Temocillin

• CAT Number: I037109
• CAS Number: 66148-78-5
• Molecular Formula: C16H18N2O7S2
• Molecular Weight: 414.45
• Purity: 98%
• Synonyms: Temocillin
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: (2S,5R,6S)-6-[(2-carboxy-2-thiophen-3-ylacetyl)amino]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• InChI: InChI=1S/C16H18N2O7S2/c1-15(2)9(12(22)23)18-13(24)16(25-3,14(18)27-15)17-10(19)8(11(20)21)7-4-5-26-6-7/h4-6,8-9,14H,1-3H3,(H,17,19)(H,20,21)(H,22,23)/t8?,9-,14+,16-/m0/s1
• InChIKey: BVCKFLJARNKCSS-DWPRYXJFSA-N
• SMILES: CC1([C@@H](N2[C@H](S1)[C@@](C2=O)(NC(=O)C(C3=CSC=C3)C(=O)O)OC)C(=O)O)C

Temocillin（Cat No.:I037109）is a beta-lactam antibiotic derived from ticarcillin, specifically designed to target gram-negative bacterial infections. Notably resistant to beta-lactamase enzymes, Temocillin remains effective against bacteria producing extended-spectrum beta-lactamases (ESBLs) and AmpC enzymes, making it valuable in treating multidrug-resistant infections. Commonly used for urinary and respiratory tract infections, it binds to penicillin-binding proteins, inhibiting cell wall synthesis and leading to bacterial death. Its selective spectrum minimizes effects on beneficial microbiota, reducing resistance risk. Temocillin is particularly valuable in managing hospital-acquired and resistant bacterial infections.

Reference

1: Alexandre K, Fantin B. Pharmacokinetics and Pharmacodynamics of Temocillin. Clin Pharmacokinet. 2018 Mar;57(3):287-296. doi: 10.1007/s40262-017-0584-7. PMID: 28849402.
2: Vallée M, Bruyère F, Roblot F, Brureau L. Place de la témocilline dans le traitement des infections urinaires [Temocillin and urinary tract infections]. Prog Urol. 2017 Oct;27(12):609-617. French. doi: 10.1016/j.purol.2017.07.242. Epub 2017 Aug 30. PMID: 28869169.
3: Balakrishnan I, Koumaki V, Tsakris A. Temocillin: is this the right momentum for its global use? Future Microbiol. 2019 Jan;14:81-83. doi: 10.2217/fmb-2018-0316. Epub 2019 Jan 15. PMID: 30644315.
4: Alexandre K, Soares A, Chau F, Fantin B, Caron F, Etienne M. Temocillin breakpoints in pyelonephritis: evaluation in a murine model due to ESBL- producing Escherichia coli clinical isolates. J Antimicrob Chemother. 2019 May 1;74(5):1323-1326. doi: 10.1093/jac/dky569. PMID: 30689887.
5: Cavaco LM, Hansen F, Mushtaq S, Hill RLR, Woodford N, Le Hello S, Hendriksen RS, Hammerum AM, Hasman H. Evaluation of temocillin for phenotypic carbapenemase screening of Escherichia coli and Salmonella enterica isolates in relation to the presence of genes encoding ESBLs and carbapenemase production. J Antimicrob Chemother. 2019 Mar 1;74(3):639-644. doi: 10.1093/jac/dky493. PMID: 30544192.
6: Soubirou JF, Rossi B, Couffignal C, Ruppé E, Chau F, Massias L, Lepeule R, Mentre F, Fantin B. Activity of temocillin in a murine model of urinary tract infection due to Escherichia coli producing or not producing the ESBL CTX-M-15. J Antimicrob Chemother. 2015 May;70(5):1466-72. doi: 10.1093/jac/dku542. Epub 2015 Jan 5. PMID: 25564564.
7: Rodríguez-Baño J, Gutiérrez-Gutiérrez B, Machuca I, Pascual A. Treatment of Infections Caused by Extended-Spectrum-Beta-Lactamase-, AmpC-, and Carbapenemase-Producing Enterobacteriaceae. Clin Microbiol Rev. 2018 Feb 14;31(2):e00079-17. doi: 10.1128/CMR.00079-17. PMID: 29444952; PMCID: PMC5967687.
8: Zeiser ET, Becka SA, Barnes MD, Taracila MA, LiPuma JJ, Papp-Wallace KM. Resurrecting Old β-Lactams: Potent Inhibitory Activity of Temocillin against Multidrug-Resistant Burkholderia Species Isolates from the United States. Antimicrob Agents Chemother. 2019 Mar 27;63(4):e02315-18. doi: 10.1128/AAC.02315-18. PMID: 30718248; PMCID: PMC6437531.
9: Ip M, Lai CK, Fung KSC, Wong KT, Zhu C, Van de Velde S, Tsang DN, Hawkey P. Activity of temocillin and 15 other agents, including fosfomycin and colistin, against Enterobacteriaceae in Hong Kong. Eur J Clin Microbiol Infect Dis. 2017 Dec;36(12):2491-2494. doi: 10.1007/s10096-017-3091-8. Epub 2017 Aug 25. PMID: 28840351; PMCID: PMC5688185.
10: Deshayes S, Coquerel A, Verdon R. Neurological Adverse Effects Attributable to β-Lactam Antibiotics: A Literature Review. Drug Saf. 2017 Dec;40(12):1171-1198. doi: 10.1007/s40264-017-0578-2. PMID: 28755095.
11: Sacco MD, Kroeck KG, Kemp MT, Zhang X, Andrews LD, Chen Y. Influence of the α-Methoxy Group on the Reaction of Temocillin with Pseudomonas aeruginosa PBP3 and CTX-M-14 β-Lactamase. Antimicrob Agents Chemother. 2019 Dec 20;64(1):e01473-19. doi: 10.1128/AAC.01473-19. PMID: 31685462; PMCID: PMC7187628.
12: Berleur M, Guérin F, Massias L, Chau F, Poujade J, Cattoir V, Fantin B, de Lastours V. Activity of fosfomycin alone or combined with temocillin in vitro and in a murine model of peritonitis due to KPC-3- or OXA-48-producing Escherichia coli. J Antimicrob Chemother. 2018 Nov 1;73(11):3074-3080. doi: 10.1093/jac/dky283. PMID: 30085154.
13: Kresken M, Körber-Irrgang B, Pfeifer Y, Werner G. Activity of temocillin against CTX-M-producing Escherichia coli and Klebsiella pneumoniae from Germany. Int J Antimicrob Agents. 2018 Jan;51(1):159-160. doi: 10.1016/j.ijantimicag.2017.06.014. Epub 2017 Jul 10. PMID: 28705669.
14: Miranda Bastos AC, Vandecasteele SJ, Spinewine A, Tulkens PM, Van Bambeke F. Temocillin dosing in haemodialysis patients based on population pharmacokinetics of total and unbound concentrations and Monte Carlo simulations. J Antimicrob Chemother. 2018 Jun 1;73(6):1630-1638. doi: 10.1093/jac/dky078. PMID: 29579214.
15: Alexandre K, Chau F, Guérin F, Massias L, Lefort A, Cattoir V, Fantin B. Activity of temocillin in a lethal murine model of infection of intra-abdominal origin due to KPC-producing Escherichia coli. J Antimicrob Chemother. 2016 Jul;71(7):1899-904. doi: 10.1093/jac/dkw066. Epub 2016 Mar 29. PMID: 27029848.
16: Shaker OA, Gomaa HE, ElMasry SA, Halim RMA, Abdelrahman AH, Kamal JS. Evaluation of Combined Use of Temocillin Disk and Mastdisks Inhibitor Combination Set Against Polymerase Chain Reaction for Detection of Carbapenem- Resistant Enterobacteriaceae. Open Access Maced J Med Sci. 2018 Feb 1;6(2):242-247. doi: 10.3889/oamjms.2018.090. PMID: 29531581; PMCID: PMC5839425.
17: Hopkins KL, Meunier D, Mustafa N, Pike R, Woodford N. Evaluation of temocillin and meropenem MICs as diagnostic markers for OXA-48-like carbapenemases. J Antimicrob Chemother. 2019 Dec 1;74(12):3641-3643. doi: 10.1093/jac/dkz383. PMID: 31730158.
18: Spencer RC. Temocillin. J Antimicrob Chemother. 1990 Dec;26(6):735-7. doi: 10.1093/jac/26.6.735. PMID: 2081715.
19: Alexandre K, Réveillon-Istin M, Fabre R, Delbos V, Etienne M, Pestel-Caron M, Dahyot S, Caron F. Temocillin against Enterobacteriaceae isolates from community-acquired urinary tract infections: low rate of resistance and good accuracy of routine susceptibility testing methods. J Antimicrob Chemother. 2018 Jul 1;73(7):1848-1853. doi: 10.1093/jac/dky101. PMID: 29635629.
20: Livermore DM, Tulkens PM. Temocillin revived. J Antimicrob Chemother. 2009 Feb;63(2):243-5. doi: 10.1093/jac/dkn511. Epub 2008 Dec 18. PMID: 19095679.