ATECEGATRAN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H21ClF2N4O4
Molecular Weight	466.866
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=N)C1=CC=C(CNC(=O)[C@@H]2CCN2C(=O)[C@H](O)C3=CC(Cl)=CC(OC(F)F)=C3)C=C1

InChI

InChIKey=QTUUCFVBSVJGOH-DLBZAZTESA-N

InChI=1S/C21H21ClF2N4O4/c22-14-7-13(8-15(9-14)32-21(23)24)17(29)20(31)28-6-5-16(28)19(30)27-10-11-1-3-12(4-2-11)18(25)26/h1-4,7-9,16-17,21,29H,5-6,10H2,(H3,25,26)(H,27,30)/t16-,17+/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19492147 | https://www.ncbi.nlm.nih.gov/pubmed/20806126https://www.ncbi.nlm.nih.gov/pubmed/19690349 | https://adisinsight.springer.com/drugs/800018351

Atecegetran metoxil (more widely known as AZD0837), an anticoagulant and a prodrug, converted to a selective and reversible direct thrombin inhibitor (AR-H067637). Atecegetran metoxil participated in phase II clinical trials to prevent the stroke and systemic embolism in patients with non-valvular atrial fibrillation. The development of atecegetran metoxil was discontinued, due to a limitation identified in the long-term stability of the extended-release drug product.

Originator

Approval Year

PubMed

Title	Date	PubMed
Oral direct thrombin inhibitor AZD0837 for the prevention of stroke and systemic embolism in patients with non-valvular atrial fibrillation: a randomized dose-guiding, safety, and tolerability study of four doses of AZD0837 vs. vitamin K antagonists.	2009 Dec	19690349
Biochemical and pharmacological effects of the direct thrombin inhibitor AR-H067637.	2009 Jun	19492147
Evaluation of AR-H067637, the active metabolite of the new direct thrombin inhibitor AZD0837, in models of venous and arterial thrombosis and bleeding in anaesthetised rats.	2010 Dec	20806126
Exposure-response for biomarkers of anticoagulant effects by the oral direct thrombin inhibitor AZD0837 in patients with atrial fibrillation.	2015 Dec	26174611

Patents

Sample Use Guides

In Vivo Use Guide

150, 300, or 450 mg once daily or 200 mg twice daily

Route of Administration: Oral

Name

Type

Language

ATECEGATRAN

Official Name

English

AR-H067637

Code

English

AR-H-067637

Code

English

ARH-067637

Code

English

AR-H 067637

Code

English

atecegatran [INN]

Common Name

English

(2S)-N-((4-CARBAMIMIDOYLPHENYL)METHYL)-1-((2R)-2-(3-CHLORO-5-(DIFLUOROMETHOXY)PHENYL)-2-HYDROXYACETYL)AZETIDINE-2-CARBOXAMIDE

Systematic Name

English

2-AZETIDINECARBOXAMIDE, N-((4-(AMINOIMINOMETHYL)PHENYL)METHYL)-1-((2R)-2-(3-CHLORO-5-(DIFLUOROMETHOXY)PHENYL)-2-HYDROXYACETYL)-

Systematic Name

English

(2S)-N-((4-(AMINOIMINOMETHYL)PHENYL)METHYL)-1-((2R)-2-(3-CHLORO-5-(DIFLUOROMETHOXY)PHENYL)-2-HYDROXYACETYL)-2-AZETIDINECARBOXAMIDE

Systematic Name

English

Atecegatran [WHO-DD]

Common Name

English

Code System Code Type Description

CAS

433937-74-7