DABIGATRAN ETEXILATE

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Search structure


Trade Names	DABIGATRAN ETEXILATE
Synonyms	BIBR 1048 BIBR 1048 BS RS1 BIBR-1048 BIBR-1048-BS-RS1 Dabigatran etexilate Dabigatran etexilate methanesulfonate Pradaxa
Status
Molecule Category	UNKNOWN
ATC	B01AE07
UNII	2E18WX195X
EPA CompTox	DTXSID4057681


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

Structure


InChI Key	KSGXQBZTULBEEQ-UHFFFAOYSA-N
Smiles	CCCCCCOC(=O)NC(=N)c1ccc(NCc2nc3cc(C(=O)N(CCC(=O)OCC)c4ccccn4)ccc3n2C)cc1
InChI	InChI=1S/C34H41N7O5/c1-4-6-7-10-21-46-34(44)39-32(35)24-12-15-26(16-13-24)37-23-30-38-27-22-25(14-17-28(27)40(30)3)33(43)41(20-18-31(42)45-5-2)29-11-8-9-19-36-29/h8-9,11-17,19,22,37H,4-7,10,18,20-21,23H2,1-3H3,(H2,35,39,44)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C34H41N7O5
Molecular Weight	627.75
AlogP	5.6
Hydrogen Bond Acceptor	9.0
Hydrogen Bond Donor	2.0
Number of Rotational Bond	15.0
Polar Surface Area	154.03
Molecular species	NEUTRAL
Aromatic Rings	4.0
Heavy Atoms	46.0

Assay Description	Organism	Bioactivity	Reference
Antiplatelet activity against rabbit platelets assessed as inhibition of thrombin-induced platelet aggregation	Oryctolagus cuniculus	326.0 nM
Binding affinity to human thrombin	Homo sapiens	4.5 nM
Inhibition of thrombin-induced rabbit platelet aggregation compound pre-incubated in rabbit liver microsomal suspension	Oryctolagus cuniculus	337.0 nM
Inhibition of thrombin-induced platelet aggregation in Sprague-Dawley rat at 3 mg/ml administered for 4 days relative to control	Rattus norvegicus	92.9 %
Inhibition of arterial/venous thromboembolic weight in Sprague-Dawley rat at 3 mg/ml administered for 4 days relative to control	Rattus norvegicus	76.0 %
Inhibition of thrombin-induced rabbit platelet aggregation after 4 hrs in presence of rabbit liver microsomes	Oryctolagus cuniculus	340.0 nM
Inhibition of human thrombin preincubated for 10 mins using Ac-FVR-AMC as substrate by chromogenic assay	Homo sapiens	2.63 nM		Inhibition of human thrombin preincubated for 10 mins using Ac-FVR-AMC as substrate by chromogenic assay	Homo sapiens	2.61 nM
Inhibition of rabbit thrombin-induced platelet aggregation in rabbit platelet-rich plasma preincubated with rabbit liver microsomes for 4 hrs followed by addition to platelet	Oryctolagus cuniculus	554.0 nM
Antiplatelet activity in New Zealand rabbit platelet rich plasma assessed as inhibition of thrombin-induced platelet aggregation preincubated for 1 min followed by thrombin addition measured after 10 mins	Oryctolagus cuniculus	0.326 nM
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	4.4 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	7.66 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	2.142 %
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	-0.13 %		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	-0.13 %		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 %

Cross References

Resources	Reference
ChEBI	70746
ChEMBL	CHEMBL539697
DrugBank	DB06695
DrugCentral	776
FDA SRS	2E18WX195X
Human Metabolome Database	HMDB0015641
Guide to Pharmacology	6379
PharmGKB	PA165958369
PubChem	213023
SureChEMBL	SCHEMBL505829
ZINC	ZINC000003943279

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).