1-(acetyloxy)ethyl (6R,7R)-3-[(carbamoyloxy)methyl]-7-{[(2Z)-2-furan-2-yl-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
Cefuroxim
CAS: 55268-75-2
Molecular Formula: C16H16N4O8S
1-(acetyloxy)ethyl (6R,7R)-3-[(carbamoyloxy)methyl]-7-{[(2Z)-2-furan-2-yl-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate - Names and Identifiers
1-(acetyloxy)ethyl (6R,7R)-3-[(carbamoyloxy)methyl]-7-{[(2Z)-2-furan-2-yl-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate - Physico-chemical Properties
| Molecular Formula | C16H16N4O8S |
| Molar Mass | 424.39 |
| Density | 1.76 |
| Melting Point | 171.5-173°C |
| Specific Rotation(α) | D20 +63.7° (c = 1.0 in 0.2M pH 7 phosphate buffer) |
| Water Solubility | 145mg/L at 25℃ |
| Solubility | Easily soluble in water or buffer solution, soluble in methanol, very slightly soluble in ethyl ethanol, ether, octanol, benzene or chloroform |
| Appearance | White crystal |
| Color | White to Off-White |
| pKa | pKa 2.5(H2O) (Uncertain) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.6000 (estimate) |
| MDL | MFCD00864889 |
| Physical and Chemical Properties | White Crystal,[α] at 63.7 °(C = 1.0,0.2mol/L phosphate buffer pH = 7). UV absorption maximum (pH = 6 phosphate buffer):274NM (Δ17600). Cefuroxime Sodium: C16H15N4aO8SNa. [56238-63-2]. White solid, soluble in water or buffer solution, soluble in methanol, very slightly soluble in ethyl alcohol, ethyl ether, octanol, benzene or chloroform, water solubility of 500mg/2.5. pKa (water):2.5;pKa(Z. Methylformamide):5.1. [Α] D 20 60 °(C = 0.91, water). |
| Use | A broad-spectrum semi-synthetic cephalosporin |
| In vitro study | Cefuroxime is highly active against S. aureus (MIC=0.25 μg/ml), regardless of whether the strains produces a penicillinase. It is against Staphylococcus aureus methicillin susceptible; S. aureus , methicillin resistant, Streptococcus pyogenes , S. pneumoniae , S. viridans , S. faecalis , and Clostridium spp with MIC values of 0.25 μg/ml, 5.9 μg/ml, 0.125 μg/ml, 0.125 μg/ml, 0.125 μg/ml, >125.0 μg/ml, and 1.2 μg/ml, respectively. Cefuroxime (10-100 μg/ml; 2-6 hours) rapidly bactericidal, its action is comparatively slow against the strains of S. aureus , but, even so, over 99% of the initial inoculum is killed by 6 h. The gram-negative organisms are killed rapidly, and in most cases over 99% of the very large inocula are killed within 2 h; the β-lactamase-producing strains are killed as quickly as non-enzyme-producing strains. |
| In vivo study | Rabbits (weighing 2.0 to 2.5 kg) are challenged intravenously with S. aureus strain 630 (a penicillinase-producing strain), the median effective dose of Cefuroxime is 3 mg/kg as a result of the protection test. |
1-(acetyloxy)ethyl (6R,7R)-3-[(carbamoyloxy)methyl]-7-{[(2Z)-2-furan-2-yl-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 42/43 - May cause sensitization by inhalation and skin contact. |
| Safety Description | S22 - Do not breathe dust. S24 - Avoid contact with skin. S37 - Wear suitable gloves. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) |
| WGK Germany | 3 |
| RTECS | XI0329000 |
1-(acetyloxy)ethyl (6R,7R)-3-[(carbamoyloxy)methyl]-7-{[(2Z)-2-furan-2-yl-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate - Reference
| Reference Show more | 1. [IF=3.681] Rao Zhi et al."Determination of Total and Unbound Meropenem, Imipenem/Cilastatin, and Cefoperazone/Sulbactam in Human Plasma: Application for Therapeutic Drug Monitoring in Critically Ill Patients."Ther Drug Monit. 2020 Aug;42(4):578-587 |
1-(acetyloxy)ethyl (6R,7R)-3-[(carbamoyloxy)methyl]-7-{[(2Z)-2-furan-2-yl-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate - Nature
Open Data Verified Data
white to light yellow powder, slightly odor, bitter taste. The absorption coefficient at 276nm was 390~420. Soluble in dioxane, acetone, more soluble in methanol, ethanol-soluble, very slightly soluble in ether, almost insoluble in water.
Last Update：2024-01-02 23:10:35
1-(acetyloxy)ethyl (6R,7R)-3-[(carbamoyloxy)methyl]-7-{[(2Z)-2-furan-2-yl-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate - Quality standards-Chinese Pharmacopoeia 2005 edition
Open Data Verified Data
Cefuroxime Axetil is A mixture of isomers A and B; The content of cefuroxime (G16 H16 N4 08 S) should not be less than 75.0% calculated as anhydrous; the clarity and color of the solution should be in accordance with the regulations; The crystallinity should be in accordance with the regulations. The ratio of the area of the isomer peak to the area and the ratio of the, B isomer peak should be 0. 48~0.55; Water content shall not exceed 1.5%, and related substances shall comply with the regulations; Ignition residue shall not pass 0. 2%; Containing heavy metals not over 0.002%.
Last Update：2022-01-01 08:52:17
1-(acetyloxy)ethyl (6R,7R)-3-[(carbamoyloxy)methyl]-7-{[(2Z)-2-furan-2-yl-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate - Preparation Method
Open Data Verified Data
cefuroxime as raw material, its sodium salt and acetic acid-1-bromoethyl Ester reaction into ester. Cefuroxime Axetil.
Last Update：2022-01-01 08:52:17
1-(acetyloxy)ethyl (6R,7R)-3-[(carbamoyloxy)methyl]-7-{[(2Z)-2-furan-2-yl-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate - Use
Open Data Verified Data
It is an esterified derivative of cefuroxime and a prodrug. Its antibacterial spectrum and antibacterial activity are similar to those of cefuroxime, but its absorption in vivo is improved. For a variety of gram-positive bacteria, gram-negative bacteria and anaerobic bacteria have antibacterial effect. It is mainly used for respiratory tract infection, urinary tract infection, Neisseria gonorrhoeae infection, skin and soft tissue infection caused by sensitive bacteria.
Last Update：2022-01-01 08:52:17
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