(2S,5R,6R)-6-[(R)-2-Amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Ampicillin
CAS: 69-53-4
Molecular Formula: C16H19N3O4S
(2S,5R,6R)-6-[(R)-2-Amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid - Names and Identifiers
(2S,5R,6R)-6-[(R)-2-Amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid - Physico-chemical Properties
| Molecular Formula | C16H19N3O4S |
| Molar Mass | 349.4 |
| Density | 1.2794 (rough estimate) |
| Melting Point | 198-200°C (dec.)(lit.) |
| Boling Point | 201.8°C (rough estimate) |
| Specific Rotation(α) | D23 +287.9° (c = 1 in water) |
| JECFA Number | 85 |
| Water Solubility | 13.9g/L(25 ºC) |
| Solubility | NH4OH 1 M: 50mg/mL, clear, colorless |
| Appearance | solid |
| Color | White to Pale Yellow |
| Merck | 13,591 |
| BRN | 1090925 |
| pKa | 2.5 (COOH)(at 25℃) |
| Storage Condition | 2-8°C |
| Stability | Stable, but may be moisture sensitive. Incopmpatible with strong oxidizing agents. |
| Refractive Index | 1.6320 (estimate) |
| Physical and Chemical Properties | Semi-synthetic, broad-spectrum penicillin antibiotics. Its free acid contains 3 molecules of crystal water for oral use; Its sodium salt for injection. White or off-white powder or crystal. Odorless, slightly bitter, soluble in water, slightly soluble in ethanol, insoluble in ether. Not resistant to enzymes, acid-stable. |
| Use | For the treatment of sensitive enterococci, Shigella, Salmonella Typhi, Escherichia coli, listeria, Aerobacter aerogenes, influenza and Proteus mirabilis |
(2S,5R,6R)-6-[(R)-2-Amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid - Risk and Safety
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R42/43 - May cause sensitization by inhalation and skin contact. R61 - May cause harm to the unborn child |
| Safety Description | S22 - Do not breathe dust. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 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.) S53 - Avoid exposure - obtain special instructions before use. |
| WGK Germany | 2 |
| RTECS | XH8425000 |
| FLUKA BRAND F CODES | 10-23 |
| HS Code | 29212900 |
| Toxicity | LD50 oral in mouse: > 5gm/kg |
(2S,5R,6R)-6-[(R)-2-Amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid - Upstream Downstream Industry
| Raw Materials | Triethylamine Trimethylacetyl chloride |
| Downstream Products | 6-Aminopenicillanic acid |
(2S,5R,6R)-6-[(R)-2-Amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid - Standard
Authoritative Data Verified Data
(2S, bR,6R)-3, 3-dimethyl-6-[(R)-2-amino-2-phenylacetylamino]-7-oxo-4-thia-1-azabicyclo [3.2.0] heptane-2-carboxylic acid trihydrate. The content of ampicillin (calculated as C16H19N304S) shall not be less than 96.0% calculated as anhydrous.
Last Update：2024-01-02 23:10:35
(2S,5R,6R)-6-[(R)-2-Amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid - Trait
Authoritative Data Verified Data
- This product is white crystalline powder; Slightly bitter taste.
- This product is slightly soluble in water, insoluble in ethanol, ether or volatile oil; Dissolved in dilute acid solution or dilute alkali solution.
specific rotation
take this product, precision weighing, add water to dissolve and quantitatively dilute to make a solution containing about 2.5mg per lml, heat on a water bath at 60°C to dissolve, cool, measured according to law (General rule 0621), the specific rotation is 280 ° to 305 °.
Last Update：2022-01-01 15:37:02
(2S,5R,6R)-6-[(R)-2-Amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid - Differential diagnosis
Authoritative Data Verified Data
- take an appropriate amount of this product and ampicillin reference, and add phosphate buffer solution (take anhydrous disodium hydrogen phosphate 0.50g and potassium dihydrogen phosphate 0.301g, add water to dissolve into 1000ml,pH 7.0) each solution containing about 1 mg per 1 ml was prepared by dissolving and diluting, and used as a test solution and a reference solution; The above two solutions were mixed in equal amounts as a mixed solution. According to the thin layer chromatography (General 0502) test, absorb the above three solutions each 2 u1, respectively, on the same silica gel G thin layer plate, with acetone-water-toluene-glacial acetic acid (65:10:10:2.5) as the developing solvent, it was developed, dried, sprayed with 0.3% ninhydrin ethanol color developing solution, and heated at 90°C until spots appeared. The main spot displayed by the mixed solution should be a single spot, and the position and color of the main spot displayed by the test solution should be the same as that of the reference solution or the mixed solution.
- 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 658).
- two items (1) and (2) above can be selected as one item.
Last Update：2022-01-01 15:37:02
(2S,5R,6R)-6-[(R)-2-Amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid - Exam
Authoritative Data Verified Data
acidity
take this product, add water to make a solution containing about 0631 mg per 1 ml, heat it in a 60°C water bath to dissolve it, let it cool, and measure it according to law (general rule), the pH should be between 3.5 and 5.5.
clarity of the solution
take 5 parts of this product, 0.6g each, add 5ml of 1 mol/L hydrochloric acid solution to dissolve it, and immediately check it. Take another 5 parts of this product, each 0.6g, add 5ml of 2mol/L ammonium hydroxide solution to dissolve, immediately check, the solution should be clear; If it is turbid, it should not be more concentrated compared with No. 2 Turbidity standard solution (General rule 0902 first method).
Related substances
new system for clinical use. Take an appropriate amount of this product, precision weighing, and add mobile phase A to dissolve and quantitatively dilute to prepare A solution containing about 3mg per lml as A test solution; Take an appropriate amount of ampicillin reference substance, precision weighing, mobile phase A was added to dissolve and quantitatively dilute to prepare A solution containing about 30ug per 1 ml as A control solution. According to the high performance liquid chromatography (General 0512) test, silica gel bonded with eighteen alkyl silane was used as filler; Mobile phase A was 12% acetic acid solution -0.2mol/L potassium dihydrogen phosphate solution-acetonitrile-water (0.5:50:50 :900) mobile phase B was 12% acetic acid solution -0.2mol/L potassium dihydrogen phosphate solution-acetonitrile-water (0.5:50:400:550); The detection wavelength was 254nm. First, the mobile phase A- mobile phase B(85:15) was used for isocratic elution, and immediately after the ampicillin peak elution was completed, the linear gradient elution was carried out according to the following table. Appropriate amount of ampicillin system applicable reference substance is taken, dissolved and diluted with mobile phase A to make A solution containing about 2mg per 1 ml, and 20ul is injected into the liquid chromatograph. The chromatogram recorded should be consistent with the standard chromatogram. 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 any impurity peaks in the chromatogram of the test solution, the single impurity shall not exceed 1.0% and the total amount of each impurity shall not exceed 3.0% based on the calculation of ampicillin peak by external standard method, the peaks in the chromatogram of the test solution which were 0.05 times smaller than the main peak area of the control solution were ignored.
N,N-dimethylaniline
take about 1.0g of this product, weigh it accurately, place it in a test tube with a stopper, add 5ml of 1 mol/L sodium hydroxide solution, and add the internal standard solution accurately (weigh the proper amount of naphthalene accurately, add cyclohexane to dissolve and dilute to make a solution containing about 50ug per lml) lml, shake strongly, stand still, take the upper liquid as the test solution; Take 50mg of N,N-dimethylaniline, add 2ml of hydrochloric acid and 20ml of water to the measuring flask, shake and mix well, dilute to the scale with water, shake well, take 5ml of the measuring flask, place it in the 250ml measuring flask, dilute to scale with water, shake well, take 1ml accurately, put it in a test tube, add 5ml of 1 mol/L sodium hydroxide solution, add 1ml of internal standard solution accurately, shake strongly, and stand still, the supernatant was taken as a control solution. According to the gas chromatography (General 0521) test, with silicone (OV-17) as stationary phase, coating concentration of 3%; Column temperature of 120°C;N, the resolution between N-dimethylaniline peak and internal standard peak shall meet the requirements. 2 u1 of the test solution and the reference solution were respectively injected into the gas chromatograph, and the chromatogram was recorded. The peak area ratio was calculated according to the internal standard method, N, the amount of N-dimethylaniline should not exceed 20 parts per million.
moisture
take this product, according to the moisture determination method (General 0832 first method 1), the moisture content should be 12.0% ~ 15.0%.
ignition residue
take l.Og of this product and check it according to law (General rule 0841). The residue left shall not exceed 0.5%.
Heavy metals
The residue left under the item of taking the ignition residue shall not contain more than 20 parts per million of heavy metal when examined by law (General rule 0821, Law II).
Last Update：2022-01-01 15:37:03
(2S,5R,6R)-6-[(R)-2-Amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid - Content determination
Authoritative Data Verified Data
- measured by high performance liquid chromatography (General 0512).
- chromatographic conditions and system applicability test using eighteen alkyl silane bonded silica gel as filler; Mobile phase A- mobile phase B(85:15) under related substances as mobile phase; the detection wavelength was 254nm. Appropriate amount of ampicillin reference substance and cefradine reference substance were taken, dissolved and diluted with mobile phase A to prepare A mixed solution containing 0.3mg of ampicillin and 0.02mg of cefradine per 1 ml. 20u1 was injected into the liquid chromatograph and the chromatogram was recorded. The resolution between ampicillin peak and cephradine peak should be greater than 3.0.
- determination about 50mg of this product is accurately weighed, placed in A 50ml measuring flask, dissolved with the mobile phase A under the item of related substances, diluted to the scale, and shaken, as a sample solution, 20ul was injected into the liquid chromatograph with precision, and the chromatogram was recorded. An appropriate amount of ampicillin reference substance was taken and determined by the same method. According to the external standard method to calculate the peak area, that is.
Last Update：2022-01-01 15:37:04
(2S,5R,6R)-6-[(R)-2-Amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid - Category
Authoritative Data Verified Data
B-lactam antibiotics, penicillins.
Last Update：2022-01-01 15:37:04
(2S,5R,6R)-6-[(R)-2-Amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid - Storage
Authoritative Data Verified Data
light-shielded, sealed, and stored in a dry place.
Last Update：2022-01-01 15:37:04
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Spot supply
Product Name: Ampicillin Visit Supplier Webpage Request for quotationCAS: 69-53-4
Tel: 0714-3999186
Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052
Wechat: 15671228036
View History
Raw Materials for (2S,5R,6R)-6-[(R)-2-Amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Downstream Products for (2S,5R,6R)-6-[(R)-2-Amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid