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avibactam tomilopil   Click here for help

GtoPdb Ligand ID: 12949

Synonyms: ARX-1796 | AV-006 | PF-07338233
Compound class: Synthetic organic
Comment: Avibactam tomilopil is an orally available prodrug of the β-lactamase inhibitor avibactam [1]. Pfizer are developing an oral combined formulation of avibactam tomilopil and ceftibuten for the treatment of complicated urinary tract infections (cUTIs) [2].

avibactam tomilopil 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 9
Hydrogen bond donors 1
Rotatable bonds 9
Topological polar surface area 153.92
Molecular weight 393.41
XLogP -2.46
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 CCOC(=O)C(C)(C)COS(=O)(=O)ON1[C@@H]2CC[C@@H](C(=O)N)N(C2)C1=O
Isomeric SMILES CCOC(=O)C(C)(C)COS(=O)(=O)ON1[C@@H]2CC[C@H](N(C2)C1=O)C(=O)N
InChI InChI=1S/C14H23N3O8S/c1-4-23-12(19)14(2,3)8-24-26(21,22)25-17-9-5-6-10(11(15)18)16(7-9)13(17)20/h9-10H,4-8H2,1-3H3,(H2,15,18)/t9-,10+/m1/s1
InChI Key JHSLCXRZVJOZQZ-ZJUUUORDSA-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. Gordon EM, Duncton MAJ, Gallop MA. (2018)
Orally Absorbed Derivatives of the β-Lactamase Inhibitor Avibactam. Design of Novel Prodrugs of Sulfate Containing Drugs.
J Med Chem, 61 (22): 10340-10344. [PMID:30296086]
2. Huband MD, Fedler KA, Sader HS, Stone GG, Castanheira M. (2023)
Determination of MIC Quality Control Ranges for Ceftibuten-Avibactam (Fixed 4 μg/mL), a Novel β-Lactam/β-Lactamase Inhibitor Combination.
J Clin Microbiol, 61 (7): e0165722. [PMID:37395644]