ampicillin   Click here for help

GtoPdb Ligand ID: 10896

Synonyms: aminobenzylpenicillin | KS-R1 | Penbritin® | Polycillin | Principen®
Approved drug PDB Ligand
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.
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2D Structure
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Physico-chemical Properties
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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
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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
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Summary of Clinical Use Click here for help
Ampicillin is administered orally (as the trihydrate) or by injection (as the sodium salt). It can be used to treat ear, nose and throat infections, bronchitis, pneumonia, urinary tract infections, gonorrhoea, gynaecological infections, septicaemia, peritonitis, endocarditis, meningitis, enteric fever, and gastro-intestinal infections.
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