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
Click here for help

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.

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

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.

✖
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
Click here for help

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/)

✖
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/)
References
1. Dunne MW, Aronin SI, Das AF, Akinapelli K, Breen J, Zelasky MT, Puttagunta S. (2023)
Sulopenem for the Treatment of Complicated Urinary Tract Infections Including Pyelonephritis: A Phase 3, Randomized Trial.
Clin Infect Dis, 76 (1): 78-88. [PMID:36068705]
2. Dunne MW, Aronin SI, Das AF, Akinapelli K, Zelasky MT, Puttagunta S, Boucher HW. (2023)
Sulopenem or Ciprofloxacin for the Treatment of Uncomplicated Urinary Tract Infections in Women: A Phase 3, Randomized Trial.
Clin Infect Dis, 76 (1): 66-77. [PMID:36069202]
3. Kosowska-Shick K, Ednie LM, McGhee P, Appelbaum PC. (2009)
Comparative antipneumococcal activities of sulopenem and other drugs.
Antimicrob Agents Chemother, 53 (6): 2239-47. [PMID:19307366]
4. Minamimura M, Taniyama Y, Inoue E, Mitsuhashi S. (1993)
In vitro antibacterial activity and beta-lactamase stability of CP-70,429 a new penem antibiotic.
Antimicrob Agents Chemother, 37 (7): 1547-51. [PMID:8363389]
5. Okamoto K, Gotoh N, Nishino T. (2001)
Pseudomonas aeruginosa reveals high intrinsic resistance to penem antibiotics: penem resistance mechanisms and their interplay.
Antimicrob Agents Chemother, 45 (7): 1964-71. [PMID:11408209]
6. thepharmaletter team. 
Iterum hopeful despite Phase III miss for sulopenem.
Accessed on 12/05/2020. Modified on 12/05/2020. thepharmaletter.com, https://www.thepharmaletter.com/article/iterum-hopeful-despite-phase-iii-miss-for-sulopenem