Molecular Formula | C13H17N5O8S2 |
Molar Mass | 435.43 |
Density | 1.83 |
Melting Point | 227°C |
Specific Rotation(α) | -28° (C=0.5,H2O) |
Water Solubility | Soluble in DMF/water (1:1) at 50 mg/ml |
Solubility | Soluble in dimethylformamide and dimethylsulfoxide; slightly soluble in water or methanol, hardly soluble in absolute ethanol, not easy to chloroform or ethyl acetate. |
Appearance | White to off-white crystals |
Color | white to beige |
Merck | 14,925 |
pKa | pKa -0.7(H2O t=RT Iunde?ned) (Uncertain);2.75(H3O t=RT Iunde?ned) (Uncertain);3.91(H4O t=RT Iunde?ne |
Storage Condition | room temp |
Refractive Index | 1.6460 (estimate) |
MDL | MFCD00072145 |
Physical and Chemical Properties | Density 1.83 |
Use | It is mainly used for infections caused by sensitive Gram-negative bacteria, including Pneumonia, pleurisy, abdominal infection, biliary tract infection, bone and joint infection, skin and soft tissue inflammation, especially for urinary tract infection, and also for sepsis. Because this product has good enzyme resistance, therefore, when the microorganisms are not sensitive to penicillins, cephalosporins, aminoglycosides and other drugs, the application of this product can often be effective. |
Hazard Symbols | Xn - Harmful |
Risk Codes | R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. 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 | UA2451400 |
HS Code | 29419000 |
Toxicity | TDLo ivn-rat: 1100 mg/kg (7-17D preg):TER NKRZAZ33(Suppl 1),203,85 |
Reference Show more | 1. [IF=4.003] Hao Tang et al.Direct-on-Target Microdroplet Growth Assay for Detection of Bacterial Resistance in Positive Blood Cultures.Infect Drug Resist. 2021 Nov;14:4611-4617 |
This product is [2s-[ 2a,3B( Z )]] -2- [[ 1-(2-amino-4-thiazolyl)-2-[(2-methyl-4-oxo-1-sulfo-3-azetidinyl) amino]-2-oxoethylidene] amino] oxy]-2-methylpropionic acid. Calculated as anhydrous, containing C13H17N508S2 should be 93.0% ~ 103.0% o
take this product, precision weighing, add water to dissolve and quantitatively dilute to make a solution containing about 5mg per lml, according to the law (General 0621), the specific rotation of a 26 ° to a 32 °.
take this product, add water to make a solution containing 5mg per lml, according to the law (General 0631),pH value should be 2.2~2.8.
take 5 parts of this product, 50mg each, respectively, and add 10ml of water to dissolve, the solution should be clear and colorless; If it is turbid, compare it with No. 1 turbidity standard solution (General rule 0902 first method), shall not be more concentrated; If the color is developed, it shall not be deeper in comparison with the yellow or yellow-green No. 2 Standard Colorimetric solution (General Principles 0901 first method).
take about 0.lg of this product, put it in A 100ml measuring flask, add mobile phase A to dissolve and dilute to the scale, shake, as A test solution; Take 1ml, set in A 100ml measuring flask, dilute to the scale with mobile phase A, and shake to serve as A control solution. According to the test of high performance liquid chromatography (General 0512), silica gel was bonded with eighteen alkyl silane as filler; 0.05mol/L potassium dihydrogen phosphate solution (adjusted to pH 3.0 with phosphoric acid)-acetonitrile (90:10) as mobile phase A, with 0.05mol/L potassium dihydrogen phosphate solution (adjusted to pH 3.0 with phosphoric acid)-acetonitrile (60:40) as mobile phase B, the linear gradient elution was carried out immediately after the elution of the aztreonam peak. The detection wavelength was 270Nm. Take an appropriate amount of aztreonam reference, make A solution containing 1 mg per 1ml with mobile phase A, put the UV lamp (254mn) under irradiation for 3 hours, as the system applicable solution, and inject 20ul into the liquid chromatograph, the separation degree between aztreonam peak and adjacent impurity peak shall meet the requirements. 20ul 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 1.5 times (1.5%) of the area of the main peak of the control solution, the sum of each impurity peak area shall not be greater than 3.5 times (3.5%) of the main peak area of the control solution, and the peaks smaller than 0.05 times of the main peak area of the control solution in the chromatogram of the test solution shall be ignored.
take this product about l. Log, precision weighing, 5ml measuring flask, add 8% sodium carbonate solution to dissolve and dilute to the scale, shake, as a sample stock solution; Precision measure 1ml, in the top empty bottle, add 1ml of 8% sodium carbonate solution accurately, mix well, seal, and use as the test solution; Accurately weigh about 60mg of methanol, about lOOmg of ethanol and about 12mg of dichloromethane, in the same 100ml measuring flask, dilute to the scale with 8% sodium carbonate solution, shake well, and use it as a reference stock solution; Take 1ml for precision measurement, and place it in the top empty bottle, then, 1ml of the stock solution of the test article was added precisely, mixed well, sealed, and used as a reference solution. Determined according to the residual solvent assay (General 0861 second method). The capillary column with 6% cyanopropylphenyl-94% dimethylpolysiloxane polymer (or similar polarity) as stationary liquid is used as the chromatographic column, and the starting temperature is 40 ° C., which is maintained for 5 minutes, to 200°C at a rate of 30°C per minute, It was maintained for 3 minutes; The inlet temperature was 150°C, the detector temperature was 250°C, the headspace bottle equilibrium temperature was 90°C, and the equilibrium time was 15 minutes. Take 1ml of the stock solution of the reference substance, place it in the top empty bottle, add 1ml of 8% sodium carbonate solution, shake well, use it as the applicable solution of the system, inject the sample in the head space, and record the chromatogram. The degree of separation between peaks shall meet the requirements. Take the reference solution and the test solution into the headspace respectively, and calculate the peak area according to the standard addition method. The residual amount of ethanol shall not exceed 2.0%, and the residual amount of methanol and dichloromethane shall meet the requirements.
take this product, according to the determination of moisture (General 0832 first method 1), the water content shall not exceed 2.0%.
take l.Og of this product and determine it according to law (General rule 0841). The remaining residue shall not exceed 0.1%.
The residue left under the ignition residue item shall not contain more than 10 parts per million of heavy metals as determined by law (general chapter 0821 second method).
take 5 parts of this product, each 2.0g, plus 2.34% arginine solution (0.45um filter) after dissolution, according to the law (General rule 0904), should comply with the provisions. (For aseptic dispensing)
Take 3 parts of this product and add 2.34% arginine solution (filtered through 0.45um filter) to make a solution containing 50mg per 1 ml, and check according to law (General rule 0903), each lg sample containing 10um and 10um above the particle shall not exceed 6000, containing 25um and 25um above the particle shall not exceed 600. (For aseptic packaging).
take this product, check according to law (General rule 1143), the amount of endotoxin per 1 mg of aztreonam should be less than 0.17EU. (For injection)
Take 9g of this product, add 2.34% sterile arginine solution to dissolve, after membrane filtration method, check according to law (General rule 1101), should comply with the provisions. (For aseptic dispensing)
monocyclic lactam antibiotics.
shade, seal, and store in a cool and dry place.
This product is a sterile powder or sterile lyophilized product made from aztreonam plus an appropriate amount of cosolvent arginine. The content of aztreonam (each C13H17N5O8S2) shall be 91.0%-103.0% based on anhydrous and arginine-free materials; The content of aztreonam (C13H17N5O8S 2) shall be 90.0%-115.0% of the standard 7K amount based on the average loading.
This product is white or off-white powder or loose lumps.
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 control solution.
Same as aztreonam.
(l ) 0.5g (2)1.0g (3)2.0g
It was sealed and kept in a cool and dark place.
Overview | , aztreonam, bacteriocan, monosamidex, and thiamethoxime monoamidophilin, in English named Aztreonam, AZACTAM, Azactam, aztreonomum, Primbactam, Primbactin, it is a new type of β-lactam antibiotic of monamide ring. It was first discovered in 1978 from the culture medium of the New Jersey soil bacterium virobacterium virobacterium virobacterium virobacterium, which has been synthesized. Aztreonam has a high degree of antibacterial activity against most aerobic Gram-negative bacteria, including Escherichia coli, Klebsiella spp. Pneumonia and ocristine, Aerobacter aerogenes, Enterobacter cloacae, Proteus spp, serratia, citrate, shigella and other Enterobacteriaceae, as well as influenza, Neisseria gonorrhoeae, Meningococcus and so on, which also has a good antibacterial effect on Pseudomonas aeruginosa, the antibacterial effect on some Pseudomonas and Acinetobacter species other than Pseudomonas aeruginosa is poor, in addition to some Pseudomonas aeruginosa other than the Pseudomonas and Acinetobacter less antibacterial effect of Staphylococcus, streptococcus and other aerobic Gram-positive bacteria and anaerobic bacteria no antibacterial activity. Aztreonam inhibits cell wall synthesis by highly affinity with penicillin binding protein 3(PBP3) on the cell membrane of sensitive aerobic Gram-negative bacteria. Aztreonam can be used to treat Upper Respiratory Infections, severe bronchitis, cystic fibrosis patients with acute severe tracheal, pulmonary Pseudomonas aeruginosa infection and chronic pulmonary Pseudomonas aeruginosa infection in cystic fibrosis patients allergic to β-lactam.|
mechanism of action | aztreonam is a bacterial fungicide. It rapidly passes through the outer membrane wall of gram-negative aerobic bacteria and has a high affinity for penicillin binding protein 3(PBP-3). By acting on PBP-3, the synthesis of the bacterial cell wall is inhibited, leading to cell lysis and death. Aztreonam antibacterial spectrum is narrow, only for aerobic Gram-negative bacteria with antibacterial effect, such as Escherichia coli, Klebsiella, Serratia, Proteus mirabilis, indole-positive Proteus, haemophilus influenzae, Pseudomonas aeruginosa and Other Pseudomonas, certain Enterobacteriaceae, Neisseria gonorrhoeae, etc. This product is highly stable against β-lactamases produced by many bacteria. No activity against Gram-positive bacteria and anaerobic bacteria. Compared with ceftazidime and gentamicin, the effect of aztreonam on aerogenes and Enterobacter cloacae was higher than that of ceftazidime, but lower than that of gentamicin. The effect on Pseudomonas aeruginosa was lower than that of ceftazidime, which was similar to that of gentamicin. |
pharmacokinetics | aztreonam can be widely distributed in tissues and body fluids, such as adipose tissue, bone, gallbladder, lung, liver, kidney, heart, abdominal tissue and prostate tissue, in saliva, sputum, bronchial secretions, bile, pericardial fluid, pleural fluid, peritoneal fluid, synovial fluid, ascites and tissue and skin edema fluid. Aztreonam and serum protein binding rate of 45% ~ 60%, initially excreted by the kidney, normal kidney, liver function adults, half-life of 0.2~0.7 h, elimination half-life of 1.3~2.2 h, patients with renal impairment had higher serum concentrations and prolonged half-life. The half-life of the drug is rarely prolonged when liver function is impaired, but the elimination half-life of aztreonam can be prolonged in alcoholic liver cirrhosis patients. |
indication | aztreonam belongs to monocyclic β-lactam antibiotics, unlike most β-lactam antibiotics, it does not induce the production of β-lactamases by the bacteria, while being highly stable against the majority of β-lactamases produced by the bacteria. Mainly for the treatment of respiratory infections caused by sensitive bacteria, urinary, reproductive system infections (including acute gonorrhea), abdominal infections, skin, soft tissue infections, pre-operative prevention of infection, other serious infections, such as sepsis. |
product features | 1. aztreonam, abbreviated as AZT, was the first monocyclic β-lactam antibiotic to be clinically used. Unlike most beta-lactam antibiotics, aztreonam does not induce the production of beta-lactamases by bacteria and is highly stable against most beta-lactamases produced by bacteria. Therefore, the use of aztreonam is effective when the microorganism is not sensitive to penicillins, cephalosporins, aminoglycosides and other drugs. Aztreonam has fewer adverse drug reactions and lower incidence of allergic reactions than penicillin and cephalosporins, so it is especially suitable for immunocompromised, elderly and penicillin allergic patients. Aztreonam has no nephrotoxic effect on patients with normal renal function and is safe and effective for severe urinary and biliary tract infections. Aztreonam can be used in combination with other antibiotics. It does not affect the antibacterial activity of these antibiotics against gram-positive bacteria when used in combination with neo-penicillin I, O-chloropenicillin, erythromycin or vancomycin. It can be used in combination with metronidazole and clindamycin to resist anaerobic infection, and has definite curative effect with aminoglycosides. |
note | 1. Contraindications: allergic to this product or to lidocaine and other local anesthetics have allergic history or other beta-lactam drugs have anaphylactic shock reactions disabled. 2. The following cases should be used with caution:(1) there is no cross allergic reaction between aztreonam and penicillin drugs, but it is used with caution in those who are allergic to penicillins and cephalosporins and those who are allergic. (2) renal dysfunction with caution. (3) aztreonam is not toxic to the liver, but its dynamic changes should be observed in patients with impaired liver function. It has been reported that the total clearance rate of alcoholic cirrhosis patients can be reduced by 20-25%. (4) pregnant women, lactating women, infants and young children with caution. 3. Effect of drugs on clinical outcome:(1) direct antiglobulin test (Coombs test) may be positive. (2) a small number of patients after the drug can appear serum alanine aminotransferase (ALT), aspartate aminotransferase (AST), lactate dehydrogenase (LDH) and serum creatinine values may have a temporary increase, partial thromboplastin time (PTT) and prothrombin time (PT) may be prolonged. (3) adverse reactions have skin symptoms such as rash, purpura, itching, etc. (a total of about 2%); Gastrointestinal symptoms such as Diarrhea, Nausea, Vomit, taste changes, jaundice and drug-induced hepatitis (about 2% of total); Local irritation symptoms such as thrombophlebitis. Injection site swelling (about 2.4%); Other symptoms of the nervous system, vaginitis, oral lesions, Fatigue, dizziness, bleeding. 4. Long-term medication should pay attention to the monitoring of liver and kidney function and hematopoietic system. |
Usage | monocyclic β-lactam antibiotics have strong antibacterial effect on Gram-negative bacteria, and is stable to β-lactamases, but slightly unstable to plasmid-or chromosome-mediated type 1 enzymes. For Gram-negative sensitive bacteria caused by respiratory infections, urinary tract infections, biliary tract infections, abdominal infections, bone and joint infections, and other drugs can be used to treat Gram-positive bacteria and anaerobic bacteria caused by infection. anti-infection. It is mainly used for infections caused by sensitive Gram-negative bacteria, including Pneumonia, pleurisy, abdominal infection, biliary tract infection, bone and joint infection, skin and soft tissue inflammation, especially for urinary tract infection, also used for sepsis. Because this product has good enzyme resistance, therefore, when the microorganisms are not sensitive to penicillins, cephalosporins, aminoglycosides and other drugs, the application of this product can often be effective. antimicrobial agent |
production method | using threonine as raw material, the acid chloride generated by chlorination is amidated to form amide, the α-amino group was protected with benzyl chloroformate, the β-hydroxyl group was esterified with methanesulfonyl chloride, the amide group was sulfonated with tetrabutyl ammonium sulfate, and then azetidine derivatives were synthesized under the action of potassium bicarbonate, re-hydrogen is freed from the protecting group to form 3-amino -2-methyl -4-oxo -1-sulfoazetidine. The azetidine derivative and the side-chain thiazole derivative obtained above are deamidated, and the protecting group is removed by hydrolysis to obtain aztreonam. |
category | toxic substances |
toxicity grade | poisoning |
Acute toxicity | intraperitoneal-rat LD50: 2549 mg/kg; Intraperitoneal-mouse LD50: 2897 mg/kg |
flammability hazard characteristics | flammability; Toxic nitrogen oxide and sulfur oxide fumes from combustion |
storage and transportation characteristics | ventilation and low temperature drying |
fire extinguishing agent | dry powder, foam, sand, carbon dioxide, water mist |