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 52 Target ID: CHEMBL215 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7490726	Inhibitor 8504		23.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Asthma 244 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9923573	Primary	Phase III 665	Unknown Approved Use Unknown
Atherosclerosis 76 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27883201 http://adisinsight.springer.com/drugs/800025272	Primary	Phase II 1147	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 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
0.17 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9569998/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	ATRELEUTON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
0.31 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9569998/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	ATRELEUTON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
0.6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9569998/	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	ATRELEUTON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
1.17 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9569998/	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:	ATRELEUTON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
1.82 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9569998/	120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered:	ATRELEUTON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
2.35 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9569998/	160 mg single, oral dose: 160 mg route of administration: Oral experiment type: SINGLE co-administered:	ATRELEUTON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

AUC

Value	Dose	Analyte	Population
3.4 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9569998/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	ATRELEUTON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
6.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9569998/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	ATRELEUTON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
12.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9569998/	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	ATRELEUTON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
26.3 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9569998/	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:	ATRELEUTON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
37.6 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9569998/	120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered:	ATRELEUTON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
53.3 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9569998/	160 mg single, oral dose: 160 mg route of administration: Oral experiment type: SINGLE co-administered:	ATRELEUTON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

T_1/2

Value	Dose	Analyte	Population
15 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9569998/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	ATRELEUTON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
15.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9569998/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	ATRELEUTON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
15 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9569998/	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	ATRELEUTON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
15.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9569998/	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:	ATRELEUTON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
13.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9569998/	120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered:	ATRELEUTON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
15.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9569998/	160 mg single, oral dose: 160 mg route of administration: Oral experiment type: SINGLE co-administered:	ATRELEUTON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

Doses

Dose	Population	Adverse events
200 mg 1 times / day multiple, oral Highest studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9542476/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/9542476/	Sources: https://pubmed.ncbi.nlm.nih.gov/9542476/
100 mg 1 times / day multiple, oral Studied dose Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9542476/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/9542476/	Disc. AE: Hyperventilation, Headache... AEs leading to discontinuation/dose reduction: Hyperventilation (grade 3, 12.5%) Headache (grade 3, 12.5%) ALT increased (grade 2, 12.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/9542476/
150 mg 1 times / day multiple, oral Studied dose Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9542476/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/9542476/	Disc. AE: Vomiting... AEs leading to discontinuation/dose reduction: Vomiting (12.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/9542476/

AEs

AE	Significance	Dose	Population
ALT increased	grade 2, 12.5% Disc. AE	100 mg 1 times / day multiple, oral Studied dose Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9542476/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/9542476/
Headache	grade 3, 12.5% Disc. AE	100 mg 1 times / day multiple, oral Studied dose Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9542476/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/9542476/
Hyperventilation	grade 3, 12.5% Disc. AE	100 mg 1 times / day multiple, oral Studied dose Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9542476/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/9542476/
Vomiting	12.5% Disc. AE	150 mg 1 times / day multiple, oral Studied dose Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9542476/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/9542476/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193	substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP1A2 1197 CYP2E1 729 CYP2C19 1119 CYP2A6 626

Drug as victim

Target	Modality	Activity
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9763401/	major
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9763401/	minor
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9763401/	weak
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9763401/	weak
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9763401/	weak
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9763401/	weak
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9763401/	weak

PubMed

Title	Date	PubMed
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.	2011-12-08	22059882
ABT-761 attenuates bronchoconstriction and pulmonary inflammation in rodents.	1997-03	9067325
The effect of ABT-761, a novel 5-lipoxygenase inhibitor, on exercise- and adenosine-induced bronchoconstriction in asthmatic subjects.	1997-03	9117020
(R)-(+)-N-[3-[5-[(4-fluorophenyl)methyl]-2-thienyl]-1-methyl- 2-propynyl]-N-hydroxyurea (ABT-761), a second-generation 5-lipoxygenase inhibitor.	1995-11-24	7490726

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 `Wed Apr 02 07:44:58 GMT 2025` Edited by `admin` on `Wed Apr 02 07:44:58 GMT 2025`
Record UNII	U301T88E1M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

A-85761

Preferred Name

English

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

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