Ketodarolutamide

• CAS: 1297537-33-7
• Catalog Number: ACM1297537337
• Category: Antagonists
• Molecular Weight: 396.84
• Molecular Formula: C19H17ClN6O2
• Description: Ketodarolutamide., also known as ORM-15341 and BAY-1896953, is a potent and full antagonist for human AR (hAR) with IC50 = 38 nM. Ketodarolutamide is a nonsteroidal antiandrogen (NSAA) and the major active metabolite of darolutamide (ODM-201, BAY-1841788), an NSAA which is used in the treatment of prostate cancer in men. Similarly to its parent compound, darolutamide acts as a highly selective, high-affinity, competitive silent antagonist of the androgen receptor (AR). Both agents show much higher affinity and more potent inhibition of the AR relative to the other NSAAs enzalutamide and apalutamide, although they also possess much shorter and comparatively less favorable elimination half-lives.
• Synonyms: BAY-1896953; BAY 1896953; BAY1896953; ORM-15341; ORM 15341; ORM15341; Ketodarolutamide
• IUPAC Name: (S)-5-acetyl-N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-1H-pyrazole-3-carboxamide
• Canonical SMILES: ClC1=C(C#N)C=CC(C2=NN(C[C@H](C)NC(C3=NNC(C(C)=O)=C3)=O)C=C2)=C1
• InChI: InChI=1S/C19H17ClN6O2/c1-11(22-19(28)18-8-17(12(2)27)23-24-18)10-26-6-5-16(25-26)13-3-4-14(9-21)15(20)7-13/h3-8,11H,10H2,1-2H3,(H,22,28)(H,23,24)/t11-/m0/s1
• InChI Key: GMBPVBVTPBWIKC-NSHDSACASA-N
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Shelf Life: >2 years if stored properly
• Storage: Dry, dark and at 0-4 °C for short term (days to weeks) or -20 °C for long term (months to years).
• Biological Target: Ketodarolutamide, also known as ORM-15341 and BAY-1896953, is a potent and full antagonist for human AR (hAR) with IC50 = 38 nM.
• Drug Formulation: This drug may be formulated in DMSO
• Elemental Analysis: C, 57.51; H, 4.32; Cl, 8.93; N, 21.18; O, 8.06
• Exact Mass: 396.1102
• HS Tariff Code: 2934.99.9001
• In Vitro Activity: The antagonistic properties of the different compounds in a cell - based transactivation assay using an MMT - driven luciferase reporter were determined. For darolutamide, the (S,R)- and (S,S)-diastereomers, and the main in vivo metabolite keto-darolutamide, a strong antagonistic activity against AR wild type, when stimulating with 1 nM R1881, was found. This was reduced but still significantly better than observed for other AR antagonists when increasing the androgen level used for stimulation to 10 nM. Strong antagonism was also measured for darolutamide, its diastereomers and for keto-darolutamide when testing the W742C and W742L forms.; Reference: Int J Cancer. 2019 Sep 1;145(5):1382-1394. https://pubmed.ncbi.nlm.nih.gov/30828788/
• In Vivo Activity: The absorption, distribution, metabolism and excretion properties of darolutamide in rats are reported. Keto-darolutamide was the most abundant metabolite in rat hepatocytes and the only major one in plasma. Interconversion between diastereoisomers was observed.; Reference: Xenobiotica. 2020 Aug;50(8):967-979. https://pubmed.ncbi.nlm.nih.gov/32003293/
• Shipping: 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.
• Stock Solution Storage: 0-4 °C for short term (days to weeks), or -20 °C for long term (months).