ANTIPYRINE

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Synonyms
Status
Molecule Category Free-form
UNII T3CHA1B51H
EPA CompTox DTXSID6021117

Structure

InChI Key VEQOALNAAJBPNY-UHFFFAOYSA-N
Smiles Cc1cc(=O)n(-c2ccccc2)n1C
InChI
InChI=1S/C11H12N2O/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C11H12N2O
Molecular Weight 188.23
AlogP 1.48
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 1.0
Polar Surface Area 26.93
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 14.0

Bioactivity

Mechanism of Action Action Reference
Cyclooxygenase-1 inhibitor INHIBITOR PubMed PubMed PubMed PubMed
Protein: Cyclooxygenase-1
Description: Prostaglandin G/H synthase 1
Organism : Homo sapiens
P23219 ENSG00000095303
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 80
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 21
Assay Description Organism Bioactivity Reference
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens 20.7 %
Inhibition of human FAAH at 1 uM Homo sapiens -5.75 %
TP_TRANSPORTER: inhibition of PAH uptake (PAH: 2 uM, Antipyrine: 1000 uM) in Xenopus laevis oocytes Xenopus laevis 37.8 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 79.71 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 82.49 %
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 9.39 %
Inhibition of NAPRT (unknown origin) Homo sapiens 1.0 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 15.26 %
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 -0.05 % 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 -0.05 %

Related Entries

Cross References

Resources Reference
ChEBI 31225
ChEMBL CHEMBL277474
DrugBank DB01435
DrugCentral 861
FDA SRS T3CHA1B51H
Human Metabolome Database HMDB0015503
KEGG C13244
PharmGKB PA448453
PubChem 2206
SureChEMBL SCHEMBL20452
ZINC ZINC000000061044
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