ampicillin   

GtoPdb Ligand ID: 10896

Synonyms: aminobenzylpenicillin | KS-R1 | Penbritin® | Polycillin | Principen®
ampicillin is an approved drug (FDA (1965))
Compound class: Synthetic organic
Comment: Ampicillin is a broad-spectrum, semi-synthetic, β-lactam penicillin class antibiotic. It is resistant to hydrolysis by a variety of β-lactamases, so can be to treat a diverse range of infections caused by Gram-positive and Gram-negative infections.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 138.03
Molecular weight 349.11
XLogP -1.73
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES N[C@H](c1ccccc1)C(=O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C
Isomeric SMILES N[C@H](c1ccccc1)C(=O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C
InChI InChI=1S/C16H19N3O4S/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/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1
InChI Key AVKUERGKIZMTKX-NJBDSQKTSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1965))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
(2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
International Nonproprietary Names
INN number INN
1339 ampicillin
Synonyms
aminobenzylpenicillin | KS-R1 | Penbritin® | Polycillin | Principen®
Database Links
BindingDB Ligand 50350465
CAS Registry No. 69-52-3 (source: WHO INN record)
ChEMBL Ligand CHEMBL174
DrugBank Ligand DB00415
GtoPdb PubChem SID 405560337
PubChem CID 6249
RCSB PDB Ligand AIC
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