(6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-{2-[(2H4)pyridin-4-ylsulfanyl]acetamido}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 163984
• Molecular Formular: C17H17N3O6S2
• Molecular Mass: 423.46338
• Monoisotopic Mass: 423.05587728
• SMILES: [C@H]1(C(=O)N2[C@@H]1SCC(=C2C(=O)O)COC(=O)C)NC(=O)CSc1ccncc1
• Canonical SMILES: O=C(N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)COC(=O)C)CSc1ccncc1
• InChI: InChI=1S/C17H17N3O6S2/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25)/t13-,16-/m1/s1
• InChIKey: UQLLWWBDSUHNEB-CZUORRHYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-{2-[(^2H₄)pyridin-4-ylsulfanyl]acetamido}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-{2-[(^2H₄)pyridin-4-ylsulfanyl]acetamido}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: (6R,7R)-3-[(Acetyloxy)methyl]-8-oxo-7-[[(4-pyridinylthio-d4)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; (6R-trans)-3-[(Acetyloxy)methyl]-8-oxo-7-[[(4-pyridinylthio-d4)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; 7-[2-(4-Pyridylthio-d4)acetamido]cephalosporanic Acid; Cefapirin-d4; Cefaprin-d4; Cephapirine-d4; Cephaprin-d4; Cephapirin-d4

Database IDs

• PubChem SID: 162258119
• PubChem CID: 71314643

CALCULATED PROPERTIES

• Acid pKa: 3.540687
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -2.5915926
• LogD (pH = 7.4): -4.131089
• Log P: -2.0011034
• Molar Refractivity: 102.4307 cm^3
• Polarizability: 39.8448 Å^3
• Polar Surface Area: 125.9 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 150-153°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - C261502

Labelled Cephapirin (C261500). An antimicrobial agent.

REFERENCES

• Tan, J.S., et al.: Antimicrob. Agents Chemother., 15, 510 (1979)