AZD5153 HNT salt
- Parent CAS: 1869912-39-9
- Optical Purity: 99.5% e.e.
- Soluble in DMSO
- MF: C25H33N7O3.C11H8O3
- MW: 667.75
Description
AZD5153 is a potent, selective, and orally available BET/BRD4 bromodomain inhibitor with a bivalent binding mode. Unlike many previously reported monovalent inhibitors, AZD5153 ligates two bromodomains in BRD4 simultaneously. The enhanced avidity afforded through bivalent binding translates into increased cellular and antitumor activity in preclinical hematologic tumor models. In vivo administration of AZD5153 led to tumor stasis or regression in multiple xenograft models of acute myeloid leukemia, multiple myeloma, and diffuse large B-cell lymphoma. The relationship between AZD5153 exposure and efficacy suggests that prolonged BRD4 target coverage is a primary efficacy driver. AZD5153 treatment markedly affects transcriptional programs of MYC, E2F, and mTOR. Transcriptional modulation of MYC and HEXIM1 was confirmed in AZD5153-treated human whole blood.
More Information
| Parent CAS No. | 1869912-39-9 |
|---|---|
| Chemical Name | (R)-4-(2-(4-(1-(3-methoxy-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)piperidin-4-yl)phenoxy)ethyl)-1,3-dimethylpiperazin-2-one 6-hydroxy-2-naphthoate |
| extra_info | Sold in collaboration with Chemietek |
| SMILES | C1C=C(OCCN2[C@H](C)C(=O)N(C)CC2)C=CC=1C1CCN(C2C=CC3=NN=C(OC)N3N=2)CC1.C1C=C2C=C(C(O)=O)C=CC2=CC=1O |&1:7,r| |
| MFCD | N.A. |
| InChi | InChI=1S/C25H33N7O3.C11H8O3/c1-18-24(33)29(2)14-15-30(18)16-17-35-21-6-4-19(5-7-21)20-10-12-31(13-11-20)23-9-8-22-26-27-25(34-3)32(22)28-23;12-10-4-3-7-5-9(11(13)14)2-1-8(7)6-10/h4-9,18,20H,10-17H2,1-3H3;1-6,12H,(H,13,14)/t18-;/m1./s1 |
| InChiKey | UNZQBHXKCHECEC-GMUIIQOCSA-N |
| CID | 118693658 |
| Short Description | BET/BRD4 bromodomain inhibitor |
References
- GW Rhyasen et al. AZD5153: A Novel Bivalent BET Bromodomain Inhibitor Highly Active against Hematologic Malignancies. Mol Cancer Ther. 2016 Nov;15(11):2563-2574.
- RH Bradbury et al.Optimization of a Series of Bivalent Triazolopyridazine Based Bromodomain and Extraterminal Inhibitors: The Discovery of (3R)-4-[2-[4-[1-(3-Methoxy-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-4-piperidyl]phenoxy]ethyl]-1,3-dimethyl-piperazin-2-one (AZD5153). J Med Chem. 2016 Sep 8;59(17):7801-17.
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