HETACILLIN POTASSIUM

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Search structure


Trade Names	VERSAPEN-K
Synonyms	Hetacillin potassium Hetacillin potassium salt Hetacin-k NSC-757046 Natacillin Potassium hetacillin Versapen-k Versatrex
Status
Molecule Category	Salt-form
UNII	95PFX5932Y
Parent Compound:	HETACILLIN


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

Structure


InChI Key	QRSPJBLLJXVPDD-XFAPPKAWSA-M
Smiles	CC1(C)S[C@@H]2[C@H](N3C(=O)[C@@H](c4ccccc4)NC3(C)C)C(=O)N2[C@H]1C(=O)[O-].[K+]
InChI	InChI=1S/C19H23N3O4S.K/c1-18(2)13(17(25)26)21-15(24)12(16(21)27-18)22-14(23)11(20-19(22,3)4)10-8-6-5-7-9-10;/h5-9,11-13,16,20H,1-4H3,(H,25,26);/q;+1/p-1/t11-,12-,13+,16-;/m1./s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C19H22KN3O4S
Molecular Weight	427.57
AlogP	1.41
Hydrogen Bond Acceptor	5.0
Hydrogen Bond Donor	2.0
Number of Rotational Bond	3.0
Polar Surface Area	89.95
Molecular species	ACID
Aromatic Rings	1.0
Heavy Atoms	27.0

Bioactivity

Mechanism of Action	Action	Reference
Penicillin-binding protein inhibitor	INHIBITOR	PubMed PubMed

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group I Nuclear hormone receptor subfamily 1 group I member 2	6300	-	-	-	-
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides	-	-	-	-	82

Assay Description	Organism	Bioactivity	Reference
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	81.9 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	89.09 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	67.14 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	18.58 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.11 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.11 %

Cross References

Resources	Reference
ChEBI	34789
ChEMBL	CHEMBL1201121
FDA SRS	95PFX5932Y
KEGG	C13980
PubChem	23678597
SureChEMBL	SCHEMBL192601

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).