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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL29
CHEMBL29
Compound Name BENZYLPENICILLIN
ChEMBL Synonyms BENETHAMINE PENICILLIN | Permapen | BENZYLPENICILLIN SODIUM | PENICILLIN G SODIUM, CRYSTALLINE | BENZETHACIL | PERMAPEN | Cilloral | Penicillin G Potassium | Pentids '400' | PENICILLIN CALCIUM | PENICILLIN G SODIUM | Pentids '200' | Pentids '800' | BICILLIN | BICILLIN L-A | Penicillin-2 | BENZATHINE BENZYLPENICILLIN | Pfizerpen-AS | Pfizerpen | Liquapen | E705 | E706 | Scotcil | PENICILLIN G BENZATHINE | E708 | Penicillin G | Pfizerpen G | PENTIDS | PENICILLIN POTASSIUM G, CRYSTALLINE | BENZYLPENICILLIN BENZATHINE | BENZATHINE PENICILLIN | Pentids '250' | Penicillin | BENZYLPENICILLIN POTASSIUM | Bicillin | BENZYLPENICILLIN
Max Phase 4 (Approved)
Trade Names Cilloral | Pentids '400' | PERMAPEN | Pentids '200' | Pentids '800' | BICILLIN | BICILLIN L-A | Penicillin | Pentids '250' | PENTIDS | Liquapen | Scotcil
Molecular Formula C16H18N2O4S

Additional synonyms for CHEMBL29 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CC1(C)S[C@@H]2[C@H](NC(=O)Cc3ccccc3)C(=O)N2[C@H]1C(=O)O
Standard InChI InChI=1S/C16H18N2O4S/c1-16(2)12(15(21)22)18-13(20)11(14(18)2 ...
Download InChI
Standard InChI Key JGSARLDLIJGVTE-MBNYWOFBSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • Curated Drug Metabolism Pathways
  • DrugMatrix
  • Gene Expression Atlas Compounds
  • HeCaToS Compounds
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL29

Molecule Features

CHEMBL29 compound icon
Drug Type:Natural Product-derived Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:Y Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Bacterial penicillin-binding protein inhibitor Bacterial penicillin-binding protein PubMed PubMed PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
CARCINOMA, SQUAMOUS CELLD002294EFO:0000181HEAD AND NECK SQUAMOUS CELL CARCINOMA1ClinicalTrials
PSORIASISD011565EFO:0000676PSORIASIS2ClinicalTrials
PNEUMONIAD011014EFO:0003106PNEUMONIA3ClinicalTrials

Clinical Data

ClinicalTrials.gov BENZYLPENICILLIN
The Cochrane Collaboration BENZYLPENICILLIN

Metabolites for CHEMBL29

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Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL29. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL321 Matrix metalloproteinase 9 Homo sapiens 0.401
CHEMBL333 Matrix metalloproteinase-2 Homo sapiens 0.206

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL321 Matrix metalloproteinase 9 Homo sapiens 0.293

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
334.4 334.0987 1.12 4 112.01 ACID


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
5 2 0 6 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
2.45 - 1.92 -1.81 1 23 0.8

Structural Alerts

There are 3 structural alerts for CHEMBL29. To view alerts please click here.

Compound Cross References

ATC S - SENSORY ORGANS
S01 - OPHTHALMOLOGICALS
S01A - ANTIINFECTIVES
S01AA - Antibiotics
S01AA14 - benzylpenicillin

J - ANTIINFECTIVES FOR SYSTEMIC USE
J01 - ANTIBACTERIALS FOR SYSTEMIC USE
J01C - BETA-LACTAM ANTIBACTERIALS, PENICILLINS
J01CE - Beta-lactamase sensitive penicillins
J01CE08 - benzathine benzylpenicillin

J - ANTIINFECTIVES FOR SYSTEMIC USE
J01 - ANTIBACTERIALS FOR SYSTEMIC USE
J01C - BETA-LACTAM ANTIBACTERIALS, PENICILLINS
J01CE - Beta-lactamase sensitive penicillins
J01CE01 - benzylpenicillin

ChemSpider ChemSpider:JGSARLDLIJGVTE-MBNYWOFBSA-N
DailyMed penicillin g benzathine penicillin g potassium penicillin g sodium
PubChem SID: 49647119
Wikipedia Benzylpenicillin

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL29



ACToR 61-33-6
Atlas Penicillin G
BindingDB 50022787
Brenda 348 125600 181 174232 11038
ChEBI 18208
DrugBank DB01053
DrugCentral 2082
EPA CompTox Dashboard DTXSID5046934
FDA SRS Q42T66VG0C
Guide to Pharmacology 4796
Human Metabolome Database HMDB0015186
IBM Patent System 8810BC350F6BED3BEC270C0D7CFF7FAF
KEGG Ligand C05551
LINCS LSM-3229
Nikkaji J2.342F
PDBe PNN
PharmGKB PA450842
PubChem 5904
PubChem: Thomson Pharma 15348041 14875396
SureChEMBL SCHEMBL3783
ZINC ZINC000003871701

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/JGSARLDLIJGVTE-MBNYWOFBSA-N spacer
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