Tebipenem | CAS#161715-21-5 | oral carbapenem antibiotic

MedKoo Cat#: 599052 | Name: Tebipenem

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Tebipenem is an oral carbapenem antibiotic, against penicillin-nonsusceptible Streptococcus pneumoniae.

Chemical Structure

Tebipenem

CAS#161715-21-5

Theoretical Analysis

MedKoo Cat#: 599052

Name: Tebipenem

CAS#: 161715-21-5

Chemical Formula: C16H21N3O4S2

Exact Mass: 383.0973

Molecular Weight: 383.48

Elemental Analysis: C, 50.11; H, 5.52; N, 10.96; O, 16.69; S, 16.72

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

161715-21-5 (Tebipenem) 161715-24-8 (pivoxil).

Synonym

Tebipenem; LJC-11036; LJC 11036; LJC11036;

IUPAC/Chemical Name

(4R,5S,6S)-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-carboxylic acid

InChi Key

GXXLUDOKHXEFBQ-YJFSRANCSA-N

InChi Code

InChI=1S/C16H21N3O4S2/c1-7-11-10(8(2)20)14(21)19(11)12(15(22)23)13(7)25-9-5-18(6-9)16-17-3-4-24-16/h7-11,20H,3-6H2,1-2H3,(H,22,23)/t7-,8-,10-,11-/m1/s1

SMILES Code

O=C1[C@H]([C@H](O)C)[C@@]2([H])[C@@H](C)C(SC3CN(C4=NCCS4)C3)=C(C(O)=O)N12

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 383.48 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Cielecka-Piontek J, Paczkowska M, Zalewski P, Talaczyńska A, Mizera M. Tebipenem pivoxyl. Derivative spectroscopy study of stability of the first oral carbapenem. Spectrochim Acta A Mol Biomol Spectrosc. 2015 Jan 25;135:14-9. doi: 10.1016/j.saa.2014.06.083. Epub 2014 Jun 23. PubMed PMID: 25036644. 2: Cielecka-Piontek J, Zalewski P, Paczkowska M. The chromatographic approach to kinetic studies of tebipenem pivoxil. J Chromatogr Sci. 2015 Feb;53(2):325-30. doi: 10.1093/chromsci/bmu063. Epub 2014 Jun 30. PubMed PMID: 24981980. 3: Mizera M, Talaczyńska A, Zalewski P, Skibiński R, Cielecka-Piontek J. Prediction of HPLC retention times of tebipenem pivoxyl and its degradation products in solid state by applying adaptive artificial neural network with recursive features elimination. Talanta. 2015 May;137:174-81. doi: 10.1016/j.talanta.2015.01.032. Epub 2015 Feb 4. PubMed PMID: 25770622. 4: Thamlikitkul V, Lorchirachoonkul N, Tiengrim S. In vitro and in vivo activity of tebipenem against ESBL-producing E. coli. J Med Assoc Thai. 2014 Dec;97(12):1259-68. PubMed PMID: 25764632. 5: Hazra S, Xu H, Blanchard JS. Tebipenem, a new carbapenem antibiotic, is a slow substrate that inhibits the β-lactamase from Mycobacterium tuberculosis. Biochemistry. 2014 Jun 10;53(22):3671-8. doi: 10.1021/bi500339j. Epub 2014 May 29. PubMed PMID: 24846409; PubMed Central PMCID: PMC4053071. 6: Talaczyńska A, Lewandowska K, Garbacki P, Zalewski P, Skibiński R, Miklaszewski A, Mizera M, Cielecka-Piontek J. Solid-state stability studies of crystal form of tebipenem. Drug Dev Ind Pharm. 2016;42(2):238-44. doi: 10.3109/03639045.2015.1044902. Epub 2015 Jun 5. PubMed PMID: 26043654. 7: Seenama C, Tiengrim S, Thamlikitkul V. In vitro activity of tebipenem against Burkholderia pseudomallei. Int J Antimicrob Agents. 2013 Oct;42(4):375. doi: 10.1016/j.ijantimicag.2013.06.016. Epub 2013 Aug 24. PubMed PMID: 23978354. 8: Li H, Wang Z, Zhang F, Wang Q, Chen H, Zhao C, Wang H. In vitro antibacterial activities of two novel oral antibiotics, tebipenem and cefditoren, and other comparators against community-acquired respiratory tract infection-associated bacterial pathogens: a multicentre study in China. Int J Antimicrob Agents. 2014 Jan;43(1):92-3. doi: 10.1016/j.ijantimicag.2013.09.009. Epub 2013 Oct 16. PubMed PMID: 24183753. 9: Cielecka-Piontek J, Zalewski P, Barszcz B, Lewandowska K, Paczkowska M. Stress Degradation Studies of Tebipenem and a Validated Stability-Indicating LC Method. Chromatographia. 2013 Apr;76(7-8):381-386. Epub 2012 Oct 5. PubMed PMID: 23555151; PubMed Central PMCID: PMC3612176. 10: Sugita R. Good transfer of tebipenem into middle ear effusion conduces to the favorable clinical outcomes of tebipenem pivoxil in pediatric patients with acute otitis media. J Infect Chemother. 2013 Jun;19(3):465-71. doi: 10.1007/s10156-012-0513-5. Epub 2013 Feb 8. PubMed PMID: 23393013. 11: Shihyakugari A, Miki A, Nakamoto N, Satoh H, Sawada Y. First case report of suspected onset of convulsive seizures due to co-administration of valproic acid and tebipenem. Int J Clin Pharmacol Ther. 2015 Jan;53(1):92-6. doi: 10.5414/CP202188. PubMed PMID: 25407257. 12: Yao Q, Wang J, Cui T, Yang Z, Su M, Zhao P, Yan H, Zhan Y, Yang H. Antibacterial Properties of Tebipenem Pivoxil Tablet, a New Oral Carbapenem Preparation against a Variety of Pathogenic Bacteria in Vitro and in Vivo. Molecules. 2016 Jan 6;21(1):62. doi: 10.3390/molecules21010062. PubMed PMID: 26751436. 13: Fujisaki M, Sadamoto S, Ikedo M, Totsuka K, Kaku M, Tateda K, Hirakata Y, Yamaguchi K. Development of interpretive criteria for tebipenem disk diffusion susceptibility testing with Staphylococcus spp. and Haemophilus influenzae. J Infect Chemother. 2011 Feb;17(1):17-23. doi: 10.1007/s10156-010-0091-3. Epub 2010 Jul 31. PubMed PMID: 20676913. 14: Kataoka H, Kasahara H, Sasagawa Y, Matsumoto M, Shimada S. [Evaluation of safety and efficacy of tebipenem pivoxil granules for pediatric in pneumonia, otitis media and sinusitis]. Jpn J Antibiot. 2016 Feb;69(1):53-76. Japanese. PubMed PMID: 27290830. 15: Muratani T, Doi K, Kobayashi T, Nakamura T, Matsumoto T. [Antimicrobial activity of tebipenem against various clinical isolates from various specimen, mainly urinary tract]. Jpn J Antibiot. 2009 Apr;62(2):116-26. Japanese. PubMed PMID: 19673353. 16: Kishii K, Chiba N, Morozumi M, Ono A, Ida T, Ubukata K. In vitro activity of tebipenem, a new oral carbapenem antibiotic, against beta-lactamase-nonproducing, ampicillin-resistant Haemophilus influenzae. Antimicrob Agents Chemother. 2010 Sep;54(9):3970-3. doi: 10.1128/AAC.00054-10. Epub 2010 Jun 28. PubMed PMID: 20585130; PubMed Central PMCID: PMC2934951. 17: Sakata H. [Clinical efficacy of tebipenem pivoxil treatment in children with pneumonia, who had no relief despite having administered oral beta-lactam antibiotics]. Jpn J Antibiot. 2011 Jun;64(3):171-7. Japanese. PubMed PMID: 21861308. 18: Kuroki H, Tateno N, Ikeda H, Saito N. Investigation of pneumonia-causing pathogenic organisms in children and the usefulness of tebipenem pivoxil for their treatment. J Infect Chemother. 2010 Aug;16(4):280-7. doi: 10.1007/s10156-010-0053-9. Epub 2010 Mar 31. PubMed PMID: 20352278. 19: Kato K, Shirasaka Y, Kuraoka E, Kikuchi A, Iguchi M, Suzuki H, Shibasaki S, Kurosawa T, Tamai I. Intestinal absorption mechanism of tebipenem pivoxil, a novel oral carbapenem: involvement of human OATP family in apical membrane transport. Mol Pharm. 2010 Oct 4;7(5):1747-56. doi: 10.1021/mp100130b. Epub 2010 Sep 3. PubMed PMID: 20735088. 20: Kobayashi R, Konomi M, Hasegawa K, Morozumi M, Sunakawa K, Ubukata K. In vitro activity of tebipenem, a new oral carbapenem antibiotic, against penicillin-nonsusceptible Streptococcus pneumoniae. Antimicrob Agents Chemother. 2005 Mar;49(3):889-94. PubMed PMID: 15728880; PubMed Central PMCID: PMC549228.