ALEGLITAZAR

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H23NO5S
Molecular Weight	437.508
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CO[C@@H](CC1=CC=C(OCCC2=C(C)OC(=N2)C3=CC=CC=C3)C4=C1SC=C4)C(O)=O

InChI

InChIKey=DAYKLWSKQJBGCS-NRFANRHFSA-N

InChI=1S/C24H23NO5S/c1-15-19(25-23(30-15)16-6-4-3-5-7-16)10-12-29-20-9-8-17(14-21(28-2)24(26)27)22-18(20)11-13-31-22/h3-9,11,13,21H,10,12,14H2,1-2H3,(H,26,27)/t21-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19349176|https://www.ncbi.nlm.nih.gov/pubmed/24467636|https://www.ncbi.nlm.nih.gov/pubmed/22489042

Aleglitazar is a dual agonist of PPARalpha/PPARgamma which was developed by Hoffmann-La Roche for the treatment of type 2 diabetes. Aleglitazar activates PPAR receptors with EC50 in nanomolar range and exerts a cardioprotective effect in vitro. The drug is currently in phase III of clinical trials.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Peroxisome proliferator-activated receptor alpha 62 Target ID: CHEMBL239 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19349176	Agonist 2678		5.0 nM [EC50]
Peroxisome proliferator-activated receptor gamma 111 Target ID: CHEMBL235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19349176	Agonist 2678		9.0 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 259 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25407798	Primary		Phase III 656	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
16.8 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20336066/	300 μg 1 times / day steady-state, oral dose: 300 μg route of administration: Oral experiment type: STEADY-STATE co-administered:	ALEGLITAZAR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
28.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20336066/	600 μg 1 times / day steady-state, oral dose: 600 μg route of administration: Oral experiment type: STEADY-STATE co-administered:	ALEGLITAZAR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.05 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20336066/	50 μg 1 times / day steady-state, oral dose: 50 μg route of administration: Oral experiment type: STEADY-STATE co-administered:	ALEGLITAZAR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
49.2 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20336066/	900 μg 1 times / day steady-state, oral dose: 900 μg route of administration: Oral experiment type: STEADY-STATE co-administered:	ALEGLITAZAR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20336066/	20 μg 1 times / day steady-state, oral dose: 20 μg route of administration: Oral experiment type: STEADY-STATE co-administered:	ALEGLITAZAR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
5.91 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20336066/	100 mg 1 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ALEGLITAZAR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
141 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20336066/	300 μg 1 times / day steady-state, oral dose: 300 μg route of administration: Oral experiment type: STEADY-STATE co-administered:	ALEGLITAZAR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
204 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20336066/	600 μg 1 times / day steady-state, oral dose: 600 μg route of administration: Oral experiment type: STEADY-STATE co-administered:	ALEGLITAZAR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
26 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20336066/	50 μg 1 times / day steady-state, oral dose: 50 μg route of administration: Oral experiment type: STEADY-STATE co-administered:	ALEGLITAZAR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
402 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20336066/	900 μg 1 times / day steady-state, oral dose: 900 μg route of administration: Oral experiment type: STEADY-STATE co-administered:	ALEGLITAZAR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
8.66 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20336066/	20 μg 1 times / day steady-state, oral dose: 20 μg route of administration: Oral experiment type: STEADY-STATE co-administered:	ALEGLITAZAR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
41.8 nmol × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20336066/	100 mg 1 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ALEGLITAZAR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
11.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20336066/	300 μg 1 times / day steady-state, oral dose: 300 μg route of administration: Oral experiment type: STEADY-STATE co-administered:	ALEGLITAZAR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
13.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20336066/	600 μg 1 times / day steady-state, oral dose: 600 μg route of administration: Oral experiment type: STEADY-STATE co-administered:	ALEGLITAZAR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
7.77 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20336066/	50 μg 1 times / day steady-state, oral dose: 50 μg route of administration: Oral experiment type: STEADY-STATE co-administered:	ALEGLITAZAR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
16.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20336066/	900 μg 1 times / day steady-state, oral dose: 900 μg route of administration: Oral experiment type: STEADY-STATE co-administered:	ALEGLITAZAR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
6.04 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20336066/	20 μg 1 times / day steady-state, oral dose: 20 μg route of administration: Oral experiment type: STEADY-STATE co-administered:	ALEGLITAZAR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
8.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20336066/	100 mg 1 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ALEGLITAZAR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY105513	https://www.001chemical.com/chem/search?q=DY105513
1PlusChem LLC	1P00DBLC	https://www.1pchem.com/search?query=1P00DBLC
AK Scientific	3431AH	https://aksci.com/item_detail.php?cat=3431AH
AstaTech	42161	http://astatechinc.com/CPSResult.php?CRNO=42161
BOC Sciences	475479-34-6	http://www.bocsci.com/description.asp?cas=475479-34-6
Chem Scene	CS-0008995	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0008995
Chem Scene	CS-1134	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-1134
Matrix Scientific	125215	http://www.matrixscientific.com/125215.html
MedChem Express	HY-14728	https://www.medchemexpress.com/search.html?q=HY-14728&ft=&fa=&fp=
MolPort	MolPort-035-683-372	https://www.molport.com/shop/molecule-link/MolPort-035-683-372
MolPort	MolPort-047-114-045	https://www.molport.com/shop/molecule-link/MolPort-047-114-045
Molcore	MC105513	http://www.molcore.com/CatMC105513.html
Molnova	M14583	https://www.molnova.com/en/serch-list.html?keywords=M14583
MuseChem	I003657	https://www.musechem.com/product/I003657.html
ShangHai Biochempartner	BCP11370	http://www.biochempartner.com/search_BCP11370
Synthonix	14579	https://synthonix.com/catalogsearch/result/?q=14579
Tetrahedron	TS88924	http://www.thsci.com/search.do?q=TS88924
eMolecules	45475563	https://orderbb.emolecules.com/search/#?query=45475563
mcule	MCULE-7615393654	https://mcule.com/MCULE-7615393654/

PubMed

Title	Date	PubMed
Effect of the dual peroxisome proliferator-activated receptor-alpha/gamma agonist aleglitazar on risk of cardiovascular disease in patients with type 2 diabetes (SYNCHRONY): a phase II, randomised, dose-ranging study.	2009 Jul 11	19515415
A cardiologic approach to non-insulin antidiabetic pharmacotherapy in patients with heart disease.	2009 Jul 20	19619327
Therapeutic potential of aleglitazar, a new dual PPAR-α/γ agonist: implications for cardiovascular disease in patients with diabetes mellitus.	2010	20653327
Pharmacokinetics, pharmacodynamics, and tolerability of aleglitazar in patients with type 2 diabetes: results from a randomized, placebo-controlled clinical study.	2010 Aug	20336066
Transcriptional regulation of human and rat hepatic lipid metabolism by the grapefruit flavonoid naringenin: role of PPARalpha, PPARgamma and LXRalpha.	2010 Aug 25	20811644
Neuropathy, retinopathy, and glucose-lowering treatments.	2010 Jun	20508223
Gateways to clinical trials.	2010 Nov	21225019
Aleglitazar, a dual PPARα and PPARγ agonist for the potential oral treatment of type 2 diabetes mellitus.	2010 Nov	21046527

Patents

Sample Use Guides

In Vivo Use Guide

Patients receive 150 mcg orally daily.

Route of Administration: Oral

In Vitro Use Guide

Aleglitazar increased cell viability and reduced apoptosis in human cardiomyocytes at concentrations of 150-600 nM.

Name

Type

Language

ALEGLITAZAR

Official Name

English

aleglitazar [INN]

Common Name

English

ALEGLITAZAR [USAN]

Common Name

English

Aleglitazar [WHO-DD]

Common Name

English

R1439

Code

English

R-1439

Code

English

(2S)-2-Methoxy-3-{4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]-benzothiophen-7-yl}propionic acid

Systematic Name

English

ALEGLITAZAR [MI]

Common Name

English

RO0728804

Code

English

RO-0728804

Code

English

BENZO(B)THIOPHENE-7-PROPANOIC ACID, .ALPHA.-METHOXY-4-(2-(5-METHYL-2-PHENYL-4-OXAZOLYL)ETHOXY)-, (.ALPHA.S)-

Common Name

English

(S)-2-METHOXY-3-(4-(2-(5-METHYL-2-PHENYLOXAZOL-4-YL-ETHOXY)BENZO(B)THIOPHEN-7-YL)PROPIONIC ACID

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C98233