sodium (2S,5R,6R)-6-[3-(2-chlorophenyl)-5-(13C)methyl(4,5-13C2)-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

• ChemBase ID: 164931
• Molecular Formular: C19H17ClN3NaO5S
• Molecular Mass: 461.83376935
• Monoisotopic Mass: 461.06093297
• SMILES: [C@H]1(C(=O)N2[C@@H]1SC([C@@H]2C(=O)[O-])(C)C)N[13C](=O)[13c]1c(no[13c]1[13CH3])c1ccccc1Cl.[Na+]
• Canonical SMILES: [O-]C(=O)[C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)N[13C](=O)[13c]1[13c]([13CH3])onc1c1ccccc1Cl.[Na+]
• InChI: InChI=1S/C19H18ClN3O5S.Na/c1-8-11(12(22-28-8)9-6-4-5-7-10(9)20)15(24)21-13-16(25)23-14(18(26)27)19(2,3)29-17(13)23;/h4-7,13-14,17H,1-3H3,(H,21,24)(H,26,27);/q;+1/p-1/t13-,14+,17-;/m1./s1/i1+1,8+1,11+1,15+1
• InChIKey: SCLZRKVZRBKZCR-QSLPWVMZSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,5R,6R)-6-[3-(2-chlorophenyl)-5-(^1^3C)methyl(4,5-^1^3C₂)-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• IUPAC Traditional name: sodium (2S,5R,6R)-6-[3-(2-chlorophenyl)-5-(^1^3C)methyl(4,5-^1^3C₂)-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• Synonyms: (2S,5R,6R)-6-[[[3-(2-Chlorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid-13C4 Sodium Salt; Ankerbin; 3-(o-Chlorophenyl)-5-methyl-4-isoxazolylpenicillin-13C4 Sodium Salt; Austrastaph-13C4; BRL 1621-13C4 Sodium Salt; Cloxapen-13C4; Ekvacillin-13C4; Gelstaph-13C4; Orbenin-13C4 Sodium; Prevencilina P; -13C4 Prostaphilin A-13C4; Prostaphlin A-13C4; Syntarpen-13C4 Sodium Salt; Tegopen-13C4; Sodium 3-(O-Chlorophenyl)-5-methyl-4-isoxazolylpenicillin-13C4; Sodium Cloxacillin-13C4; 6-[3-(o-Chlorophenyl)-5-methyl-4-isoxazolecarboxamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid-13C4 Monosodium Salt; Staphybiotic-13C4; Cloxacillin-13C4 Sodium Salt

Database IDs

• PubChem SID: 162259065
• PubChem CID: 71314965

CALCULATED PROPERTIES

• Acid pKa: 3.7497845
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.55099535
• LogD (pH = 7.4): -0.9830029
• Log P: 2.3017397
• Molar Refractivity: 117.4742 cm^3
• Polarizability: 41.823692 Å^3
• Polar Surface Area: 115.57 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C587462

Labelled analogue of Cloxacillin, an antibiotic that belongs to the group of the isoxazolylpenicillins. Cloxacillin is used to treat infections caused by species of staphylococci that produce beta-lactamase due to its inhibitory effects on beta-lactamase

REFERENCES

• Gibbs, D.L. et al.: Curr. Microbiol., 2, 239 (1979)
• Dmitrova, D. et al.: Farmat., 48, 28 (1979)
• CRaven, N. et al.: Res. Vet. Sci., 29, 57 (1979)