sodium (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(2H3)methoxyimino]acetamido]-3-[(Z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

• ChemBase ID: 163901
• Molecular Formular: C19H17N6NaO5S3
• Molecular Mass: 528.56025
• Monoisotopic Mass: 528.03202496
• SMILES: S1[C@H]2N(C(=C(C1)/C=C\c1c(ncs1)C)C(=O)[O-])C(=O)[C@H]2NC(=O)/C(=N\OC)/c1csc(n1)N.[Na+]
• Canonical SMILES: CO/N=C(\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])/C=C\c1scnc1C)/c1csc(n1)N.[Na+]
• InChI: InChI=1S/C19H18N6O5S3.Na/c1-8-11(33-7-21-8)4-3-9-5-31-17-13(16(27)25(17)14(9)18(28)29)23-15(26)12(24-30-2)10-6-32-19(20)22-10;/h3-4,6-7,13,17H,5H2,1-2H3,(H2,20,22)(H,23,26)(H,28,29);/q;+1/p-1/b4-3-,24-12-;/t13-,17-;/m1./s1
• InChIKey: VFUMWBZIKOREOO-WSWQWPGSSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(^2H₃)methoxyimino]acetamido]-3-[(Z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• IUPAC Traditional name: sodium (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(^2H₃)methoxyimino]acetamido]-3-[(Z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• Synonyms: (6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)methoxyimino-d3)acetyl]amino]-3-[(1Z)-2-(4-methyl-5-thiazolyl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Sodium Salt; ME 1206-d3; Cefditoren Acid-d3 Sodium Salt

Database IDs

• PubChem SID: 162258036
• PubChem CID: 71314601

CALCULATED PROPERTIES

• Acid pKa: 3.395358
• H Acceptors: 9
• H Donor: 2
• LogD (pH = 5.5): -1.4440151
• LogD (pH = 7.4): -2.6541753
• Log P: -0.4207479
• Molar Refractivity: 135.0168 cm^3
• Polarizability: 46.19558 Å^3
• Polar Surface Area: 162.93 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Pale Yellow Crystalline Solid
• Melting Point: 195-200°C

DETAILS

Toronto Research Chemicals - C242702

Labelled Cefditoren. Third generation cephalosporin; active metabolite of orally absorbed pivaloyloxymethyl ester prodrug. An antibacterial.

REFERENCES

• Sakagami, K., et al.: J. Antibiot., 43, 1047 (1990)
• Felmingham, D., Drugs Exp. Clin. Res., 20, 127 (1990)
• Iwai, N., et al.: Japan J. Antibiot., 47, 181 (1994)