CAS 94935-63-4

Ampicillin-sulbactam

Description:

Ampicillin-sulbactam is a combination antibiotic that consists of ampicillin, a penicillin derivative, and sulbactam, a beta-lactamase inhibitor. This combination enhances the efficacy of ampicillin against a broader spectrum of bacteria, particularly those that produce beta-lactamase enzymes, which can inactivate many penicillins. Ampicillin itself is effective against various gram-positive and some gram-negative bacteria, while sulbactam protects ampicillin from degradation. The substance is typically administered via injection and is used to treat a range of infections, including respiratory tract infections, urinary tract infections, and skin infections. Its mechanism of action involves inhibiting bacterial cell wall synthesis, leading to cell lysis and death. Ampicillin-sulbactam is generally well-tolerated, but potential side effects may include allergic reactions, gastrointestinal disturbances, and alterations in liver function tests. The combination is particularly valuable in clinical settings due to its ability to combat resistant strains of bacteria, making it an important tool in the treatment of infectious diseases.

Formula: C₁₆H₁₉N₃O₄S·C₈H₁₁NO₅S

InChI: InChI=1S/C16H19N3O4S.C8H11NO5S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8;1-8(2)6(7(11)12)9-4(10)3-5(9)15(8,13)14/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23);5-6H,3H2,1-2H3,(H,11,12)/t9-,10-,11+,14-;5-,6+/m11/s1

InChI key: InChIKey=XBKAJGGBQLRIFJ-OUPOZMNRSA-N

SMILES: C(O)(=O)[C@@H]1N2[C@](S(=O)(=O)C1(C)C)(CC2=O)[H].C(O)(=O)[C@@H]1N2[C@@]([C@H](NC([C@H](N)C3=CC=CC=C3)=O)C2=O)(SC1(C)C)[H]

Synonyms:

• 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2R)-aminophenylacetyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-, mixt. with (2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide
• 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-, 4,4-dioxide, (2S-cis)-, mixt. contg.
• 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-, mixt. with (2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide
• 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-, 4,4-dioxide, (2S,5R)-, mixt. contg.
• 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-, [2S-[2α,5α,6β(S*)]]-, mixt. with (2S-cis)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide

Ampicillin-sulbactam

CAS: 94935-63-4

Ampicillin-sulbactam is a combination antibiotic, which is a pharmaceutical product derived from the penicillin class of beta-lactam antibiotics. Its source involves semi-synthetic processes, combining ampicillin with sulbactam. The mode of action of this compound is through the inhibition of bacterial cell wall synthesis. Ampicillin specifically binds to penicillin-binding proteins, thereby disrupting the cross-linking process essential for maintaining cell wall structural integrity, leading to bacterial lysis. Sulbactam functions as a beta-lactamase inhibitor, enhancing the efficacy of ampicillin by preventing its degradation by beta-lactamase enzymes produced by certain resistant bacterial strains.

Formula: C₂₅H₃₁N₃O₉S₂

Purity: Min. 95%

Molecular weight: 581.7 g/mol

Ref: 3D-UDA93563