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MedKoo Cat#: 526472 | Name: Tomopenem

Description:

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

Tomopenem is a novel penem antibiotic. Tomopenem has improved activity against diverse hospital pathogens, including Pseudomonas aeruginosa and methicillin-resistant Staphylococcus aureus (MRSA), and has a half-life about twice longer than the half-lives of other carbapenems such as imipenem (IPM) and meropenem (MEM).

Chemical Structure

Tomopenem
CAS#222400-20-6

Theoretical Analysis

MedKoo Cat#: 526472

Name: Tomopenem

CAS#: 222400-20-6

Chemical Formula: C23H35N7O6S

Exact Mass: 537.2370

Molecular Weight: 537.64

Elemental Analysis: C, 51.38; H, 6.56; N, 18.24; O, 17.85; S, 5.96

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 #
No Data
Synonym
Tomopenem; CS-023; RO-4908463; R-1558;
IUPAC/Chemical Name
1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-(((3S,5S)-5-(((3S)-3-((((aminoiminomethyl)amino)acetyl)amino)-1-pyrrolidinyl)carbonyl)-1-methyl-3-pyrrolidinyl)thio)-6-((1R)-1-hydroxyethyl)-4-methyl-7-oxo-, (4R,5S,6S)-
InChi Key
KEDAXBWZURNCHS-GPODMPQUSA-N
InChi Code
InChI=1S/C23H35N7O6S/c1-10-17-16(11(2)31)21(34)30(17)18(22(35)36)19(10)37-13-6-14(28(3)9-13)20(33)29-5-4-12(8-29)27-15(32)7-26-23(24)25/h10-14,16-17,31H,4-9H2,1-3H3,(H,27,32)(H,35,36)(H4,24,25,26)/t10-,11-,12+,13+,14+,16-,17-/m1/s1
SMILES Code
O=C(C(N12)=C(S[C@@H]3CN(C)[C@H](C(N4C[C@@H](NC(CNC(N)=N)=O)CC4)=O)C3)[C@H](C)[C@]2([H])[C@@H]([C@H](O)C)C1=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
Soluble in DMSO
Shelf Life
>2 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

Preparing Stock Solutions

The following data is based on the product molecular weight 537.64 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.

Recalculate based on batch purity %
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: Ansari MA, Shaikh S, Shakil S, Rizvi SM. An enzoinformatics study for prediction of efficacies of three novel penem antibiotics against New Delhi metallo-β-lactamase-1 bacterial enzyme. Interdiscip Sci. 2014 Sep;6(3):208-15. doi: 10.1007/s12539-013-0202-9. PubMed PMID: 25205498. 2: Ansari MA, Shaikh S, Shakil S, Rizvi SM. An enzoinformatics study for prediction of efficacies of three novel penem antibiotics against New Delhi metallo-β-lactamase-1 bacterial enzyme. Interdiscip Sci. 2014 Aug 9. [Epub ahead of print] PubMed PMID: 25118651. 3: Sugihara K, Tateda K, Yamamura N, Koga T, Sugihara C, Yamaguchi K. Efficacy of human-simulated exposures of tomopenem (formerly CS-023) in a murine model of Pseudomonas aeruginosa and methicillin-resistant Staphylococcus aureus infection. Antimicrob Agents Chemother. 2011 Nov;55(11):5004-9. doi: 10.1128/AAC.00068-11. PubMed PMID: 21844314; PubMed Central PMCID: PMC3195026. 4: Sugihara K, Sugihara C, Matsushita Y, Yamamura N, Uemori M, Tokumitsu A, Inoue H, Kakuta M, Namba E, Nasu H, Koga T. In vivo pharmacodynamic activity of tomopenem (formerly CS-023) against Pseudomonas aeruginosa and methicillin-resistant Staphylococcus aureus in a murine thigh infection model. Antimicrob Agents Chemother. 2010 Dec;54(12):5298-302. doi: 10.1128/AAC.00267-10. PubMed PMID: 20921311; PubMed Central PMCID: PMC2981229. 5: El-Gamal MI, Oh CH. Current status of carbapenem antibiotics. Curr Top Med Chem. 2010;10(18):1882-97. Review. PubMed PMID: 20615191. 6: Tomozawa T, Sugihara C, Kakuta M, Sugihara K, Koga T. In vitro postantibiotic effects of tomopenem (CS-023) against Staphylococcus aureus and Pseudomonas aeruginosa. J Med Microbiol. 2010 Apr;59(Pt 4):438-41. doi: 10.1099/jmm.0.017905-0. PubMed PMID: 20093378. 7: Mallalieu NL, Lennon S, Guy T, Liu M, Luedin E, Davies BE. Lack of age and gender effects on single-dose pharmacokinetics of tomopenem (RO4908463/CS-023), a novel carbapenem. Br J Clin Pharmacol. 2009 Apr;67(4):469-72. doi: 10.1111/j.1365-2125.2009.03367.x. PubMed PMID: 19371322; PubMed Central PMCID: PMC2679112. 8: Bassetti M, Nicolini L, Esposito S, Righi E, Viscoli C. Current status of newer carbapenems. Curr Med Chem. 2009;16(5):564-75. Review. PubMed PMID: 19199922. 9: Koga T, Sugihara C, Kakuta M, Masuda N, Namba E, Fukuoka T. Affinity of Tomopenem (CS-023) for penicillin-binding proteins in Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa. Antimicrob Agents Chemother. 2009 Mar;53(3):1238-41. doi: 10.1128/AAC.01433-08. PubMed PMID: 19104025; PubMed Central PMCID: PMC2650550. 10: Tanaka K, Mikamo H, Nakao K, Ichiishi T, Goto T, Yamagishi Y, Watanabe K. In vitro activity of tomopenem (CS-023/RO4908463) against anaerobic bacteria. Antimicrob Agents Chemother. 2009 Jan;53(1):319-22. doi: 10.1128/AAC.00595-08. PubMed PMID: 18955522; PubMed Central PMCID: PMC2612141. 11: Morinaga Y, Yanagihara K, Nakamura S, Yamamoto K, Izumikawa K, Seki M, Kakeya H, Yamamoto Y, Yamada Y, Kohno S, Kamihira S. In vivo efficacy and pharmacokinetics of tomopenem (CS-023), a novel carbapenem, against Pseudomonas aeruginosa in a murine chronic respiratory tract infection model. J Antimicrob Chemother. 2008 Dec;62(6):1326-31. doi: 10.1093/jac/dkn411. PubMed PMID: 18835805. 12: Koga T, Masuda N, Kakuta M, Namba E, Sugihara C, Fukuoka T. Potent in vitro activity of tomopenem (CS-023) against methicillin-resistant Staphylococcus aureus and Pseudomonas aeruginosa. Antimicrob Agents Chemother. 2008 Aug;52(8):2849-54. doi: 10.1128/AAC.00413-08. PubMed PMID: 18519723; PubMed Central PMCID: PMC2493143. 13: Mallalieu NL, Lennon S, Liu M, Kirkpatrick C, Robson R, Luedin E, Davies BE. Effect of impaired renal function on the pharmacokinetics of tomopenem (RO4908463/CS-023), a novel carbapenem. Antimicrob Agents Chemother. 2008 Jul;52(7):2360-6. doi: 10.1128/AAC.01249-07. PubMed PMID: 18443123; PubMed Central PMCID: PMC2443904. 14: Vergidis PI, Falagas ME. Multidrug-resistant Gram-negative bacterial infections: the emerging threat and potential novel treatment options. Curr Opin Investig Drugs. 2008 Feb;9(2):176-83. Review. PubMed PMID: 18246520. 15: MacGowan AP, Bowker KE, Noel AR. Pharmacodynamics of the antibacterial effect and emergence of resistance to tomopenem, formerly RO4908463/CS-023, in an in vitro pharmacokinetic model of Staphylococcus aureus infection. Antimicrob Agents Chemother. 2008 Apr;52(4):1401-6. doi: 10.1128/AAC.01153-07. PubMed PMID: 18227179; PubMed Central PMCID: PMC2292562. 16: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2007 Apr;29(3):231-45. PubMed PMID: 17520107. 17: Shibayama T, Sugiyama D, Kamiyama E, Tokui T, Hirota T, Ikeda T. Characterization of CS-023 (RO4908463), a novel parenteral carbapenem antibiotic, and meropenem as substrates of human renal transporters. Drug Metab Pharmacokinet. 2007 Feb 25;22(1):41-7. PubMed PMID: 17329910. 18: Shibayama T, Matsushita Y, Kurihara A, Hirota T, Ikeda T. Prediction of pharmacokinetics of CS-023 (RO4908463), a novel parenteral carbapenem antibiotic, in humans using animal data. Xenobiotica. 2007 Jan;37(1):91-102. PubMed PMID: 17178636. 19: Shibayama T, Yamamura N, Matsushita Y, Tokui T, Hirota T, Ikeda T. Renal handling of CS-023 (RO4908463), a novel parenteral carbapenem antibiotic, in rabbits in comparison with meropenem. Xenobiotica. 2006 Dec;36(12):1273-87. PubMed PMID: 17162472. 20: Shibayama T, Matsushita Y, Kawai K, Hirota T, Ikeda T, Kuwahara S. Pharmacokinetics and disposition of CS-023 (RO4908463), a novel parenteral carbapenem, in animals. Antimicrob Agents Chemother. 2007 Jan;51(1):257-63. PubMed PMID: 17074792; PubMed Central PMCID: PMC1797684.