bacampicillin   Click here for help

GtoPdb Ligand ID: 12292

Synonyms: Penglobe® | Spectrobid®
Approved drug
bacampicillin is an approved drug (FDA (1980))
Compound class: Synthetic organic
Comment: Bacampicillin is a semisynthetic penicillin belonging to the β-lactam group of antibacterial compounds. It is a prodrug that is hydrolysed to ampicillin following absorption from the gastrointestinal tract [1].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 10
Hydrogen bond donors 2
Rotatable bonds 11
Topological polar surface area 162.56
Molecular weight 465.16
XLogP 1.98
No. Lipinski's rules broken 0
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Canonical SMILES CCOC(=O)OC(OC(=O)[C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)NC(=O)[C@@H](c1ccccc1)N)C
Isomeric SMILES CCOC(=O)OC(C)OC(=O)[C@H]1C(S[C@H]2N1C(=O)[C@H]2NC(=O)[C@@H](c1ccccc1)N)(C)C
InChI InChI=1S/C21H27N3O7S/c1-5-29-20(28)31-11(2)30-19(27)15-21(3,4)32-18-14(17(26)24(15)18)23-16(25)13(22)12-9-7-6-8-10-12/h6-11,13-15,18H,5,22H2,1-4H3,(H,23,25)/t11?,13-,14-,15+,18-/m1/s1
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1980))
Is prodrug? Yes
Active form ampicillin
IUPAC Name Click here for help
1-ethoxycarbonyloxyethyl (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
International Nonproprietary Names Click here for help
INN number INN
3630 bacampicillin
Synonyms Click here for help
Penglobe® | Spectrobid®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Bacampicillin
Other databases
CAS Registry No. 50972-17-3 (source: Scifinder)
ChEMBL Ligand CHEMBL1583
DrugBank Ligand DB01602
DrugCentral Ligand 280
GtoPdb PubChem SID 479821083
PubChem CID 441397
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UniChem Compound Search for chemical match using the InChIKey PFOLLRNADZZWEX-FFGRCDKISA-N
UniChem Connectivity Search for chemical match using the InChIKey PFOLLRNADZZWEX-FFGRCDKISA-N