LETAXABAN

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Search structure


Synonyms	Letaxaban TAK 442 TAK-442
Status
Molecule Category	UNKNOWN
UNII	Y3WB03966W


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

Structure


InChI Key	GEHAEMCVKDPMKO-HXUWFJFHSA-N
Smiles	O=C([C@H](O)CS(=O)(=O)c1ccc2cc(Cl)ccc2c1)N1CCC(N2CCCNC2=O)CC1
InChI	InChI=1S/C22H26ClN3O5S/c23-17-4-2-16-13-19(5-3-15(16)12-17)32(30,31)14-20(27)21(28)25-10-6-18(7-11-25)26-9-1-8-24-22(26)29/h2-5,12-13,18,20,27H,1,6-11,14H2,(H,24,29)/t20-/m1/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C22H26ClN3O5S
Molecular Weight	479.99
AlogP	2.03
Hydrogen Bond Acceptor	5.0
Hydrogen Bond Donor	2.0
Number of Rotational Bond	5.0
Polar Surface Area	107.02
Molecular species	NEUTRAL
Aromatic Rings	2.0
Heavy Atoms	32.0

Bioactivity

Mechanism of Action	Action	Reference
Coagulation factor X inhibitor	INHIBITOR	PubMed


Protein: Coagulation factor X Description: Coagulation factor X Organism : Homo sapiens P00742 ENSG00000126218

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Protease Serine protease Serine protease PA clan Serine protease S1A subfamily	-	2-4	-	2	-

Assay Description	Organism	Bioactivity	Reference
Inhibition of human factor 10a assessed as p-nitroanilide release using S2765 as substrate by chromogenic assay	Homo sapiens	3.5 nM
Anticoagulant activity in rabbit venous thrombosis model assessed as inhibition of venous thrombus formation at 50 mg/kg, iv administered as bolus infusion for 1 hr	Oryctolagus cuniculus	50.0 %
Anticoagulant activity in rabbit venous thrombosis model assessed as inhibition of venous thrombus formation at 100 mg/kg, iv administered as bolus infusion for 1 hr	Oryctolagus cuniculus	81.0 %
Inhibition of human factor 10a using S2222 as substrate after 10 mins by chromogenic assay	Homo sapiens	2.2 nM
Inhibition of factor 10a	None	3.5 nM		Inhibition of factor 10a	None	1.8 nM

Cross References

Resources	Reference
ChEMBL	CHEMBL1095032
DrugBank	DB11984
FDA SRS	Y3WB03966W
PDB	443
PubChem	11641515
SureChEMBL	SCHEMBL766143
ZINC	ZINC000013986542

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).