PENICILLIN V

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Trade Names	V-CILLIN
Synonyms	Distaquaine v Penapar-VK Penicillin phenoxymethyl Penicillin v Penicillin-VK Phenomycilline Phenoxymethylpenicillin Phenoxymethylpenicillinum V-cillin Vebecillin Veetids
Status
Molecule Category	UNKNOWN
UNII	Z61I075U2W
EPA CompTox	DTXSID3023429


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	BPLBGHOLXOTWMN-MBNYWOFBSA-N
Smiles	CC1(C)S[C@@H]2[C@H](NC(=O)COc3ccccc3)C(=O)N2[C@H]1C(=O)O
InChI	InChI=1S/C16H18N2O5S/c1-16(2)12(15(21)22)18-13(20)11(14(18)24-16)17-10(19)8-23-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C16H18N2O5S
Molecular Weight	350.4
AlogP	0.7
Hydrogen Bond Acceptor	5.0
Hydrogen Bond Donor	2.0
Number of Rotational Bond	5.0
Polar Surface Area	95.94
Molecular species	ACID
Aromatic Rings	1.0
Heavy Atoms	24.0

Pharmacology

Mechanism of Action	Action	Reference
Bacterial penicillin-binding protein inhibitor	INHIBITOR	DailyMed Wikipedia

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters	-	48600	-	-	-

Assay Description	Organism	Bioactivity	Reference
Inhibition of Staphylococcus aureus PBP2a	Staphylococcus aureus	5.0 /M/s
Inhibition of Bacillus subtilis 168 PBP5 after 30 mins by SDS-PAGE	Bacillus subtilis subsp. subtilis str. 168	620.0 /M/s
Inhibition of Bacillus subtilis 168 PBP4 after 30 mins by SDS-PAGE	Bacillus subtilis subsp. subtilis str. 168	1.9 10'4/M/s
Inhibition of Bacillus subtilis 168 PBP3 after 30 mins by SDS-PAGE	Bacillus subtilis subsp. subtilis str. 168	28.0 /M/s
Inhibition of Bacillus subtilis 168 PBP2 after 30 mins by SDS-PAGE	Bacillus subtilis subsp. subtilis str. 168	1.9 10'4/M/s
Inhibition of Escherichia coli PBP5/6 after 30 mins by SDS-PAGE	Escherichia coli	96.0 /M/s
Inhibition of Bacillus subtilis 168 PBP1 after 30 mins by SDS-PAGE	Bacillus subtilis subsp. subtilis str. 168	1.1 10'5/M/s
Inhibition of Escherichia coli PBP3 after 30 mins by SDS-PAGE	Escherichia coli	420.0 /M/s
Inhibition of Escherichia coli BL21(DE3) PBP2 after 30 mins by SDS-PAGE	Escherichia coli BL21(DE3)	128.0 /M/s
Inhibition of Escherichia coli PBP1a/1b after 30 mins by SDS-PAGE	Escherichia coli	184.0 /M/s

Related Entries

Cross References

Resources	Reference
ChEBI	27446
ChEMBL	CHEMBL615
DrugBank	DB00417
DrugCentral	2083
FDA SRS	Z61I075U2W
Human Metabolome Database	HMDB0014561
Guide to Pharmacology	10920
KEGG	C08126
PDB	PNV
PharmGKB	PA164745442
PubChem	6869
SureChEMBL	SCHEMBL49223
ZINC	ZINC000003831282

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).