penicillin G   Click here for help

GtoPdb Ligand ID: 4796

Synonyms: penicillin G sodium | penicillin-G potassium
Approved drug PDB Ligand
penicillin G is an approved drug (FDA (1947))
Compound class: Synthetic organic
Comment: Penicillin G (benzylpenicillin) is a narrow spectrum penicillin antibacterial.
Penicillin G is is one of the access group antibacterials on the World Health Organization's Model List of Essential Medicines (link provided in the Classification table under the Summary tab).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 112.01
Molecular weight 334.1
XLogP 1.49
No. Lipinski's rules broken 0
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Canonical SMILES O=C(Cc1ccccc1)NC1C(=O)N2C1SC(C2C(=O)O)(C)C
Isomeric SMILES O=C(Cc1ccccc1)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C
InChI InChI=1S/C16H18N2O4S/c1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1947))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
Prodrug penamecillin
IUPAC Name Click here for help
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
221 benethamine penicillin
203 benzathine benzylpenicillin
58 benzylpenicillin
827 clemizole penicillin
736 phenyracillin
Synonyms Click here for help
penicillin G sodium | penicillin-G potassium
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Penicillin G (Benzylpenicillin)
Other databases
CAS Registry No. 61-33-6 (source: Scifinder)
DrugBank Ligand DB01053
DrugCentral Ligand 2082
GtoPdb PubChem SID 178101498
Immunopaedia Search penicillin
PubChem CID 5904
Search Google for chemical match using the InChIKey JGSARLDLIJGVTE-MBNYWOFBSA-N
Search Google for chemicals with the same backbone JGSARLDLIJGVTE
Search PubMed clinical trials phenyracillin
Search PubMed titles phenyracillin
Search PubMed titles/abstracts phenyracillin
UniChem Compound Search for chemical match using the InChIKey JGSARLDLIJGVTE-MBNYWOFBSA-N
UniChem Connectivity Search for chemical match using the InChIKey JGSARLDLIJGVTE-MBNYWOFBSA-N
Wikipedia Penicillin_G