sodium (2S,5R,6R)-6-[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

• ChemBase ID: 169024
• Molecular Formular: C19H16ClFN3NaO5S
• Molecular Mass: 475.8536132
• Monoisotopic Mass: 475.03809181
• SMILES: [C@H]1(C(=O)N2[C@@H]1SC([C@@H]2C(=O)[O-])(C)C)NC(=O)c1c(noc1C)c1c(cccc1Cl)F.[Na+]
• Canonical SMILES: O=C1[C@@H](NC(=O)c2c(C)onc2c2c(F)cccc2Cl)[C@@H]2N1[C@@H](C(=O)[O-])C(S2)(C)C.[Na+]
• InChI: InChI=1S/C19H17ClFN3O5S.Na/c1-7-10(12(23-29-7)11-8(20)5-4-6-9(11)21)15(25)22-13-16(26)24-14(18(27)28)19(2,3)30-17(13)24;/h4-6,13-14,17H,1-3H3,(H,22,25)(H,27,28);/q;+1/p-1/t13-,14+,17-;/m1./s1
• InChIKey: OTEANHMVDHZOPB-SLINCCQESA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,5R,6R)-6-[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• IUPAC Traditional name: sodium flucloxacillin(1-)
• Synonyms: (2S,5R,6R)-6-[[[3-(2-Chloro-6-fluorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Sodium; Floxacillin Sodium; Floxapen Sodium; Staphylex Sodium; Flucloxacillin Sodium

Database IDs

• CAS Number: 1847-24-1
• PubChem SID: 162263156
• PubChem CID: 23667629

CALCULATED PROPERTIES

• Acid pKa: 3.7475462
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.6915611
• LogD (pH = 7.4): -0.841252
• Log P: 2.4444416
• Molar Refractivity: 117.6906 cm^3
• Polarizability: 41.600456 Å^3
• Polar Surface Area: 115.57 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: 176-178°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - F419200

Flucloxacillin, a new semisynthetic penicillin.

REFERENCES

• Markovich, M., et al.: Antibiot. Med. Biotekhnol., 31, 603 (1986)
• Rahman, M., et al.: Biochem. Pharmacol., 46, 1721 (1986)
• Silva, D., et al.: Med. Biol. Res., 37, 963 (1986)