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.
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) |
Biological Activity
| 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]. |
| 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 a temocillin(2-). |
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 |