(5-methyl-2-oxo-2H-1,3-dioxol-4-yl)methyl (2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate hydrochloride

• ChemBase ID: 172260
• Molecular Formular: C21H24ClN3O7S
• Molecular Mass: 497.94916
• Monoisotopic Mass: 497.1023488
• SMILES: [C@H]1(C(=O)N2[C@@H]1SC([C@@H]2C(=O)OCc1oc(=O)oc1C)(C)C)NC(=O)[C@H](N)c1ccccc1.Cl
• Canonical SMILES: O=C([C@@H](c1ccccc1)N)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)OCc1oc(=O)oc1C)(C)C.Cl
• InChI: InChI=1S/C21H23N3O7S.ClH/c1-10-12(31-20(28)30-10)9-29-19(27)15-21(2,3)32-18-14(17(26)24(15)18)23-16(25)13(22)11-7-5-4-6-8-11;/h4-8,13-15,18H,9,22H2,1-3H3,(H,23,25);1H/t13-,14-,15+,18-;/m1./s1
• InChIKey: FXXSETTYJSGMCR-GLCLSGQWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5-methyl-2-oxo-2H-1,3-dioxol-4-yl)methyl (2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate hydrochloride
• IUPAC Traditional name: (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate hydrochloride
• Synonyms: (2S,5R,6R)-6-[[(2R)-Aminophenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid (5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl Ester Hydrochloride; KB 1585; KBT 1585; Takacillin; Varacillin; [2S-[2α,5α,6β(S*)]]-6-[(Aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid (5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl Ester MonoHydrochloride; Lenampicillin Hydrochloride

Database IDs

• CAS Number: 80734-02-7
• PubChem SID: 164228170
• PubChem CID: 6917773

CALCULATED PROPERTIES

• Acid pKa: 11.720702
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -0.90083975
• LogD (pH = 7.4): 0.6886881
• Log P: 1.0089236
• Molar Refractivity: 113.6582 cm^3
• Polarizability: 44.89514 Å^3
• Polar Surface Area: 137.26 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L328100

An oral ampicillin prodrug. Antibiotic used in the treatment of respiratory tract infections and urinary tract infections.

REFERENCES

• Saito, A. et al.: Chemother., 42, 209 (1983)
• Tsukamoto, G. et al.: Curr. Chemother. Immunother. Proc. Int. Congr. Chemother., 1, 142 (1983)
• Yamabe, S. et al.: Chemioterapia, 3, 60 (1983)