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Details

Stereochemistry ACHIRAL
Molecular Formula C19H20N2O3
Molecular Weight 324.3737
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BINDARIT

SMILES

CC(C)(OCC1=NN(CC2=CC=CC=C2)C3=C1C=CC=C3)C(O)=O

InChI

InChIKey=MTHORRSSURHQPZ-UHFFFAOYSA-N
InChI=1S/C19H20N2O3/c1-19(2,18(22)23)24-13-16-15-10-6-7-11-17(15)21(20-16)12-14-8-4-3-5-9-14/h3-11H,12-13H2,1-2H3,(H,22,23)

HIDE SMILES / InChI
Molecular Formula C19H20N2O3
Molecular Weight 324.3737
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/15691869

Bindarit (2-Methyl-2-[[1-(phenylmethyl)-1H-indazol-3yl]methoxy]propanoic acid; AF-2838) is an indazolic derivative that is devoid of any immunosuppressive effects and has no effect on arachidonic acid metabolism. It has been proved to have anti-inflammatory activity in a number of experimental diseases, including pancreatitis, arthritis, and lupus nephritis. This therapeutic effect has been associated with its ability to interfere selectively with monocyte recruitment, although the underlying molecular mechanisms are unknown. Bindarit selectively inhibits the production of the monocyte chemotactic protein subfamily of CC inflammatory chemokines (MCP-1/CCL2, MCP-3/CCL7, MCP-2/CCL8) without affecting the production of the cytokines IL-1, IL-6, or the chemokines IL-8, MIP-1α.

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Inhibitor
8297
C-C motif chemokine 8
1
Target ID: P80075
Gene ID: 6355.0
Gene Symbol: CCL8
Target Organism: Homo sapiens (Human)
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Phase II
1132
Unknown

Approved Use

Unknown
Palliative
Phase II
1132
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
50 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21852559
25 mg/kg single, oral
dose: 25 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
BINDARIT plasma
Sus scrofa
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
10 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21852559
25 mg/kg single, oral
dose: 25 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
BINDARIT plasma
Sus scrofa
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
600 mg 2 times / day multiple, oral
Highest studied dose
Dose: 600 mg, 2 times / day
Route: oral
Route: multiple
Dose: 600 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/21876349
Page: p.370
unhealthy, ADULT
n = 11
Health Status: unhealthy
Condition: lupus nephritis
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources:
https://pubmed.ncbi.nlm.nih.gov/21876349
Page: p.370
Sources:
https://pubmed.ncbi.nlm.nih.gov/21876349
Page: p.370
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P000V78
https://www.1pchem.com/search?query=1P000V78
AChemBlock
10234
http://www.achemblock.com/catalogsearch/result/?q=10234
AK Scientific
X6136
https://aksci.com/item_detail.php?cat=X6136
Alfa Chemistry
ACM130641382
http://www.alfa-chemistry.com/search.aspx?q=ACM130641382
ApexBio Technology
B2156
https://www.apexbt.com/catalogsearch/result/?q=B2156
AstaTech
A12002
http://astatechinc.com/CPSResult.php?CRNO=A12002
BOC Sciences
130641-38-2
http://www.bocsci.com/description.asp?cas=130641-38-2
Capot Chemical
26565
https://www.capotchem.com/search.do?q=26565
Cayman Chemical
11479
http://www.caymanchem.com/app/template/Product.vm/catalog/11479
Chem Scene
CS-2620
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-2620
ChemShuttle
151797
https://www.chemshuttle.com/catalogsearch/result/?q=151797
KeyOrganics
AS-72769
http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-72769
Lab Network
LN01273472
https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01273472
MedChem Express
HY-B0498
https://www.medchemexpress.com/search.html?q=HY-B0498&ft=&fa=&fp=
MolPort
MolPort-019-879-260
https://www.molport.com/shop/molecule-link/MolPort-019-879-260
Molnova
M11224
https://www.molnova.com/en/serch-list.html?keywords=M11224
MuseChem
A000871
https://www.musechem.com/product/A000871.html
ShangHai Biochempartner
BCP000527
http://www.biochempartner.com/search_BCP000527
ShangHai Biochempartner
BCP22728
http://www.biochempartner.com/search_BCP22728
TargetMol
T6413
https://www.targetmol.com/search?keyword=T6413
Tetrahedron
TS77487
http://www.thsci.com/search.do?q=TS77487
Toronto Research Chemicals
B387050
https://www.trc-canada.com/product-detail/?CatNum=B387050
Wonderchem
WD02KT3
http://www.wonder-chem.com/search.html?text=WD02KT3
eMolecules
43607616
https://orderbb.emolecules.com/search/#?query=43607616
eNovation Chemicals
D541007
https://www.enovationchem.com/Products.asp?SEARCHTEXT=D541007&searchbtn.x=0&searchbtn.y=0
mcule
MCULE-4362111701
https://mcule.com/MCULE-4362111701/
PubMed

PubMed

TitleDatePubMed
Treatment with bindarit, a blocker of MCP-1 synthesis, protects mice against acute pancreatitis.
2005 Jun
The anti-inflammatory agent bindarit inhibits neointima formation in both rats and hyperlipidaemic mice.
2009 Dec 1
Patents

Patents

08350052
2
JP2006516202A
24

Sample Use Guides

In Vivo Use Guide
2x300 mg bid (two times a day); duration:12 weeks
Route of Administration: Oral
In Vitro Use Guide
Acini were preincubated with/without bindarit (460 μM) for 30 min, and further incubated with caerulein (10−12-10−7 M) for 30 min. The dose of bindarit was chosen based on earlier reports in which it was shown to inhibit MCP-1 synthesis. Bindarit has been shown to preferentially inhibit MCP-1 production in vitro in monocytes without affecting the production of the cytokines IL-1, IL-6, or the chemokines IL-8, protein macrophage inflammatory-1alpha.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:40:29 GMT 2023
Edited
by admin
on Fri Dec 15 15:40:29 GMT 2023
Record UNII
JQ11LH711M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BINDARIT
INN   USAN  
INN   USAN  
Official Name English
BINDARIT [USAN]
Common Name English
AF-2838
Code English
PROPANOIC ACID, 2-METHYL-2-((1-(PHENYLMETHYL)-1H-INDAZOL-3-YL)METHOXY)-
Common Name English
bindarit [INN]
Common Name English
AF 2838
Code English
Classification Tree Code System Code
NCI_THESAURUS C29634
Created by admin on Fri Dec 15 15:40:29 GMT 2023 , Edited by admin on Fri Dec 15 15:40:29 GMT 2023
FDA ORPHAN DRUG 110097
Created by admin on Fri Dec 15 15:40:29 GMT 2023 , Edited by admin on Fri Dec 15 15:40:29 GMT 2023
Code System Code Type Description
EVMPD
SUB05834MIG
Created by admin on Fri Dec 15 15:40:29 GMT 2023 , Edited by admin on Fri Dec 15 15:40:29 GMT 2023
PRIMARY
SMS_ID
100000085886
Created by admin on Fri Dec 15 15:40:29 GMT 2023 , Edited by admin on Fri Dec 15 15:40:29 GMT 2023
PRIMARY
INN
6689
Created by admin on Fri Dec 15 15:40:29 GMT 2023 , Edited by admin on Fri Dec 15 15:40:29 GMT 2023
PRIMARY
DRUG BANK
DB12739
Created by admin on Fri Dec 15 15:40:29 GMT 2023 , Edited by admin on Fri Dec 15 15:40:29 GMT 2023
PRIMARY
PUBCHEM
71354
Created by admin on Fri Dec 15 15:40:29 GMT 2023 , Edited by admin on Fri Dec 15 15:40:29 GMT 2023
PRIMARY
FDA UNII
JQ11LH711M
Created by admin on Fri Dec 15 15:40:29 GMT 2023 , Edited by admin on Fri Dec 15 15:40:29 GMT 2023
PRIMARY
EPA CompTox
DTXSID30156660
Created by admin on Fri Dec 15 15:40:29 GMT 2023 , Edited by admin on Fri Dec 15 15:40:29 GMT 2023
PRIMARY
CAS
130641-38-2
Created by admin on Fri Dec 15 15:40:29 GMT 2023 , Edited by admin on Fri Dec 15 15:40:29 GMT 2023
PRIMARY
ChEMBL
CHEMBL2107549
Created by admin on Fri Dec 15 15:40:29 GMT 2023 , Edited by admin on Fri Dec 15 15:40:29 GMT 2023
PRIMARY
NCI_THESAURUS
C96701
Created by admin on Fri Dec 15 15:40:29 GMT 2023 , Edited by admin on Fri Dec 15 15:40:29 GMT 2023
PRIMARY
USAN
EE-27
Created by admin on Fri Dec 15 15:40:29 GMT 2023 , Edited by admin on Fri Dec 15 15:40:29 GMT 2023
PRIMARY
Related Record Type Details
C-C MOTIF CHEMOKINE 2
TARGET -> INHIBITOR
Related Record Type Details
Structure of BINDARIT
ACTIVE MOIETY
NIH
NCATS
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DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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