ATRELEUTON

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H15FN2O2S
Molecular Weight	318.366
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H](C#CC1=CC=C(CC2=CC=C(F)C=C2)S1)N(O)C(N)=O

InChI

InChIKey=MMSNEKOTSJRTRI-LLVKDONJSA-N

InChI=1S/C16H15FN2O2S/c1-11(19(21)16(18)20)2-7-14-8-9-15(22-14)10-12-3-5-13(17)6-4-12/h3-6,8-9,11,21H,10H2,1H3,(H2,18,20)/t11-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C16H15FN2O2S
Molecular Weight	318.366
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/7490726
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/27883201 | https://www.ncbi.nlm.nih.gov/pubmed/25752438

Atreleuton is a potent, orally administered, selective 5-Lipoxygenase inhibitor. Atreleuton had been in phase III clinical trials for the treatment of asthma and phase II clinical trials for the treatment of acute coronary syndrome and atherosclerosis. However, this research has been discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Arachidonate 5-lipoxygenase 49 Target ID: CHEMBL215 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7490726	Inhibitor 8297		23.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Asthma 241 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9923573	Primary	Phase III 656	Unknown Approved Use Unknown
Atherosclerosis 74 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27883201 http://adisinsight.springer.com/drugs/800025272	Primary	Phase II 1132	Unknown Approved Use Unknown
Acute coronary syndrome 33 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20190281 https://www.ncbi.nlm.nih.gov/pubmed/25752438	Primary	Phase II 1132	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
(R)-(+)-N-[3-[5-[(4-fluorophenyl)methyl]-2-thienyl]-1-methyl- 2-propynyl]-N-hydroxyurea (ABT-761), a second-generation 5-lipoxygenase inhibitor.	1995 Nov 24	7490726
ABT-761 attenuates bronchoconstriction and pulmonary inflammation in rodents.	1997 Mar	9067325
5-Lipoxygenase-activating protein (FLAP) inhibitors. Part 4: development of 3-[3-tert-butylsulfanyl-1-[4-(6-ethoxypyridin-3-yl)benzyl]-5-(5-methylpyridin-2-ylmethoxy)-1H-indol-2-yl]-2,2-dimethylpropionic acid (AM803), a potent, oral, once daily FLAP inhibitor.	2011 Dec 8	22059882

Patents

Sample Use Guides

In Vivo Use Guide

200 mg once daily

Route of Administration: Oral

In Vitro Use Guide

Inhibition of LTB4 formation in calcium ionophore-stimulated purified human neutrophils from four donors gave a mean IC50 of 23 nM. In the more complex medium of human whole blood, Atreleuton was a selective inhibitor of calcium ionophorestimulated LTB4 formation with an IC50 of 150 nM (95%, cl 100-200). In the same assay an IC50 of 11 uM (95%, cl 8-12) was measured for 12-HETE, 50% inhibition of 15-HETE was observed at the highest dose tested of 100 uM, and an IC50 of 50 uM (95%, cl 37-78) was found for the formation of TXB2.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 16:21:30 UTC 2023` Edited by `admin` on `Sat Dec 16 16:21:30 UTC 2023`
Record UNII	U301T88E1M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ATRELEUTON

Official Name

English

ABBOTT-85761

Code

English

(R)-N-(3-(5-(4-FLUOROBENZYL) THIEN-2-YL)-1-METHYL-2-PROPYN- YL)-N-HYDROXY-UREA

Systematic Name

English

A-85761

Code

English

ATRELEUTON [USAN]

Common Name

English

ABT-761

Code

English

atreleuton [INN]

Common Name

English

Atreleuton [WHO-DD]

Common Name

English

VIA-2291

Code

English

A-85761.0

Code

English

1-((R)-3-(5-(P-FLUOROBENZYL)-2-THIENYL)-1-METHYL-2-PROPYNYL)-1-HYDROXYUREA

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1322