LETAXABAN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H26ClN3O5S
Molecular Weight	479.977
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[C@H](CS(=O)(=O)C1=CC=C2C=C(Cl)C=CC2=C1)C(=O)N3CCC(CC3)N4CCCNC4=O

InChI

InChIKey=GEHAEMCVKDPMKO-HXUWFJFHSA-N

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

HIDE SMILES / InChI

Molecular Formula	C22H26ClN3O5S
Molecular Weight	479.977
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/30568593 | https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=NCI_Thesaurus&code=C96541 | https://www.pharmacodia.com/yaodu/html/v1/chemicals/f67fe69d3660b4d35a731817b538b21d.html | https://adisinsight.springer.com/drugs/800027537

Letaxaban is an orally active, tetrahydropyrimidin-2(1H)-one derivative and inhibitor of coagulation factor Xa (activated factor X) with anticoagulant activity. Letaxaban may have anti-inflammatory potential in addition to its anti-thrombotic effects. Letaxaban had been in phase II clinical trials by Takeda for the treatment of venous thromboembolism (VTE). However, this research has been discontinued. Takeda had discontinued their phase II clinical trials for the treatment of acute coronary syndrome (ACS) since the results failed to meet the target efficacy and safety profile.

Approval Year

PubMed

Title	Date	PubMed
Synergistic effect of a factor Xa inhibitor, TAK-442, and antiplatelet agents on whole blood coagulation and arterial thrombosis in rats.	2010 Aug	20452654
Anti-thrombotic effect of a factor Xa inhibitor TAK-442 in a rabbit model of arteriovenous shunt thrombosis stimulated with tissue factor.	2018 Oct 30	30376878

Patents

Sample Use Guides

In Vivo Use Guide

Doses of Letaxaban escalated from 10 mg BID, 20 mg twice-daily (BID), or 40 mg once-daily (QD) in stage 1; to 40 mg BID, 80 mg QD, or 80 mg BID in stage 2; and to 160 mg QD or 120 mg BID in stage 3.

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:13:44 UTC 2023` Edited by `admin` on `Fri Dec 15 19:13:44 UTC 2023`
Record UNII	Y3WB03966W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LETAXABAN

Official Name

English

2(1H)-PYRIMIDINONE, 1-(1-((2S)-3-((6-CHLORO-2-NAPHTHALENYL)SULFONYL)-2-HYDROXY-1-OXOPROPYL)-4-PIPERIDINYL)TETRAHYDRO-

Systematic Name

English

1-(1-{(2S)-3-[(6-Chloronaphthalen-2-yl)sulfonyl]-2-hydroxypropanoyl}piperidin-4-yl)tetrahydropyrimidin-2(1H)-one

Systematic Name

English

PIPERIDINE, 1-((2S)-3-((6-CHLORO-2-NAPHTHALENYL)SULFONYL)-2-HYDROXY-1-OXOPROPYL)-4-(TETRAHYDRO-2-OXO-1(2H)-PYRIMIDINYL)-

Systematic Name

English

LETAXABAN [USAN]

Common Name

English

TAK442

Code

English

letaxaban [INN]

Common Name

English

Letaxaban [WHO-DD]

Common Name

English

TAK-442

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C29750