penamecillin

Also known as acetyloxymethyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Penamecillin, an acetoxymethyl ester of benzylpenicillin, is a prodrug processed to benzylpenicillin by esterases. It has no detectable teratogenic risk to the fetus.

In the Vinony graph

Within Vinony's link graph, penamecillin is referenced by 185 other articles, and connects out to antibiotic, ceftolozane/tazobactam and penicillin.

It sits within the topics Chemical pages without DrugBank identifier, Drugboxes which contain changes to verified fields and Drugboxes which contain changes to watched fields.

Its subject is documented across 9 Wikipedia language editions.

Chemical data

Formula: C19H22N2O6S
Molecular weight: 406.5 g/mol
IUPAC name: acetyloxymethyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
SMILES: CC(=O)OCOC(=O)[C@H]1C(S[C@H]2N1C(=O)[C@H]2NC(=O)CC3=CC=CC=C3)(C)C
InChIKey: NLOOMWLTUVBWAW-HLLBOEOZSA-N
XLogP: 2.1
Polar surface area: 127 Å²
H-bond donors: 1
H-bond acceptors: 7
Formal charge: 0

via PubChem

Wikidata facts

Subclass of: chemical compound
Mass: 406.119857

Show 4 more facts

chemical formula: C₁₉H₂₂N₂O₆S
canonical SMILES: CC(=O)OCOC(=O)C1C(SC2N1C(=O)C2NC(=O)CC3=CC=CC=C3)(C)C
isomeric SMILES: CC(=O)OCOC(=O)[C@H]1C(S[C@H]2N1C(=O)[C@H]2NC(=O)CC3=CC=CC=C3)(C)C
Commons category: Penamecillin

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Encyclopedic overview

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Contents

References

Penamecillin, an acetoxymethyl ester of benzylpenicillin, is a prodrug processed to benzylpenicillin by esterases. It has no detectable teratogenic risk to the fetus.

== References ==

Excerpted from Wikipedia’s “penamecillin” article, available under the CC BY-SA 4.0 licence.