Lenapenem
Basic information
- CAS
149882-71-3- Standard SMILES
CNCC[C@@H](O)[C@@H]1C[C@H](SC2=C(C(=O)O)N3C(=O)[C@H]([C@@H](C)O)[C@H]3[C@H]2C)CN1- InChIKey
PZLOCBSBEUDCPF-YJIVIRPOSA-N- Molecular formula
- C18H29N3O5S
- Average molar mass
- 399.5 g/mol
- Monoisotopic mass
- 399.18279221
Overview
Lenapenem is a broad-spectrum, carbapenem antibiotic with bactericidal activity. Lenapenem binds to penicillin binding proteins (PBPs) located on the bacterial cell wall, thereby inhibiting the final transpeptidation step in the synthesis of peptidoglycan, an essential component of the bacterial cell wall. This inhibition weakens the bacterial cell wall and leads to lytic cell death in a wide range of Gram-positive and Gram-negative aerobic and anaerobic pathogens.
Names & identifiers
- Preferred name
- Lenapenem
- IUPAC
- (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-3-[(3S,5S)-5-[(1R)-1-hydroxy-3-(methylamino)propyl]pyrrolidin-3-yl]sulfanyl-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Names & synonyms
Lenapenem149951-16-6Lenapenem [INN](4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-3-[(3S,5S)-5-[(1R)-1-hydroxy-3-(methylamino)propyl]pyrrolidin-3-yl]sulfanyl-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acidD6NBQ3H12U(+)-(4R,5S,6S)-6-((R)-1-Hydroxyethyl)-3-(((3S,5S)-5-((R)-1-hydroxy-3-(methylamino)propyl)-3-pyrrolidinyl)thio)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid149882-71-3UNII-D6NBQ3H12U6-(1-hydroxyethyl)-2-(5-(1-hydroxy-3-N-methylaminopropyl)pyrrolidin-3-ylthio)1-methyl-1-carbapen-2-em-3-carboxylic acid hydrochloride hydrateSCHEMBL75702CHEMBL3989459GTPL10825
Show more names
DTXSID701031259BO2727(4R,5S,6S)-3-(((3S,5S)-5-((R)-1-hydroxy-3-(methylamino)propyl)pyrrolidin-3-yl)thio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acidDA-64916HY-105180CS-0025215NS00124580L-739,428
Database identifiers
Properties
Computed structural properties
- XLogP
- -2.5
- Topological polar surface area
- 147 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 8
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 642
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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