1033000

Ampicillin

United States Pharmacopeia (USP) Reference Standard

• Synonym(s): D-(−)-α-Aminobenzylpenicillin
• Empirical Formula (Hill Notation): C₁₆H₁₉N₃O₄S
• CAS Number: 69-53-4
• Molecular Weight: 349.40
• Beilstein: 1090925
• MDL number: MFCD00005175
• UNSPSC Code: 41116107
• PubChem Substance ID: 329749022
• NACRES: NA.24

Properties

• grade: pharmaceutical primary standard
• description: API family: ampicillin
• API family: ampicillin
• manufacturer/tradename: USP
• mp: 208 °C (dec.) (lit.)
• application(s): pharmaceutical (small molecule)
• format: neat
• storage temp.: 2-8°C
• SMILES string: [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)c3ccccc3)C(O)=O
• InChI: 1S/C16H19N3O4S/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-/m1/s1
• InChI key: AVKUERGKIZMTKX-NJBDSQKTSA-N

Description

General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

Application

Ampicillin USP reference standard, intended for use in specified quality tests and assays as specified in the USP compendia.
Also, for use with USP monographs such as:

• Ampicillin Sodium
• Ampicillin Capsules
• Ampicillin Tablets
• Ampicillin Boluses
• Ampicillin for Injection
• Ampicillin Soluble Powder
• Ampicillin for Oral Suspension

Biochem/physiol Actions

Mode of Action: Ampicillin is a semisynthetic penicillin and a ß-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 ß-lactamase cleaves the ß-lactam ring of Ampicillin and inactivates it.

Antimicrobial Spectrum: Effective against both Gram-positive (similar to benzylpenicillin) and Gram-negative bacteria (similar to tetracyclines and chloramphenicol.

Caution

This product has been reported stable as supplied at 25°C at 43% and 81% relative humidity for six weeks. Additional studies have shown that the stability of Ampicillin in solution is a function of pH, temperature and the identity of the buffer. It′s activity is quickly lost when stored above pH 7. Optimal storage conditions are suggested as 2-8°C, and pH 3.8-5 where its activity was retained at 90%+ for a week.

Preparation Note

Ampicillin is reported as slightly soluble in water, practically insoluble in alcohol, chloroform, ether and fixed oils but soluble in dilute acids or bases. The solution should not be autoclaved; a stock solution should be sterilized through filtration and stored frozen, where it will be stable for months.

Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Legal Information

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

Safety Information

• Pictograms: GHS08
• Signal Word: Danger
• Hazard Statements: H317,H334
• Precautionary Statements: P261 - P272 - P280 - P284 - P302 + P352 - P333 + P313
• Hazard Classifications: Resp. Sens. 1 - Skin Sens. 1
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 2
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable