AMINOPYRINE

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Search structure


Synonyms	4-dimethylaminoantipyrine Amidazophene Amidopyrazoline Amidopyrine Aminophenazone Aminopyrine Brufaneuxol Dereuma Febron Itamidone Mamallet a NSC-4993 Netsusarin
Status
Molecule Category	UNKNOWN
UNII	01704YP3MO
EPA CompTox	DTXSID7020504


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

Structure


InChI Key	RMMXTBMQSGEXHJ-UHFFFAOYSA-N
Smiles	Cc1c(N(C)C)c(=O)n(-c2ccccc2)n1C
InChI	InChI=1S/C13H17N3O/c1-10-12(14(2)3)13(17)16(15(10)4)11-8-6-5-7-9-11/h5-9H,1-4H3

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C13H17N3O
Molecular Weight	231.3
AlogP	1.55
Hydrogen Bond Acceptor	4.0
Hydrogen Bond Donor	0.0
Number of Rotational Bond	2.0
Polar Surface Area	30.17
Molecular species	NEUTRAL
Aromatic Rings	2.0
Heavy Atoms	17.0

Assay Description	Organism	Bioactivity	Reference
Compound was tested for antiinflammatory activity and the % inhibition was reported 3 hr after carrageenan injection in the hind paw edema test in rats: dose=80 mg/kg	Rattus norvegicus	17.5 %
Neuronal protective effect of compound against ischemic brain damage in rat t-MCAO model	Rattus norvegicus	21.0 %
TP_TRANSPORTER: inhibition of PAH uptake (PAH: 2 uM, Amimopyrine: 1000 uM) in Xenopus laevis oocytes	Xenopus laevis	23.8 %
Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 100 mg/kg, po pretreated for 30 mins followed by carrageenan challenge measured after 3 hrs relative to control	Rattus norvegicus	48.2 %
Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 50 mg/kg, po pretreated for 30 mins followed by carrageenan challenge measured after 3 hrs relative to control	Rattus norvegicus	25.0 %
Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 25 mg/kg, po pretreated for 30 mins followed by carrageenan challenge measured after 3 hrs relative to control	Rattus norvegicus	11.0 %
Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced hind paw edema at 100 mg/kg, po administered as gum arabic suspension 30 mins prior to carrageenin injection measured 3 hrs post-carrageenin injection	Rattus norvegicus	66.0 %
Time dependent inhibition of CYP1A2 (unknown origin) at 100 uM by LC/MS system	Homo sapiens	10.0 %
Time dependent inhibition of CYP2B6 (unknown origin) at 100 uM by LC/MS system	Homo sapiens	10.0 %
Time dependent inhibition of CYP2C9 (unknown origin) at 100 uM by LC/MS system	Homo sapiens	10.0 %
Time dependent inhibition of CYP2C19 in human liver microsomes at 100 uM by LC/MS system	Homo sapiens	10.0 %
Time dependent inhibition of CYP2D6 (unknown origin) at 100 uM by LC/MS system	Homo sapiens	10.0 %
Time dependent inhibition of CYP3A4 (unknown origin) at 100 uM by LC/MS system	Homo sapiens	10.0 %
Time dependent inhibition of CYP2C8 (unknown origin) at 100 uM by LC/MS system	Homo sapiens	10.0 %
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	23.9 %
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	27.62 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	16.17 %
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	-0.03 %		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	-0.04 %		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	-0.03 %		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	-0.04 %

Related Entries

Cross References

Resources	Reference
ChEBI	160246
ChEMBL	CHEMBL288470
DrugBank	DB01424
DrugCentral	171
FDA SRS	01704YP3MO
Human Metabolome Database	HMDB0015493
KEGG	C07539
PharmGKB	PA164748135
SureChEMBL	SCHEMBL26293
ZINC	ZINC000000057115

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).