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Tebipenem pivoxil

Chemical compound From Wikipedia, the free encyclopedia

Tebipenem pivoxil, sold under the brand name Orapenem among others, is a beta-lactam antibiotic medication used for the treatment of complicated urinary tract infections, including pyelonephritis.[1] It is a broad-spectrum orally-administered antibiotic, from the carbapenem subgroup of beta-lactam antibiotics.[1] It was developed as a novel drug to combat bacteria that had acquired antibiotic resistance to commonly used antibiotics.[2][3] Tebipenem is the first carbapenem whose prodrug form is orally available.[4]

Trade namesOrapenem, others
Other namesTebipenem pivoxil hydrobromide (USAN US)
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Quick facts Clinical data, Trade names ...
Tebipenem pivoxil
Tebipenem pivoxil
Clinical data
Trade namesOrapenem, others
Other namesTebipenem pivoxil hydrobromide (USAN US)
AHFS/Drugs.comutebzi
License data
Routes of
administration
By mouth
Drug classBeta-lactam antibiotic
ATC code
Legal status
Legal status
Identifiers
  • (4R,5S,6S)-(Pivaloyloxy)methyl 3-((1-(4,5-dihydrothiazol-2-yl)azetidin-3-yl)thio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
CAS Number
PubChem CID
UNII
KEGG
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H31N3O6S2
Molar mass497.63 g·mol−1
3D model (JSmol)
  • [H][C@]12N(C(C(OCOC(C(C)(C)C)=O)=O)=C(SC3CN(C4=NCCS4)C3)[C@@H]2C)C([C@@]1([C@H](O)C)[H])=O
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The most common side effects include diarrhea, headache, nausea, abdominal pain, increased liver enzymes, and Clostridioides difficile infection.[5]

Medical uses

Tebipenem pivoxil is indicated for the treatment of complicated urinary tract infections, including pyelonephritis, caused by the following susceptible microorganisms: Escherichia coli, Klebsiella pneumoniae, Enterobacter cloacae species complex, Klebsiella oxytoca, and Enterococcus faecalis in adults who have limited or no alternative oral treatment options.[1]

In Japan, tebipenem pivoxil is approved for the treatment of haemophilus infections and streptococcal infections.[6]

Side effects

The most common side effects include diarrhea, headache, nausea, abdominal pain, increased liver enzymes, and Clostridioides difficile infection.[5]

History

The efficacy of tebipenem pivoxil was evaluated in adults with cUTI, including pyelonephritis, in a global, randomized, double-blind, double-dummy, noninferiority trial (NCT06059846).[5] In this trial, 1,690 hospitalized participants were randomly assigned to receive tebipenem pivoxil 600 mg orally every 6 hours or imipenem-cilastatin 500 mg intravenously every 6 hours for 7 to 10 days.[5] A total of 929 participants were considered the “intent-to-treat” population.[5]

Society and culture

Tebipenem pivoxil was approved for medical use in Japan in April 2009,[7] and in the United States in June 2026.[5]

Names

Tebipenem pivoxil is the international nonproprietary name.[8]

Tebipenem pivoxil is sold under the brand names Orapenem and Utebzi.[1][9]

References

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