69-52-3

Name	Ampicillin sodium
CAS	69-52-3
EINECS(EC#)	200-708-1
Molecular Formula	C16H18N3NaO4S
MDL Number	MFCD00064313
Molecular Weight	371.39
MOL File	69-52-3.mol

Synonyms

6-[D(-)-ALPHA-AMINOPHENYLACETAMIDO]PENICILLANIC ACID, NA 6-[D(-)-ALPHA-AMINO-PHENYLACETAMIDO]-PENICILLANIC ACID SODIUM SALT AMPICILLIN AMPICILLIN NA-SALT AMPICILLIN SODIUM AMPICILLIN SODIUM SALT AMPICILLIN, SODIUM SALT, GAMMA IRRADIATED D(-)-ALPHA-AMINOBENZYLPENICILLIN SODIUM SALT sodium [2s-[2alpha,5alpha,6beta(s*)]]-6-(aminophenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate XLD AGAR 6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-,sodiumsalt,d-(-)-4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid Alpen-n Amcill-s Binotalsodium Citteral D-6-(-Amino-phenylacetamido)penicillanicacidsodiumsalt Domicillin omnipen-n pena/n penbritin-s

Chemical Properties

Appearance	White powder
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
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. less more
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 Data

Hazard Codes	Xi
Risk Statements	R42/43:May cause sensitization by inhalation and skin contact . R36/37/38:Irritating to eyes, respiratory system and skin . R22:Harmful if swallowed. less more
Safety Statements	S22:Do not breathe dust . S36/37:Wear suitable protective clothing and gloves . S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . S36:Wear suitable protective clothing . S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . less more
WGK Germany	2
RTECS	XH8400000
F	3-10
HS Code	29411000
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. less more
Toxicity	LD50 oral in rat: > 5314mg/kg less more

Raw materials And Preparation Products

Hazard Information

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.

storage

+4°C

Material Safety Data Sheet(MSDS)

Questions And Answer

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. ;

Spectrum Detail

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69-52-3

Chemical Properties

Safety Data

Raw materials And Preparation Products

Raw materials

Hazard Information

Definition

Brand name

General Description

Biological Activity

Biochem/physiol Actions

storage

Material Safety Data Sheet(MSDS)

Questions And Answer

Broad-spectrum penicillin

Chemical Properties

Uses

production method

Category

Toxicity grading

Acute toxicity

Flammability and hazard characteristics

Storage Characteristics

Extinguishing agent

Spectrum Detail

Well-known Reagent Company Product Information

Supplier

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