69-52-3 Usage
Uses
Used in Pharmaceutical Industry:
Ampicillin sodium is used as an antibiotic for the treatment of infections caused by penicillin-sensitive gram-positive bacteria, Escherichia coli, Proteus, Salmonella, and Shigella. It is effective against a wide range of bacterial infections due to its ability to inhibit bacterial cell wall synthesis.
Used in Medical Applications:
Ampicillin sodium is used as a penicillin antibacterial agent, helping to combat various bacterial infections and promoting overall health and well-being.
Used in Cardiovascular Health:
Ampicillin sodium is used as a diuretic and anti-hypertensive, assisting in the management of high blood pressure and fluid retention in the body.
Used in Biotechnology Research:
Ampicillin sodium salt is used as a reagent for transformed cells expressing beta-lactamase. It acts as a structural analogue of acyl-D-alanyl-D-alanine, acylating the transpeptidase enzyme and preventing the cross-linking of the peptidoglycan of the cell wall necessary for bacterial growth. This makes it a valuable tool in genetic research and the development of antibiotic-resistant strains.
Broad-spectrum penicillin
Ampicillin sodium is a broad-spectrum penicillin, its antibacterial spectrum is broader than penicillin , it has antibacterial activity on some gram-negative bacteria (such as Haemophilus influenzae, Escherichia coli, Proteus mirabilis) . Its effects on gram-positive cocci are similar to penicillin. Enzymatic hydrolysis of penicillin produced by bacteria may also make it inactive. It is clinically applicable in the treatment of respiratory infections, urinary tract infections, gastrointestinal tract infections, skin and soft tissue infections, meningitis, septicemia, endocarditis caused by sensitive bacteria. This product is a drug of choice for enterococcal infections.
The above information is edited by the lookchem of Tian Ye.
production method
It is derived from the ampicillin salifying : Ampicillin is suspended in water, adjust to pH 9 with sodium hydroxide solution, dissolve and filter . The filtrate is added active carbon, and is filtered and the filtrate is dried at a low temperature, to obtain the product.
Toxicity grading
Low toxic
Acute toxicity
Oral-rat LD50:> 5314 mg/kg; Oral-Mouse LD50:> 5314 mg/kg.
Flammability and hazard characteristics
Combustion produces toxic sodium oxide, nitrogen oxide and sulfur oxide gases.
Storage Characteristics
Ventilated, low-temperature ,dry storeroom.
Extinguishing agent
Water, dry powder, foam, sand.
Biological Activity
ampicillin sodium is a competitive inhibitor of the enzyme transpeptidase with ic50 value of 1.8 μg/ml [1].ampicillin is a β-lactam antibiotic that kills bacteria by inhibiting transpeptidase reactions. transpeptidase is involved in the final stages of cell wall biosynthesis and inhibition of it ultimately leads to cell lysis [1].in e. coli 146 cells treated with ether, ampicillin showed no significant inhibition on the transpeptidase reaction at concentrations below 0.5 μg/ml, but exhibited 50% inhibition at the concentration of 1.8 μg/ml. in e. coli 146 cells, the minimal inhibitory concentration (mic) of ampicillin was 3.1 μg/ml [1]. in e. coli and s. typhi, ampicillin and epicillin at concentrations close to mic values killed bacteria at slower rates than amoxycillin [2].in experimental mouse infections, oral or subcutaneous treatment of ampicillin at the dose of 0.2 ml/20 g was significantly more effective than epicillin and amoxycillin against the majority of infections [2].[1]. moore b a, jevons s, brammer k w. inhibition of transpeptidase activity in escherichia coli by thienamycin. antimicrobial agents and chemotherapy, 1979, 15(6): 831-833.[2]. basker m j, gwynn m n, white a r. comparative activities of ampicillin, epicillin and amoxycillin in vitro and in vivo. chemotherapy, 1979, 25(3): 170-180.
Biochem/physiol Actions
Mode of Action: This is a ?-lactam antibiotic that inhibits bacterial cell-wall synthesis by inactivating transpeptidases on the inner surface of the bacterial cell membrane. Mode of Resistance: Administration with ?-lactamase cleaves the ?-lactam ring of Ampicillin and inactivates it. Antimicrobial Spectrum: Includes both gram-positive (similar to benzylpenicillin) and gram-negative bacteria (similar to tetracyclines and chloramphenicol.
Contact allergens
Ampicillin caused contact dermatitis in a nurse also
sensitized to amoxicillin (with tolerance to oral phenoxymethylpenicillin)
and in a pharmaceutical factory
worker. Systemic drug reactions are common. Crossreactivity
is regular with ampicillin and can occur with
other penicillins.
Safety Profile
Moderately toxic by intraperitoneal route. Human systemic effects by ingestion: hypermotility, diarrhea, and other gastrointestinal changes. Questionable carcinogen. When heated to decomposition it emits very toxic fumes of NOx, Na2O, and SOx.
Check Digit Verification of cas no
The CAS Registry Mumber 69-52-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 9 respectively; the second part has 2 digits, 5 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 69-52:
(4*6)+(3*9)+(2*5)+(1*2)=63
63 % 10 = 3
So 69-52-3 is a valid CAS Registry Number.
InChI:InChI=1/C16H19N3O4S.Na/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8;/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23);/q;+1/t9-,10-,11+,14-;/m1./s1
69-52-3Relevant articles and documents
Ampicillin sodium and sulbactam sodium pharmaceutical composition
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Paragraph 0049; 0050, (2016/11/17)
The present invention discloses an ampicillin sodium and sulbactam sodium pharmaceutical composition comprising sulbactam sodium and ampicillin sodium with the specific optical rotation of + 264 degrees to + 269 degrees, and the mass ratio of ampicillin sodium to sulbactam sodium is 2: 1. The ampicillin sodium and sulbactam sodium pharmaceutical composition is prepared from the sulbactam sodium and the ampicillin sodium with the particular specific optical rotation, the drug stability is improved, and drug safety is improved.
A solvent crystallization method for preparing sodium ampicillin
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Paragraph 0005; 0029-0033, (2017/05/04)
The invention discloses a method for preparing ampicillin sodium by a menstruum crystallization method. The method comprises the following steps: firstly, dissolving sodium 2-ethylhexanoate into methanol, controlling the temperature to 15 DEG C, adding ampicillin acid into dichloromethane, and dripping diisopropylamine for a dissolution reaction; adding a sodium 2-ethylhexanoate solution into a crystallization tank, then adding a dichloromethane liquation agent in a flowing manner, and adding a seed crystal for growing crystals in a standing manner; then adding the dichloromethane liquation agent for crystallization; controlling the crystallization temperature to 20-25 DEG C; controlling the flowing acceleration of the liquation agent to 100 ml/h; after the crystallization reaction is completed, discharging materials, filtering the discharged materials, and drying the filtered materials to obtain the ampicillin sodium. According to the method, the methanol solvent, in which the ampicillin sodium is easy to dissolve, is selected for use, and then the dichloromethane solvent is used for dissolving out products, so that the crystallization speed of the product can be controlled; in addition, measures of adding the seed crystal for growing the crystal, controlling the dissolving temperature and the crystallization temperature, controlling the flowing acceleration of the liquation agent and the like are taken, so that the crystallization speed can be controlled, the crystal nucleus of the product are enlarged and uniform, the product purity is high, the dissolving residue is low, and the quality is stable.
Protection of functional groups during reaction and their subsequent restoration
-
, (2008/06/13)
In the process for preparing an organic compound of the formula in which X is an amino group, a hydroxyl group or a carboxyl group, and A' is the remainder of the molecule, from an organic compound of the formula in which A is the remainder of the molecule which can undergo reaction to form A', by converting A -- X into a compound of the formula in which Z is --NH--, --O-- or a direct C--C bond, and R is a radical of the formula STR1 IN WHICH Y is a direct C--C single bond, the --CH=CH-- group or an arylene group, R1 to R4 each independently is hydrogen, halogen or an alkyl, aryl, aralkyl, alkoxycarbonyl, alkylaminocarbonyl, arylaminocarbonyl or cycloalkylaminocarbonyl radical, or R1 + r2 and R3 + R4 each independently completes a 5- or 6-membered carbocyclic ring, or R1 and R3 conjointly with the grouping --C--Y--C-- forms a carbocyclic ring with 5 or 6 carbon atoms, and Hal is halogen, Thereby to protect X, then converting A -- Z -- COOR into a compound of the formula and then treating the compound A' -- Z -- COOR to restore the group X, the improvement which comprises effecting the treatment of the compound A' -- Z -- COOR with an alkali metal compound of a complex of monovalent cobalt. The process is applicable particularly to aminocarboxylic acids including intermediates from various stages of the synthesis of penicillins and cephalosporins.
