1-{[(6R,7R)-7-[(2E)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}imidazo[1,2-b]pyridazin-1-ium

• ChemBase ID: 163925
• Molecular Formular: C19H17N9O5S2
• Molecular Mass: 515.52558
• Monoisotopic Mass: 515.07940669
• SMILES: [C@H]1(C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])C[n+]1c2n(cc1)nccc2)NC(=O)/C(=N/OC)/c1nc(sn1)N
• Canonical SMILES: CO/N=C(\c1nsc(n1)N)/C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])C[n+]1ccn2c1cccn2
• InChI: InChI=1S/C19H17N9O5S2/c1-33-24-11(14-23-19(20)35-25-14)15(29)22-12-16(30)28-13(18(31)32)9(8-34-17(12)28)7-26-5-6-27-10(26)3-2-4-21-27/h2-6,12,17H,7-8H2,1H3,(H3-,20,22,23,25,29,31,32)/b24-11+/t12-,17-/m1/s1
• InChIKey: QDUIJCOKQCCXQY-HEOFFLBTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{[(6R,7R)-7-[(2E)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}imidazo[1,2-b]pyridazin-1-ium
• IUPAC Traditional name: 1-{[(6R,7R)-7-[(2E)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}imidazo[1,2-b]pyridazin-1-ium
• Synonyms: 1-[[(6R,7R)-7-[[2Z)-(5-Amino-1,2,4-thiadiazol-3-yl)(methoxyimino)acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]imidazo[1,2-b]pyridazinium Inner Salt Dihydrochloride; SCE-1787 Dihydrochloride; Firstcin Dihydrochloride; Cefozopran Dihydrochloride

Database IDs

• PubChem SID: 162258060
• PubChem CID: 5464317

CALCULATED PROPERTIES

• Acid pKa: 2.8961968
• H Acceptors: 10
• H Donor: 2
• LogD (pH = 5.5): -4.6335845
• LogD (pH = 7.4): -4.6303
• Log P: -5.1394553
• Molar Refractivity: 147.3731 cm^3
• Polarizability: 46.495483 Å^3
• Polar Surface Area: 184.11 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White To Pale-Yellow Solid
• Melting Point: >175°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under inert atmosphere

DETAILS

Toronto Research Chemicals - C243300

Antibacterial.

REFERENCES

• Iwahi, T., et al.: Antimicrob. Agents Chemother., 36, 1358 (1992)
• Miyake, A., et al.: J. Antibiot., 45, 709 (1992)