Ketodarolutamide | CAS#1297537-33-7

Ketodarolutamide
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 555933

CAS#: 1297537-33-7

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.

Chemical Structure

Ketodarolutamide

CAS# 1297537-33-7

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 555933
Name: Ketodarolutamide
CAS#: 1297537-33-7
Chemical Formula: C19H17ClN6O2
Exact Mass: 396.11
Molecular Weight: 396.835
Elemental Analysis: C, 57.51; H, 4.32; Cl, 8.93; N, 21.18; O, 8.06

Price and Availability

Size	Price	Availability
10mg	USD 150	Ready to ship
25mg	USD 250	Ready to ship
50mg	USD 450	Ready to ship
100mg	USD 750	Ready to ship
200mg	USD 1250	Ready to ship
500mg	USD 2650	Ready to ship
1g	USD 3950	Ready to ship
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 1297537-33-7

Synonym: BAY-1896953; BAY 1896953; BAY1896953; ORM-15341; ORM 15341; ORM15341; Ketodarolutamide;

IUPAC/Chemical Name: (S)-5-acetyl-N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-1H-pyrazole-3-carboxamide

InChi Key: GMBPVBVTPBWIKC-NSHDSACASA-N

InChi Code: 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

SMILES Code: ClC1=C(C#N)C=CC(C2=NN(C[C@H](C)NC(C3=NNC(C(C)=O)=C3)=O)C=C2)=C1

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: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

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

More Info:

Product Data:

Product Data

Certificate of Analysis:

View CoA: current batch, Lot#C21R12B30

QC Data:

View QC data: current batch, Lot#C21R12B30

Safety Data Sheet (SDS):

View Safety Data Sheet (SDS)

Instruction:

View handling instruction

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.
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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	100.0	252.00

Preparing Stock Solutions

The following data is based on the product molecular weight 396.84 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.

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:	1. Sugawara T, Baumgart SJ, Nevedomskaya E, Reichert K, Steuber H, Lejeune P, Mumberg D, Haendler B. Darolutamide is a potent androgen receptor antagonist with strong efficacy in prostate cancer models. Int J Cancer. 2019 Sep 1;145(5):1382-1394. doi: 10.1002/ijc.32242. Epub 2019 Mar 23. PMID: 30828788; PMCID: PMC6766977. 2. Taavitsainen P, Gieschen H, Korjamo T, Kähkönen M, Malmström C, Prien O, Niehues M, Sandmann S, Janssen W, Koskinen M. Absorption, distribution, metabolism and excretion of darolutamide (a novel non-steroidal androgen receptor antagonist) in rats. Xenobiotica. 2020
In vitro protocol:	1. Sugawara T, Baumgart SJ, Nevedomskaya E, Reichert K, Steuber H, Lejeune P, Mumberg D, Haendler B. Darolutamide is a potent androgen receptor antagonist with strong efficacy in prostate cancer models. Int J Cancer. 2019 Sep 1;145(5):1382-1394. doi: 10.1002/ijc.32242. Epub 2019 Mar 23. PMID: 30828788; PMCID: PMC6766977.
In vivo protocol:	1. Taavitsainen P, Gieschen H, Korjamo T, Kähkönen M, Malmström C, Prien O, Niehues M, Sandmann S, Janssen W, Koskinen M. Absorption, distribution, metabolism and excretion of darolutamide (a novel non-steroidal androgen receptor antagonist) in rats. Xenobiotica. 2020

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1: Saini NK, Gabani BB, Todmal U, Sulochana SP, Kiran V, Zainuddin M, Balaji N, Polina SB, Srinivas NR, Mullangi R. Pharmacokinetics of Darolutamide in Mouse - Assessment of the Disposition of the Diastereomers, Key Active Metabolite and Interconversion Phenomenon: Implications to Cancer Patients. Drug Metab Lett. 2020 May 20. doi: 10.2174/1872312814666200521091236. Epub ahead of print. PMID: 32436836.

2: Zakkula A, Kiran V, Todmal U, Sulochana SP, Mullangi R. RP-HPLC-UV Method for Simultaneous Quantification of Second Generation Non-Steroidal Antiandrogens Along with their Active Metabolites in Mice Plasma: Application to a Pharmacokinetic Study. Drug Res (Stuttg). 2019 Oct;69(10):537-544. doi: 10.1055/a-0790-8309. Epub 2018 Dec 10. PMID: 30536259.

3: Sulochana SP, Saini NK, Daram P, Polina SB, Mullangi R. Validation of an LC- MS/MS method for simultaneous quantitation of enzalutamide, N-desmethylenzalutamide, apalutamide, darolutamide and ORM-15341 in mice plasma and its application to a mice pharmacokinetic study. J Pharm Biomed Anal. 2018 Jul 15;156:170-180. doi: 10.1016/j.jpba.2018.04.038. Epub 2018 Apr 24. PMID: 29709784.

4: Balaji N, Sulochana SP, Saini NK, A SK, Mullangi R. Validated Chiral LC-ESI- MS/MS Method for the Simultaneous Quantification of Darolutamide Diastereomers and Its Active Metabolite in Mice Plasma: Application to a Pharmacokinetic Study. Drug Res (Stuttg). 2018 Nov;68(11):615-624. doi: 10.1055/a-0580-7218. Epub 2018 Mar 20. PMID: 29558780.

5: Dittakavi S, Nagasuri PKVSP, Sulochana SP, Saim SM, Mallurwar SR, Zainuddin M, Dewang P, Rajagopal S, Mullangi R. LC-MS/MS-ESI method for simultaneous quantification of darolutamide and its active metabolite, ORM-15341 in mice plasma and its application to a pharmacokinetic study. J Pharm Biomed Anal. 2017 Oct 25;145:454-461. doi: 10.1016/j.jpba.2017.06.074. Epub 2017 Jul 13. PMID: 28743076.

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