Cefmetazole sodium (U-72791A sodium; CS-1170) is a potent 2nd-generation, semi-synthetic, beta-lactam cephalosporin antibiotic with antibacterial activity. It acts by binding to penicillin-binding proteins (PBPs) which are enzymes responsible for crosslinking of peptidoglycan. By preventing crosslinking of peptidoglycan, cell wall integrity is disrupted and cell wall synthesis is halted.
Physicochemical Properties
| Molecular Formula | C15H16N7NAO5S3 |
| Molecular Weight | 493.52 |
| Exact Mass | 493.027 |
| Elemental Analysis | C, 36.51; H, 3.27; N, 19.87; Na, 4.66; O, 16.21; S, 19.49 |
| CAS # | 56796-39-5 |
| Related CAS # | Cefmetazole;56796-20-4 |
| PubChem CID | 23666711 |
| Appearance | Solid powder |
| Density | 1.75 g/cm3 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 12 |
| Rotatable Bond Count | 9 |
| Heavy Atom Count | 31 |
| Complexity | 824 |
| Defined Atom Stereocenter Count | 2 |
| SMILES | S1C([H])([H])C(C([H])([H])SC2=NN=NN2C([H])([H])[H])=C(C(=O)[O-])N2C([C@]([C@@]12[H])(N([H])C(C([H])([H])SC([H])([H])C#N)=O)OC([H])([H])[H])=O.[Na+] |
| InChi Key | BITQGIOJQWZUPL-PBCQUBLHSA-M |
| InChi Code | InChI=1S/C15H17N7O5S3.Na/c1-21-14(18-19-20-21)30-6-8-5-29-13-15(27-2,17-9(23)7-28-4-3-16)12(26)22(13)10(8)11(24)25/h13H,4-7H2,1-2H3,(H,17,23)(H,24,25)/q+1/p-1/t13-,15+/m1./s1 |
| Chemical Name | 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((((cyanomethyl)thio)acetyl)amino)-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-, monosodium salt, (6R-cis)- |
| Synonyms | CMZ sodium; U72791A; U 72791A; U-72791A |
| 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 and light. |
| 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
| Targets | β-lactam | |
| ln Vitro |
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| ln Vivo |
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| Animal Protocol |
Animal Model: Male ICR mice[3] Dosage: 100 mg/kg Administration: Subcutaneous injection; twice a day, for 7 days Result: decreased numbers of Peyer's patch (PP) lymphocyte cells and fewer small-intestine bacteria. |
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| References |
[1].Truesdell SE, et, al. Interaction of cephalosporins with penicillin-binding proteins of methicillin-resistant Staphylococcus aureus. J Antimicrob Chemother. 1989 Apr;23 Suppl D:13-9. [2].Schentag JJ. Cefmetazole sodium: pharmacology, pharmacokinetics, and clinical trials. Pharmacotherapy. 1991;11(1):2-19. [3].Yaguchi Y, et, al. Influences of long-term antibiotic administration on Peyer's patch lymphocytes and mucosal immunoglobulin A levels in a mouse model. JPEN J Parenter Enteral Nutr. 2006 Sep-Oct;30(5):395-8; discussion 399. |
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| Additional Infomation |
Cefmetazole sodium is an organic sodium salt that is the sodium salt of cefmetazole. It has a role as an antimicrobial agent. It contains a cefmetazole(1-). Cefmetazole Sodium is the sodium salt form of cefmetazole, a second-generation, semi-synthetic, beta-lactam cephalosporin antibiotic with antibacterial activity. Cefmetazole binds to penicillin-binding proteins (PBPs), transpeptidases that are responsible for crosslinking of peptidoglycan. By preventing crosslinking of peptidoglycan, cell wall integrity is lost and cell wall synthesis is halted. A semisynthetic cephamycin antibiotic with a broad spectrum of activity against both gram-positive and gram-negative microorganisms. It has a high rate of efficacy in many types of infection and to date no severe side effects have been noted. |
Solubility Data
| Solubility (In Vitro) |
DMSO : ~125 mg/mL (~253.28 mM) H2O : ~100 mg/mL (~202.63 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (4.21 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (4.21 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.08 mg/mL (4.21 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.0263 mL | 10.1313 mL | 20.2626 mL | |
| 5 mM | 0.4053 mL | 2.0263 mL | 4.0525 mL | |
| 10 mM | 0.2026 mL | 1.0131 mL | 2.0263 mL |