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

• ChemBase ID: 103102
• Molecular Formular: C16H17N3O5S
• Molecular Mass: 363.38828
• Monoisotopic Mass: 363.08889166
• SMILES: O=C1N2C(=C(CS[C@@H]2[C@@H]1NC(=O)[C@@H](c1ccc(O)cc1)N)C)C(=O)O
• Canonical SMILES: O=C([C@@H](c1ccc(cc1)O)N)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)C
• InChI: InChI=1S/C16H17N3O5S/c1-7-6-25-15-11(14(22)19(15)12(7)16(23)24)18-13(21)10(17)8-2-4-9(20)5-3-8/h2-5,10-11,15,20H,6,17H2,1H3,(H,18,21)(H,23,24)/t10-,11-,15-/m1/s1
• InChIKey: BOEGTKLJZSQCCD-UEKVPHQBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: cephadroxil; (6R,7R)-7-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: Cefadroxil; p-Hydroxycephalexine; Cefamox; CEFADROXIL; (6R,7R)-7-((R)-2-amino-2-(4-hydroxyphenyl)acetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; Cephadroxil; Baxan; Bidocef; Cefadril; Cefadrox; Cefroxil; Duricef; 头孢羟氨苄

Database IDs

• CAS Number: 50370-12-2
• EC Number: 256-555-6
• MDL Number: MFCD00865091
• PubChem SID: 162091217; 24892921
• PubChem CID: 47965

CALCULATED PROPERTIES

• Acid pKa: 3.4454033
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.4450464
• LogD (pH = 7.4): -2.7044444
• Log P: -2.4485235
• Molar Refractivity: 90.9545 cm^3
• Polarizability: 35.27431 Å^3
• Polar Surface Area: 132.96 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 197°C

Safety Information

• Storage Condition: 2-8°C
• RTECS: XI0337000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 36/37/38-42/43
• Safety Statements: 26-36
• 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
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Pharmacology Properties

• Mechanism of Action: Cell wall synthesis inhibitor; Mucopeptide-synthesis inhibitor;

Product Information

• Application(s): Broad-spectrum antibiotic effective in Gram-positive and Gram-negative bacterial infections.; It is a bactericidal antibiotic

DETAILS

MP Biomedicals - 02150581

White crystalline powder
m.p. 197°C

Sigma Aldrich - C7020

Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C7020.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

REFERENCES

• Ger. Pat., 1973, 2 263 861; CA, 79, 78822, (synth)
• Ger. Pat., 1975, 2 460 607; CA, 83, 145764, (synth)
• Dunn, G. et al., J. Antibiot., 1976, 29, 65, (synth)
• Neuman, M., Drugs of Today (Barcelona), 1977, 13, 471, (rev)
• U.S. Pat., 1979, 4 160 863; CA, 91, 175376, (synth, cryst struct)
• Leitner, F. et al., J. Antimicrob. Chemother., Suppl. B, 1982, 10, 1, (numerous papers)
• Tanrisever, B. et al., Drugs, 1986, 32, 1, (rev)
• Shin, W. et al., Acta Cryst. C, 1992, 48, 1454, (cryst struct)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 5179, (synonyms)
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 163
• Kemperman, G.J. et al., Eur. J. Org. Chem., 2001, 1817-1820, (synth)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DYF700