ATECEGATRAN METOXIL

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H23ClF2N4O5
Molecular Weight	496.892
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CONC(=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=XSNMGLZVFNDDPW-ZWKOTPCHSA-N

InChI=1S/C22H23ClF2N4O5/c1-33-28-19(26)13-4-2-12(3-5-13)11-27-20(31)17-6-7-29(17)21(32)18(30)14-8-15(23)10-16(9-14)34-22(24)25/h2-5,8-10,17-18,22,30H,6-7,11H2,1H3,(H2,26,28)(H,27,31)/t17-,18+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C22H23ClF2N4O5
Molecular Weight	496.892
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
Exposure-response for biomarkers of anticoagulant effects by the oral direct thrombin inhibitor AZD0837 in patients with atrial fibrillation.	2015-12	26174611
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.	2010-12	20806126
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.	2009-12	19690349
Biochemical and pharmacological effects of the direct thrombin inhibitor AR-H067637.	2009-06	19492147

Patents

Sample Use Guides

In Vivo Use Guide

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

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Mon Mar 31 20:04:18 GMT 2025` Edited by `admin` on `Mon Mar 31 20:04:18 GMT 2025`
Record UNII	4GU1D587JV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AZD-0837

Preferred Name

English

ATECEGATRAN METOXIL

Official Name

English

ATECEGATRAN FEXENETIL

Common Name

English

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

Systematic Name

English

atecegatran metoxil [INN]

Common Name

English

Atecegatran metoxil [WHO-DD]

Common Name

English

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

Systematic Name

English

AZD0837

Code

English

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

Systematic Name

English

AZD 0837 [WHO-DD]

Common Name

English

Code System Code Type Description

DRUG BANK

DB12507