sulopenem   Click here for help

GtoPdb Ligand ID: 10862

Synonyms: CP-70,429 | CP-70429 | CP70429 | Orlynvah® (sulopenem etzadroxil and probenecid)
Approved drug
sulopenem is an approved drug (FDA (2024))
Compound class: Synthetic organic
Comment: Sulopenem is a β-lactam (carbapenem) antibacterial [4]. It has a broad-spectrum of activity against Gram-negative, Gram-positive and anaerobic bacteria, including multi-drug resistant Gram-negative infections in both the hospital and community settings. Sulopenem is relatively stable against hydrolysis by various β-lactamases. It is being developed for oral and parenteral administration.

sulopenem 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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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 4
Topological polar surface area 164.72
Molecular weight 349.01
XLogP -0.9
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 O=[S@@]1CC[C@@H](C1)SC1=C(C(=O)O)N2[C@H](S1)[C@H](C2=O)[C@H](O)C
Isomeric SMILES O=[S@@]1CC[C@@H](C1)SC1=C(C(=O)O)N2[C@H](S1)[C@H](C2=O)[C@H](O)C
InChI InChI=1S/C12H15NO5S3/c1-5(14)7-9(15)13-8(11(16)17)12(20-10(7)13)19-6-2-3-21(18)4-6/h5-7,10,14H,2-4H2,1H3,(H,16,17)/t5-,6+,7+,10-,21-/m1/s1
InChI Key FLSUCZWOEMTFAQ-PRBGKLEPSA-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/)
No information available.
Summary of Clinical Use Click here for help
Oral and i.v. sulopenem are being evaluated in three pivotal Phase 3 clinical trials of uncomplicated urinary tract infections, complicated urinary tract infections and complicated intra-abdominal infections (cIAI). All of these trials have been completed. Updates released online (in late 2019) indicate that the drug narrowly missed its primary endpoint in the cIAI study [6]. Results from the UTI studies have been posted with ClinicalTrials.gov.
The FDA approved use of sulopenem etzadroxil and probenecid (a renal tubular transport inhibitor) in October 2024, to treat women with uncomplicated urinary tract infections caused by certain susceptible microorganisms (Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis) for which there are limited/no alternative oral antibacterial treatments available.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT03354598 Oral Sulopenem-etzadroxil/Probenecid Versus Ciprofloxacin for Uncomplicated Urinary Tract Infection in Adult Women Phase 3 Interventional Iterum Therapeutics, International Limited
NCT03357614 Sulopenem Followed by Sulopenem-etzadroxil/Probenecid vs Ertapenem Followed by Cipro for Complicated UTI in Adults Phase 3 Interventional Iterum Therapeutics, International Limited 1-2
NCT03358576 Sulopenem Versus Ertapenem for Complicated Intra-abdominal Infection (cIAI) Phase 3 Interventional Iterum Therapeutics, International Limited