Ampicillin

• (2S, 5R, 6R ) -6 - (2-amino -2-phenyl -acetyl ) amino -3 ,3-dimethyl -7- oxo-4 -thia -1 -azabicyclo [3.2.0 ] heptane - 2-carboxylic acid (IUPAC)
• Ampicillinum (Latin )

• C16H19N3O4S ( ampicillin)
• C16H18N3NaO4S

• 69-53-4 (Ampicillin )
• 69-52-3 ( ampicillin sodium salt)

• J01CA01
• S01AA19

Antibiotics

199-202 ° C ( decomposition)

Slightly soluble in water

Risk

Template: Infobox chemical / molecular formula search available

Ampicillin is a semi- synthetic antibiotic effective drug from the group of β -lactam antibiotics ( aminopenicillins ). Because of its effectiveness against gram- positive pathogens ( as well as some gram-negative rods ) referred to it as a broad-spectrum antibiotic or broadband penicillin.

Chemically counts ampicillin to aminopenicillins and was first synthesized by John C. Sheehan.

Pharmacology

Areas of application

Broadband penicillins are used for infections of all kinds, against the " conventional " penicillins are ineffective. These include, inter alia, certain infections of the gastrointestinal tract, the respiratory tract, the middle ear, biliary tract and urinary tract. They are particularly suitable for the treatment of infections with gram-negative rods, which have a natural resistance to penicillins standard.

Mechanism of action

The bactericidal effect of ampicillin based like all β -lactam antibiotics work by blocking a necessary for the formation of a new cell wall at present in the partition phase the bacterial enzyme, the D -alanine transpeptidase, β - lactam ring by addition of their. This prevents the de novo synthesis of the cell wall, the cells are thus unable to divide, but continue to live. Dividing human cells is not hindered, because human cells, only one cell membrane but do not have the cell wall and therefore no D-alanine transpeptidase.

The β -lactam antibiotic ampicillin blocked not only the division of bacteria, including cyanobacteria, but also the division of cyanelles, the photosynthetic organelles of Glaucocystaceae, and the chloroplasts of Physcomitrella mosses, liverworts ( Marchantia polymorpha ) and moss ferns ( Selaginella nipponica ). However, on the division of plastids of the highly developed vascular plants such as tomatoes in it have no effect. This is an indication that at higher plants show took place through evolutionary changes in the Plastidteilung β -lactam antibiotics generally chloroplasts no longer effective.

Tolerability, side effects

Ampicillin is worse tolerated in oral dosing compared to other broadband penicillins such as amoxicillin, since it is of the intestinal wall relatively poorly absorbed, resulting in a high percentage of the drug remains in the gut to the digestive microbial colonization ( intestinal flora ) damages.

As with all penicillins may also ampicillin trigger an allergy that can lead to a (very rarely occurring ) anaphylactic shock. Frequently - and not to be confused with an allergy - is a measles -like drug eruption ( " Ampicillinexanthem " ), which occurs a few days after the first dose. This is particularly pronounced in connection with mononucleosis. An occurrence of this rash does not invalidate the subsequent intake of penicillin or its derivatives ( such as ampicillin ).

Other possible side effects include diarrhea, nausea and vomiting. Rare ( vasculitis), interstitial nephritis (kidney inflammation) and laryngeal edema was reported in the airways of blood disorders, inflammatory reaction of the blood vessels.

Interactions with other drugs

When oral contraceptives ( contraceptives in tablet form; " pill " ) may by influencing the gut flora come to a decreased uptake of contraceptives in the blood and thus to a reduced efficacy.

Bacteriostatic antibiotics (antibiotics that prevent pathogens from reproducing ), generally may not be combined with penicillins, as they limit their effectiveness. The reason for this is that penicillins intervene in the division phase of the bacteria and thus find no point of attack, if the division is prevented by bacteriostatic agents.

Indomethacin, phenylbutazone, probenecid, sulfinpyrazone, salicylates, and lead to a longer and higher concentration of penicillin in the blood and therefore should not be taken together with penicillins.

Contraindications

Penicillin allergy, hypersensitivity to the active ingredient ampicillin.

Application

Given the primary amino group of ampicillin is also orally ingestible unlike benzylpenicillin (penicillin G). The intake of ampicillin is carried out orally or parenterally, several times a day over a period of several days.

Molecular Biology

Ampicillin is one of the most widely used in molecular biology selection agent. It is added in the transformation of vectors in bacterial cells the culture medium in which the cells are to be increased. Only those cells can survive, who have taken up the vector in the transformation which carries the ampicillin resistance. To such transgenic E. coli bacteria in LB medium, for example, to cultivate selectively up to a final concentration of 0.2 mg / ml of the medium is used. Other antibiotics such as kanamycin or tetracycline are used for selection media.