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faropenem   Click here for help

GtoPdb Ligand ID: 10808

Synonyms: compound 1 [PMID: 9216830] | faropenem medoxomil | fropenem
Approved drug PDB Ligand
faropenem is an approved drug (Japan)
Compound class: Synthetic organic
Comment: Faropenem is a β-lactam antibacterial with Gram-negative activity. It was developed for the treatment of community acquired pneumonia.

faropenem is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 112.37
Molecular weight 285.07
XLogP -0.22
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES C[C@H]([C@H]1C(=O)N2[C@@H]1SC(=C2C(=O)O)[C@H]1CCCO1)O
Isomeric SMILES C[C@H]([C@H]1C(=O)N2[C@@H]1SC(=C2C(=O)O)[C@H]1CCCO1)O
InChI InChI=1S/C12H15NO5S/c1-5(14)7-10(15)13-8(12(16)17)9(19-11(7)13)6-3-2-4-18-6/h5-7,11,14H,2-4H2,1H3,(H,16,17)/t5-,6-,7+,11-/m1/s1
InChI Key HGGAKXAHAYOLDJ-FHZUQPTBSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Gandra S, Takahashi S, Mitrani-Gold FS, Mulgirigama A, Ferrinho DA. (2022)
A systematic scoping review of faropenem and other oral penems: treatment of Enterobacterales infections, development of resistance and cross-resistance to carbapenems.
JAC Antimicrob Resist, 4 (6): dlac125. [PMID:36570688]
2. Ishiguro M, Tanaka R, Namikawa K, Nasu T, Inoue H, Nakatsuka T, Oyama Y, Imajo S. (1997)
5,6-Cis-penems: broad-spectrum anti-methicillin-resistant Staphylococcus aureus beta-lactam antibiotics.
J Med Chem, 40 (14): 2126-32. [PMID:9216830]
3. (2008)
Faropenem medoxomil: A0026, BAY 56-6854, BAY 566854, faropenem daloxate, SUN 208, SUN A0026.
Drugs R D, 9 (2): 115-24. [PMID:18298129]