ampicillin

[Blend of AMINO- and PENICILLIN.]

An acid-stable semisynthetic penicillin antibiotic with a broader spectrum of effectiveness than penicillin G.

Brand names: Principen®

Chemical formula:

Drug Forms:
• Ampicillin trihydrate Oral capsule (below)
• Ampicillin trihydrate Oral suspension
• Ampicillin Sodium Solution for injection

Español:
• Ampicilina Trihidrato, Cápsula oral
• Ampicilina Trihidrato, Suspensión oral
• Ampicilina Sódica, Solución para inyección

Ampicillin trihydrate Oral capsule

What is this medicine?

AMPICILLIN (am pi SILL in) is a penicillin antibiotic. It is used to treat certain kinds of bacterial infections. It will not work for colds, flu, or other viral infections.
 
This medicine may be used for other purposes; ask your health care provider or pharmacist if you have questions.

What should I tell my health care provider before I take this medicine?

They need to know if you have any of these conditions:
•bowel disease, like colitis
•heart disease
•kidney disease
•liver disease
•seizures disorder
•an unusual or allergic reaction to ampicillin, other penicillins or antibiotics, other medicines, foods, dyes, or preservatives
•pregnant or trying to get pregnant
•breast-feeding

How should I use this medicine?

Take this medicine by mouth with a full glass of water. Follow the directions on the prescription label. Take this medicine on an empty stomach, at least 30 minutes before or 2 hours after food. Do not take with food. Take your medicine at regular intervals. Do not take your medicine more often than directed. Take all of your medicine as directed even if you think you are better. Do not skip doses or stop your medicine early.

Talk to your pediatrician regarding the use of this medicine in children. Special care may be needed.

Overdosage: If you think you have taken too much of this medicine contact a poison control center or emergency room at once.
NOTE: This medicine is only for you. Do not share this medicine with others.

What if I miss a dose?

What may interact with this medicine?

•allopurinol
•birth control pills
•chloroquine
•methotrexate
•probenecid
•some other antibiotics like erythromycin, tetracycline

This list may not describe all possible interactions. Give your health care provider a list of all the medicines, herbs, non-prescription drugs, or dietary supplements you use. Also tell them if you smoke, drink alcohol, or use illegal drugs. Some items may interact with your medicine.

What should I watch for while using this medicine?

Tell your doctor or health care professional if your symptoms do not improve or if you get new symptoms.

Do not treat diarrhea with over the counter products. Contact your doctor if you have diarrhea that lasts more than 2 days or if it is severe and watery.

This medicine can interfere with some urine glucose tests. If you use such tests, talk with your health care professional.

Birth control pills may not work properly while you are taking this medicine. Talk to your doctor about using an extra method of birth control.

What side effects may I notice from receiving this medicine?

Side effects that you should report to your doctor or health care professional as soon as possible:
•allergic reactions like skin rash, itching or hives, swelling of the face, lips, or tongue
•breathing problems
•dark urine
•fever
•pain or difficulty passing urine
•pain when swallowing
•redness, blistering, peeling or loosening of the skin, including inside the mouth
•seizures
•unusual bleeding, bruising
•unusually weak or tired

Side effects that usually do not require medical attention (report to your doctor or health care professional if they continue or are bothersome):
•diarrhea
•dizziness
•headache
•loss of appetite
•nausea, vomiting
•sore mouth, tongue
•stomach upset

This list may not describe all possible side effects. Call your doctor for medical advice about side effects. You may report side effects to FDA at 1-800-FDA-1088.

Where should I keep my medicine?

Keep out of the reach of children.

Store at room temperature between 20 and 25 degrees C (68 and 77 degrees F). Keep container tightly closed. Throw away any unused medicine after the expiration date.

Last updated: 7/1/2002

Important Disclaimer: The drug information provided here is for educational purposes only. It is intended to supplement, not substitute for, the diagnosis, treatment and advice of a medical professional. This drug information does not cover all possible uses, precautions, side effects and interactions. It should not be construed to indicate that this or any drug is safe for you. Consult your medical professional for guidance before using any prescription or over the counter drugs.

An aminopenicillin of synthetic origin, susceptible to β-lactamase, with activity similar to amoxicillin but shorter duration of activity. It can be administered orally or parenterally.

Ampicillin
Systematic (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
Identifiers
CAS number	69-53-4
ATC code	J01CA01 S01AA19 QJ51CA01
PubChem	6249
DrugBank	APRD00320
ChemSpider	6013
Chemical data
Formula	C16H19N3O4S
Mol. mass	349.41 g·mol−1
SMILES	eMolecules & PubChem
Pharmacokinetic data
Bioavailability	40% (oral)
Protein binding	15 to 25%
Metabolism	12 to 50%
Half life	approx 1 hour
Excretion	75 to 85% renal
Therapeutic considerations
Pregnancy cat.	A (Au), B (U.S.)
Legal status
Routes	Oral, intravenous
Y(what is this?)  (verify)

Ampicillin is a beta-lactam antibiotic that has been used extensively to treat bacterial infections since 1961. Until the introduction of ampicillin by the British company, Beecham, penicillin therapies had only been effective against Gram-positive organisms such as Staphylococci and Streptococci. Ampicillin (originally branded as 'Penbritin') also demonstrated activity against Gram-negative organisms such as H. influenzae, coliforms and Proteus spp. Ampicillin was the first of a number of so-called broad spectrum penicillins subsequently introduced by Beecham. Ampicillin is part of the aminopenicillin family and is roughly equivalent to its successor,amoxicillin in terms of spectrum and level of activity^[1]. It can sometimes result in reactions that range in severity from a non-in allergic rash (in the case of patients that may unwitting have mononucleosis) to potentially lethal allergic reactions such as anaphylaxis. However, as with other penicillin drugs, it is relatively non-toxic and adverse effects of a serious nature are encountered only infrequently.

Contents 1 Mechanism of action 1.1 Effects on chloroplasts division 2 Application 2.1 Use in research 3 External links 4 References

Mechanism of action

Belonging to the penicillin group of beta-lactam antibiotics, ampicillin is able to penetrate Gram-positive and some Gram-negative bacteria. It differs from penicillin only by the presence of an amino group. That amino group helps the drug penetrate the outer membrane of gram-negative bacteria.

Ampicillin acts as a competitive inhibitor of the enzyme transpeptidase, which is needed by bacteria to make their cell walls.^[1] It inhibits the third and final stage of bacterial cell wall synthesis in binary fission, which ultimately leads to cell lysis.

Effects on chloroplasts division

Ampicillin, like other β-lactam antibiotics, not only blocks the division of bacteria, but also the division of chloroplasts of the Glaucophytes (called cyanelles) and chloroplasts of the moss Physcomitrella patens, a bryophyte. In contrast, it has no effect on the plastids of the higher developed vascular plant Lycopersicon esculentum L. (tomato) ^[2].

Application

Ampicillin is closely related to amoxicillin, another type of penicillin, and both are used to treat urinary tract infections, otitis media, uncomplicated community-acquired pneumonia, Haemophilus influenzae, salmonellosis and Listeria meningitis. It is used with flucloxacillin in the combination antibiotic co-fluampicil for empiric treatment of cellulitis; providing cover against Group A streptococcal infection whilst the flucloxacillin acts against the Staphylococcus aureus bacterium. Of concern is the number of bacteria that become resistant to Ampicillin necessitating combination therapy or use of other antibiotics.

All Pseudomonas and most strains of Klebsiella and Aerobacter are considered resistant.^[3]

Use in research

Ampicillin is often used as a selective agent in molecular biology to select for and to confirm the uptake of genes (e.g., of plasmids) by bacteria (e.g., E. coli). A gene that is to be inserted into a bacterium is coupled to a gene coding for an ampicillin resistance (in E. coli, usually the bla (TEM-1) gene, coding for β-lactamase). The treated bacteria are then grown in a medium containing ampicillin (typically 50-100mg/L). Only the bacteria that successfully take up the desired genes become ampicillin resistant, and therefore contain the other desired gene as well. It can be used with Cloaxicillin as well. As a powder ampicillin is white with slight yellow cast and is soluble in water (150mg/ml).

External links

References

1. ^ ^{a b} AHFS DRUG INFORMATION 2006 (2006 ed ed.). American Society of Health-System Pharmacists. 2006. 
2. ^ Britta Kasten und Ralf Reski (1997): β-lactam antibiotics inhibit chloroplast division in a moss (Physcomitrella patens) but not in tomato (Lycopersicon esculentum). Journal of Plant Physiology 150, 137-140. [1]
3. ^ Mosby's Drug Consult 2006 (16 ed ed.). Mosby, Inc.. 2006. 

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