CEFOXITIN

/static/temp/default.svg

Search structure


Synonyms	Cefoxitin Cenomycin J01DC01 Mefoxin Mefoxitin
Status
Molecule Category	Free-form
ATC	J01DC01
UNII	6OEV9DX57Y
EPA CompTox	DTXSID1022764


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

Structure


InChI Key	WZOZEZRFJCJXNZ-ZBFHGGJFSA-N
Smiles	CO[C@@]1(NC(=O)Cc2cccs2)C(=O)N2C(C(=O)O)=C(COC(N)=O)CS[C@@H]21
InChI	InChI=1S/C16H17N3O7S2/c1-25-16(18-10(20)5-9-3-2-4-27-9)13(23)19-11(12(21)22)8(6-26-15(17)24)7-28-14(16)19/h2-4,14H,5-7H2,1H3,(H2,17,24)(H,18,20)(H,21,22)/t14-,16+/m1/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C16H17N3O7S2
Molecular Weight	427.46
AlogP	0.1
Hydrogen Bond Acceptor	8.0
Hydrogen Bond Donor	3.0
Number of Rotational Bond	7.0
Polar Surface Area	148.26
Molecular species	ACID
Aromatic Rings	1.0
Heavy Atoms	28.0

Assay Description	Organism	Bioactivity	Reference
Inhibition of Citrobacter freundii PER2 beta lactamase	Citrobacter freundii	140.0 nM
Antimicrobial activity against methicillin-susceptible Staphylococcus aureus ATCC 25923 infected in human keratinocytes assessed as change in bacterial count after 24 hrs	Staphylococcus aureus	0.55 ug.mL-1
Inhibition of Escherichia coli MC4100 Beta-Lactamase CMY-30 using cephalothin as reporter substrate	Escherichia coli	170.0 nM
Inhibition of Escherichia coli MC4100 Beta-Lactamase CMY-2 using cephalothin as reporter substrate	Escherichia coli	150.0 nM
Activity of Acinetobacter baumannii ADC-33 beta-lactamase	Acinetobacter baumannii	100.0 nM
Activity of Acinetobacter baumannii ADC-11 beta-lactamase	Acinetobacter baumannii	500.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	4.46 %
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	0.25 %		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	0.25 %

Cross References

Resources	Reference
ChEBI	209807
ChEMBL	CHEMBL996
DrugBank	DB01331
DrugCentral	550
FDA SRS	6OEV9DX57Y
Human Metabolome Database	HMDB0015426
Guide to Pharmacology	10937
KEGG	C06887
PDB	CFX
PharmGKB	PA448856
PubChem	441199
SureChEMBL	SCHEMBL15971
ZINC	ZINC000003830449

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).