sodium (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(2R)-oxolan-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate hydrate

• ChemBase ID: 154833
• Molecular Formular: C12H16NNaO6S
• Molecular Mass: 325.31331
• Monoisotopic Mass: 325.05960252
• SMILES: C[C@H]([C@@H]1[C@@H]2N(C1=O)C(=C(S2)[C@H]1CCCO1)C(=O)[O-])O.O.[Na+]
• Canonical SMILES: C[C@H]([C@H]1C(=O)N2[C@@H]1SC(=C2C(=O)[O-])[C@H]1CCCO1)O.O.[Na+]
• InChI: InChI=1S/C12H15NO5S.Na.H2O/c1-5(14)7-10(15)13-8(12(16)17)9(19-11(7)13)6-3-2-4-18-6;;/h5-7,11,14H,2-4H2,1H3,(H,16,17);;1H2/q;+1;/p-1/t5-,6-,7+,11-;;/m1../s1
• InChIKey: FHSVCMPZCIOKGW-VIDQLUEFSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(2R)-oxolan-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate hydrate
• IUPAC Traditional name: sodium (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(2R)-oxolan-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate hydrate
• Synonyms: (5R,6S,8R,2′R)-2-(2′-tetrahydrofuryl)-6-hydroxyethylpenem-3-carboxylate sodium salt; ALP 201; Farom; Fropenem; Furopenem; SUN 5555; SY 5555; Wy 49605; Faropenem sodium hydrate

Database IDs

• CAS Number: 122547-49-3(anhydrous)
• MDL Number: MFCD17215925
• PubChem SID: 162248971
• PubChem CID: 71311999

CALCULATED PROPERTIES

• Acid pKa: 4.1632895
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -2.1061792
• LogD (pH = 7.4): -3.8107867
• Log P: -0.7526909
• Molar Refractivity: 80.0927 cm^3
• Polarizability: 26.562815 Å^3
• Polar Surface Area: 89.9 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥20 mg/mL; H2O: ≥20 mg/mL
• Apperance: off-white to light brown powder
• Optical Rotation: [α]/D +110 to 130°, c = 1 in H2O

Safety Information

• Storage Condition: desiccated
• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C12H14NNaO5S · xH2O

DETAILS

Sigma Aldrich - F8182

Biochem/physiol Actions
Faropenem sodium is an ultra-broad spectrum, β-lactamase resistant, β-lactam antibiotic active against both Gram-positive and Gram-negative bacteria.