1-{[(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-5,6,7,8-tetrahydroquinolin-1-ium; sulfuric acid

• ChemBase ID: 163931
• Molecular Formular: C23H26N6O9S3
• Molecular Mass: 626.68234
• Monoisotopic Mass: 626.09233944
• SMILES: [C@H]1(C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])C[n+]1c2c(ccc1)CCCC2)NC(=O)/C(=N\OC)/c1nc(N)sc1.S(=O)(=O)(O)O
• Canonical SMILES: OS(=O)(=O)O.CO/N=C(/c1csc(n1)N)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])C[n+]1cccc2c1CCCC2
• InChI: InChI=1S/C23H24N6O5S2.H2O4S/c1-34-27-16(14-11-36-23(24)25-14)19(30)26-17-20(31)29-18(22(32)33)13(10-35-21(17)29)9-28-8-4-6-12-5-2-3-7-15(12)28;1-5(2,3)4/h4,6,8,11,17,21H,2-3,5,7,9-10H2,1H3,(H3-,24,25,26,30,32,33);(H2,1,2,3,4)/b27-16-;/t17-,21-;/m1./s1
• InChIKey: KYOHRXSGUROPGY-OFNLCGNNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{[(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-5,6,7,8-tetrahydroquinolin-1-ium; sulfuric acid
• IUPAC Traditional name: cefquinome; sulfuric acid
• Synonyms: 1-[[(6R,7R)-7-[[(2Z)-2-(2-Amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-5,6,7,8-tetrahydro-quinolinium Sulfate; Cefquinome Sulphate; HR 111V Sulfate; [6R-[6α,7β(Z)]]-1-[[7-[[(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-5,6,7,8-tetrahydro-quinolinium Sulfate; Cefquinome Sulfate

Database IDs

• CAS Number: 118443-89-3
• PubChem SID: 162258066
• PubChem CID: 9577261

CALCULATED PROPERTIES

• Acid pKa: 3.1466074
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -3.2246041
• LogD (pH = 7.4): -3.2095468
• Log P: -3.521601
• Molar Refractivity: 145.897 cm^3
• Polarizability: 50.696644 Å^3
• Polar Surface Area: 153.92 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C244000

An antibacterial used in veterinary medicine. Used in the treatment of infections caused by pathogens such as S. aureus, E. coli, Streptococcus, P. multocida and A. pleuropneumoniae. Also used to treat mastitis in dairy cows.

REFERENCES

• Bottner, A. et al.: J. Vet. Med., 42, 377 (1995)
• Fan, X. et al.: Xumu Yu Shouyi, 40, 78 (1995)
• Shpigel, N.Y. et al.: J. Dairy Sci., 80, 318 (1995)