Penam: Difference between revisions

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'''Penam''' is a term that can refer to several different concepts, depending on the context. It may refer to a brand of pharmaceuticals, a type of bread, or a location in Slovakia. This article will provide a detailed overview of each of these potential meanings.
{{Chembox
| Name          = Penam
| ImageFile      = File:Penam.svg
| ImageSize      = 150px
| Caption        = Structure of the penam backbone
| IUPACName      = (5R)-4-thia-1-azabicyclo[3.2.0]heptan-7-one
| OtherNames    = 1-Aza-7-oxo-4-thiabicyclo[3.2.0]heptane
| Section1      = {{Chembox Identifiers
| CASNo          = 53908-04-6
| CASNo_Ref      = {{Cascite|changed|ChemSpider}}
| PubChem        = 9548842
| Beilstein      = 4374479
| ChemSpiderID  = 7827765
| ChEBI          = 35991
| SMILES        = C1CSC2N1C(=O)C2
| InChI          = 1S/C5H7NOS/c7-4-3-5-6(4)1-2-8-5/h5H,1-3H2/t5-/m1/s1
| InChIKey      = WSHJJCPTKWSMRR-RXMQYKEDSA-N
| StdInChI      = 1S/C5H7NOS/c7-4-3-5-6(4)1-2-8-5/h5H,1-3H2/t5-/m1/s1
| StdInChIKey    = WSHJJCPTKWSMRR-RXMQYKEDSA-N
}}
| Section2      = {{Chembox Properties
| C              = 5
| H              = 7
| N              = 1
| O              = 1
| S              = 1
| Appearance    = Colorless crystalline solid
| Density        =
| MeltingPtC    =
| BoilingPtC    =
| Solubility    = Soluble in water and organic solvents
}}
| Section3      = {{Chembox Hazards
| MainHazards    = May cause allergic reactions
| FlashPt        =
| AutoignitionPt =
}}
| Section8      = {{Chembox Related
| OtherCompounds = Clavam, Penem, Carbapenem
}}
}}


== Penam Pharmaceuticals ==
[[File:Penicillin-G.svg|thumb|[[Benzylpenicillin]], an example of a penam]]
[[Penam Pharmaceuticals]] is a pharmaceutical company that specializes in the production of various types of medicines and healthcare products. The company is known for its commitment to quality and innovation, and it has a wide range of products that cater to different healthcare needs. Some of its most popular products include [[antibiotics]], [[analgesics]], and [[vitamins]].


== Penam Bread ==
'''Penams''' represent the structural core of the [[penicillin]] subclass of [[β-lactam antibiotics]]. They are bicyclic compounds characterized by a [[β-lactam]] ring fused to a five-member [[thiazolidine]] ring. The [[penam]] skeleton is integral to the activity of these antibiotics, which disrupt bacterial cell wall synthesis.
[[Penam Bread]] is a type of bread that is popular in several countries around the world. It is known for its unique taste and texture, which is achieved through a special baking process. The bread is often used in a variety of dishes, from sandwiches to toast, and is a staple in many households.


== Penam, Slovakia ==
== Structure and Properties ==
[[Penam, Slovakia]] is a small village located in the [[Trencin Region]] of Slovakia. The village is known for its picturesque scenery and peaceful atmosphere. It is a popular destination for tourists who are looking to experience the natural beauty of Slovakia.
The penam structure consists of:
* A [[β-lactam ring]]: A four-membered cyclic amide responsible for antibacterial activity.
* A [[thiazolidine ring]]: A sulfur-containing five-membered ring fused to the β-lactam ring.


== See Also ==
Penams exhibit:
* [[Pharmaceutical industry]]
* '''High strain energy''': The 90º bond angles in the β-lactam ring deviate significantly from the ideal sp² or sp³ bond angles, causing [[angle strain]].
* [[Bread]]
* '''Limited resonance stabilization''': The amide bond between the β-lactam carbonyl group and nitrogen is distorted, reducing overlap between lone pair and π orbitals.
* [[Slovakia]]
 
These features make penams highly reactive, especially to [[β-lactamase]] enzymes and acidic or basic conditions.
 
== Biological Significance ==
Penams are critical components of penicillin antibiotics, which target the [[bacterial cell wall]]. Their mode of action involves:
* 1. Binding to [[penicillin-binding proteins]] (PBPs) in bacteria.
* 2. Inhibiting the final steps of [[peptidoglycan]] synthesis, weakening the cell wall.
* 3. Inducing bacterial cell lysis.
 
Examples of penam antibiotics include:
* [[Benzylpenicillin]] (penicillin G)
* [[Phenoxymethylpenicillin]] (penicillin V)
 
== Chemical Reactivity ==
Penams are susceptible to hydrolysis by [[β-lactamases]], enzymes produced by resistant bacteria. This reaction cleaves the β-lactam ring, rendering the antibiotic inactive. To counteract this, β-lactamase inhibitors such as [[clavulanic acid]] are used in combination therapies.


== References ==
== Applications ==
<references />
Penams are used in the treatment of:
* [[Bacterial infections]] such as [[streptococcal pharyngitis]], [[syphilis]], and [[endocarditis]].
* Conditions caused by penicillin-sensitive organisms.


[[Category:Disambiguation pages]]
== Related Compounds ==
[[Category:Pharmaceutical companies]]
Penams are part of a broader family of [[β-lactam antibiotics]], which includes:
[[Category:Bread]]
* [[Penems]]
[[Category:Villages in Slovakia]]
* [[Carbapenems]]
* [[Cephalosporins]]


{{disambiguation}}
== See Also ==
{{pharma-stub}}
* [[Antibiotic resistance]]
{{food-stub}}
* [[Penicillin-binding protein]]
{{Slovakia-geo-stub}}
* [[β-lactamase inhibitors]]
* [[Sulbactam]]
* [[Tazobactam]]
== External Links ==
* [https://www.ncbi.nlm.nih.gov/pmc/articles/PMC Penicillin Mechanisms - PubMed]
* [https://www.sciencedirect.com/topics/penam Penam Studies on ScienceDirect]
[[Category:Beta-lactam antibiotics]]
[[Category:Sulfur heterocycles]]
[[Category:Nitrogen heterocycles]]
[[Category:Heterocyclic compounds with 2 rings]]
[[Category:Ketones]]
[[Category:Antibiotics]]

Latest revision as of 14:21, 11 December 2024

Chemical Compound
Identifiers
CAS Number
PubChem CID
ChemSpider ID
UNII
ChEBI
ChEMBL
Properties
Chemical Formula
Molar Mass
Appearance
Density
Melting Point
Boiling Point
Hazards
GHS Pictograms [[File:|50px]]
GHS Signal Word
GHS Hazard Statements
NFPA 704 [[File:|50px]]
References
Benzylpenicillin, an example of a penam

Penams represent the structural core of the penicillin subclass of β-lactam antibiotics. They are bicyclic compounds characterized by a β-lactam ring fused to a five-member thiazolidine ring. The penam skeleton is integral to the activity of these antibiotics, which disrupt bacterial cell wall synthesis.

Structure and Properties[edit]

The penam structure consists of:

  • A β-lactam ring: A four-membered cyclic amide responsible for antibacterial activity.
  • A thiazolidine ring: A sulfur-containing five-membered ring fused to the β-lactam ring.

Penams exhibit:

  • High strain energy: The 90º bond angles in the β-lactam ring deviate significantly from the ideal sp² or sp³ bond angles, causing angle strain.
  • Limited resonance stabilization: The amide bond between the β-lactam carbonyl group and nitrogen is distorted, reducing overlap between lone pair and π orbitals.

These features make penams highly reactive, especially to β-lactamase enzymes and acidic or basic conditions.

Biological Significance[edit]

Penams are critical components of penicillin antibiotics, which target the bacterial cell wall. Their mode of action involves:

Examples of penam antibiotics include:

Chemical Reactivity[edit]

Penams are susceptible to hydrolysis by β-lactamases, enzymes produced by resistant bacteria. This reaction cleaves the β-lactam ring, rendering the antibiotic inactive. To counteract this, β-lactamase inhibitors such as clavulanic acid are used in combination therapies.

Applications[edit]

Penams are used in the treatment of:

Related Compounds[edit]

Penams are part of a broader family of β-lactam antibiotics, which includes:

See Also[edit]

External Links[edit]

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