Methanone, [2-(1H-indol-3-yl)-1H-imidazol-5-yl](3,4,5-trimethoxyphenyl)-
- Product Name
- Methanone, [2-(1H-indol-3-yl)-1H-imidazol-5-yl](3,4,5-trimethoxyphenyl)-
- CAS No.
- 1332881-26-1
- Chemical Name
- Methanone, [2-(1H-indol-3-yl)-1H-imidazol-5-yl](3,4,5-trimethoxyphenyl)-
- Synonyms
- ABI-231;Sabizabulin;sabizabulin(VERU-111);Sabizabulin/VERU-111/ABI-231;Sabizabulin (Synonyms: VERU-111;2-(1H-indol-3-yl)-1H-imidazol-5-yl](3,4,5-trimethoxyphenyl)-Methanone;Methanone, [2-(1H-indol-3-yl)-1H-imidazol-5-yl](3,4,5-trimethoxyphenyl)-;VERU-111 (1H-indol-3-yl)-1H-imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanone
- CBNumber
- CB05569748
- Molecular Formula
- C21H19N3O4
- Formula Weight
- 377.39
- MOL File
- 1332881-26-1.mol
Methanone, [2-(1H-indol-3-yl)-1H-imidazol-5-yl](3,4,5-trimethoxyphenyl)- Property
- Boiling point:
- 688.1±55.0 °C(Predicted)
- Density
- 1.306±0.06 g/cm3(Predicted)
- storage temp.
- 4°C, away from moisture and light
- solubility
- Soluble in DMSO
- pka
- 10.82±0.10(Predicted)
- form
- Solid
- color
- Light yellow to yellow
- InChI
- InChI=1S/C21H19N3O4/c1-26-17-8-12(9-18(27-2)20(17)28-3)19(25)16-11-23-21(24-16)14-10-22-15-7-5-4-6-13(14)15/h4-11,22H,1-3H3,(H,23,24)
- InChIKey
- WQGVHOVEXMOLOK-UHFFFAOYSA-N
- SMILES
- C(C1NC(C2C3=C(NC=2)C=CC=C3)=NC=1)(C1=CC(OC)=C(OC)C(OC)=C1)=O
N-Bromosuccinimide Price
- Product number
- CS-0078414
- Product name
- VERU-111
- Packaging
- 5mg
- Price
- $380
- Updated
- 2021/12/16
- Product number
- CS-0078414
- Product name
- VERU-111
- Packaging
- 10mg
- Price
- $600
- Updated
- 2021/12/16
- Product number
- CS-0078414
- Product name
- VERU-111
- Packaging
- 25mg
- Price
- $1150
- Updated
- 2021/12/16
- Product number
- CS-0078414
- Product name
- VERU-111
- Packaging
- 50mg
- Price
- $1800
- Updated
- 2021/12/16
- Product number
- CS-0078414
- Product name
- VERU-111
- Packaging
- 100mg
- Price
- $2850
- Updated
- 2021/12/16
Methanone, [2-(1H-indol-3-yl)-1H-imidazol-5-yl](3,4,5-trimethoxyphenyl)- Chemical Properties,Usage,Production
Description
Sabizabulin (VERU-111) is a potent, orally bioavailable, and well-tolerated microtubule inhibitor that Veru Inc. is currently developing. It can inhibit the growth of ovarian tumors and completely suppress tumor metastasis in vivo, with efficacy comparable to that of paclitaxel, the current first-line treatment for ovarian cancer. VERU-111 can block the polymerization of tubulin and is not a substrate for multi-drug resistance mechanisms.
Uses
VERU-111 (ABI-231) is a potent and orally active α and β tubulin inhibitor, which displays strong antiproliferative activity, with an average IC50 of 5.2 nM against panels of melanoma and prostate cancer cell lines. VERU-111 (ABI-231) suppresses tumor growth and metastatic phenotypes of cervical cancer cells via targeting HPV E6 and E7, and has potential for the treatment of prostate cancer[1][2][3].
in vitro
In vitro experiments have shown that VERU-111 has a significant inhibitory effect on the ovarian cancer cell lines SKOV3 and OVCAR3. It can effectively inhibit colony formation, proliferation, invasion, and migration of cells at nanomolar levels. In addition, VERU-111 can induce apoptosis in a concentration-dependent manner, with an effect comparable to that of the standard chemotherapeutic drug paclitaxel.
in vivo
In vivo experiments have also shown VERU-111 to have strong anti-tumor and anti-metastatic activity. In a mouse model with orthotopic transplantation of SKOV3 ovarian cancer tumor cells, VERU-111 significantly inhibited tumor growth and completely blocked tumor metastasis to distant organs. Importantly, VERU-111 showed good tolerability during the treatment process, without systemic toxicity.
Clinical claims and research
Sabizabulin has entered Phase II clinical trials for the treatment of ER+ HER2- metastatic breast cancer (NCT05079360), Phase III clinical trials for the treatment of metastatic castration-resistant prostate cancer (mCRPC) (NCT04844749), and Phase III clinical trials for the treatment of COVID-19 (NCT04842747).
References
[1] Wang Q, et al. Structure-Guided Design, Synthesis, and Biological Evaluation of (2-(1H-Indol-3-yl)-1H-imidazol-4-yl)(3,4,5-trimethoxyphenyl) Methanone (ABI-231) Analogues Targeting the Colchicine Binding Site in Tubulin. J Med Chem. 2019 Jul 12. DOI:10.1021/acs.jmedchem.9b00706
[2] Qinghui Wang, et al. Discovery of ABI-231 analogs targeting the colchicine site in tubulin for advanced melanoma. Cancer Research 76(14 Supplement):4848-4848.
[3] Vivek Kashyap, et al. ABI-231: A novel small molecule suppresses tumor growth and metastatic phenotypes of cervical cancer cells via targeting Human papilloma virus (HPV) E6 and E7. Cancer Research 78(13 Supplement):679-679.
[4] Kashyap VK, et al. Therapeutic efficacy of a novel βIII/βIV-tubulin inhibitor (VERU-111) in pancreatic cancer. J Exp Clin Cancer Res. 2019 Jan 23;38(1):29. DOI:10.1186/s13046-018-1009-7
Methanone, [2-(1H-indol-3-yl)-1H-imidazol-5-yl](3,4,5-trimethoxyphenyl)- Preparation Products And Raw materials
Raw materials
Preparation Products
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