Temocillin
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| Category | Antibiotics |
| Catalog number | BBF-03770 |
| CAS | 66148-78-5 |
| Molecular Weight | 414.45 |
| Molecular Formula | C16H18N2O7S2 |
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Description
Temocillin is a β-lactamase-resistant penicillin that effects against gram-negative bacteria.
Specification
| Synonyms | Temocillinum; BRL 17421; Negaban |
| Storage | Store at -20°C |
| 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 |
| Canonical SMILES | CC1(C(N2C(S1)C(C2=O)(NC(=O)C(C3=CSC=C3)C(=O)O)OC)C(=O)O)C |
| 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 |
| InChI Key | BVCKFLJARNKCSS-DWPRYXJFSA-N |
Properties
| Appearance | White to Light Yellow Solid |
| Antibiotic Activity Spectrum | Gram-negative bacteria |
| Boiling Point | 761.9°C at 760 mmHg |
| Density | 1.6 g/cm3 |
Reference Reading
1. [Temocillin and urinary tract infections]
L Brureau, F Bruyère, M Vallée, F Roblot Prog Urol . 2017 Oct;27(12):609-617. doi: 10.1016/j.purol.2017.07.242.
Introduction:Temocillin is an alternative to treat urinary tract infections with bacteria producing extended spectrum beta-lactamase (ESBL). The objective is to evaluate the use of temocillin in urinary tract infections.Materials and methods:A systematic review of literature was carried out according to PRISMA criteria. All national and international recommendations have been reviewed regarding the indication of the use of temocillin in urology. Data collection on the use of temocillin in urinary tract infection has been performed from the Cochrane, LILACS and the Medline database. The following keywords were used: temocillin, extended spectrum beta-lactamase, urinary tract infections, urine, prostate, epididymis, testis, diffusion, pharmacokinetics, pharmacodynamics. The selection was based on the methodology, language of publication (English/French), relevance to the topic and date of publication of the articles collected. The endpoint was to provide exhaustive scientific information allowing urologists to use this antibiotic in febrile urinary infections.Results:Bacteria producing ESBL has a relatively high susceptible to temocillin, ranging from 61 % to 90 %. These rates would allow its use in probabilistic. The dosage recommended is currently, in the normo-renal patient, 4g per day by intermittent infusion or continuously after a loading dose of 2g. Some studies argue, particularly in case of difficult clinical situations or obese patients, for administration of high doses (6g/24h) rather continuous infusion. There is no evident relationship between high doses and side effects. With an excellent urinary and prostatic diffusion, temocilllin might be recommend for the treatment of ESBL prostatitis.Conclusion:Temocillin is known to have good urinary and prostatic diffusion. According to our results, this antibiotics is now a reliable alternative for the treatment of documented ESBL urinary tract infections.Level of evidence:4.
2. Temocillin revived
David M Livermore, Paul M Tulkens J Antimicrob Chemother . 2009 Feb;63(2):243-5. doi: 10.1093/jac/dkn511.
Resistance in Gram-negative pathogens is an increasing concern, with carbapenems often appearing as the only acceptable treatment option in serious infections. Reviving older compounds that have fallen into disuse may help to alleviate this burden. Temocillin (6-alpha-methoxy-ticarcillin) is resistant to most if not all classical and extended-spectrum beta-lactamases and to AmpC enzymes. It is also chemically stable, allowing administration by continuous infusion. Pharmacokinetic/pharmacodynamic analysis, aided by Monte-Carlo simulations, suggests a breakpoint of 8 mg/L for the registered maximum dosage of 4 g daily. Temocillin's weaknesses, explaining its limited previous use, are a lack of activity against Gram-positive organisms, anaerobes and Pseudomonas. In settings where these are unlikely or are covered by other agents, temocillin may be useful, potentially 'sparing' carbapenems and having little apparent potential to select for Clostridium difficile.
3. Temocillin: Applications in Antimicrobial Stewardship as a Potential Carbapenem-Sparing Antibiotic
Verena Zerbato, Barbara Rizzello, Francesco Giuseppe De Rosa, Stefano Di Bella, Silvia Corcione, Simone Mornese Pinna, Roberta Bosio, Ilaria De Benedetto, Tommaso Lupia, Giacomo Stroffolini, Nour Shbaklo Antibiotics (Basel) . 2022 Apr 7;11(4):493. doi: 10.3390/antibiotics11040493.
Temocillin is an old antibiotic, but given its particular characteristics, it may be a suitable alternative to carbapenems for treating infections due to ESBL-producingEnterobacteralesand uncomplicated UTI due to KPC-producers. In this narrative review, the main research question was to summarize current evidence on temocillin and its uses in infectious diseases. A search was run on PubMed using the terms ('Temocillin' [Mesh]) AND ('Infection' [Mesh]). Current knowledge regarding temocillin in urinary tract infection, blood-stream infections, pneumonia, intra-abdominal infections, central nervous system infections, skin and soft tissues infections, surgical sites infections and osteoarticular Infections were summarized. Temocillin retain a favourable profile on microbiota and risk ofClostridioides difficileinfections and could be an option for treating outpatients. Temocillin may be a valuable tool to treat susceptible pathogens and for which a carbapenem could be spared. Other advantages in temocillin use are that it is well-tolerated; it is associated with a low rate ofC. difficileinfections; it is active against ESBL, AmpC, and KPC-producingEnterobacterales; and it can be used in the OPAT clinical setting.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
