keflor; Raniclor; Cefaclor Monohydrate

Database IDs

• CAS Number: 70356-03-5
• PubChem SID: 162258002
• PubChem CID: 51038

CALCULATED PROPERTIES

• Acid pKa: 3.0266292
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.3069453
• LogD (pH = 7.4): -2.5625703
• Log P: -2.3063354
• 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: DMSO; Water
• Apperance: Pale Yellow Solid
• Melting Point: >180°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C235250

Second-generation cephalosporin antibiotic. Antibacterial.

REFERENCES

• Gray, B.M., et al.: Antimicrob. Agents Chemother., 13, 988 (1978)
• Lorenz, L.J., et al.: Anal. Profiles Drug Subs., 9, 107 (1978)
• Hori, R., et al.: J. Pharm. Pharmacol., 40, 646 (1978)