 Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C16H16N4O8S |
| Molecular Weight | 424.39 |
| Exact Mass | 424.068 |
| CAS # | 55268-75-2 |
| Related CAS # | Cefuroxime sodium;56238-63-2;Cefuroxime-d3;1803240-98-3 |
| PubChem CID | 5479529 |
| Appearance | White to light yellow solid powder |
| Density | 1.8±0.1 g/cm3 |
| Melting Point | 171.5-173°C |
| Index of Refraction | 1.735 |
| LogP | 0.47 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 10 |
| Rotatable Bond Count | 8 |
| Heavy Atom Count | 29 |
| Complexity | 798 |
| Defined Atom Stereocenter Count | 2 |
| SMILES | CO/N=C(/C1=CC=CO1)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)N)C(=O)O |
| InChi Key | JFPVXVDWJQMJEE-IZRZKJBUSA-N |
| InChi Code | InChI=1S/C16H16N4O8S/c1-26-19-9(8-3-2-4-27-8)12(21)18-10-13(22)20-11(15(23)24)7(5-28-16(17)25)6-29-14(10)20/h2-4,10,14H,5-6H2,1H3,(H2,17,25)(H,18,21)(H,23,24)/b19-9-/t10-,14-/m1/s1 |
| Chemical Name | (6R,7R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
| 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 |
| 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 | Cefuroxime has a strong anti-S effect. aureus (MIC=0.25 μg/ml), irrespective of the strains' penicillinase production. It works against methicillin-susceptible Staphylococcus aureus; S. methicillin-resistant, Streptococcus pyogenes, S. aureus, and S. pneumoniae, S. viridans, S. Clostridium spp., faecalis, and >125.0 μg/ml had MIC values of 0.25 μg/ml, 5.9 μg/ml, 0.125 μg/ml, 0.125 μg/ml, and 1.2 μg/ml, respectively[1]. Cefuroxime (10–100 μg/ml; 2–6 hours) acts bactericidally quickly, although it acts more slowly on S strains. aureus, but even so, by six hours, more than 99% of the original inoculum has been destroyed. Gram-negative organisms are eliminated fast; typically, more than 99% of the big inocula are eliminated in less than two hours; strains that produce β-lactamase are eliminated just as quickly as bacteria that do not produce enzymes[1]. |
| ln Vivo | Intravenous administration of S is used to challenge rabbits weighing 2.0 to 2.5 kg. The protection test results indicate that the median effective dose of Cefuroxime for the penicillinase-producing strain 630 is 3 mg/kg[2]. |
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion Absorbed from the gastrointestinal tract. Absorption is greater when taken after food (absolute bioavailability increases from 37% to 52%). Metabolism / Metabolites The axetil moiety is metabolized to acetaldehyde and acetic acid. Biological Half-Life Approximately 80 minutes following intramuscular or intravenous injection. |
| Toxicity/Toxicokinetics |
Effects During Pregnancy and Lactation ◉ Summary of Use during Lactation Limited information indicates that cefuroxime produces low levels in milk that are not expected to cause severe adverse effects in breastfed infants. Cefuroxime does not appear to alter the flora of breastmilk when used alone, but it can alter the infant’s fecal flora.[1] Occasionally, diarrhea or thrush have been reported with cephalosporins, but these effects have not been adequately evaluated. Cefuroxime is acceptable in nursing mothers. ◉ Effects in Breastfed Infants A prospective, controlled study asked mothers who called an information service about adverse reactions experience by their breastfed infants. Mothers were taking either cephalexin or cefuroxime. No statistical difference was found in the rate of adverse reactions in the 2 groups, with 1 case of diarrhea in each. This amounted to 2.6% of the cefuroxime-exposed infants.[8] ◉ Effects on Lactation and Breastmilk Relevant published information was not found as of the revision date. Protein Binding 50% to serum protein |
| References |
[1]. Cefuroxime, a New Cephalosporin Antibiotic: Activity in Vitro. Antimicrob Agents Chemother. 1976 Mar;9(3):511-9. [2]. Cefuroxime, a New Cephalosporin Antibiotic: Activity in Vivo. Antimicrob Agents Chemother. 1976 Mar;9(3):520-5. |
| Additional Infomation |
Cefuroxime is a 3-(carbamoyloxymethyl)cephalosporin compound having a 7-(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido side chain. It has a role as a drug allergen. It is a 3-(carbamoyloxymethyl)cephalosporin, a member of furans and an oxime O-ether. Broad-spectrum cephalosporin antibiotic resistant to beta-lactamase. It has been proposed for infections with gram-negative and gram-positive organisms, gonorrhea, and haemophilus. Cefuroxime is a Cephalosporin Antibacterial. Cefuroxime has been reported in Apis cerana with data available. Cefuroxime is a semisynthetic, broad-spectrum, beta-lactamase-resistant, second-generation cephalosporin with antibacterial activity. Cefuroxime binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Inactivation of PBPs interferes with the cross-linkage 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. Broad-spectrum cephalosporin antibiotic resistant to beta-lactamase. It has been proposed for infections with gram-negative and gram-positive organisms, GONORRHEA, and HAEMOPHILUS. See also: Cefuroxime Sodium (has salt form); Cefuroxime Axetil (active moiety of). Drug Indication For the treatment of many different types of bacterial infections such as bronchitis, sinusitis, tonsillitis, ear infections, skin infections, gonorrhea, and urinary tract infections. FDA Label Mechanism of Action Cefuroxime, like the penicillins, is a beta-lactam antibiotic. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cefuroxime interferes with an autolysin inhibitor. |
Solubility Data
| Solubility (In Vitro) | May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *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. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.3563 mL | 11.7816 mL | 23.5632 mL | |
| 5 mM | 0.4713 mL | 2.3563 mL | 4.7126 mL | |
| 10 mM | 0.2356 mL | 1.1782 mL | 2.3563 mL |