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Details

Stereochemistry ABSOLUTE
Molecular Formula C29H32O7S
Molecular Weight 524.625
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FASIGLIFAM

SMILES

CC1=CC(OCCCS(C)(=O)=O)=CC(C)=C1C2=CC(COC3=CC=C4[C@H](CC(O)=O)COC4=C3)=CC=C2

InChI

InChIKey=BZCALJIHZVNMGJ-HSZRJFAPSA-N
InChI=1S/C29H32O7S/c1-19-12-25(34-10-5-11-37(3,32)33)13-20(2)29(19)22-7-4-6-21(14-22)17-35-24-8-9-26-23(15-28(30)31)18-36-27(26)16-24/h4,6-9,12-14,16,23H,5,10-11,15,17-18H2,1-3H3,(H,30,31)/t23-/m1/s1

HIDE SMILES / InChI
Molecular Formula C29H32O7S
Molecular Weight 524.625
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including: https://www.takeda.com/news/2013/20131227_6117.html | https://www.aasld.org/sites/default/files/documents/DILI/2016/IV_6_Dragan_ppt.pdf | https://www.ncbi.nlm.nih.gov/pubmed/25604916

TAK-875 (Fasiglifam) is the potent, selective and orally bioavailable GPR40 agonist. The drug was in Phase III clinical trials for the treatment of type 2 diabetes mellitus. Termination phase III development of TAK-875 for the potential treatment of type-2 diabetes mellitus was announced in 2013 due to concerns about liver safety.

Originator

Takeda Pharmaceutical
69
Curator's Comment: # Takeda Pharmaceutical Company, Ltd.

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 0.038 µM [Ki]
Inhibitor
8297
 2.28 µM [IC50]
Inhibitor
8297
 3.98 µM [IC50]
Inhibitor
8297
 2.41 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
656
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.3 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/22669289
25 mg 1 times / day steady-state, oral
dose: 25 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FASIGLIFAM HEMIHYDRATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/22669289
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FASIGLIFAM HEMIHYDRATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
17.6 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/22669289
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FASIGLIFAM HEMIHYDRATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
13 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/22669289
100 mg 1 times / day steady-state, oral
dose: 100 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FASIGLIFAM HEMIHYDRATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
30.8 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/22669289
400 mg 1 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FASIGLIFAM HEMIHYDRATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
5.5 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/22669289
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FASIGLIFAM HEMIHYDRATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
40.3 nmol × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/22669289
25 mg 1 times / day steady-state, oral
dose: 25 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FASIGLIFAM HEMIHYDRATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
13.7 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/22669289
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FASIGLIFAM HEMIHYDRATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
230 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/22669289
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FASIGLIFAM HEMIHYDRATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
235.5 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/22669289
100 mg 1 times / day steady-state, oral
dose: 100 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FASIGLIFAM HEMIHYDRATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
549.9 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/22669289
400 mg 1 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FASIGLIFAM HEMIHYDRATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
71.2 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/22669289
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FASIGLIFAM HEMIHYDRATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
44.7 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/22669289
25 mg 1 times / day steady-state, oral
dose: 25 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FASIGLIFAM HEMIHYDRATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
45.8 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/22669289
100 mg 1 times / day steady-state, oral
dose: 100 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FASIGLIFAM HEMIHYDRATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
31.5 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/22669289
400 mg 1 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FASIGLIFAM HEMIHYDRATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Sourcing

Sourcing

Vendor/AggregatorIDURL
001 Chemical
DY116257
https://www.001chemical.com/chem/search?q=DY116257
1PlusChem LLC
1P00013A
https://www.1pchem.com/search?query=1P00013A
AChemBlock
10392
http://www.achemblock.com/catalogsearch/result/?q=10392
AK Scientific
X7587
https://aksci.com/item_detail.php?cat=X7587
AOBIOUS INC
AOB2992
http://aobious.com/aobious/search?search_query=AOB2992
Angene
AGN-PC-0OPDC8
http://www.angenechemical.com/productshow/AGN-PC-0OPDC8.html
Angene
AGN-PC-0WCXV8
http://www.angenechemical.com/productshow/AGN-PC-0WCXV8.html
ApexBio Technology
A8339
https://www.apexbt.com/catalogsearch/result/?q=A8339
AstaTech
31406
http://astatechinc.com/CPSResult.php?CRNO=31406
AstaTech
F18436
http://astatechinc.com/CPSResult.php?CRNO=F18436
BLD Pharm
BD247920
http://www.bldpharm.com/search/Search.html?keyword=BD247920
BOC Sciences
1000413-72-8
http://www.bocsci.com/description.asp?cas=1000413-72-8
BioSynth
J-501277
https://www.biosynth.com/en/products/life-science/other-biochemicals/products/J-501277
Capot Chemical
24441
https://www.capotchem.com/search.do?q=24441
Cayman Chemical
17335
http://www.caymanchem.com/app/template/Product.vm/catalog/17335
ChemShuttle
102928
https://www.chemshuttle.com/catalogsearch/result/?q=102928
ChemShuttle
185391
https://www.chemshuttle.com/catalogsearch/result/?q=185391
Combi-Blocks
QJ-8851
http://www.combi-blocks.com/cgi-bin/find.cgi?QJ-8851
Debye Scientific
DA-45543
https://www.debyesci.com/index.php?id=product&ext[cno]=DA-45543
Hairui
HR150849
http://www.hairuichem.com/en/product/search.do?q=HR150849
Lab Seeker
SC-86271
http://www.labseeker.com/search.php?keywords=SC-86271&category=0
Lab Seeker
SC-95595
http://www.labseeker.com/search.php?keywords=SC-95595&category=0
LabSeeker
SC-86271
http://www.labseeker.com/search.php?keywords=SC-86271&category=0
LabSeeker
SC-95595
http://www.labseeker.com/search.php?keywords=SC-95595&category=0
Matrix Scientific
144401
http://www.matrixscientific.com/144401.html
MedChem Express
HY-10480
https://www.medchemexpress.com/search.html?q=HY-10480&ft=&fa=&fp=
MolPort
MolPort-023-293-501
https://www.molport.com/shop/molecule-link/MolPort-023-293-501
MolPort
MolPort-035-395-707
https://www.molport.com/shop/molecule-link/MolPort-035-395-707
Molcore
MC116257
http://www.molcore.com/CatMC116257.html
Molnova
M10006
https://www.molnova.com/en/serch-list.html?keywords=M10006
Molnova
M11546
https://www.molnova.com/en/serch-list.html?keywords=M11546
MuseChem
I000065
https://www.musechem.com/product/I000065.html
MuseChem
M125695
https://www.musechem.com/product/M125695.html
MuseChem
R026077
https://www.musechem.com/product/R026077.html
Ryan Scientific
Clemizole
https://ryansci.com/products?q=Clemizole&list_q=&search_type=exact
Selleck Chemicals
S2637
http://www.selleckchem.com/search.html?searchDTO.searchParam=S2637
ShangHai Biochempartner
BCP000363
http://www.biochempartner.com/search_BCP000363
ShangHai Biochempartner
BCP02430
http://www.biochempartner.com/search_BCP02430
Synthonix
15656
https://synthonix.com/catalogsearch/result/?q=15656
TargetMol
T2351
https://www.targetmol.com/search?keyword=T2351
TargetMol
T2351L
https://www.targetmol.com/search?keyword=T2351L
Tetrahedron
TS89067
http://www.thsci.com/search.do?q=TS89067
Toronto Research Chemicals
T004915
https://www.trc-canada.com/product-detail/?CatNum=T004915
eMolecules
108760723
https://orderbb.emolecules.com/search/#?query=108760723
eMolecules
195149271
https://orderbb.emolecules.com/search/#?query=195149271
eMolecules
275021242
https://orderbb.emolecules.com/search/#?query=275021242
eMolecules
300725680
https://orderbb.emolecules.com/search/#?query=300725680
eMolecules
44833695
https://orderbb.emolecules.com/search/#?query=44833695
eNovation Chemicals
D372369
https://www.enovationchem.com/Products.asp?SEARCHTEXT=D372369&searchbtn.x=0&searchbtn.y=0
eNovation Chemicals
D500334
https://www.enovationchem.com/Products.asp?SEARCHTEXT=D500334&searchbtn.x=0&searchbtn.y=0
eNovation Chemicals
D516275
https://www.enovationchem.com/Products.asp?SEARCHTEXT=D516275&searchbtn.x=0&searchbtn.y=0
mcule
MCULE-3608941093
https://mcule.com/MCULE-3608941093/
mcule
MCULE-5860324700
https://mcule.com/MCULE-5860324700/
mcule
MCULE-6544081391
https://mcule.com/MCULE-6544081391/
PubMed

PubMed

TitleDatePubMed
Free fatty acids regulate insulin secretion from pancreatic beta cells through GPR40.
2003 Mar 13
TAK-875, an orally available G protein-coupled receptor 40/free fatty acid receptor 1 agonist, enhances glucose-dependent insulin secretion and improves both postprandial and fasting hyperglycemia in type 2 diabetic rats.
2011 Oct
Identification of a potent and selective free fatty acid receptor 1 (FFA1/GPR40) agonist with favorable physicochemical and in vitro ADME properties.
2011 Oct 13
Patents

Patents

07732626
2
08088821
4
08492430
3
08598226
2
20100004312
2
20100197761
2
20120046338
2
20120121530
2
20130090341
2

Sample Use Guides

In Vivo Use Guide
25 mg or 50 mg once-daily
Route of Administration: Oral
In Vitro Use Guide
IC50 of TAK-875 for inhibiting Madin-Darby canine kidney (MDCK) cells overexpressing MRP2 (MDCK-MRP2 cells) was 2.41 ± 0.50 uM.
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:59:57 UTC 2023
Edited
by admin
on Sat Dec 16 01:59:57 UTC 2023
Record UNII
GLP1W4JXAH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FASIGLIFAM
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
FASIGLIFAM [USAN]
Common Name English
((3S)-6-(((2',6'-DIMETHYL-4'-(3-(METHANESULFONYL)PROPOXY)-(1,1'-BIPHENYL)-3-YL))METHOXY)-2,3-DIHYDRO-1-BENZOFURAN-3-YL)ACETIC ACID
Systematic Name English
Fasiglifam [WHO-DD]
Common Name English
TAK-875 ANHYDROUS
Common Name English
3-BENZOFURANACETIC ACID, 6-((2',6'-DIMETHYL-4'-(3-(METHYLSULFONYL)PROPOXY)(1,1'-BIPHENYL)-3-YL)METHOXY)-2,3-DIHYDRO-, (3S)-
Common Name English
fasiglifam [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29711
Created by admin on Sat Dec 16 01:59:57 UTC 2023 , Edited by admin on Sat Dec 16 01:59:57 UTC 2023
Code System Code Type Description
PUBCHEM
24857286
Created by admin on Sat Dec 16 01:59:57 UTC 2023 , Edited by admin on Sat Dec 16 01:59:57 UTC 2023
PRIMARY
SMS_ID
100000175100
Created by admin on Sat Dec 16 01:59:57 UTC 2023 , Edited by admin on Sat Dec 16 01:59:57 UTC 2023
PRIMARY
NCI_THESAURUS
C132780
Created by admin on Sat Dec 16 01:59:57 UTC 2023 , Edited by admin on Sat Dec 16 01:59:57 UTC 2023
PRIMARY
FDA UNII
GLP1W4JXAH
Created by admin on Sat Dec 16 01:59:57 UTC 2023 , Edited by admin on Sat Dec 16 01:59:57 UTC 2023
PRIMARY
USAN
ZZ-123
Created by admin on Sat Dec 16 01:59:57 UTC 2023 , Edited by admin on Sat Dec 16 01:59:57 UTC 2023
PRIMARY
INN
9651
Created by admin on Sat Dec 16 01:59:57 UTC 2023 , Edited by admin on Sat Dec 16 01:59:57 UTC 2023
PRIMARY
ChEMBL
CHEMBL1829174
Created by admin on Sat Dec 16 01:59:57 UTC 2023 , Edited by admin on Sat Dec 16 01:59:57 UTC 2023
PRIMARY
DRUG BANK
DB12491
Created by admin on Sat Dec 16 01:59:57 UTC 2023 , Edited by admin on Sat Dec 16 01:59:57 UTC 2023
PRIMARY
CAS
1000413-72-8
Created by admin on Sat Dec 16 01:59:57 UTC 2023 , Edited by admin on Sat Dec 16 01:59:57 UTC 2023
PRIMARY
EPA CompTox
DTXSID601025726
Created by admin on Sat Dec 16 01:59:57 UTC 2023 , Edited by admin on Sat Dec 16 01:59:57 UTC 2023
PRIMARY
Related Record Type Details
Structure of FASIGLIFAM HEMIHYDRATE
SALT/SOLVATE -> PARENT
Structure of FASIGLIFAM HEMIHYDRATE
SOLVATE->ANHYDROUS
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
FREE FATTY ACID RECEPTOR 1
TARGET -> AGONIST
Related Record Type Details
Structure of DES(BENZOFURANACETIC ACID) FASIGLIFAM BENZOIC ACID
METABOLITE INACTIVE -> PARENT
Related Record Type Details
Structure of FASIGLIFAM
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