Tebipenem hydrate | CAS#unknown | Carbenapenem antibiotic

MedKoo Cat#: 464716 | Name: Tebipenem hydrate

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Description:

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

Tebipenem is a carbenapenem antibiotic. It is active against a panel of clinical isolates from a variety of bacterial species (MIC50s = ≤0.0039-8 µg/ml), including methicillin-resistant strains of S. aureus and S. epidermidis and penicillin-resistant S. pneumoniae. Tebipenem inhibits β-lactamase in a concentration-dependent manner. It decreases the number of colony forming units (CFUs) in the lungs in a mouse model of penicillin-resistant S. pneumoniae infection when administered at doses ranging from 0.32 to 3.2 mg/kg.

Chemical Structure

Tebipenem hydrate

CAS#unknown

Theoretical Analysis

MedKoo Cat#: 464716

Name: Tebipenem hydrate

CAS#: unknown

Chemical Formula: C16H23N3O6S2

Exact Mass: 417.1028

Molecular Weight: 417.50

Elemental Analysis: C, 46.03; H, 5.55; N, 10.07; O, 22.99; S, 15.36

Price and Availability

Size	Price	Availability
250mg	USD 550.00	2 Weeks
500mg	USD 950.00	2 Weeks
1g	USD 1,650.00	2 Weeks

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Related CAS #

161715-21-5 (free)

Synonym

Tebipenem hydrate; LJC 11,036; LJC11,036; LJC-11,036; SPR859; SPR 859; SPR-859; TBPM;

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-carboperoxoic acid hydrate

InChi Key

KHAOTBZKZPHGEU-PIFQMSPBSA-N

InChi Code

InChI=1S/C16H21N3O5S2.H2O/c1-7-11-10(8(2)20)14(21)19(11)12(15(22)24-23)13(7)26-9-5-18(6-9)16-17-3-4-25-16;/h7-11,20,23H,3-6H2,1-2H3;1H2/t7-,8-,10-,11-;/m1./s1

SMILES Code

OOC(C1=C([C@@H]([C@@]([H])(N1C2=O)[C@@]2([H])[C@@H](C)O)C)SC3CN(C3)C4=NCCS4)=O.O

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

	Solvent	mg/mL	mM
Solubility
	DMSO	1.0	2.40
	PBS (pH 7.2)	1.0	2.40

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 417.50 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: Chatwin CL, Hamrick JC, Trout REL, Myers CL, Cusick SM, Weiss WJ, Pulse ME, Xerri L, Burns CJ, Moeck G, Daigle DM, John K, Uehara T, Pevear DC. Microbiological characterization of VNRX-5236: a broad spectrum β-lactamase inhibitor for rescue of the orally bioavailable cephalosporin ceftibuten as a carbapenem-sparing agent against strains of Enterobacterales expressing extended spectrum β-lactamases and serine carbapenemases. Antimicrob Agents Chemother. 2021 May 17:AAC.00552-21. doi: 10.1128/AAC.00552-21. Epub ahead of print. PMID: 34001510. 2: Gupta VK, Maier G, Eckburg P, Morelli L, Lei Y, Jain A, Manyak E, Melnick D. A Randomized, Double-blind, Placebo- and Positive-controlled Crossover Study of the Effects of Tebipenem Pivoxil Hydrobromide on QT/QTc Intervals in Healthy Subjects. Antimicrob Agents Chemother. 2021 Apr 19:AAC.00145-21. doi: 10.1128/AAC.00145-21. Epub ahead of print. PMID: 33875429. 3: Clayton NP, Jain A, Halasohoris SA, Pysz LM, Lembirik S, Zumbrun SD, Kane CD, Hackett MJ, Pfefferle D, Smiley MA, Anderson MS, Heine H, Meister GT, Pucci MJ. In Vitro and In Vivo Characterization of Tebipenem (TBP), an Orally Active Carbapenem, against Biothreat Pathogens. Antimicrob Agents Chemother. 2021 Feb 16;65(5):e02385-20. doi: 10.1128/AAC.02385-20. Epub ahead of print. PMID: 33593844; PMCID: PMC8092902. 4: Cotroneo N, Rubio A, Critchley IA, Pillar C, Pucci MJ. In Vitro and In Vivo Characterization of Tebipenem, an Oral Carbapenem. Antimicrob Agents Chemother. 2020 Jul 22;64(8):e02240-19. doi: 10.1128/AAC.02240-19. PMID: 32423950; PMCID: PMC7526814. 5: Lomovskaya O, Tsivkovski R, Nelson K, Rubio-Aparicio D, Sun D, Totrov M, Dudley MN. Spectrum of Beta-Lactamase Inhibition by the Cyclic Boronate QPX7728, an Ultrabroad-Spectrum Beta-Lactamase Inhibitor of Serine and Metallo-Beta- Lactamases: Enhancement of Activity of Multiple Antibiotics against Isogenic Strains Expressing Single Beta-Lactamases. Antimicrob Agents Chemother. 2020 May 21;64(6):e00212-20. doi: 10.1128/AAC.00212-20. PMID: 32229489; PMCID: PMC7269471. 6: Gumbo T, Cirrincione K, Srivastava S. Repurposing drugs for treatment of Mycobacterium abscessus: a view to a kill. J Antimicrob Chemother. 2020 May 1;75(5):1212-1217. doi: 10.1093/jac/dkz523. PMID: 32016429. 7: Eckburg PB, Jain A, Walpole S, Moore G, Utley L, Manyak E, Dane A, Melnick D. Safety, Pharmacokinetics, and Food Effect of Tebipenem Pivoxil Hydrobromide after Single and Multiple Ascending Oral Doses in Healthy Adult Subjects. Antimicrob Agents Chemother. 2019 Aug 23;63(9):e00618-19. doi: 10.1128/AAC.00618-19. PMID: 31262768; PMCID: PMC6709501. 8: McEntee L, Johnson A, Farrington N, Unsworth J, Dane A, Jain A, Cotroneo N, Critchley I, Melnick D, Parr T, Ambrose PG, Das S, Hope W. Pharmacodynamics of Tebipenem: New Options for Oral Treatment of Multidrug-Resistant Gram-Negative Infections. Antimicrob Agents Chemother. 2019 Jul 25;63(8):e00603-19. doi: 10.1128/AAC.00603-19. PMID: 31109982; PMCID: PMC6658774. 9: Ubukata K, Morozumi M, Sakuma M, Adachi Y, Mokuno E, Tajima T, Iwata S; AOM Surveillance Study Group. Genetic characteristics and antibiotic resistance of Haemophilus influenzae isolates from pediatric patients with acute otitis media after introduction of 13-valent pneumococcal conjugate vaccine in Japan. J Infect Chemother. 2019 Sep;25(9):720-726. doi: 10.1016/j.jiac.2019.03.019. Epub 2019 Apr 12. PMID: 30987951. 10: Arends SJR, Rhomberg PR, Cotroneo N, Rubio A, Flamm RK, Mendes RE. Antimicrobial Activity Evaluation of Tebipenem (SPR859), an Orally Available Carbapenem, against a Global Set of Enterobacteriaceae Isolates, Including a Challenge Set of Organisms. Antimicrob Agents Chemother. 2019 May 24;63(6):e02618-18. doi: 10.1128/AAC.02618-18. PMID: 30936096; PMCID: PMC6535533. 11: Xue S, Qin Z, Ren G, Yang Z, Lu Y, Zhang Y, Li N, Chen X, Zhao D. A validated UPLC-MS/MS method for determination of tebipenem in human plasma and its application to a pharmacokinetic study in healthy volunteers. J Pharm Biomed Anal. 2019 Jun 5;170:30-39. doi: 10.1016/j.jpba.2019.03.010. Epub 2019 Mar 6. PMID: 30903927. 12: Lacasse E, Brouillette E, Larose A, Parr TR Jr, Rubio A, Malouin F. In Vitro Activity of Tebipenem (SPR859) against Penicillin-Binding Proteins of Gram-Negative and Gram-Positive Bacteria. Antimicrob Agents Chemother. 2019 Mar 27;63(4):e02181-18. doi: 10.1128/AAC.02181-18. PMID: 30718255; PMCID: PMC6437484. 13: Paczkowska M, Szymanowska-Powałowska D, Mizera M, Siąkowska D, Błaszczak W, Piotrowska-Kempisty H, Cielecka-Piontek J. Cyclodextrins as multifunctional excipients: Influence of inclusion into β-cyclodextrin on physicochemical and biological properties of tebipenem pivoxil. PLoS One. 2019 Jan 25;14(1):e0210694. doi: 10.1371/journal.pone.0210694. PMID: 30682086; PMCID: PMC6347292. 14: Tang C, Cai L, Liu S, Zheng Z, Li G, Chen J, Sui Q. Crystal structure of tebipenem pivoxil. Acta Crystallogr E Crystallogr Commun. 2018 Aug 10;74(Pt 9):1215-1217. doi: 10.1107/S2056989018010770. PMID: 30225102; PMCID: PMC6127708. 15: Rubio A, Pucci MJ, Jain A. Characterization of SPR994, an Orally Available Carbapenem, with Activity Comparable to Intravenously Administered Carbapenems. ACS Infect Dis. 2018 Oct 12;4(10):1436-1438. doi: 10.1021/acsinfecdis.8b00188. Epub 2018 Aug 17. PMID: 30118209. 16: Li F, Wan L, Xiao T, Liu H, Jiang Y, Zhao X, Wang R, Wan K. In Vitro Activity of β-Lactams in Combination with β-Lactamase Inhibitors against Mycobacterium tuberculosis Clinical Isolates. Biomed Res Int. 2018 Jul 2;2018:3579832. doi: 10.1155/2018/3579832. PMID: 30065936; PMCID: PMC6051288. 17: Jain A, Utley L, Parr TR, Zabawa T, Pucci MJ. Tebipenem, the first oral carbapenem antibiotic. Expert Rev Anti Infect Ther. 2018 Jul;16(7):513-522. doi: 10.1080/14787210.2018.1496821. Epub 2018 Jul 27. PMID: 30014729. 18: Ntombela T, Fakhar Z, Ibeji CU, Govender T, Maguire GEM, Lamichhane G, Kruger HG, Honarparvar B. Molecular insight on the non-covalent interactions between carbapenems and L,D-transpeptidase 2 from Mycobacterium tuberculosis: ONIOM study. J Comput Aided Mol Des. 2018 Jun;32(6):687-701. doi: 10.1007/s10822-018-0121-2. Epub 2018 May 29. PMID: 29845435. 19: Hagiya H, Kimura K, Nishi I, Yoshida H, Yamamoto N, Akeda Y, Tomono K. Emergence of Carbapenem Non-susceptible Campylobacter coli after Long-term Treatment against Recurrent Bacteremia in a Patient with X-linked Agammaglobulinemia. Intern Med. 2018 Jul 15;57(14):2077-2080. doi: 10.2169/internalmedicine.0312-17. Epub 2018 Feb 28. PMID: 29491300; PMCID: PMC6096023. 20: Huang W, Briffotaux J, Wang X, Liu L, Hao P, Cimino M, Buchieri MV, Namouchi A, Ainsa JA, Gicquel B. Ionophore A23187 shows anti-tuberculosis activity and synergy with tebipenem. Tuberculosis (Edinb). 2017 Dec;107:111-118. doi: 10.1016/j.tube.2017.09.001. Epub 2017 Sep 6. PMID: 29050757.