SULFINPYRAZONE

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Search structure


Trade Names	ANTURANE SULFINPYRAZONE
Synonyms	Anturan Anturane NSC-75925 Sulfinpyrazone Sulphinpyrazone
Status
Molecule Category	Free-form
ATC	M04AB02
UNII	V6OFU47K3W
EPA CompTox	DTXSID0023618


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

Structure


InChI Key	MBGGBVCUIVRRBF-UHFFFAOYSA-N
Smiles	O=C1C(CC[S+]([O-])c2ccccc2)C(=O)N(c2ccccc2)N1c1ccccc1
InChI	InChI=1S/C23H20N2O3S/c26-22-21(16-17-29(28)20-14-8-3-9-15-20)23(27)25(19-12-6-2-7-13-19)24(22)18-10-4-1-5-11-18/h1-15,21H,16-17H2

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C23H20N2O3S
Molecular Weight	404.49
AlogP	3.8
Hydrogen Bond Acceptor	3.0
Hydrogen Bond Donor	0.0
Number of Rotational Bond	6.0
Polar Surface Area	57.69
Molecular species	ACID
Aromatic Rings	3.0
Heavy Atoms	29.0

Bioactivity

Mechanism of Action	Action	Reference
Solute carrier family 22 member 12 inhibitor	INHIBITOR	PubMed PubMed Wikipedia


Protein: Solute carrier family 22 member 12 Description: Solute carrier family 22 member 12 Organism : Homo sapiens Q96S37 ENSG00000197891

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Oxidoreductase	-	-	-	-	83
Enzyme Protease Serine protease Serine protease PA clan Serine protease S1A subfamily	-	-	-	-	27
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) N-formyl methionyl peptide receptor N-formyl methionyl peptide receptor	-	10000	-	-	-
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides	-	-	-	-	44
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters	-	100000	-	-	-
Transporter Primary active transporter ATP-binding cassette ABCB subfamily	-	11000	-	-	-

Assay Description	Organism	Bioactivity	Reference
Inhibition of beta-lactamase at 100 uM	None	5.0 %
Inhibition of chymotrypsin at 250 uM	unidentified	27.0 %
Inhibition of malate dehydrogenase (MDH) at 400 uM	None	83.0 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	55.19 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	43.93 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600)	Staphylococcus aureus subsp. aureus	18.52 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600)	Escherichia coli	6.57 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600)	Klebsiella pneumoniae	13.98 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600)	Pseudomonas aeruginosa	20.19 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600	Acinetobacter baumannii	24.87 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630	Candida albicans	4.96 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570)	Cryptococcus neoformans	-8.91 %
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	-0.47 %
Inhibition of NAPRT (unknown origin)	Homo sapiens	0.5 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	-10.54 %
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	0.02 %		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	0.02 %

Related Entries

Cross References

Resources	Reference
ChEBI	9342
ChEMBL	CHEMBL832
DrugBank	DB01138
DrugCentral	2528
FDA SRS	V6OFU47K3W
Human Metabolome Database	HMDB0015269
Guide to Pharmacology	5826
KEGG	C07317
PharmGKB	PA451550
PubChem	5342
SureChEMBL	SCHEMBL34421
ZINC	ZINC03831483

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).