Bavdegalutamide
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MedKoo CAT#: 207155

CAS#: 2222112-77-6

Description: Bavdegalutamide, also known as ARV-110, is a first-in-class PROTAC that effectively targets the wild type Androgen Receptor (AR) and certain genomic alterations of the AR (amplification, T878A, H875Y, F877L, M895V, but not L702H or AR-V7) for degradation in both enzalutamide sensitive and resistant preclinical models. ARV-110 showed promising anti-tumor activity in heavily pretreated men with metastatic castration-resistant prostate cancer (mCRPC),


Chemical Structure

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Bavdegalutamide
CAS# 2222112-77-6

Theoretical Analysis

MedKoo Cat#: 207155
Name: Bavdegalutamide
CAS#: 2222112-77-6
Chemical Formula: C41H43ClFN9O6
Exact Mass: 811.3009
Molecular Weight: 812.3004
Elemental Analysis: C, 60.62; H, 5.34; Cl, 4.36; F, 2.34; N, 15.52; O, 11.82

Price and Availability

Size Price Availability Quantity
10.0mg USD 250.0 2 Weeks
25.0mg USD 450.0 2 Weeks
50.0mg USD 750.0 2 Weeks
100.0mg USD 1250.0 2 Weeks
200.0mg USD 2250.0 2 Weeks
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Synonym: ARV-110; ARV 110; ARV110; Bavdegalutamide;

IUPAC/Chemical Name: N-((1r,4r)-4-(3-chloro-4-cyanophenoxy)cyclohexyl)-6-(4-((4-(2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindolin-5-yl)piperazin-1-yl)methyl)piperidin-1-yl)pyridazine-3-carboxamide

InChi Key: CLCTZVRHDOAUGJ-SYVGMNBRSA-N

InChi Code: InChI=1S/C41H43ClFN9O6/c42-31-19-28(4-1-25(31)22-44)58-27-5-2-26(3-6-27)45-38(54)33-7-9-36(48-47-33)51-13-11-24(12-14-51)23-49-15-17-50(18-16-49)35-21-30-29(20-32(35)43)40(56)52(41(30)57)34-8-10-37(53)46-39(34)55/h1,4,7,9,19-21,24,26-27,34H,2-3,5-6,8,10-18,23H2,(H,45,54)(H,46,53,55)/t26-,27-,34?

SMILES Code: ClC1=CC(O[C@H]2CC[C@@H](CC2)NC(C3=CC=C(N=N3)N4CCC(CC4)CN5CCN(CC5)C6=CC(C(N7C8CCC(NC8=O)=O)=O)=C(C=C6F)C7=O)=O)=CC=C1C#N

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Product Data:

Biological target: Androgen receptor (AR) PROTAC degrader.
In vitro activity: PROTAC-mediated AR degradation suppresses the expression of the AR-target genes PSA and FKBP5, inhibits AR-dependent cell proliferation, and induces potent apoptosis in VCaP cells. ARV-110 degrades clinically relevant mutant AR proteins and retains activity in a high androgen environment. In mouse xenograft studies, greater than 90% AR degradation is observed at a 1 mg/kg PO QD dose. Significant inhibition of tumor growth and AR signaling can be achieved in both an intact and castrate setting. Further, ARV-110 demonstrates in vivo efficacy and reduction of oncogenic Erg protein in a long term, castrate, enzalutamide-resistant VCaP tumor model. DMPK and exploratory toxicology studies show robust oral, dose proportional drug exposure in rodent and non-rodent species. Reference:Taavi Neklesa, et al. ARV-110: An androgen receptor PROTAC degrader for prostate cancer. American Association for Cancer Research. 2018. 78 (13): pp. 5236.
In vivo activity: ARV-110 robustly degrades AR in all cell lines tested, with an observed halfmaximal degradation concentration (DC50) of ~1 nM. ARV-110 treatment leads to highly selective AR degradation, as demonstrated by proteomic studies. In VCaP cells, PROTAC-mediated AR degradation suppresses the expression of the AR-target gene PSA, inhibits AR-dependent cell proliferation, and induces apoptosis at low nanomolar concentrations. Further, ARV-110 degrades clinically relevant mutant AR proteins and retains activity in a high androgen environment. In mouse xenograft studies, greater than 90% AR degradation is observed at a 1 mg/kg PO QD dose. Significant inhibition of tumor growth and AR signaling has been achieved in LNCaP, VCaP and prostate cancer patient derived xenograft (PDX) models. Notably, ARV-110 demonstrates in vivo efficacy and reduction of AR-target gene expression in a long term, castrate, enzalutamide-resistant VCaP tumor model. Reference: Taavi K Neklesa,et al. ARV-110: an oral androgen receptor PROTAC degrader for prostate cancer. GU ASCO 2019

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 26.67 32.83

Preparing Stock Solutions

The following data is based on the product molecular weight 812.3004 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: Taavi Neklesa, et al. ARV-110: An androgen receptor PROTAC degrader for prostate cancer. American Association for Cancer Research. 2018. 78 (13): pp. 5236.
In vitro protocol: Taavi Neklesa, et al. ARV-110: An androgen receptor PROTAC degrader for prostate cancer. American Association for Cancer Research. 2018. 78 (13): pp. 5236.
In vivo protocol: Taavi K Neklesa,et al. ARV-110: an oral androgen receptor PROTAC degrader for prostate cancer. GU ASCO 2019

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1: Zeng S, Huang W, Zheng X, Liyan Cheng, Zhang Z, Wang J, Shen Z. Proteolysis targeting chimera (PROTAC) in drug discovery paradigm: Recent progress and future challenges. Eur J Med Chem. 2021 Jan 15;210:112981. doi: 10.1016/j.ejmech.2020.112981. Epub 2020 Oct 31. PMID: 33160761.

2: Proof-of-Concept with PROTACs in Prostate Cancer. Cancer Discov. 2020 Aug;10(8):1084. doi: 10.1158/2159-8290.CD-NB2020-054. Epub 2020 Jun 5. PMID: 32503798.

3: Wang Y, Jiang X, Feng F, Liu W, Sun H. Degradation of proteins by PROTACs and other strategies. Acta Pharm Sin B. 2020 Feb;10(2):207-238. doi: 10.1016/j.apsb.2019.08.001. Epub 2019 Aug 13. PMID: 32082969; PMCID: PMC7016280.