| Identification | More | [Name]
Ampicillin sodium | [CAS]
69-52-3 | [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 | [EINECS(EC#)]
200-708-1 | [Molecular Formula]
C16H18N3NaO4S | [MDL Number]
MFCD00064313 | [Molecular Weight]
371.39 | [MOL File]
69-52-3.mol |
| Chemical Properties | Back Directory | [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. | [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 | Back Directory | [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. | [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 . | [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. | [Toxicity]
LD50 oral in rat: > 5314mg/kg |
| Questions And Answer | Back Directory | [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.
|
| Hazard Information | Back Directory | [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 |
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