Ampicillin
Ampicillin
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Ampicillin

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Catalog Number PR69534
CAS 69-53-4
Description Ampicillin is a penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-phenylacetamido group. It has a role as an antibacterial drug. It is a penicillin, a penicillin allergen and a beta-lactam antibiotic. It is a conjugate acid of an ampicillin(1-).
Synonyms Aminobenzylpenicillin; Ampicillin acid; Tokiocillin; Omnipen
IUPAC Name (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Molecular Weight 349.4
Molecular Formula C16H19N3O4S
InChI AVKUERGKIZMTKX-NJBDSQKTSA-N
InChI Key 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
Drug Categories Amides; Aminopenicillins; Anti-Bacterial Agents; Anti-Infective Agents; Antibacterials for Systemic Use; Antiinfectives for Systemic Use; Beta-Lactam Antibacterials; beta-Lactams; Drugs that are Mainly Renally Excreted; Heterocyclic Compounds, Fused-Ring; Lactams; Ophthalmologicals; Penicillin G; Penicillins; Penicillins With Extended Spectrum; Sensory Organs; Sulfur Compounds
Drug Interactions Abacavir-Ampicillin may decrease the excretion rate of Abacavir which could result in a higher serum level.
Aceclofenac-Aceclofenac may decrease the excretion rate of Ampicillin which could result in a higher serum level.
Acemetacin-Acemetacin may decrease the excretion rate of Ampicillin which could result in a higher serum level.
Acenocoumarol-Ampicillin may increase the anticoagulant activities of Acenocoumarol.
Acetaminophen-Acetaminophen may decrease the excretion rate of Ampicillin which could result in a higher serum level.
Isomeric SMILES CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)O)C
Type Small Molecule
Pharmacology

Indications

Ampicillin is indicated for the treatment of infections caused by various bacterial pathogens. These include respiratory, gastrointestinal, urinary tract infections (UTIs), and mening·he antibiotic is effective against a rang·h as Escherichia coli, Proteus mirabilis, enterococci, Shigella, Salmonella typhosa and other Salmonella species, non-penicillinase-producing·hoeae, Haemophilus influenzae, staphylococci, and streptococci.

Pharmacodynamics

As a beta-lactam antibiotic in the penicillin group, Ampicillin exerts its bactericidal effects by inhibiting·hesis of susceptible bacteria. It is primarily effective against gram-positive bacteria, although it also has activity against certain gram-negative aerobic and anaerobic bacteria. The mechanism of action involves binding·he disruption of cell wall synthesis. Ampicillin demonstrates stability against hydrolysis by a variety of beta-lactamases, including·halosporinases, and extended-spectrum beta-lactamases, enhancing its effectiveness against resistant bacterial strains.

Mechanism of Action

Ampicillin functions by targeting and binding to specific penicillin-binding proteins (PBPs) within the bacterial cell wall, thus obstructing the third and final phase of bacterial cell wall synthesis. This inhibition leads to cell lysis, which is facilitated by the bacterial wall's own autolytic enzymes, including autolysins. There is a possibility that Ampicillin also disrupts an autolysin inhibitor, further contributing to its bactericidal effect.

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