Ampicillin sodium Chemical Properties

Melting point:

215 °C (dec.)(lit.)

alpha 

+246～+272°

storage temp. 

2-8°C

solubility 

H₂O: 50 mg/mL, clear, very faintly yellow

form 

powder

color 

white with slight yellow cast

PH

pH(100g/l, 25℃):8.0～10.0

Water Solubility 

Freely soluble in water. Sparingly soluble in acetone

BRN 

4119211

InChI

InChI=1/C16H19N3O4S.Na.H/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);;/t9-,10-,11+,14-;;/s3

InChIKey

XCZQUQSOMVIRFX-AGYZSTNLNA-N

SMILES

C([C@H]1C(S[C@]2([H])[C@H](NC(=O)[C@@H](C3C=CC=CC=3)N)C(=O)N12)(C)C)(=O)O.[NaH] |&1:1,4,6,10,r|

CAS DataBase Reference

69-52-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

42/43-36/37/38-22

Safety Statements 

22-36/37-45-36-26

WGK Germany 

2

RTECS 

XH8400000

F 

3-10

HS Code 

29419000

Toxicity

LD50 oral in rat: > 5314mg/kg

MSDS

• Language:English Provider:Ampicillin sodium
• Language:English Provider:SigmaAldrich

Ampicillin sodium Usage And Synthesis

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 chemicalbook of Tian Ye.

Chemical Properties

White or almost white powder or crystal. Soluble in water, slightly soluble in ethanol, insoluble in ether. Hygroscopic, when it is set at room temperature in an aqueous solution ,it gradually turns yellow,produces turbidity, decreases potency. Odorless, slightly bitter taste.

Uses

A semi-synthetic broad-spectrum penicillin,it is mainly used for treatment of penicillin-sensitive gram-positive bacteria, Escherichia coli, Proteus, Salmonella, Shigella and other.

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.

Category

Toxic substances

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.

Chemical Properties

White or almost white powder, hygroscopic.

Uses

Penicillin antibacterial.

Uses

Ampicillin sodium salt is a reagent for transformed cells expressing beta-lactamase. It acts as a structural analogue of acyl-D-alanyl-D-alanine, acylates the transpeptidase enzyme and prevents the cross-linking of the peptidoglycan of the cell wall necessary for the growth of the bacterium.

Uses

diuretic, anti-hypertensive

Definition

ChEBI: Ampicillin sodium is an organic sodium salt. It contains an ampicillin(1-).

brand name

Polycillin-N (Bristol-Myers Squibb).

General Description

Chemical structure: ?-lactam

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.

storage

+4°C

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