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A9393

Sigma-Aldrich

Ampicillin

anhydrous, 96.0-102.0% (anhydrous basis)

Synonym(s):

(-)-6-(2-Amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, Ampicillin acid, Ampicillin anhydrous, D-(−)-α-Aminobenzylpenicillin

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About This Item

Empirical Formula (Hill Notation):
C16H19N3O4S
CAS Number:
69-53-4
Molecular Weight:
349.40
Beilstein:
1090925
EC Number:
200-709-7
MDL number:
MFCD00005175
UNSPSC Code:
51101500
PubChem Substance ID:
24891442
NACRES:
NA.85

Quality Level

200

Assay

96.0-102.0% (anhydrous basis)

form

solid

pKa (25 °C)

2.5 (COOH)
7.3 (NH2)

mp

208 °C (dec.) (lit.)

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

cell wall synthesis | interferes

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

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General description

Chemical structure: ß-lactam

Application

Ampicillin has been used to study antibiotic resistance and penetration limitations, the synergy between multiple antibiotics, certain bloodstream infections, and has been used to develop PCR assays to detect resistance genes in cerebrospinal fluid.

Biochem/physiol Actions

β-lactams are inactivated by β-lactamases and for this reason ampicillin is used with a β-lactamase inhibitor.
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.

Other Notes

Store under argon. Keep container tightly closed in a dry and well-ventilated place, hygroscopic.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H317,H334

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. Is Ampicillin product stable in solution?

    We recommend using freshly prepared solutions. A concentrated solution of sodium ampicillin in water (approximately 330 mg/mL) may be expected to lose about 10% potency in 20 hours at -20°C.

  3. How do I use Ampicllin in agar plates?

    For plates, add ampicillin to autoclaved media cooled to 48°C, to a final concentration of 35-50 μg/mL. Pour the plates, and allow them to cool completely. Plates may be stored at 2-8°C for up to only 1-2 weeks before use.

  4. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  5. What is the solubility of Product A9393, Ampicillin?

    The solubility of ampicillin is tested at 50 mg/mL in 1M ammonium hydroxide. Additional solubility information can be found on the product information sheet (under Documents, above).

  6. Which Ampicillin product has higher water solubility, Product A9393 or Product A9518?

    Product No. A9518 (Ampicillin, sodium salt) is soluble at 50 mg/mL in water.

  7. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  8. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  9. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Comparative evaluation of a new beta-lactamase inhibitor, YTR 830, combined with different beta-lactam antibiotics against bacteria harboring known beta-lactamases.
Antimicrobial Agents and Chemotherapy, 29, 955-957 (1986)
Laurent Poirel et al.
Antimicrobial agents and chemotherapy, 52(5), 1613-1617 (2008-02-27)
The basis of the beta-lactam resistance of 39 multidrug-resistant Acinetobacter baumannii isolates recovered from hospitalized patients was studied. These isolates were collected from 2001 to 2005 at the Sahloul Hospital in Sousse, Tunisia. They belonged to two distinct clones. One
J N Anderl et al.
Antimicrobial agents and chemotherapy, 44(7), 1818-1824 (2000-06-20)
The penetration of two antibiotics, ampicillin and ciprofloxacin, through biofilms developed in an in vitro model system was investigated. The susceptibilities of biofilms and corresponding freely suspended bacteria to killing by the antibiotics were also measured. Biofilms of Klebsiella pneumoniae
Kenneth H Rand et al.
The Journal of antimicrobial chemotherapy, 53(3), 530-532 (2004-02-14)
We used a novel screening method to look for synergy between daptomycin and 18 other antibiotics against 19 strains of high-level vancomycin-resistant enterococci (VRE) (vancomycin MIC > or = 256 mg/L). In this approach, daptomycin was incorporated into Ca(2+)-supplemented Mueller-Hinton
M R Jacobs et al.
Antimicrobial agents and chemotherapy, 29(6), 980-985 (1986-06-01)
The in vitro synergistic activities of the beta-lactamase inhibitors YTR 830, clavulanate, and sulbactam, combined with ampicillin, ticarcillin, mezlocillin, azlocillin, piperacillin, and apalcillin, were determined against 34 strains of members of the Enterobacteriaceae family, Pseudomonas aeruginosa, Aeromonas hydrophila, and Haemophilus
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