4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid,6-[[(2R)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]aMino]-2-phenylacetyl]aMino]-3,3-diMethyl-7-oxo-,(2S,5R,6R)-
Piperacillin
CAS: 61477-96-1
Molecular Formula: C23H27N5O7S
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid,6-[[(2R)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]aMino]-2-phenylacetyl]aMino]-3,3-diMethyl-7-oxo-,(2S,5R,6R)- - Names and Identifiers
| Name | Piperacillin |
| Synonyms | PIPC Pipracil Piperacillin Piperacillin (Acid) Monohydrate 6α-[[(R)-(4-Ethyl-2,3-dioxo-1-piperazinylcarbonylamino)phenylacetyl]amino]penicillanic acid 6α-[[(R)-α-Oxo-β-[[(2,3-dioxo-4-ethyl-1-piperazinyl)carbonyl]amino]phenethyl]amino]penicillanic acid (2S,5R,6R)-6-[[(2R)-[[(4-Ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid,6-[[(2R)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]aMino]-2-phenylacetyl]aMino]-3,3-diMethyl-7-oxo-,(2S,5R,6R)- |
| CAS | 61477-96-1 |
| EINECS | 262-811-8 |
| InChI | InChI=1/C23H27N5O7S/c1-4-26-10-11-27(19(32)18(26)31)22(35)25-13(12-8-6-5-7-9-12)16(29)24-14-17(30)28-15(21(33)34)23(2,3)36-20(14)28/h5-9,13-15,20H,4,10-11H2,1-3H3,(H,24,29)(H,25,35)(H,33,34)/t13-,14-,15+,20-/m1/s1 |
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid,6-[[(2R)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]aMino]-2-phenylacetyl]aMino]-3,3-diMethyl-7-oxo-,(2S,5R,6R)- - Physico-chemical Properties
| Molecular Formula | C23H27N5O7S |
| Molar Mass | 517.55 |
| Density | 1.51±0.1 g/cm3(Predicted) |
| Melting Point | 183-185?C (dec.) |
| Water Solubility | 256.8mg/L at 20℃ |
| Solubility | Freely soluble in methanol. Only sparingly soluble in aqueous solution at 0.119 mg/mL |
| Vapor Presure | 0Pa at 20℃ |
| Appearance | Solid |
| Color | White to Off-White |
| pKa | 2.44±0.50(Predicted) |
| Storage Condition | Sealed in dry,2-8°C |
| Stability | Hygroscopic |
| Physical and Chemical Properties | As the drug, its sodium salt, I .e., oxypiperazine penicillin sodium, is a white crystalline powder. Melting point 183-185 °c (decomposition). Soluble in water and methanol, soluble in ethanol, insoluble in acetone, ethyl acetate, almost insoluble in chloroform. |
| Use | Has a broad-spectrum antibacterial effect, gram-positive and gram-negative bacteria have good antibacterial activity |
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid,6-[[(2R)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]aMino]-2-phenylacetyl]aMino]-3,3-diMethyl-7-oxo-,(2S,5R,6R)- - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 42/43 - May cause sensitization by inhalation and skin contact. |
| Safety Description | 36/37 - Wear suitable protective clothing and gloves. |
| RTECS | XH8952200 |
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid,6-[[(2R)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]aMino]-2-phenylacetyl]aMino]-3,3-diMethyl-7-oxo-,(2S,5R,6R)- - Upstream Downstream Industry
| Raw Materials | Acetone Diethyl oxalate Carbon Dioxide Carbon Dioxide Sodium bicarbonate Bromoethane Bromoethane Ethylenediamine |
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid,6-[[(2R)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]aMino]-2-phenylacetyl]aMino]-3,3-diMethyl-7-oxo-,(2S,5R,6R)- - Reference
| Reference Show more | Liu Chen-hui, Cao Jing, Jing Zhao-Yu et al. Low-adhesiveness electropositive nanocapsules for the treatment of bacterial biofilm infection [J]. Acta polymerica Sinica 2019(3):300-310. |
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid,6-[[(2R)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]aMino]-2-phenylacetyl]aMino]-3,3-diMethyl-7-oxo-,(2S,5R,6R)- - Standard
Authoritative Data Verified Data
(2S, 5R,6R)-3, 3-dimethyl-6-[(R)-2-(4-ethyl-2, 3-dioxo-1-piperazinylamino)-2-phenylacetamido]-7-oxo-4-thia-1-azabicyclo [3.2.0] heptane-2-carboxylic acid monohydrate. Calculated as anhydrous, containing piperacillin (C23H27N507S) shall not be less than 92.0%.
Last Update：2024-01-02 23:10:35
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid,6-[[(2R)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]aMino]-2-phenylacetyl]aMino]-3,3-diMethyl-7-oxo-,(2S,5R,6R)- - Trait
Authoritative Data Verified Data
- This product is white crystalline powder; Odorless; Slightly hygroscopic.
- This product is soluble in methanol, soluble in anhydrous ethanol or acetone, and slightly soluble in water.
specific rotation
take this product, precision weighing, plus absolute ethanol dissolution and quantitative dilution of the solution containing about 10 mg per 1 ml, according to the law (General 0621), specific rotation from +160 ° to 178% °
Last Update：2022-01-01 13:40:00
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid,6-[[(2R)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]aMino]-2-phenylacetyl]aMino]-3,3-diMethyl-7-oxo-,(2S,5R,6R)- - Differential diagnosis
Authoritative Data Verified Data
- Take 10 mg of this product, add 2ml of water and hydroxylamine hydrochloride solution [take 1 part of 34.8% hydroxylamine hydrochloride solution, sodium acetate-sodium hydroxide solution (take 10.3g of sodium acetate and 86.5g of sodium hydroxide, add water to make it 1000ml)l part and 4 parts of ethanol, mix well] 3ml, shake to dissolve, place for 5 minutes, add acid ammonium ferric sulfate test solution 1 ml, shake well, red-brown.
- 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 product of the infrared absorption spectrum with the control of the map (spectral set 621 a) consistent.
Last Update：2022-01-01 13:40:01
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid,6-[[(2R)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]aMino]-2-phenylacetyl]aMino]-3,3-diMethyl-7-oxo-,(2S,5R,6R)- - Exam
Authoritative Data Verified Data
acidity
take this product, add water to make each lml containing lOmg suspension, according to the law (General 0631),pH value should be 2.5~4.0.
clarity and color of solution
take 5 parts of this product, each 0.55g, respectively, add methanol 5M l dissolved, the solution should be clear and colorless; If it is turbid, and 1 turbidity standard solution (General Principles 0902 first method) comparison, shall not be more concentrated; If color, with yellow-green or yellow No. 2 Standard Colorimetric liquid (General Principles 0901 first method), shall not be deeper.
Related substances I
take an appropriate amount of this product, add an appropriate amount of methanol to dissolve, dilute with mobile phase to make about 2.0 mg of the solution was used as a test solution; An appropriate amount of the solution was quantitatively diluted with a mobile phase to prepare a solution containing about 20ug per 1 ml as a control solution. According to the chromatographic conditions under the item of content determination, each lol of the test solution and the control solution is accurately weighed and injected into the human liquid chromatograph respectively, and the chromatogram is recorded to 1.1 times of the retention time of the main component peak. If there are impurity peaks in the chromatogram of the test solution, the peak area of ampicillin (relative retention time is about 0.31) shall not be greater than 0.2 times (0.2%) of the main peak area of the control solution, impurity A (relative retention time is about 0.62) calculated by the corrected peak area (multiplied by the correction factor of 1.4), and shall not be greater than the main peak area of the control solution (1.0% ) , the Peak area of other individual impurities shall not be more than 2 times (2.0%) of the main peak area of the control solution.
Related substances II
take an appropriate amount of this product, add an appropriate amount of methanol to dissolve, dilute with mobile phase to make 2.0 mg of the solution was used as a test solution; An appropriate amount of the solution was quantitatively diluted with a mobile phase to prepare a solution containing about 20ug per 1 ml as a control solution. According to high performance liquid chromatography (General 0512) determination, with eighteen alkyl silane bonded silica gel as filler; methanol-water -0.2mol/L sodium dihydrogen phosphate solution -0.4mol/L tetrabutylammonium hydroxide solution (615:282:100:3) (pH adjusted to 5.50±0.02 with phosphoric acid) as mobile phase, the detection wavelength was 220nm. The sample solution and the control solution were respectively injected into the liquid chromatograph at 10ug, and the chromatogram was recorded to 3 times of the retention time of the main component peak. If there are impurity peaks in the chromatogram of the test solution, the impurity D (relative retention time is about 2.55) shall be calculated according to the corrected peak area (multiplied by the correction factor of 1.47), not more than 2 times (2.0%) the area of the main peak of the control solution. The sum of impurities of related substances I and related substances II shall not exceed 3.8%.
moisture
take this product, according to the determination of moisture (General 0832 first method 1), the water content shall not exceed 5.0%.
bacterial endotoxin
take this product, add an appropriate amount of lmol/L sodium hydroxide solution to dissolve and adjust the pH value to near neutral, check according to law (General rule 1143), every lmg piperacillin (according to C23H27N5O7S) the amount of endotoxin contained in should be less than 0.050EU. (For injection)
Last Update：2022-01-01 13:40:02
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid,6-[[(2R)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]aMino]-2-phenylacetyl]aMino]-3,3-diMethyl-7-oxo-,(2S,5R,6R)- - Content determination
Authoritative Data Verified Data
measured by high performance liquid chromatography (General 0512).
chromatographic conditions and system suitability test
silica gel bonded with octylsilane as filler; Methanol-water -0.2mol/L sodium dihydrogen phosphate solution -0.4mol/L tetrabutylammonium hydroxide solution (450:447:100:3) (with phosphoric acid to adjust the pH value to 5.50±0.02) as mobile phase, the detection wavelength was 254nm. An appropriate amount of ampicillin and piperacillin control was taken, dissolved and diluted with mobile phase to prepare 0.2mg of ampicillin (according to C16H19N3O4S) and piperacillin (according to C23H27N5O7S) per lml. 0.4mg mixed solution, take 10u1 injection human liquid chromatograph, record chromatogram, ampicillin peak relative retention time is about 0.31, impurity A peak relative retention time is about 0.62, the separation degree of piperacillin peak and ampicillin peak should be greater than 16, and the tailing factor of piperacillin peak should not be greater than 1.2.
assay
take about 40mg of this product, accurately weigh it, put it in a 100ml measuring flask, add an appropriate amount of methanol to dissolve it, dilute it to the scale with mobile phase, shake it well, and use it as a test solution, precision amount of 10ul injection of human liquid chromatography; Another piperacillin standard amount, the same method for determination. The content of C23H27N5O7S in the sample was calculated by the peak area according to the external standard method.
Last Update：2022-01-01 13:40:03
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid,6-[[(2R)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]aMino]-2-phenylacetyl]aMino]-3,3-diMethyl-7-oxo-,(2S,5R,6R)- - Category
Authoritative Data Verified Data
B-lactam antibiotics, penicillins.
Last Update：2022-01-01 13:40:03
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid,6-[[(2R)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]aMino]-2-phenylacetyl]aMino]-3,3-diMethyl-7-oxo-,(2S,5R,6R)- - Storage
Authoritative Data Verified Data
sealed and stored in a cool, dark and dry place.
Last Update：2022-01-01 13:40:03
![4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid,6-[[(2R)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]aMino]-2-phenylacetyl]aMino]-3,3-diMethyl-7-oxo-,(2S,5R,6R)-](http://res.chembk.com/assets/str/2d/6/61/61477-96-1.png)
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View History
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid,6-[[(2R)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]aMino]-2-phenylacetyl]aMino]-3,3-diMethyl-7-oxo-,(2S,5R,6R)-
VITAMIN K5
布美他尼对照品
丙环定杂质4
2-(3-Formylphenyl)thiophene-3-carboxylic acid
青阳参苷元B
METHACHOLINE BROMIDE
2,4,5,6-四氨基嘧啶硫酸盐(甲氨碟呤的中间体)
COBALTOUS ACETATE TETRAHYDRATE, CRYSTALL IZED
4-BUTOXYBENZOIC ACID
VITAMIN K5
布美他尼对照品
丙环定杂质4
2-(3-Formylphenyl)thiophene-3-carboxylic acid
青阳参苷元B
METHACHOLINE BROMIDE
2,4,5,6-四氨基嘧啶硫酸盐(甲氨碟呤的中间体)
COBALTOUS ACETATE TETRAHYDRATE, CRYSTALL IZED
4-BUTOXYBENZOIC ACID
Raw Materials for 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid,6-[[(2R)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]aMino]-2-phenylacetyl]aMino]-3,3-diMethyl-7-oxo-,(2S,5R,6R)-