Physicochemical Properties
| Molecular Formula | C16H16N5NAO7S2 |
| Molecular Weight | 477.4473 |
| Exact Mass | 477.038 |
| Elemental Analysis | C, 40.25; H, 3.38; N, 14.67; Na, 4.82; O, 23.46; S, 13.43 |
| CAS # | 64485-93-4 |
| Related CAS # | Cefotaxime;63527-52-6;Cefotaxime-d3 sodium |
| PubChem CID | 10695961 |
| Appearance | White to off-white solid powder |
| Density | 1.8 g/cm3 |
| Melting Point | 162-163ºC(lit.) |
| Index of Refraction | 61 ° (C=1， H2O) |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 12 |
| Rotatable Bond Count | 8 |
| Heavy Atom Count | 31 |
| Complexity | 839 |
| Defined Atom Stereocenter Count | 2 |
| SMILES | S1C([H])([H])C(C([H])([H])OC(C([H])([H])[H])=O)=C(C(=O)[O-])N2C([C@]([H])([C@@]12[H])N([H])C(/C(/C1=C([H])SC(N([H])[H])=N1)=N/OC([H])([H])[H])=O)=O.[Na+] |
| InChi Key | AZZMGZXNTDTSME-JUZDKLSSSA-M |
| InChi Code | InChI=1S/C16H17N5O7S2.Na/c1-6(22)28-3-7-4-29-14-10(13(24)21(14)11(7)15(25)26)19-12(23)9(20-27-2)8-5-30-16(17)18-8;/h5,10,14H,3-4H2,1-2H3,(H2,17,18)(H,19,23)(H,25,26);/q;+1/p-1/b20-9-;/t10-,14-;/m1./s1 |
| Chemical Name | sodium;(6R,7R)-3-(acetyloxymethyl)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate |
| Synonyms | Cefotaxime Sodium; CEFOTAXIME SODIUM SALT; Cefotaxim sodium salt; Cefotax; CHEBI:3498; Merck Brand of Cefotaxime Sodium; Pisa Brand of Cefotaxime Sodium; Primafen; Ru 24756; Ru-24756; Ru24756; Sodium, Cefotaxime; Taporin; Viken Brand of Cefotaxime Sodium; |
| 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, 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
| Targets | β-lactam |
| ln Vitro | MIC for cefotaxime sodium against V. vulnificus CMCP6 is 0.0625 mg/L[4]. |
| ln Vivo | Compared to earlier regimens, the combination of ciprofloxacin and cefotaxime is more effective in eliminating V. vulnificus in vivo[4]. |
| Animal Protocol |
Animal Model: 8-week-old female BALB/c mice that are free of a particular pathogen[4]. Dosage: 30 mg/kg. Administration: IP every 6 h. Result: Mice treated with cefotaxime-plus-ciprofloxacin had fewer viable bacterial counts in their livers than mice treated with cefotaxime alone (P<0.001 at 24 and 48 hours, respectively). |
| Toxicity/Toxicokinetics |
Effects During Pregnancy and Lactation ◉ Summary of Use during Lactation Cefotaxime is no longer marketed in the United States. Limited information indicates that cefotaxime produces low levels in milk that are not expected to cause adverse effects in breastfed infants. Occasionally disruption of the infant's gastrointestinal flora, resulting in diarrhea or thrush have been reported with cephalosporins, but these effects have not been adequately evaluated. Cefotaxime is acceptable in nursing mothers. ◉ Effects in Breastfed Infants Relevant published information was not found as of the revision date. ◉ Effects on Lactation and Breastmilk Relevant published information was not found as of the revision date. |
| References |
[1]. A comparison of the prophylactic efficacy of ceftriaxone and cefotaxime in abdominal surgery. Am J Surg. 2003 Jan;185(1):45-9. [2]. Prospective comparison of ceftriaxone and cefotaxime for the short-term treatment of bacterial meningitis in children. Chemotherapy. 1998 Mar-Apr;44(2):142-7. [3]. Use of cefotaxime, a beta-lactamase stable cephalosporin, in the therapy of serious infections, including those due to multiresistant organisms. Am J Med. 1981 Sep;71(3):435-42. [4]. Differences between ceftriaxone and cefotaxime: microbiological inconsistencies. Ann Pharmacother. 2008 Jan;42(1):71-9. |
| Additional Infomation |
Cefotaxime sodium is a cephalosporin organic sodium salt having acetoxymethyl and [2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino side-groups. It contains a cefotaxime(1-). Cefotaxime Sodium is the sodium salt form of cefotaxime, a beta-lactam, third-generation cephalosporin antibiotic with bactericidal activity. Cefotaxime sodium binds to and inactivates penicillin-binding proteins (PBP) located on the inner membrane of the bacterial cell wall. Inactivation of PBPs interferes with the cross-linking of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis. Compared to the second and first generation cephalosporins, cefotaxime sodium is more active against gram-negative bacteria and less active against gram-positive bacteria. Semisynthetic broad-spectrum cephalosporin. See also: Cefotaxime (has active moiety). |
Solubility Data
| Solubility (In Vitro) |
H2O : 50~95 mg/mL (104.72~198.97 mM ) DMSO : ~45 mg/mL (~94.25 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.24 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 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 2: ≥ 2.08 mg/mL (4.36 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 3: 2.08 mg/mL (4.36 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. 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 4: 10% DMSO+90% Corn Oil: ≥ 2.5 mg/mL (5.24 mM) Solubility in Formulation 5: 100 mg/mL (209.45 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.0945 mL | 10.4723 mL | 20.9446 mL | |
| 5 mM | 0.4189 mL | 2.0945 mL | 4.1889 mL | |
| 10 mM | 0.2094 mL | 1.0472 mL | 2.0945 mL |