(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-8-oxo-3-(sulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 166281
• Molecular Formular: C14H15N5O5S3
• Molecular Mass: 429.4944
• Monoisotopic Mass: 429.02353161
• SMILES: [C@H]1(C(=O)N2[C@@H]1SCC(=C2C(=O)O)CS)NC(=O)/C(=N\OC)/c1nc(sc1)N
• Canonical SMILES: CO/N=C(/c1csc(n1)N)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CS
• InChI: InChI=1S/C14H15N5O5S3/c1-24-18-7(6-4-27-14(15)16-6)10(20)17-8-11(21)19-9(13(22)23)5(2-25)3-26-12(8)19/h4,8,12,25H,2-3H2,1H3,(H2,15,16)(H,17,20)(H,22,23)/b18-7-/t8-,12-/m1/s1
• InChIKey: OITCOWCNESRWSM-GHXIOONMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-8-oxo-3-(sulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-8-oxo-3-(sulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: (6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-(mercaptomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; DFC; Defuroylceftiofur; Desfuroyl Ceftiofur; (6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)(methoxyimino-d3)acetyl]amino]-3-(mercaptomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; DFC-d3; Defuroylceftiofur-d3; Desfuroyl Ceftiofur-d3

Database IDs

• CAS Number: 120882-22-6
• PubChem SID: 162260414
• PubChem CID: 5487205

CALCULATED PROPERTIES

• Polarizability: 38.57763 Å^3
• Polar Surface Area: 147.21 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true
• Acid pKa: 3.2316525
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -2.130897
• LogD (pH = 7.4): -3.3491664
• Log P: -1.0852633
• Molar Refractivity: 101.9854 cm^3

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: Off-White Solid; White to Off-White Solid
• Melting Point: >175°C (dec); >195°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -86?C Freezer, Under Inert Atmosphere; Hygroscopic, -86°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D289980

A metabolite of Ceftiofur (C244700), which is microbiologic active.

Toronto Research Chemicals - D289982

A metabolite of Ceftiofur (C244700), which is microbiologic active.

REFERENCES

• Washburn, K., et al.: J. Vet. Pharm. Ther., 28, 247 (2005)
• Washburn, K., et al.: J. Vet. Pharm. Ther., 28, 247 (2005)