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 antibacterial. 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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1965))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
Prodrug hetacillinmetampicillintalampicillinsultamicillinbacampicillinpivampicillin
IUPAC Name Click here for help
(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 Click here for help
INN number INN
1339 ampicillin
Synonyms Click here for help
aminobenzylpenicillin | KS-R1 | Penbritin® | Polycillin | Principen®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Ampicillin
Other databases
BindingDB Ligand 50350465
CAS Registry No. 69-52-3 (source: WHO INN record)
DrugBank Ligand DB00415
DrugCentral Ligand 198
GtoPdb PubChem SID 405560337
PubChem CID 6249
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UniChem Compound Search for chemical match using the InChIKey AVKUERGKIZMTKX-NJBDSQKTSA-N
UniChem Connectivity Search for chemical match using the InChIKey AVKUERGKIZMTKX-NJBDSQKTSA-N