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ARV-471 - CAS 2229711-68-4

Inquiry

ARV-471, an oral estrogen receptor PROTAC protein degrader for the treatment of breast cancer, is an heterobifunctional molecule that promotes the interaction between estrogen receptor alpha and intracellular E3 ligase complexes. It leads to ubiquitylation and subsequent degradation of estrogen receptors through the proteasome. In ER positive breast cancer cell lines, it has a strong ability to degrade ER with a half-maximal degradation concentration (DC50) of ~2 nM.

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Molecular Formula

C45H49N5O4

Molecular Weight

723.90

ARV-471

- Specification
  - Related CAS
    
    2614417-52-4 (rel-isomer) 2229713-26-0 (formic acid) 2763249-93-8 (D-tartaric acid)
    
    Purity
    
    ≥95%
    
    Solubility
    
    Soluble in DMSO
    
    Storage
    
    Store at -20°C, sealed storage, away from moisture and light
    
    IUPAC Name
    
    (3S)-3-[6-[4-[[1-[4-[(1R,2S)-6-hydroxy-2-phenyl-1,2,3,4-tetrahydronaphthalen-1-yl]phenyl]piperidin-4-yl]methyl]piperazin-1-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione
    
    Synonyms
    
    ARV471; ARV 471; (S)-3-(5-(4-((1-(4-((1R,2S)-6-hydroxy-2-phenyl-1,2,3,4-tetrahydronaphthalen-1-yl)phenyl)piperidin-4-yl)methyl)piperazin-1-yl)-1-oxoisoindolin-2-yl)piperidine-2,6-dione; 2,6-Piperidinedione, 3-[1,3-dihydro-1-oxo-5-[4-[[1-[4-[(1R,2S)-1,2,3,4-tetrahydro-6-hydroxy-2-phenyl-1-naphthalenyl]phenyl]-4-piperidinyl]methyl]-1-piperazinyl]-2H-isoindol-2-yl]-, (3S)-; Vepdegestrant; (3S)-3-[1,3-Dihydro-1-oxo-5-[4-[[1-[4-[(1R,2S)-1,2,3,4-tetrahydro-6-hydroxy-2-phenyl-1-naphthalenyl]phenyl]-4-piperidinyl]methyl]-1-piperazinyl]-2H-isoindol-2-yl]-2,6-piperidinedione
- Properties
  - Density
    
    1.275±0.06 g/cm3
    
    InChI Key
    
    TZZDVPMABRWKIZ-XMOGEVODSA-N
    
    InChI
    
    InChI=1S/C45H49N5O4/c51-37-12-15-39-33(27-37)8-13-38(31-4-2-1-3-5-31)43(39)32-6-9-35(10-7-32)48-20-18-30(19-21-48)28-47-22-24-49(25-23-47)36-11-14-40-34(26-36)29-50(45(40)54)41-16-17-42(52)46-44(41)53/h1-7,9-12,14-15,26-27,30,38,41,43,51H,8,13,16-25,28-29H2,(H,46,52,53)/t38-,41+,43+/m1/s1
    
    Canonical SMILES
    
    C1CC2=C(C=CC(=C2)O)C(C1C3=CC=CC=C3)C4=CC=C(C=C4)N5CCC(CC5)CN6CCN(CC6)C7=CC8=C(C=C7)C(=O)N(C8)C9CCC(=O)NC9=O
- Reference Reading
  - 1. Abstract P5-04-18: ARV-471, an oral estrogen receptor PROTAC degrader for breast cancer.
    
    Flanagan, J.J., Qian, Y., Gough, S.M., Andreoli, M., Bookbinder, M., Cadelina, G., Bradley, J., Rousseau, E., Willard, R., Pizzano, J. and Crews, C.M., 2019. Cancer research, 79(4_Supplement), pp.P5-04.
    
    ARV-471, an estrogen receptor (ER) alpha PROTAC, is a hetero-bifunctional molecule that facilitates the interactions between estrogen receptor alpha and an intracellular E3 ligase complex, leading to the ubiquitylation and subsequent degradation of estrogen receptors via the proteasome. ARV-471 robustly degrades ER in ER-positive breast cancer cell lines with a half-maximal degradation concentration (DC50) of ˜ 2 nM. PROTAC-mediated ER degradation decreases the expression of classically-regulated ER-target genes (PR, GREB1, TFF) and inhibits cell proliferation of ER-dependent cell lines (MCF7, T47D). Additionally, ARV-471 degrades clinically-relevant ESR1 variants (Y537S and D538G) and inhibits growth of cell lines expressing those variants. In an immature rat uterotrophic model, ARV-471 degrades rat uterine ER and demonstrates no agonist activity. Daily, oral-administration of single agent ARV-471 (3, 10, and 30 mpk) leads to significant tumor volume regressions of estradiol-dependent MCF7 xenografts and concomitant tumor ER protein reductions of >90% at study termination. Moreover, when a CDK4/6 inhibitor is combined with ARV-471 in the MCF7 model, even more pronounced tumor growth inhibition is observed (˜130% TGI), accompanied by significant reductions in ER protein levels. In an ESR1 Y537S, hormone-independent patient-derived xenograft model, ARV-471 at 10 mpk completely inhibited growth and also reduced mutant ER protein levels. Taken together, the preclinical data of ARV-471 supports its continued development as a best-in-class oral ER PROTAC-degrader.

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