From August 18th 2026, GtoPdb will require users to register to use the website. Please see our blog post for more information.

tebipenem pivoxil   Click here for help

GtoPdb Ligand ID: 10864

Synonyms: L-084 | LJC 11,084 | LJC-11,084 | LJC-11084 | Orapenem® | TBPM-PI
Approved drug
tebipenem pivoxil is an approved drug (Japan)
Compound class: Synthetic organic
Comment: Tebipenem pivoxil is an orally available pivaloyloxymethyl ester prodrug of the β-lactam antibacterial tebipenem [1-2]. The ester bond is cleaved, releasing active tebipenem (PubChem CID 9800194; LJC-11036). The drug has Gram-negative activity. Tebipenem pivoxil hydrobromide (SPR994) is another formulation of the same drug.

tebipenem pivoxil 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 9
Hydrogen bond donors 1
Rotatable bonds 10
Topological polar surface area 159.34
Molecular weight 497.17
XLogP 1.96
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 C[C@H]([C@H]1C(=O)N2[C@@H]1[C@@H](C)C(=C2C(=O)OCOC(=O)C(C)(C)C)SC1CN(C1)C1=NCCS1)O
Isomeric SMILES C[C@H]([C@H]1C(=O)N2[C@@H]1[C@@H](C)C(=C2C(=O)OCOC(=O)C(C)(C)C)SC1CN(C1)C1=NCCS1)O
InChI InChI=1S/C22H31N3O6S2/c1-11-15-14(12(2)26)18(27)25(15)16(19(28)30-10-31-20(29)22(3,4)5)17(11)33-13-8-24(9-13)21-23-6-7-32-21/h11-15,26H,6-10H2,1-5H3/t11-,12-,14-,15-/m1/s1
InChI Key SNUDIPVBUUXCDG-QHSBEEBCSA-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/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. Japan PMDA (0)
IUPAC Name Click here for help
2,2-dimethylpropanoyloxymethyl (4R,5S,6S)-3-[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
International Nonproprietary Names Click here for help
INN number INN
7924 tebipenem pivoxil
Synonyms Click here for help
L-084 | LJC 11,084 | LJC-11,084 | LJC-11084 | Orapenem® | TBPM-PI
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Tebipenem
Other databases
CAS Registry No. 161715-24-8 (source: WHO INN record)
DrugCentral Ligand 2574
GtoPdb PubChem SID 405560305
PubChem CID 9892071
Search Google for chemical match using the InChIKey SNUDIPVBUUXCDG-QHSBEEBCSA-N
Search Google for chemicals with the same backbone SNUDIPVBUUXCDG
Search PubMed clinical trials tebipenem pivoxil
Search PubMed titles tebipenem pivoxil
Search PubMed titles/abstracts tebipenem pivoxil
UniChem Compound Search for chemical match using the InChIKey SNUDIPVBUUXCDG-QHSBEEBCSA-N
UniChem Connectivity Search for chemical match using the InChIKey SNUDIPVBUUXCDG-QHSBEEBCSA-N

Product suppliers

View disclaimer

Sponsored products disclaimer

Product supplier links are provided as a service to assist in identifying commercial suppliers of reagents that are mentioned on the IUPHAR/BPS Guide to PHARMACOLOGY database website, and do not imply their endorsement by NC-IUPHAR.

Links are provided in return for sponsorship, used to fund improvements to this database. The sponsorship account is managed and audited by the University of Edinburgh, a charitable body registered in Scotland, SC005336. If you are interested in sponsoring the database, please contact us.

✖

MedChemExpress
Tebipenem pivoxil (links to external site)
Cat. No. HY-B0396