MilliporeSigma
All Photos(1)

Documents

A9393

Sigma-Aldrich

Ampicillin

anhydrous, 96.0-102.0% (anhydrous basis)

Sign Into View Organizational & Contract Pricing

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
Empirical Formula (Hill Notation):
C16H19N3O4S
CAS Number:
Molecular Weight:
349.40
Beilstein/REAXYS Number:
1090925
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.85

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
PHR2838A159359349
vibrant-m

A9393

Ampicillin

vibrant-m

PHR2838

Ampicillin

vibrant-m

A1593

Ampicillin

vibrant-m

59349

Ampicillin

Quality Level

200

Quality Level

300

Quality Level

200

Quality Level

100

form

solid

form

solid

form

solid

form

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

assay

96.0-102.0% (anhydrous basis)

assay

-

assay

-

assay

≥95.0% anhydrous basis (NT)

mp

208 °C (dec.) (lit.)

mp

208 °C (dec.) (lit.)

mp

198-200 °C (dec.) (lit.)

mp

208 °C (dec.) (lit.)

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

signalword

Danger

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves


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’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

Customers Also Viewed

Slide 1 of 8

1 of 8

Ampicillin sodium United States Pharmacopeia (USP) Reference Standard

USP

1033203

Ampicillin sodium

Ampicillin, Sodium Salt Ampicillin salt is an antibiotic that inhibits bacterial cell-wall synthesis. Active against Gram-negative bacteria. Inactivated by lactamases. Suitable for use in research that uses ampicillin-resistant plasmids.

Millipore

171254

Ampicillin, Sodium Salt

Kanamycin sulfate mixture of Kanamycin A (main component) and Kanamycin B and C

Sigma-Aldrich

60615

Kanamycin sulfate

Amoxicillin 95.0-102.0% anhydrous basis

Sigma-Aldrich

A8523

Amoxicillin

Ampicillin Sodium Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1424

Ampicillin Sodium

Chloramphenicol ≥98% (HPLC)

Sigma-Aldrich

C0378

Chloramphenicol

Ampicillin trihydrate VETRANAL®, analytical standard

Supelco

31591

Ampicillin trihydrate

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)
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
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
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
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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service