Overview
| IUPAC Name: | (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid |
|---|---|
| Trade Names: | Abbocillin; Ayercillin; Benzopenicillin; Benzylpenicillin; Benzylpenicillin G; Benzylpenicillinic Acid; Bicillin; Bicillin L-A; Cillora; Cilloral; Cilopen; Compocillin G; Cosmopen; Crysticillin 300 A.S.; Dropcillin; Free Benzylpenicillin; Free Penicillin G; Free Penicillin Ii; Galofak; Gelacillin; Liquacillin; Megacillin; Pencillin G; Penicillin; Penicillin G Potassium; Penicillin G Potassium in Plastic Container; Penicillin G Sodium; Penicillin-G Potassium; Penicillinic Acid, Benzyl-; Pentids; Pentids '200'; Permapen; Pfizerpen; Pfizerpen G; Pharmacillin; Phenylacetamidopenicillanic Acid; Pradupen; Specilline G; Ursopen; Wycillin |
| PharmGKB Accession Id: | PA450842 |
Description
A penicillin derivative commonly used in the form of its sodium or potassium salts in the treatment of a variety of infections. It is effective against most gram-positive bacteria and against gram-negative cocci. It has also been used as an experimental convulsant because of its actions on gamma-aminobutyric acid mediated synaptic transmission. [PubChem]
Indication
For use in the treatment of severe infections caused by penicillin G-susceptible microorganisms when rapid and high penicillin levels are required.
ATC Therapeutic Categories
- J01CE:Beta-lactamase sensitive penicillins
- S01AA:Antibiotics
Pharmacology and Interactions
Mechanism Of Action
By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, penicillin G inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that penicillin G interferes with an autolysin inhibitor.
Pharmacology
Penicillin G is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Penicillin G has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of penicillin G results from the inhibition of cell wall synthesis and is mediated through penicillin G binding to penicillin binding proteins (PBPs). Penicillin G is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases.
Absorption, Distribution, Metabolism, Elimination & Toxicity
Protein Binding
Bind to serum proteins, mainly albumin.
Absorption
Rapidly absorbed following both intramuscular and subcutaneous injection. Initial blood levels following parenteral administration are high but transient.
Toxicity
Oral LD50 in rat is 8900 mk/kg. Neurological adverse reactions, including convulsions, may occur with the attainment of high CSF levels of beta-lactams.
Chemical Properties
Chemical Formula:
C16H18N2O4S
SMILES Code:
CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)Cc3ccccc3)C(=O)O)C
(Format: OpenEye Isomeric)
Molecular Weight ( average / monoisotopic )
334.39 / 334.0987
Curated Information
The following genes are in curated knowledge about this drug.
| Gene | Relationship | Evidence | |
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IFNAR1 |
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SLCO1B1 |
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SLCO2B1 |
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SLCO3A1 |
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SLCO4A1 |
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Non-Curated Information
A list of non-curated publications that mention this drug along with other genes is available.
Non-Curated Information
A list of non-curated publications that mention this drug along with other drugs is available.
Drug Interactions
| acenocoumarol | The IV penicillin increases the anticoagulant effect |
| anisindione | The IV penicillin increases the anticoagulant effect |
| demeclocycline | Possible antagonism of action |
| dicumarol | The IV penicillin increases the anticoagulant effect |
| doxycycline | Possible antagonism of action |
| ethinyl estradiol | This anti-infectious agent could decreases the effect of the oral contraceptive |
| mestranol | This anti-infectious agent could decreases the effect of the oral contraceptive |
| methacycline | Possible antagonism of action |
| methotrexate | The penicillin increases the effect and toxicity of methotrexate |
| minocycline | Possible antagonism of action |
| oxytetracycline | Possible antagonism of action |
| rolitetracycline | Possible antagonism of action |
| tetracycline | Possible antagonism of action |
| warfarin | The IV penicillin increases the anticoagulant effect |
Curated Information
The following diseases are in curated knowledge about this drug.
| Disease | Relationship | Evidence | |
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Drug Hypersensitivity |
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Publications |
Non-Curated Information
A list of non-curated publications that mention this drug along with other diseases is available.
Additional Datasets
These datasets are minimally curated and are sorted alphabetically by title.
LinkOuts
Common Searches
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Non-Curated Publications
A list of non-curated publications that mention this drug is available.
