SML0328
Indazole-Cl
≥98% (HPLC)
Synonym(s):
3-Chloro-2-(4-hydroxyphenyl)-2H-indazol-5-ol
Sign Into View Organizational & Contract Pricing
All Photos(1)
About This Item
Empirical Formula (Hill Notation):
C13H9ClN2O2
CAS Number:
Molecular Weight:
260.68
MDL number:
UNSPSC Code:
51111800
PubChem Substance ID:
assay
≥98% (HPLC)
form
powder
color
white to brown
solubility
DMSO: >5 mg/mL
storage temp.
2-8°C
SMILES string
Oc1ccc(cc1)-n2nc3ccc(O)cc3c2Cl
InChI
1S/C13H9ClN2O2/c14-13-11-7-10(18)5-6-12(11)15-16(13)8-1-3-9(17)4-2-8/h1-7,17-18H
InChI key
ZNHQDSBJVFFIAK-UHFFFAOYSA-N
Biochem/physiol Actions
Indazole-Cl is a selective estrogen receptor modifier (SERM), a selective ERβ agonist with > 100-fold selectivity for ERβ over Erα. In a recent study reported in Cell, Indazole-Cl, but not structurally distinct ERβ-specific ligands DPN and ERB-041, blocked the expression of proinflammatory genes in microglia and astrocytes, repressing induction of factors that promote Th17 T cell differentiation and activation. Indazole-Cl is believed to bind to the ERβ that is part of an ADIOL-ERβ-CtBP transrepression pathway that mediates recruitment of CtBP corepressor complexes to AP-1-dependent promoters, repressing genes that amplify inflammatory responses and activate Th17 T cells. In studies of experimental autoimmune encephalitis (EAE), a mouse model of Multiple sclerosis, Indazole-Cl both prevented the development of EAE when given prophylactically and caused significant improvement of EAE when provided to mice after they exhibited symptoms of disease.
Features and Benefits
This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
Choose from one of the most recent versions:
Certificates of Analysis (COA)
Lot/Batch Number
Don't see the Right Version?
If you require a particular version, you can look up a specific certificate by the Lot or Batch number.
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
Indazole estrogens: highly selective ligands for the estrogen receptor beta.
De Angelis M, Stossi F, Carlson KA, Katzenellenbogen BS, Katzenellenbogen JA.
Journal of Medicinal Chemistry, 4, 1132-1144 (2005)
An ADIOL-ERβ-CtBP transrepression pathway negatively regulates microglia-mediated inflammation.
Saijo K, Collier JG, Li AC, Katzenellenbogen JA, Glass CK.
Cell, 4, 584-595 (2011)
Estrogen receptor transrepresses brain inflammation.
Gosselin D, Rivest S.
Cell, 4, 495-497 (2011)
Christin Rakers et al.
The Journal of biological chemistry, 291(1), 58-71 (2015-11-07)
Acting during phase II metabolism, sulfotransferases (SULTs) serve detoxification by transforming a broad spectrum of compounds from pharmaceutical, nutritional, or environmental sources into more easily excretable metabolites. However, SULT activity has also been shown to promote formation of reactive metabolites
Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.
Contact Technical Service
