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Aminopenicillin
The aminopenicillins are a group of antibiotics in the penicillin family that are structural analogs of ampicillin (which is the 2- amino derivative of benzylpenicillin, hence the name). Like other penicillins and beta-lactam antibiotics, they contain a beta-lactam ring that is crucial to its antibacterial activity. Aminopenicillins feature a positively charged amino group that enhances their uptake through bacterial porin channels. This does not, however, prevent resistance conferred by bacterial beta-lactamases. Members of this family include ampicillin, amoxicillin and bacampicillin. See also * Penicillin * Extended-spectrum penicillin The extended-spectrum penicillins are a group of antibiotics that have the widest antibacterial spectrum of all penicillins. Some sources identify them with antipseudomonal penicillins, others consider these types to be distinct. This group include ... * Carboxypenicillin References Penicillins {{antibiotic-stub ...
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Aminopenicillin
The aminopenicillins are a group of antibiotics in the penicillin family that are structural analogs of ampicillin (which is the 2- amino derivative of benzylpenicillin, hence the name). Like other penicillins and beta-lactam antibiotics, they contain a beta-lactam ring that is crucial to its antibacterial activity. Aminopenicillins feature a positively charged amino group that enhances their uptake through bacterial porin channels. This does not, however, prevent resistance conferred by bacterial beta-lactamases. Members of this family include ampicillin, amoxicillin and bacampicillin. See also * Penicillin * Extended-spectrum penicillin The extended-spectrum penicillins are a group of antibiotics that have the widest antibacterial spectrum of all penicillins. Some sources identify them with antipseudomonal penicillins, others consider these types to be distinct. This group include ... * Carboxypenicillin References Penicillins {{antibiotic-stub ...
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Ampicillin Structure
Ampicillin is an antibiotic used to prevent and treat a number of bacterial infections, such as respiratory tract infections, urinary tract infections, meningitis, salmonellosis, and endocarditis. It may also be used to prevent group B streptococcal infection in newborns. It is used by mouth, by injection into a muscle, or intravenously. Common side effects include rash, nausea, and diarrhea. It should not be used in people who are allergic to penicillin. Serious side effects may include ''Clostridium difficile'' colitis or anaphylaxis. While usable in those with kidney problems, the dose may need to be decreased. Its use during pregnancy and breastfeeding appears to be generally safe. Ampicillin was discovered in 1958 and came into commercial use in 1961. It is on the World Health Organization's List of Essential Medicines. The World Health Organization classifies ampicillin as critically important for human medicine. It is available as a generic medication. Medical u ...
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Ampicillin
Ampicillin is an antibiotic used to prevent and treat a number of bacterial infections, such as respiratory tract infections, urinary tract infections, meningitis, salmonellosis, and endocarditis. It may also be used to prevent group B streptococcal infection in newborns. It is used by mouth, by injection into a muscle, or intravenously. Common side effects include rash, nausea, and diarrhea. It should not be used in people who are allergic to penicillin. Serious side effects may include ''Clostridium difficile'' colitis or anaphylaxis. While usable in those with kidney problems, the dose may need to be decreased. Its use during pregnancy and breastfeeding appears to be generally safe. Ampicillin was discovered in 1958 and came into commercial use in 1961. It is on the World Health Organization's List of Essential Medicines. The World Health Organization classifies ampicillin as critically important for human medicine. It is available as a generic medication. Medical u ...
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Bacampicillin
Bacampicillin (INN) is a penicillin antibiotic. It is a prodrug of ampicillin with improved oral bioavailability. It was sold under the brand names Spectrobid (Pfizer) and Penglobe (AstraZeneca).In 2015, Pfizer discontinued Spectrobid, and no generic manufacturer has taken over production. Bacampicillin is thus unavailable in the United States, and is no longer FDA approved. Synthesis Semi-synthetic antibiotic related to penicillin. The relatively small chemical difference between ampicillin and benzylpenicillin not only allows for substantial oral activity but also results in a substantial broadening of antimicrobial spectrum so as to allow for use against many Gram-negative bacteria. Many devices have been employed in order to enhance still further the oral absorption of ampicillin. Bacampicillin is a prodrug of ampicillin designed for this purpose. An azidopenicillin sodium salt (1) is reacted with mixed carbonate ester 2 (itself prepared from acetaldehyde and ethyl chloro ...
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Extended-spectrum Penicillin
The extended-spectrum penicillins are a group of antibiotics that have the widest antibacterial spectrum of all penicillins. Some sources identify them with antipseudomonal penicillins, others consider these types to be distinct. This group includes the carboxypenicillins and the ureidopenicillins. Aminopenicillins, in contrast, do not have activity against ''Pseudomonas'' species, as their positively charged amino group does not hinder degradation by bacterially produced beta-lactamases. Products * Ureidopenicillins **Azlocillin ** Mezlocillin **Piperacillin *Carboxypenicillins **Ticarcillin (generally in the combination ticarcillin/clavulanic acid) **Carbenicillin Carbenicillin is a bactericidal antibiotic belonging to the carboxypenicillin subgroup of the penicillins. It was discovered by scientists at Beecham and marketed as Pyopen. It has Gram-negative coverage which includes ''Pseudomonas aeruginosa'' ... * Mecillinam See also * ''Pseudomonas aeruginosa'' § Treatme ...
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Carboxypenicillin
The carboxypenicillins are a group of antibiotics. They belong to the penicillin family and comprise the members carbenicillin and ticarcillin. Chemical structure The carboxypenicillins feature the beta-lactam backbone of all penicillins but also feature a carboxylic acid or carboxylic acid ester group in the variable side-chain. Spectrum The carboxypenicillins exhibit activity against Gram negative organisms including ''Pseudomonas aeruginosa'' and ''Proteus'' species. They are inactive against certain Gram positive pathogens such as ''Staphylococcus aureus'', ''Enterococcus faecalis'', and '' L. monocytogenes''. The carboxypenicillins are beta-lactamase sensitive. See also * Aminopenicillin The aminopenicillins are a group of antibiotics in the penicillin family that are structural analogs of ampicillin (which is the 2- amino derivative of benzylpenicillin, hence the name). Like other penicillins and beta-lactam antibiotics, they c ... References {{Cell wall ...
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Antibiotic
An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting bacterial infections, and antibiotic medications are widely used in the treatment and prevention of such infections. They may either kill or inhibit the growth of bacteria. A limited number of antibiotics also possess antiprotozoal activity. Antibiotics are not effective against viruses such as the common cold or influenza; drugs which inhibit viruses are termed antiviral drugs or antivirals rather than antibiotics. Sometimes, the term ''antibiotic''—literally "opposing life", from the Greek roots ἀντι ''anti'', "against" and βίος ''bios'', "life"—is broadly used to refer to any substance used against microbes, but in the usual medical usage, antibiotics (such as penicillin) are those produced naturally (by one microorganism fighting another), whereas non-antibiotic antibacterials (such as sulfonamides and antise ...
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Penicillin
Penicillins (P, PCN or PEN) are a group of β-lactam antibiotics originally obtained from '' Penicillium'' moulds, principally '' P. chrysogenum'' and '' P. rubens''. Most penicillins in clinical use are synthesised by P. chrysogenum using deep tank fermentation and then purified. A number of natural penicillins have been discovered, but only two purified compounds are in clinical use: penicillin G (intramuscular or intravenous use) and penicillin V (given by mouth). Penicillins were among the first medications to be effective against many bacterial infections caused by staphylococci and streptococci. They are still widely used today for different bacterial infections, though many types of bacteria have developed resistance following extensive use. 10% of the population claims penicillin allergies but because the frequency of positive skin test results decreases by 10% with each year of avoidance, 90% of these patients can tolerate penicillin. Additionally, those wi ...
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Structural Analogs
A structural analog (analogue in modern traditional English; Commonwealth English), also known as a chemical analog or simply an analog, is a compound having a structure similar to that of another compound, but differing from it in respect to a certain component. It can differ in one or more atoms, functional groups, or substructures, which are replaced with other atoms, groups, or substructures. A structural analog can be imagined to be formed, at least theoretically, from the other compound. Structural analogs are often isoelectronic. Despite a high chemical similarity, structural analogs are not necessarily functional analogs and can have very different physical, chemical, biochemical, or pharmacological properties. In drug discovery, either a large series of structural analogs of an initial lead compound are created and tested as part of a structure–activity relationship study or a database is screened for structural analogs of a lead compound. Chemical analogues of ill ...
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Amino
In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group (these may respectively be called alkylamines and arylamines; amines in which both types of substituent are attached to one nitrogen atom may be called alkylarylamines). Important amines include amino acids, biogenic amines, trimethylamine, and aniline; Inorganic derivatives of ammonia are also called amines, such as monochloramine (). The substituent is called an amino group. Compounds with a nitrogen atom attached to a carbonyl group, thus having the structure , are called amides and have different chemical properties from amines. Classification of amines Amines can be classified according to the nature and number of substituents on nitrogen. Aliphatic amines contain only H and alkyl substituents. Arom ...
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Benzylpenicillin
Benzylpenicillin, also known as penicillin G (PenG) or BENPEN, and in military slang "Peanut Butter Shot" is an antibiotic used to treat a number of bacterial infections. This includes pneumonia, strep throat, syphilis, necrotizing enterocolitis, diphtheria, gas gangrene, leptospirosis, cellulitis, and tetanus. It is not a first-line agent for pneumococcal meningitis. Due to Benzylpenicillin's limited bioavailability for oral medications, it is generally taken as an injection in the form of a sodium, potassium, benzathine, or procaine salt. Benzylpenicillin is given by injection into a vein or muscle. Two long-acting forms benzathine benzylpenicillin and procaine benzylpenicillin are available for use by injection into a muscle. Side effects include diarrhea, seizures, and allergic reactions including anaphylaxis. When used to treat syphilis or Lyme disease a reaction known as Jarisch–Herxheimer may occur. It is not recommended in those with a history of penicillin allergy. U ...
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Beta-lactam
A beta-lactam (β-lactam) ring is a four-membered lactam. A ''lactam'' is a cyclic amide, and ''beta''-lactams are named so because the nitrogen atom is attached to the β-carbon atom relative to the carbonyl. The simplest β-lactam possible is 2-azetidinone. β-lactams are significant structural units of medicines as manifested in many β-lactam antibiotics Up to 1970, most β-lactam research was concerned with the penicillin and cephalosporin groups, but since then, a wide variety of structures have been described. Clinical significance The β-lactam ring is part of the core structure of several antibiotic families, the principal ones being the penicillins, cephalosporins, carbapenems, and monobactams, which are, therefore, also called β-lactam antibiotics. Nearly all of these antibiotics work by inhibiting bacterial cell wall biosynthesis. This has a lethal effect on bacteria, although any given bacteria population will typically contain a subgroup that is resistant ...
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