Basic information
- CAS
42190-91-0- Standard SMILES
CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@H](N)c3ccccc3)[C@H]2SC1(C)C.CCCN(CCC)S(=O)(=O)c1ccc(C(=O)O)cc1- InChIKey
LKZFWYIOFQDUMO-GLCLSGQWSA-N- Molecular formula
- C35H48N4O10S2
- Average molar mass
- 748.9 g/mol
- Monoisotopic mass
- 748.28118609
Overview
Pivampicillin Probenate is the probenate salt form of pivampicillin, a semisynthetic, orally active pivalate ester of ampenicillin with antibacterial activity. Upon absorption, pivampicillin is hydrolyzed into its active form ampicillin by esterases. Ampicillin binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This interrupts bacterial cell wall synthesis and results in the weakening of the bacterial cell wall and eventually causing cell lysis.
Names & identifiers
- Preferred name
- Pivampicillin Probenate
- IUPAC
- 2,2-dimethylpropanoyloxymethyl (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;4-(dipropylsulfamoyl)benzoic acid
Names & synonyms
Pivampicillin probenate42190-91-0M3MYK6R22UDTXSID00195021RefChem:174633DTXCID10117512(2S-(2 alpha,5 alpha,6 beta(S*)))-6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, (2,2-dimethyl-1-oxopropoxy)methyl ester, mono(4-((dipropylamino)sulfonyl)benzoate)Pivampicillin probenate [USAN]2,2-dimethylpropanoyloxymethyl (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;4-(dipropylsulfamoyl)benzoic acidPivampicillin probenate (USAN)UNII-M3MYK6R22USCHEMBL192174
Show more names
MK 356Hydroxymethyl D-(-)-6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate pivalate (ester) compound with p-(dipropylsulfamoyl)benzoic acid (1:1)D05521Q27283448(2S-(2alpha,5alpha,6beta(S*)))-6-((Aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, (2,2-dimethyl-1-oxopropoxy)methyl ester, mono(4-((dipropylamino)sulfonyl)benzoate)4-(Dipropylsulfamoyl)benzoic acid--[(2,2-dimethylpropanoyl)oxy]methyl (2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate (1/1)4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, (2S-(2alpha,5alpha,6beta(S*)))-, mono(4-((dipropylamino)sulfonyl)benzoate) (1:1)
Properties
Computed structural properties
- Topological polar surface area
- 236 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 13
- Rotatable bonds
- 16
- Heavy atoms
- 51
- Formal charge
- 0
- Complexity
- 1,150
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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