CAS 87-53-6

Penicillanic acid

Description:

Penicillanic acid, with the CAS number 87-53-6, is a beta-lactam compound that serves as a key structural component of penicillin antibiotics. It is characterized by its bicyclic structure, which includes a thiazolidine ring fused to a beta-lactam ring. This compound is primarily known for its role in the synthesis of various penicillin derivatives, which exhibit antibacterial properties by inhibiting bacterial cell wall synthesis. Penicillanic acid is typically a white to off-white crystalline solid, and it is soluble in water and polar organic solvents. Its molecular structure allows it to interact with penicillin-binding proteins in bacteria, leading to cell lysis and death. The compound is sensitive to hydrolysis, particularly in the presence of acids or bases, which can affect its stability and efficacy. Due to its importance in medicinal chemistry, penicillanic acid is a crucial intermediate in the production of antibiotics used to treat a wide range of bacterial infections.

Formula: C₈H₁₁NO₃S

InChI: InChI=1S/C8H11NO3S/c1-8(2)6(7(11)12)9-4(10)3-5(9)13-8/h5-6H,3H2,1-2H3,(H,11,12)/t5-,6+/m1/s1

InChI key: InChIKey=RBKMMJSQKNKNEV-RITPCOANSA-N

SMILES: C(O)(=O)[C@@H]1N2[C@](SC1(C)C)(CC2=O)[H]

Synonyms:

• (2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-
• 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-, (2S,5R)-
• 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-, (2S-cis)-
• Penicillanic acid

(2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

CAS: 87-53-6

Formula: C₈H₁₁NO₃S

Molecular weight: 201.2428

Ref: IN-DA004DE5

Penicillanic Acid Sodium Salt-d2

Controlled Product

CAS: 4027-62-7, 77741-85-6, 87-53-6

Applications Penicillanic Acid Sodium Salt-d2 is an intermediate in the synthesis of Tazobactam-d4 which is the labeled analog of Tazobactam (T010095), a β-Lactamase inhibitor, used with β-lactam antibiotics to enhance their effect.
References Gould, I.M., et al.: Drugs Exp. Clin. Res., 17, 187 (1991); Roland, R.K., et al.: J. Infect. Dis., 4, 226 (2000); Bonomo, R.A., et al.: Biochim. Biophys. Acta, 1547, 196 (2001)

Formula: C₈H₈D₂NNaO₃S

Color and Shape: Neat

Molecular weight: 225.24

Ref: TR-P223537