AZELIRAGON

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C32H38ClN3O2
Molecular Weight	532.116
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCC1=NC(=CN1C2=CC=C(OC3=CC=C(Cl)C=C3)C=C2)C4=CC=C(OCCCN(CC)CC)C=C4

InChI

InChIKey=KJNNWYBAOPXVJY-UHFFFAOYSA-N

InChI=1S/C32H38ClN3O2/c1-4-7-9-32-34-31(25-10-16-28(17-11-25)37-23-8-22-35(5-2)6-3)24-36(32)27-14-20-30(21-15-27)38-29-18-12-26(33)13-19-29/h10-21,24H,4-9,22-23H2,1-3H3

HIDE SMILES / InChI

Molecular Formula	C32H38ClN3O2
Molecular Weight	532.116
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.alzforum.org/therapeutics/azeliragon | http://vtvtherapeutics.com/pipeline/azeliragon

Azeliragon is an orally bioavailable small molecule that inhibits the receptor for advanced glycation endproducts (RAGE). RAGE has been proposed to contribute to Alzheimer's disease pathology by promoting vascular leakage, promoting influx of peripheral amyloid beta into brain, mediating amyloid beta induced oxidative stress, mediating AGE induced hyperphosphorylation of tau and amyloid beta mediated neuronal death. Azeliragon is in Phase III clinical trial for the treatment of mild Alzheimer's disease.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Advanced glycosylation end product-specific receptor 1 Target ID: CHEMBL2176846 Sources: http://vtvtherapeutics.com/pipeline/azeliragon	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Alzheimer’s disease 278 Sources: http://vtvtherapeutics.com/pipeline/azeliragon	Primary		Phase III 665	AZELIRAGON Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
0.7 ng/mL CLINICAL TRIAL https://alz-journals.onlinelibrary.wiley.com/doi/epdf/10.1016/j.jalz.2017.06.673	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:		AZELIRAGON plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
0.58 ng/mL CLINICAL TRIAL https://alz-journals.onlinelibrary.wiley.com/doi/epdf/10.1016/j.jalz.2017.06.673	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:		AZELIRAGON plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
1.72 ng/mL CLINICAL TRIAL https://vtvtherapeutics.com/wp-content/uploads/pdf/ctad_hepatic_impairment_poster_25oct2017_final.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:		AZELIRAGON plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1.77 ng/mL CLINICAL TRIAL https://vtvtherapeutics.com/wp-content/uploads/pdf/ctad_hepatic_impairment_poster_25oct2017_final.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:		AZELIRAGON plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1.72 ng/mL CLINICAL TRIAL https://vtvtherapeutics.com/wp-content/uploads/pdf/ctad_hepatic_impairment_poster_25oct2017_final.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:		AZELIRAGON plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2.29 ng/mL CLINICAL TRIAL https://vtvtherapeutics.com/wp-content/uploads/pdf/ctad_hepatic_impairment_poster_25oct2017_final.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:		AZELIRAGON plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
4 ng/mL REVIEW https://link.springer.com/article/10.14283/jpad.2018.18	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:		AZELIRAGON plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
8.62 ng/mL CLINICAL TRIAL https://vtvtherapeutics.com/wp-content/uploads/pdf/ctad_ddi_poster_25oct2017_final.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: Gemfibrozil	Gemfibrozil	AZELIRAGON plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
10.4 ng/mL CLINICAL TRIAL https://vtvtherapeutics.com/wp-content/uploads/pdf/ctad_ddi_poster_25oct2017_final.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: Gemfibrozil	Gemfibrozil	AZELIRAGON plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
3.36 ng/mL CLINICAL TRIAL https://vtvtherapeutics.com/wp-content/uploads/pdf/ctad_ddi_poster_25oct2017_final.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: Nefazodone	Nefazodone	AZELIRAGON plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
9.11 ng/mL CLINICAL TRIAL https://vtvtherapeutics.com/wp-content/uploads/pdf/ctad_ddi_poster_25oct2017_final.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: Rifampin	Rifampin	AZELIRAGON plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
113 ng × h/mL CLINICAL TRIAL https://alz-journals.onlinelibrary.wiley.com/doi/epdf/10.1016/j.jalz.2017.06.673	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:		AZELIRAGON plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
90 ng × h/mL CLINICAL TRIAL https://alz-journals.onlinelibrary.wiley.com/doi/epdf/10.1016/j.jalz.2017.06.673	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:		AZELIRAGON plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
474 ng × h/mL CLINICAL TRIAL https://vtvtherapeutics.com/wp-content/uploads/pdf/ctad_hepatic_impairment_poster_25oct2017_final.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:		AZELIRAGON plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
451 ng × h/mL CLINICAL TRIAL https://vtvtherapeutics.com/wp-content/uploads/pdf/ctad_hepatic_impairment_poster_25oct2017_final.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:		AZELIRAGON plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
474 ng × h/mL CLINICAL TRIAL https://vtvtherapeutics.com/wp-content/uploads/pdf/ctad_hepatic_impairment_poster_25oct2017_final.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:		AZELIRAGON plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
500 ng × h/mL CLINICAL TRIAL https://vtvtherapeutics.com/wp-content/uploads/pdf/ctad_hepatic_impairment_poster_25oct2017_final.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:		AZELIRAGON plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
185 ng × h/mL CLINICAL TRIAL https://vtvtherapeutics.com/wp-content/uploads/pdf/ctad_ddi_poster_25oct2017_final.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: Gemfibrozil	Gemfibrozil	AZELIRAGON plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
228 ng × h/mL CLINICAL TRIAL https://vtvtherapeutics.com/wp-content/uploads/pdf/ctad_ddi_poster_25oct2017_final.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: Gemfibrozil	Gemfibrozil	AZELIRAGON plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
69.2 ng × h/mL CLINICAL TRIAL https://vtvtherapeutics.com/wp-content/uploads/pdf/ctad_ddi_poster_25oct2017_final.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: Nefazodone	Nefazodone	AZELIRAGON plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
195 ng × h/mL CLINICAL TRIAL https://vtvtherapeutics.com/wp-content/uploads/pdf/ctad_ddi_poster_25oct2017_final.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: Rifampin	Rifampin	AZELIRAGON plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
228 h REVIEW https://link.springer.com/article/10.14283/jpad.2018.18	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:		AZELIRAGON plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
336 h REVIEW https://link.springer.com/article/10.14283/jpad.2018.18	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:		AZELIRAGON plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00ECVW	https://www.1pchem.com/search?query=1P00ECVW
AChemBlock	O33796	http://www.achemblock.com/catalogsearch/result/?q=O33796
Alfa Chemistry	603148-36-3	http://www.alfa-chemistry.com/search.aspx?q=603148-36-3
Alfa Chemistry	ACM603148363	http://www.alfa-chemistry.com/search.aspx?q=ACM603148363
Ambeed	A124655	http://www.ambeed.com/search/Search.html?keyword=A124655
AstaTech	N11192	http://astatechinc.com/CPSResult.php?CRNO=N11192
BLD Pharm	BD583929	http://www.bldpharm.com/search/Search.html?keyword=BD583929
Chem Scene	CS-5117	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-5117
ChemShuttle	138994	https://www.chemshuttle.com/catalogsearch/result/?q=138994
Combi-Blocks	QW-1950	http://www.combi-blocks.com/cgi-bin/find.cgi?QW-1950
eMolecules	72973158	https://orderbb.emolecules.com/search/#?query=72973158
eNovation Chemicals	D509236	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D509236&searchbtn.x=0&searchbtn.y=0
Excenen	EX-A1834	http://www.excenen.com/searchresultlist.php?id=EX-A1834
Hairui	AZXM008	http://www.hairuichem.com/en/product/search.do?q=AZXM008
KeyOrganics	AS-49837	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-49837
mcule	MCULE-2610188504	https://mcule.com/MCULE-2610188504/
MedChem Express	HY-50682	https://www.medchemexpress.com/search.html?q=HY-50682&ft=&fa=&fp=
Molnova	M15253	https://www.molnova.com/en/serch-list.html?keywords=M15253
MolPort	MolPort-042-676-233	https://www.molport.com/shop/molecule-link/MolPort-042-676-233
MuseChem	I004271	https://www.musechem.com/product/I004271.html
MuseChem	I006440	https://www.musechem.com/product/I006440.html
Selleck Chemicals	S6415	http://www.selleckchem.com/search.html?searchDTO.searchParam=S6415
ShangHai Biochempartner	BCP16862	http://www.biochempartner.com/search_BCP16862
TargetMol	T2507	https://www.targetmol.com/search?keyword=T2507
Tetrahedron	TS94700	http://www.thsci.com/search.do?q=TS94700

PubMed

Title	Date	PubMed
Effect of TTP488 in patients with mild to moderate Alzheimer's disease.	2014-01-15	24423155
New therapeutic approaches for Alzheimer's disease and cerebral amyloid angiopathy.	2014	25368578
RAGE mediates amyloid-beta peptide transport across the blood-brain barrier and accumulation in brain.	2003-07	12808450

Patents

Sample Use Guides

In Vivo Use Guide

Azeliragon 5 mg orally once daily for 2 years.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:43:07 GMT 2025` Edited by `admin` on `Wed Apr 02 09:43:07 GMT 2025`
Record UNII	LPU25F15UQ
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

azeliragon [INN]

Preferred Name

English

AZELIRAGON

Official Name

English

TTP-488

Code

English

1-PROPANAMINE, 3-(4-(2-BUTYL-1-(4-(4-CHLOROPHENOXY)PHENYL)-1H-IMIDAZOL-4-YL)PHENOXY)-N,N-DIETHYL-

Systematic Name

English

TTP488

Code

English

3-(4-{2-Butyl-1-[4-(4-chlorophenoxy)phenyl]-1H-imidazol-4-yl}phenoxy)-N,N-diethylpropan-1-amine

Systematic Name

English

Azeliragon [WHO-DD]

Common Name

English

AZELIRAGON [USAN]

Common Name

English

PF-04494700

Code

English

Classification Tree Code System Code

FDA ORPHAN DRUG

915922