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Temocillin disodium salt

Alias: Temocillin sodium; temocillin disodium; 96IIP39ODH; disodium
Cat No.:V40841 Purity: ≥98%
Temocillin disodium saltis a semisynthetic, narrow-spectrum andβ-lactamase-resistant penicillin introduced by Beecham, marketed by Eumedica Pharmaceuticals as Negaban.
Temocillin disodium salt
Temocillin disodium salt Chemical Structure CAS No.: 61545-06-0
Product category: Bacterial
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
25mg
Other Sizes

Other Forms of Temocillin disodium salt:

  • Temocillin
Official Supplier of:
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Product Description
Temocillin disodium salt is a semisynthetic, narrow-spectrum and β-lactamase-resistant penicillin introduced by Beecham, marketed by Eumedica Pharmaceuticals as Negaban. It is used primarily for the treatment of multiple drug-resistant, Gram-negative bacteria. It is a 6-methoxy penicillin; it is also a carboxypenicillin. Temocillin binds to and inactivates penicillin -binding proteins (PBPs) located on the inner membrane of the bacterial cell wall.
Temocillin disodium salt is a semisynthetic, narrow-spectrum, β-lactamase-resistant penicillin (a 6-α-methoxy penicillin). It is a carboxypenicillin marketed as Negaban. It is used primarily for the treatment of infections caused by multidrug-resistant, Gram-negative bacteria, including Escherichia coli, Klebsiella pneumoniae, and Proteus mirabilis.
Biological Activity I Assay Protocols (From Reference)
Targets
Temocillin targets penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. By binding to and inactivating these PBPs, it inhibits bacterial cell wall synthesis, which is essential for the growth and survival of bacterial cells. Its resistance to β-lactamases makes it effective against many β-lactamase-producing organisms.
ln Vitro
In vitro, temocillin possesses antibacterial activity against a range of Gram-negative bacteria. It is effective against many multidrug-resistant strains. Its in vitro activity is typically assessed by determining the minimum inhibitory concentration (MIC) against a panel of bacterial isolates.
ln Vivo
With no discernible difference between the parental strain and its transconjugant, temocillin dosage regimens of 200 mg/kg every 4 and 6 hours continued to be highly effective in lowering bacterial titres in kidneys against the two strains[2].
In vivo, temocillin is used as an alternative to carbapenems and is indicated for the treatment of septicemia, urinary tract infections, and lower respiratory tract infections. In animal models, temocillin dosage regimens of 200 mg/kg every 4 and 6 hours have been shown to be highly effective in lowering bacterial titers in kidneys.
Enzyme Assay
The in vitro assay for temocillin is a standard antimicrobial susceptibility test. The minimum inhibitory concentration (MIC) is determined by broth microdilution or disk diffusion methods according to CLSI or EUCAST guidelines. The compound's activity is evaluated against a panel of Gram-negative bacterial strains, including both β-lactamase-producing and non-producing organisms.
Cell Assay
In vitro cellular studies are not applicable for temocillin, as it is an antibiotic that targets bacteria, not mammalian cells. Its activity is assessed in bacterial cultures, not in eukaryotic cell lines.
Animal Protocol
In vivo animal experiments are performed in models of bacterial infection. For example, in a murine model of kidney infection, temocillin is administered to infected animals at various doses and frequencies. The primary endpoint is the reduction of bacterial titers in target organs, such as the kidneys.
ADME/Pharmacokinetics
Temocillin disodium salt has a molecular formula of C16H16N2Na2O7S2 and a molecular weight of 458.42 g/mol. It is an organic sodium salt. It is soluble in water and DMSO. For research purposes, it is typically stored as a powder at -20°C. Its purity is generally ≥98%. It appears as an off-white to yellow solid powder.
Toxicity/Toxicokinetics
As a β-lactam antibiotic, temocillin is generally well-tolerated, but can cause hypersensitivity reactions. It is contraindicated in patients with a known allergy to penicillins. Comprehensive toxicological data would be available from its clinical use. For research purposes, standard laboratory safety precautions should be followed.
References

[1]. Antibacterial activity and beta-lactamase stability of temocillin. Antimicrob Agents Chemother. 1982 Sep;22(3):453-60.

[2]. 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.

Additional Infomation
Temocillin disodium is an organic sodium salt. It contains Temocillin (2-).
Temocillin disodium salt is also known as Temocillin sodium and has the UNII code 96IIP39ODH. It is a 6-α-methoxy penicillin, which confers resistance to many β-lactamases. It is used as an alternative to carbapenems for treating infections caused by susceptible Gram-negative pathogens. It is supplied as a research-grade compound with high purity.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C16H16N2O7S2-2.2[NA+]
Molecular Weight
458.41704
Exact Mass
414.056
CAS #
61545-06-0
Related CAS #
Temocillin;66148-78-5
PubChem CID
11583399
Appearance
Off-white to yellow solid powder
Density
1.6g/cm3
Boiling Point
761.9ºC at 760mmHg
Flash Point
414.6ºC
LogP
1.3
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
9
Rotatable Bond Count
4
Heavy Atom Count
29
Complexity
689
Defined Atom Stereocenter Count
3
SMILES
[Na+].[Na+].O=C(C(C(N[C@@]1(C(=O)N2[C@H](C(S[C@H]12)(C)C)C([O-])=O)OC)=O)C1C=CSC=1)[O-]
InChi Key
MRGCZDWBFFUEES-CWBCWDDISA-L
InChi Code
InChI=1S/C16H18N2O7S2.2Na/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);;/q;2*+1/p-2/t8?,9-,14+,16-;;/m0../s1
Chemical Name
disodium;(2S,5R,6S)-6-[(2-carboxylato-2-thiophen-3-ylacetyl)amino]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Synonyms
Temocillin sodium; temocillin disodium; 96IIP39ODH; disodium
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
H2O : ~250 mg/mL (~545.35 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 50 mg/mL (109.07 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.1814 mL 10.9070 mL 21.8141 mL
5 mM 0.4363 mL 2.1814 mL 4.3628 mL
10 mM 0.2181 mL 1.0907 mL 2.1814 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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