sodium (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
Cefuroxime Sodium
CAS: 56238-63-2
Molecular Formula: C16H15N4O8S.Na
sodium (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
sodium (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 | C16H15N4O8S.Na |
| Molar Mass | 446.37 |
| Melting Point | 240-245°C(dec) |
| Specific Rotation(α) | D20 +60° (c = 0.91 in water) |
| Water Solubility | Freely soluble in water |
| Solubility | Easily soluble in water, very slightly soluble in ethanol (96%). |
| Appearance | White crystalline solid |
| Color | White to Pale Beige |
| pKa | pKa (water): 2.5; (DMF): 5.1(at 25℃) |
| Storage Condition | Inert atmosphere,2-8°C |
| MDL | MFCD09878727 |
| Use | Belonging to antibiotics |
sodium (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 | R42/43 - May cause sensitization by inhalation and skin contact. R36/37/38 - Irritating to eyes, respiratory system and skin. R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
| Safety Description | S22 - Do not breathe dust. S36/37 - Wear suitable protective clothing and gloves. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 2 |
| RTECS | XI0330000 |
| HS Code | 29419000 |
sodium (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. Liu Min-Xuan, Zhao Xing-ran, Yu Lu, Lu Hao-Zhi, Wang Xiang-hong. Rapid detection of cefalexin residues in animal derived food by colloidal gold strip [J]. Food Research and Development, 2020,41(15):150-155. 2. [IF = 6.331] Wei Guo et al.. "J Mater Chem B. 2021 Dec;: |
sodium (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 crystals, UV maximum absorption (pH 6 phosphate buffer):274nm(17600).
cefuroxime sodium (cefuroxime sodiumsalt): white, off-white or yellowish powder or crystalline powder, odorless, bitter, with hygroscopicity. Soluble in water or buffer solution, soluble in methanol, very slightly soluble in ethyl alcohol, ethyl ether, octanol, benzene or chlorine
The solubility in water is 500mg/2. SmL. pK. (Water):2.5;pK. (Dimethylformamide):5.1. UV absorption maximum (water):274NM (e17400).
Last Update：2024-01-02 23:10:35
sodium (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 Sodium: calculated as anhydrous, containing cefuroxime (C16 H16 N4 08S) shall not be less than 86.0%; The clarity and color of the solution shall be in accordance with the provisions; the pH value should be 6.0~8. 5 (10 mg of the product dissolved in 1ml of water), impurities should not be greater than 3%, containing water should not exceed 3.5%; The amount of endotoxin in cefuroxime per 1RNG should be less than 0. 10EU; Sterility should be met.
Last Update：2022-01-01 08:52:14
sodium (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 - Standard
Authoritative Data Verified Data
This product is (6R,7R)-7-[2-(furan-2-yl)-2-(methoxyimino) acetamido]-3-carbamoyloxymethyl-8-oxo-5-thia-1-azabicyclo [4.2.0] oct-2-ene-2-carboxylic acid sodium salt. Calculated as anhydrous, containing no less than 86.0% of cefuroxime (C16H16N408S).
Last Update：2024-01-02 23:10:35
sodium (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 - Trait
Authoritative Data Verified Data
- This product is a white to yellowish powder or crystalline powder; Odorless; With hygroscopicity.
- This product is soluble in water, slightly soluble in methanol, insoluble in ethanol.
specific rotation
take this product, precision weighing, add water to dissolve and quantitatively dilute to about 10 mg of solution per lml, according to the law (General 0621), the specific rotation of 55 ° to 65 °.
absorption coefficient
take this product, precision weighing, adding water to dissolve and quantitative dilution to prepare 10ug solution per lml, according to UV-visible spectrophotometry (General 0401), the absorbance was measured at a wavelength of 274nm, and the absorption coefficient was 390 to 425.
Last Update：2022-01-01 11:40:17
sodium (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
(1) synthesis of cefuroxime: 2 acetyl furan as raw material, in the presence of hydrochloric acid and sodium nitrite reaction to generate 2 furylglyoxylic acid, then react with methoxyamine hydrochloride to generate (Z) a 2 methoxyimino-2-(furan-2-yl) acetic acid, and then with 7 aminocephalosporanic acid (7-ACA) cefuroxime was prepared by isometric reaction.
(2) There are two methods for the preparation of cefuroxime sodium.
① with cefalotin sodium as raw material, the acetyl group on the side chain was removed by enzyme hydrolysis, and then reacted with diphenyl methylene chloride and trichloroacetyl isocyanate in turn, the carboxyl group and the alcohol are protected, and treated with phosphorus pentachloride, and the obtained compound is first hydrolyzed with a weak base in methanol solution, then hydrolyzed with a strong acid, the protecting group is removed, and cefuroxime can be obtained by continuing the side chain reaction. Cefuroxime and 2 ethyl hexanoate sodium, cefuroxime sodium available.
(2) with 7 aminocephalosporanic acid as raw material, with triethylamine as acid binding agent, reaction in dichloromethane, reaction solution with dilute hydrochloric acid washed to alkali compounds, with sodium bicarbonate solution extraction and treatment. The resulting compound was fermented with a yellow enzyme to remove the acetyl group. The fermentation broth was centrifuged to remove the enzyme, and acid was added for crystallization. Then, it is reacted sequentially with trichloroacetyl isocyanate (or chlorosulfonyl isocyanate; Or dichlorophosphoryl isocyanate) and sodium 2-ethylhexanoate to obtain cefuroxime sodium.
Last Update：2022-01-01 08:52:14
sodium (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 - Differential diagnosis
Authoritative Data Verified Data
- in the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution.
- The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 721).
- This product shows the reaction of sodium salt identification (1) (General rule 0301).
Last Update：2022-01-01 11:40:18
sodium (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
The second generation cephalosporin antibiotics, gram-positive bacteria and negative bacteria have a strong antibacterial or bactericidal effect on α-lactamase stability, injection administration. For urinary tract infections caused by sensitive bacteria, respiratory infections, soft tissue infections, infections of obstetrics and gynecology diseases, gonorrhea, meningitis and so on. Cefuroxime and its sodium salt and esterified substance are cephalosporin antibiotics developed by British GlaxoSmithKline company. It has won the general recognition of the market for its good clinical application effect, annual global sales of this product have been among the best for several years. Cefuroxime sodium and cefuroxime axetil are widely used in the second generation cephalosporins in China.
Last Update：2022-01-01 08:52:15
sodium (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 - Exam
Authoritative Data Verified Data
pH
take this product, add water to make a solution containing 0.lg per lml, according to the law (General 0631),pH value should be 6.0~8.5.
clarity of the solution
take 5 parts of this product, each 0.6g, respectively, add water 0902 to dissolve, the solution should be clear; If it is turbid, compare with No. 1 turbidity standard solution (General rule first method), none should be more concentrated.
color of solution
take 5 parts of this product, each 0.6g, add 0.05mol/L ethylenediamine tetraacetic acid disodium solution 5ml to dissolve, the solution should be colorless; If color, no deeper color shall be compared with the yellow or yellow-green standard colorimetric solution No. 6 (General rule 0901, Method 1).
Related substances
take an appropriate amount of this product, add water to dissolve and dilute to make a solution containing 0.5mg per lml, as a test solution (with new or stored at 2~8°C); the appropriate amount of the test solution was accurately taken and diluted with water to prepare a solution containing 5ug per 1 ml as a control solution. According to the determination of high performance liquid chromatography (General rule 0512), octyl silane bonded silica gel is used as filler; Acetate buffer solution (0.68g of sodium acetate, 5.8g of glacial acetic acid, diluted with water to 1000ml, using glacial acetic acid to adjust the pH value to 3.4) as mobile phase A, acetonitrile as mobile Phase B, the flow rate was 1.5ml per minute, and the linear gradient elution was carried out according to the following table. The detection wavelength was 273nm. A suitable amount of cefuroxime reference substance was taken, dissolved with water and diluted to make a solution containing 0.5mg per lml, placed in a water bath at 60°C for 30 minutes, and allowed to cool, so that the cefuroxime was partially converted into decarbamyl cefuroxime, as the applicable solution of the system, 20u1 was injected into the human liquid chromatograph, and the chromatogram was recorded. The separation degree between the peak of cefuroxime and the peak of decarbamyl cefuroxime should be greater than 3.0. The separation degree between cefuroxime peak and the adjacent impurity peak should meet the requirements. 20 u1 of the test solution and the control solution were respectively injected into the liquid chromatograph, and the chromatograms were recorded. If there are impurity peaks in the chromatogram of the test solution, the area of a single impurity peak shall not be greater than the area of the main peak of the control solution (1.0% ), the sum of each impurity peak area shall not be greater than 3 times (3.0%) of the main peak area of the control solution, and the peaks in the chromatogram of the test solution which are smaller than 0.05 times of the main peak area of the control solution are ignored.
cefuroxime polymer
measured by size exclusion chromatography (General 0514).
chromatographic conditions and system suitability test
A glass column using dextran gel G-10(40-1.0 um) as a filler, having an inner diameter of 1.4 to and a column length of 30-40cm. Mobile phase A was 7.0 mol/L phosphate buffer (pH 0.025) [0.025mol/L disodium hydrogen phosphate solution -0.025mol/L sodium dihydrogen phosphate solution (61:39 )], mobile phase B was water, the flow rate was about 1.5ml per minute and the detection wavelength was 254nm. 0.5 ~ 200ul of 2000 mg/ml Blue dextran 100 solution was injected into human Liquid Chromatograph. Mobile phase A and B were used as mobile phase for determination, and the chromatogram was recorded. The number of theoretical plates is not less than 2000 calculated by the Blue dextran 400 peak, and the tailing factor should be less than 2.0. The ratio of the Blue dextran 2000 peak retention times in the two mobile phase systems should be between 0.93 and 1.07. The ratio of the retention time of the main peak of the control solution and the polymer peak in the test solution to the Blue dextran 2000 peak in the corresponding chromatography system should be between 0.93 and 1.07. Weigh about 0.2g of cefuroxime sodium, put it in a 10ml measuring flask, dissolve it in 2000 mg /ml Blue dextran solution, dilute it to the scale, and shake it well. Measure 100-200ul and inject it into human liquid chromatograph, measure with mobile phase A, and record chromatogram. The ratio of the peak height of the polymer to the valley height between the monomer and the polymer should be greater than 2.0. In addition, the mobile phase B is used as the mobile phase, and the relative standard deviation of the peak area value should not be more than 100 by taking 200 ~ 5.0% u1 of the control solution for 5 consecutive injections.
preparation of control solution
an appropriate amount of cefuroxime reference substance was accurately weighed, dissolved with water and quantitatively diluted to prepare a solution containing about 40ug per 1 ml.
assay
take about 0.2g of this product, weigh it accurately, put it in a 10ml measuring flask, add water to dissolve and dilute it to the scale, shake it well. Immediately inject 100~200u1 into human liquid chromatograph, use mobile phase A as mobile phase for measurement, and record chromatogram. In addition, 100~200u1 of the control solution was injected into the human liquid chromatograph, and the mobile phase B was used as the mobile phase to record the chromatogram. According to the external standard method to calculate the peak area of cefuroxime, the amount of cefuroxime polymer should not exceed 0.2%.
residual solvent
take about 1.Og of this product, weigh it accurately, put it in a 10ml measuring flask, add water to dissolve and dilute it to the scale, shake it well, and use it as a stock solution for test, precisely measure lml into the top empty bottle, precisely add water lml, seal, as a test solution; Precisely weigh the appropriate amount of each solvent, quantitatively dilute with water to make methanol 0.3mg per lml, ethanol 0.5mg, acetone 0.5mg, isopropanol 0.5mg, dichloromethane 60mg, n-propanol 0.5mg, ethyl acetate 0.5mg, tetrahydrofuran 70mg, n-butanol 0.5mg, A mixed solution of 0.3mg of cyclohexane and 0.5mg of methyl isobutyl ketone was shaken, and 1ml of the mixed solution was accurately measured. The mixed solution was placed in a top empty bottle, and 1ml of the sample stock solution was added, sealed and used as a reference solution. According to the determination method of residual solvent (General 0861 second method), the capillary column with 100% dimethylpolysiloxane (or similar polarity) as the stationary liquid is used as the column; The initial temperature is 35°C, and the maintenance time is 15 minutes, the temperature was raised to 150°C at a rate of 10°C per minute; The inlet temperature was 200°C; The detector temperature was 250°C; The headspace bottle equilibrium temperature was 70°C for 30 minutes. Take the reference solution into the headspace, the peak order is methanol, ethanol, acetone, isopropanol, dimethane, n-propanol, ethyl acetate, Tetrahydrofuran, n-butanol, cyclohexane, methyl isobutyl ketone, the degree of separation between peaks shall meet the requirements. Measure the reference solution and the test solution by Headspace injection, record the chromatogram, calculate the peak area according to the standard addition method, methanol, ethanol, acetone, isopropanol, dichloromethane, n-propanol, ethyl acetate, residues of tetrahydrofuran, n-butanol, cyclohexane and methyl isobutyl ketone shall comply with the regulations.
2-ethylhexanoic acid
take this product, determination according to law (General Principles 0873), not over 0.5%.
moisture
take this product, according to the moisture determination method (General 0832 first method 1), the water content shall not exceed 3.5%.
visible foreign body
take 5 parts of this product, each 3.Og, plus particle inspection water dissolution, inspection according to law (General 0904), should comply with the provisions. (For aseptic dispensing)
insoluble particles
Take 3 parts of this product, and make a solution containing 50mg per lml of water for particle inspection, and check it according to law (General rule 0903). In each lg sample, no more than 6000 particles containing lOum and more than 10um, and no more than 600 particles containing 25um and more than 25um. (For aseptic dispensing)
bacterial endotoxin
take this product, check according to law (General rule 1143), the amount of endotoxin per 1 mg cefuroxime should be less than 0.10EU. (For injection)
sterile
take this product, dissolve and dilute it with 0.9% sterile gasification sodium solution to 50mg per 1 ml, and treat it by membrane filtration, washing with sterile gasification sodium-peptone buffer at pH 7.0 (not less than 3 million per membrane), adding not less than units of penicillinase per tube of culture medium, with Staphylococcus aureus as positive control bacteria, inspection in accordance with the law (General rule 1101), should comply with the provisions. (For aseptic dispensing)
Last Update：2022-01-01 11:40:19
sodium (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 - Content determination
Authoritative Data Verified Data
measured by high performance liquid chromatography (General 0512).
chromatographic conditions and system suitability test
with octanosilane bonded silica gel as filler; With acetate buffer solution (sodium gallate 0.68g, glacial acetic acid 5.8g, diluted with water to 1000ml, with glacial acetic acid to adjust the pH value to 3.4)-Acetonitrile (85:15) as mobile phase, the detection wavelength was 273mn. Take an appropriate amount of this product, add water to dissolve and dilute to make a solution containing 0.5mg per lml, place it in a 60°C water bath for 30 minutes, and let it cool, so that the Cefuroxime is partially converted into decarbamyl cefuroxime, as the system applicable solution, 20u1 was injected into the human liquid chromatograph, and the chromatogram was recorded. The separation degree of cefuroxime peak and decarbamyl cefuroxime peak should be greater than 3.0. The separation degree between cefuroxime peak and impurity peak with relative retention time of about 1.1 should meet the requirements.
assay
take an appropriate amount of this product, weigh it accurately, add water to dissolve and quantitatively dilute it to make it contain 0. The lmg solution is used as a test solution (in the case of a new preparation or storage at 2~8°C), and 20M1 is accurately measured and injected into the liquid chromatograph, and the chromatogram is recorded; the appropriate amount of cefuroxime reference substance was taken and determined by the same method. The content of Cl6H16N4O8S in the sample was calculated by the peak area according to the external standard method.
Last Update：2022-01-01 11:40:20
sodium (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 - Category
Authoritative Data Verified Data
B-lactam antibiotics, cephalosporins.
Last Update：2022-01-01 11:40:20
sodium (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 - Storage
Authoritative Data Verified Data
shade, seal, and store in a cool place.
Last Update：2022-01-01 11:40:20
sodium (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 - Cefuroxime sodium for injection
Authoritative Data Verified Data
This product is a sterile powder of cefuroxime sodium. Calculated as anhydrous, containing cefuroxime (Cl6Hl6N408S) shall not be less than 86.0%; Calculated as the average loading, containing cefuroxime (C16H16N408S) shall be 90.0% ~ 110.0% of the labeled amount.
trait
This product is white to yellowish powder or crystalline powder.
identification
take this product, according to the identification of cefuroxime sodium under the item (1), (3) test, the results were asked.
examination
- clarity of solution take 5 bottles of this product, and add water separately according to the labeled amount to make 0 per 1 ml. lg of the solution, the solution should be clear; If it is turbid, compared with No. 1 turbidity standard solution (General 0902 first method), should not be more concentrated.
- the color of the solution of this product 5 bottles, according to the label amount were added 0.05mol/L ethylenediamine tetraacetic acid disodium solution made per 1 ml containing 0.lg of the solution, the solution should be colorless; If the color, and yellow or yellow-green No. 8 Standard Colorimetric liquid (General Principles 0901 first method), are not deeper.
- cefuroxime polymer precise weighing the appropriate amount of the content of this product, according to the method under the item of cefuroxime sodium determination, according to the external standard method to calculate the peak area of cefuroxime, cefuroxime polymer amount shall not exceed 0.3% of the label amount.
- insoluble particles this product is taken, and the labeled amount is added to the particle inspection water to make a solution containing 60mg per 1 ml, which is inspected according to law (General rule 0903), and the labeled amount is l. The conversion below Og is per l. No more than 6000 particles in the Og sample containing lOum and l0um, no more than 600 particles containing 25um or more than 25um; The labeled amount is more than 1.0g (including g). No more than 6000 particles of 10um or more and no more than 600 particles of 25um or more should be contained in each sample container.
- the pH, related substances, moisture, bacterial endotoxin and sterility should be checked according to the method of cefuroxime sodium.
- others should comply with the relevant provisions under injection (General 0102).
Content determination
The content under the item of loading amount difference was obtained by measuring according to the method under the item of cefuroxime sodium.
category
Same as cefuroxime sodium.
specification
Based on (Cl6Hl6N408S) (1) 0.5g (2) 0.75g(3) 1.0g (4) 1.25g (5) 1.5g (6) 1.75g (7) g(8)2.Og (9)2.25g (10)2.5g (11) 3.og
storage
shade, seal, and store in a cool place.
Last Update：2022-01-01 11:40:21
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