tazobactam acid
Tazobactam
CAS: 89786-04-9
Molecular Formula: C10H12N4O5S
tazobactam acid - Names and Identifiers
tazobactam acid - Physico-chemical Properties
| Molecular Formula | C10H12N4O5S |
| Molar Mass | 300.29 |
| Density | 1.92±0.1 g/cm3(Predicted) |
| Melting Point | 115-145℃ |
| Boling Point | 77℃ |
| Flash Point | >110°(230°F) |
| Water Solubility | Soluble in water |
| Solubility | Almost insoluble in water |
| Vapor Presure | 5.55E-21mmHg at 25°C |
| Appearance | White or off-white powder |
| Color | White to Off-White |
| pKa | 2.33±0.40(Predicted) |
| Storage Condition | Sealed in dry,Store in freezer, under -20°C |
| Stability | Light Sensitive |
| Refractive Index | 1.817 |
| MDL | MFCD00867002 |
| Physical and Chemical Properties | Trizobactam sodium (Tazobactam Sodium):C10H11N4NaO5S. [89785-84-2]. Amorphous solid, melting point> 170 ℃ (decomposition). |
| Use | As a beta-lactamase inhibitor, as the third generation of antibacterial potentiator, combined with piperacillin or cefoperazone can enhance the efficacy of the two and prolong the duration of action |
tazobactam acid - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| RTECS | XI0191400 |
| HS Code | 2941106000 |
tazobactam acid - Reference
| Reference Show more | 1. Liu Chenhui, Cao, Jing, Jing, Zhao, Yu, et al. Low adhesion positive Nano capsule for the treatment of drug resistant bacterial biofilm infection [J]. Chinese Journal of Polymer Science 2019(3):300-310. 2. [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 relevant." Ther Drug Monit. 2020 Aug;42(4):578-587 |
tazobactam acid - Nature
Open Data Verified Data
Tazobactam sodiumsalt: Cio HU N4NaoS.CAS accession number [89785-84-2]. Amorphous solid, melting point> 170 °c (decomposition). Soluble in water, slightly soluble in methanol, ethanol, insoluble in acetone, ethyl acetate, ether.
Last Update：2024-01-02 23:10:35
tazobactam acid - Preparation Method
Open Data Verified Data
with sulbactam as raw material, the carboxyl group was protected by alcoholization, and then reacted with sodium azide to introduce an azide group on the methyl group. Reaction with vinyl acetate to form a triazole compound, and finally the hydrogen is freed from the protecting group to give tazobactam. Alternatively, 6-APA (6-aminopenicillanic acid) is used as a raw material, which is subjected to diazotization, bromination, peracetic acid oxidation, and then alcoholization, and then debromination is carried out under the action of zinc. It is then reacted with the trimethylsilyltriazole compound, the triazole compound is introduced, the potassium permanganate is oxidized, and finally the sodium tazobactam is hydrolyzed.
Last Update：2022-01-01 08:52:36
tazobactam acid - Use
Open Data Verified Data
Japan Dapeng (Taiho) company research and development. p-lactamase inhibitors. For clinically important beta-lactamases such as penicillinase produced by S. Aureus, Proteus, Bacteroides, the chromosome-mediated p-lactamases produced by Klebsiella pneumoniae have a strong inhibitory effect. The width of the enzyme spectrum and the intensity of inhibition of enzyme activity were better than those of clavulanic acid and sulbactam. Its low toxicity, good stability, strong inhibition of enzyme activity. For the treatment of a variety of bacteria including aerobic and anaerobic bacteria caused by infection, including lower respiratory tract infections, skin and abdominal infections.
Last Update：2022-01-01 08:52:37
tazobactam acid - Reference Information
| pharmacological action | This product is also called tazobactam, which is a derivative of sulbactam, it is an irreversible competitive β-lactamase inhibitor against penicillinase produced by Staphylococcus aureus, plasmid-mediated β-lactamase produced by Gram-negative bacilli and Proteus, Bacteroides, chromosome-mediated β-lactamases produced by Klebsiella and other bacteria have strong inhibitory effect. The inhibition of enzyme is better than that of clavulanic acid and sulbactam, and it also has inhibitory effect on some chromosome-mediated type I enzyme. It has little effect on Pseudomonas aeruginosa and serratia. Only weak antibacterial activity. |
| Use | penicillane sulfone β-lactamase inhibitor, effective for type I ~ vi 3-lactamase, in particular, it is more effective for type I enzymes. Its low toxicity, good stability, strong inhibition of enzyme activity. It is clinically used to treat infections caused by a variety of bacteria including aerobes and anaerobes, including lower respiratory tract infections, skin and abdominal infections, etc. β-lactamase inhibitor, the third generation of antibacterial potentiator, combined with piperacillin or cefoperazone can enhance the efficacy and prolong the duration of action. Tazobactam sodium and piperacillin sodium when used in combination, produce obvious synergistic effect, widely used in the treatment of severe systemic and local infection, abdominal infection, lower respiratory tract infection, soft tissue infection, sepsis, etc, it has a wider antibacterial spectrum and indications than other antibacterial compounds that have been used, and it shows great advantages in overcoming drug resistance. as a β-lactamase inhibitor, it is the third generation of antibacterial potentiator. The combination with piperacillin or cefoperazone can enhance the efficacy and prolong the action time of the two |
| production method | Method 1: sulbactam was used as raw material, the carboxyl group was protected by esterification, and then reacted with sodium azide, an azido group is introduced at one of the methyl groups at position 3. Reaction with vinyl acetate to form a triazole compound, and finally the hydrogen is freed from the protecting group to give tazobactam. The final deprotecting group may also be removed by the action of sodium hydroxide. Method 2: 6-APA was used as raw material, after diazotization and bromination, bromine was introduced at the 6-position. After oxidation with peracetic acid and esterification, the bromine is removed under the action of zinc. It is then reacted with the trimethylsilyltriazole compound, the triazole compound is introduced, the potassium permanganate is oxidized, and finally the sodium tazobactam is hydrolyzed. Method 3: under ice-cooling and stirring, 6-APA, potassium bromide and 95% ethanol were added to sulfuric acid, and sodium nitrite solution was added dropwise at 5-7 ° C., and the reaction was stirred. Chloroform extraction 3 times, the combined extracts, washed with saturated salt water, concentrated to about 1/3 volume, get Intermediate Chloroform solution of (I). Water was added, 40% peroxyacetic acid was added dropwise at 0 °c, and the reaction was stirred at 0-5 °c. Diphenylhydrazone and potassium iodide were added, a second portion of 40% peroxyacetic acid and 10% sulfuric acid were added at 0 °c, the reaction was stirred, and the reaction was continued at 20-25 °c. The chloroform layer was separated and treated to give intermediate (II). The intermediate (II) was dissolved in Tetrahydrofuran, an aqueous solution of ammonium acetate was added, and zinc powder was added in portions under stirring at 0-5 °c, and the reaction was stirred at 20-25 °c. Activated Carbon and Diatomite were added, stirred, decolorized and suction filtered, and tetrahydrofuran was distilled off. The remaining aqueous solution was extracted with ethyl acetate, the extract was washed with saturated sodium chloride, dried, concentrated, cooled, suction filtered and dried to obtain an intermediate (III) in a yield of 44.4% based on 6-APA. For the preparation of intermediate (IV) from intermediate (III), see Synthesis,1986,(4):292, yield 93.9%, content 88%. Intermediate (V) is prepared from intermediate (IV), see above, content 88%. The intermediate (V) was dissolved in dimethylformamide and ethanol, and an aqueous solution of sodium azide was added under stirring at 5 °c, and the reaction was stirred at 20-25 °c. It was poured into ice water and extracted with ethyl acetate. The extract was washed with brine, dried and concentrated to obtain (Ⅵ a). The mixed oil of (VI B) and (vi B) is directly used for the next reaction. The mixture of the intermediate (VI) was dissolved in glacial acetic acid, water was added, and potassium permanganate was added in portions under stirring and below 10 °c, and stirred at room temperature. Hydrogen peroxide was added dropwise to decompose excess oxidant. The resultant was poured into ice water, suction filtered, washed with cold water, and dried. After remixing with ether and refluxing, the mixture was allowed to stand in a refrigerator overnight. (VII B) was insoluble in cold diethyl ether and removed by filtration. The filtrate was concentrated to obtain crude product (VII a), which was refined with benzene-n-hexane to obtain fine product with content of 92%. The intermediate (VIIa) was dissolved in ethyl acetate and stirred at 80-85 °c under a pressure of 0.18-0.20MPA in pure acetylene. After cooling, most of the ethyl acetate was distilled off, the crystals were collected by filtration, washed with chloroform, and dried to obtain diphenylmethyl trizobactam, The yield was 78%. The diphenylmethyl ester of tazobactam is dissolved in m-cresol, a sodium bicarbonate solution is added, and the reaction is stirred at 50-55 °c. Methyl isobutyl ketone was added and extracted at 0-5 °c with additional sodium bicarbonate solution. The separated organic layer was further extracted with sodium bicarbonate solution. The basic aqueous layers were combined and washed with methyl isobutyl ketone. Under cooling and stirring, the Ph was adjusted to 1-1.5 with hydrochloric acid, and the white solid obtained was washed with a small amount of ice water and acetone, and dried to give tazobactam in a yield of 86%-91% and a content of 99.1%. Tazobactam was dissolved in ethyl acetate and a solution of sodium isooctanoate in ethyl acetate was added and stirred. Suction filtration, ethyl acetate washing, drying, trizobactam sodium, yield 85.7%, content 98.6%, melting point 167~169 ℃ (decomposition). |
Last Update：2024-04-09 02:00:12
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