Tebipenem

Tebipenem

Tebipenem pivoxil
Systematic (IUPAC) name
(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
Clinical data
Trade names	Orapenem
Legal status	Prescription-only in Japan; investigational elsewhere
Routes of administration	Oral
Identifiers
CAS Number	161715-24-8
PDB ligand ID	1TE (PDBe, RCSB PDB)
Chemical data
Formula	C22H31N3O6S2
Molar mass	497.63 g/mol
SMILES [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

Tebipenem (brand name: Orapenem) is a broad-spectrum orally-administered antibiotic, from the carbapenem subgroup of β-lactam antibiotics. It was developed as a replacement drug to combat bacteria that had acquired antibiotic resistance to commonly used antibiotics.^[1][2] Tebipenem is formulated as the ester tebipenem pivoxil due to the better absorption and improved bioavailability of this form.^[3] It has performed well in clinical trials for ear infection and looks likely to be further developed in future.^[4] It is only marketed in Japan.^[5] Tebipenem is the first carbapenem whose prodrug form, the pivalyl ester, is orally available.^[6]

References

1. El-Gamal, M. I.; Oh, C. H. (2010). "Current status of carbapenem antibiotics". Current topics in medicinal chemistry 10 (18): 1882–1897. doi:10.2174/156802610793176639. PMID 20615191.
2. Fujimoto, K.; Takemoto, K.; Hatano, K.; Nakai, T.; Terashita, S.; Matsumoto, M.; Eriguchi, Y.; Eguchi, K.; Shimizudani, T.; Sato, K.; Kanazawa, K.; Sunagawa, M.; Ueda, Y. (2012). "Novel Carbapenem Antibiotics for Parenteral and Oral Applications: In Vitro and in Vivo Activities of 2-Aryl Carbapenems and Their Pharmacokinetics in Laboratory Animals". Antimicrobial Agents and Chemotherapy 57 (2): 697–707. doi:10.1128/AAC.01051-12. PMC 3553697. PMID 23147735.
3. Kato, K.; Shirasaka, Y.; Kuraoka, E.; Kikuchi, A.; Iguchi, M.; Suzuki, H.; Shibasaki, S.; Kurosawa, T.; Tamai, I. (2010). "Intestinal Absorption Mechanism of Tebipenem Pivoxil, a Novel Oral Carbapenem: Involvement of Human OATP Family in Apical Membrane Transport". Molecular Pharmaceutics 7 (5): 1747–1756. doi:10.1021/mp100130b. PMID 20735088.
4. Sugita, R. (2013). "Good transfer of tebipenem into middle ear effusion conduces to the favorable clinical outcomes of tebipenem pivoxil in pediatric patients with acute otitis media". Journal of Infection and Chemotherapy 19 (3): 465–471. doi:10.1007/s10156-012-0513-5. PMID 23393013.
5. Rossi, S, ed. (7 August 2014). "Tebipenem Pivoxil". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 6 April 2015.
6. Hazra, S; Xu, H; Blanchard, J (June 2014). "Tebipenem, a New Carbapenem Antibiotic is a Slow Substrate that Inhibits the β-Lactamase from Mycobacterium tuberculosis" (PDF). Biochemistry. 53(22): 3671–3678. doi:10.1021/bi500339j. PMID 24846409.