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

• ChemBase ID: 163915
• Molecular Formular: C16H17N9O5S3
• Molecular Mass: 511.55848
• Monoisotopic Mass: 511.05147769
• SMILES: S1[C@H]2N(C(=C(C1)CSc1nnnn1C)C(=O)O)C(=O)[C@H]2NC(=O)/C(=N\OC)/c1nc(sc1)N
• Canonical SMILES: CO/N=C(\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nnnn1C)/c1csc(n1)N
• InChI: InChI=1S/C16H17N9O5S3/c1-24-16(20-22-23-24)33-4-6-3-31-13-9(12(27)25(13)10(6)14(28)29)19-11(26)8(21-30-2)7-5-32-15(17)18-7/h5,9,13H,3-4H2,1-2H3,(H2,17,18)(H,19,26)(H,28,29)/b21-8-/t9-,13-/m1/s1
• InChIKey: HJJDBAOLQAWBMH-YCRCPZNHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: cefmenoxime
• Synonyms: (6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Hemihydrochloride; Abbott 50192; Bestcall; Bestron; Cefmax; Cefmenoxime hemihydrochloride; Cefmenoxime hydrochloride; Cemix; Tacef; Cefmenoxime Hydrochloride

Database IDs

• CAS Number: 75738-58-8
• PubChem SID: 162258050
• PubChem CID: 9570757

CALCULATED PROPERTIES

• Acid pKa: 3.0366993
• H Acceptors: 11
• H Donor: 3
• LogD (pH = 5.5): -2.4868429
• LogD (pH = 7.4): -3.553978
• Log P: -1.4007788
• Molar Refractivity: 133.5115 cm^3
• Polarizability: 45.1463 Å^3
• Polar Surface Area: 190.81 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C242835

A third generation cephalosporin antibiotic with strong antimicrobial activities against Streptococcus pneumoniae, Haemophilus influenzae and Moraxella subgenus Branhamella catarrhalis that were 3 major aerobic bacteria from sinusitis.

REFERENCES

• Yakota, N. et al.: Jpn. J. Antibiot., 48, 602 (1995)
• Fukuda, M. et al.: Jpn. J. Ophthamol., 46, 384 (1995)