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MedKoo Cat#: 206514 | Name: ODM-201
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Description:

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

ODM-201, also known as Darolutamide, is a new-generation, potent and selective androgen receptor (AR) inhibitor which is potential useful for treatment of castration-resistant prostate cancer (CRPC). ODM-201 is a full and high-affinity AR antagonist that, similar to second-generation antiandrogens enzalutamide and ARN-509, inhibits testosterone-induced nuclear translocation of AR. Importantly, ODM-201 also blocks the activity of the tested mutant ARs arising in response to antiandrogen therapies, including the F876L mutation that confers resistance to enzalutamide and ARN-509. In addition, ODM-201 reduces the growth of AR-overexpressing VCaP prostate cancer cells both in vitro and in a castration-resistant VCaP xenograft model. ODM-201 overcomes resistance to AR-targeted therapies by antagonizing both overexpressed and mutated ARs. ODM-201 is currently in a phase 3 trial in CRPC.

Chemical Structure

ODM-201
ODM-201
CAS#1297538-32-9

Theoretical Analysis

MedKoo Cat#: 206514

Name: ODM-201

CAS#: 1297538-32-9

Chemical Formula: C19H19ClN6O2

Exact Mass: 398.1258

Molecular Weight: 398.85

Elemental Analysis: C, 57.22; H, 4.80; Cl, 8.89; N, 21.07; O, 8.02

Price and Availability

Size Price Availability Quantity
10mg USD 90.00 Ready to Ship
25mg USD 150.00 Ready to ship
50mg USD 250.00 Ready to ship
100mg USD 450.00 Ready to ship
200mg USD 750.00 Ready to ship
500mg USD 1,650.00 Ready to ship
1g USD 2,950.00 Ready to Ship
2g USD 5,250.00 Ready to Ship
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No Data
Synonym
ODM-201; ODM 201; ODM201; Darolutamide; Nubeqa.
IUPAC/Chemical Name
N-((S)-1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-5-(1-hydroxyethyl)-1H-pyrazole-3-carboxamide
InChi Key
ANGUXJDGJCHGOG-UHFFFAOYSA-N
InChi Code
InChI=1S/C25H29N5O/c1-19-8-9-22-23(27-19)6-3-7-24(22)29-16-14-28(15-17-29)12-10-20-4-2-5-21(18-20)30-13-11-26-25(30)31/h2-9,18H,10-17H2,1H3,(H,26,31)
SMILES Code
O=C(C1=NNC(C(O)C)=C1)N[C@@H](C)CN2N=C(C3=CC=C(C#N)C(Cl)=C3)C=C2
Appearance
White to off-white 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, not in water
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
Biological target:
Darolutamide (ODM-201, BAY-1841788) is a novel androgen receptor (AR) antagonist that blocks AR nuclear translocation with Ki of 11 nM.
In vitro activity:
In competitive AR binding assays, the inhibition constant (Ki) values of Darolutamide (ODM-201) are 11 nM. ODM-201and ORM-15341 suppresse androgen-induced cell proliferation more efficaciously than enzalutamide or ARN-509, IC50 values being 230 and 170 nM for Darolutamide and ORM-15341 vs. 410 and 420 nM for enzalutamide and ARN-509. Darolutamide has no effect on the viability of AR-negative cell lines tested, DU-145 prostate cancer cells and H1581 lung cancer cells confirming that the antiproliferative properties of Darolutamide and ORM-15341 are specific to AR-dependent PC cells. Reference: Sci Rep. 2015 Jul 3;5:12007. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/26137992/
In vivo activity:
Darolutamide (ODM-201) showes a significant antitumor activity with both doses, 50 mg/kg twice daily being more efficacious compared to castrated, untreated mice (p<0.001) or Enzalutamide (p=0.0245), which also showes inhibition of tumor growth (p<0.05) vs. castrated, untreated mice. Further, there is no sign of treatment-related toxicities; the body weights of mice treated with Darolutamide twice daily do not decrease significantly during the treatment. Reference: Sci Rep. 2015 Jul 3;5:12007. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/26137992/
Solvent mg/mL mM
Solubility
DMSO 100.0 256.50
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 398.85 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:
1. Moilanen AM, Riikonen R, Oksala R, Ravanti L, Aho E, Wohlfahrt G, Nykänen PS, Törmäkangas OP, Palvimo JJ, Kallio PJ. Discovery of ODM-201, a new-generation androgen receptor inhibitor targeting resistance mechanisms to androgen signaling-directed prostate cancer therapies. Sci Rep. 2015 Jul 3;5:12007. doi: 10.1038/srep12007. PMID: 26137992; PMCID: PMC4490394. 2. Borgmann H, Lallous N, Ozistanbullu D, Beraldi E, Paul N, Dalal K, Fazli L, Haferkamp A, Lejeune P, Cherkasov A, Gleave ME. Moving Towards Precision Urologic Oncology: Targeting Enzalutamide-resistant Prostate Cancer and Mutated Forms of the Androgen Receptor Using the Novel Inhibitor Darolutamide (ODM-201). Eur Urol. 2018 Jan;73(1):4-8. doi: 10.1016/j.eururo.2017.08.012. Epub 2017 Aug 26. PMID: 28851578.
In vitro protocol:
1. Moilanen AM, Riikonen R, Oksala R, Ravanti L, Aho E, Wohlfahrt G, Nykänen PS, Törmäkangas OP, Palvimo JJ, Kallio PJ. Discovery of ODM-201, a new-generation androgen receptor inhibitor targeting resistance mechanisms to androgen signaling-directed prostate cancer therapies. Sci Rep. 2015 Jul 3;5:12007. doi: 10.1038/srep12007. PMID: 26137992; PMCID: PMC4490394. 2. Borgmann H, Lallous N, Ozistanbullu D, Beraldi E, Paul N, Dalal K, Fazli L, Haferkamp A, Lejeune P, Cherkasov A, Gleave ME. Moving Towards Precision Urologic Oncology: Targeting Enzalutamide-resistant Prostate Cancer and Mutated Forms of the Androgen Receptor Using the Novel Inhibitor Darolutamide (ODM-201). Eur Urol. 2018 Jan;73(1):4-8. doi: 10.1016/j.eururo.2017.08.012. Epub 2017 Aug 26. PMID: 28851578.
In vivo protocol:
1. Moilanen AM, Riikonen R, Oksala R, Ravanti L, Aho E, Wohlfahrt G, Nykänen PS, Törmäkangas OP, Palvimo JJ, Kallio PJ. Discovery of ODM-201, a new-generation androgen receptor inhibitor targeting resistance mechanisms to androgen signaling-directed prostate cancer therapies. Sci Rep. 2015 Jul 3;5:12007. doi: 10.1038/srep12007. PMID: 26137992; PMCID: PMC4490394. 2. Borgmann H, Lallous N, Ozistanbullu D, Beraldi E, Paul N, Dalal K, Fazli L, Haferkamp A, Lejeune P, Cherkasov A, Gleave ME. Moving Towards Precision Urologic Oncology: Targeting Enzalutamide-resistant Prostate Cancer and Mutated Forms of the Androgen Receptor Using the Novel Inhibitor Darolutamide (ODM-201). Eur Urol. 2018 Jan;73(1):4-8. doi: 10.1016/j.eururo.2017.08.012. Epub 2017 Aug 26. PMID: 28851578.
1: Fujiwara R, Yamamoto S, Takemura K, Yuasa T, Numao N, Oguchi T, Yasuda Y, Yoneoka Y, Yonese J. Clinical Outcomes and Prognostic Factors in Nonmetastatic Castration-Resistant Prostate Cancer Treated with Androgen Receptor Signaling Inhibitors Therapy. Cancers (Basel). 2024 Jul 26;16(15):2659. doi: 10.3390/cancers16152659. PMID: 39123387; PMCID: PMC11312153. 2: Huang PC, Huang LH, Yang CK, Li JR, Chen CS, Wang SS, Chiu KY, Ou YC, Lin CY. Comparative analysis of novel hormonal agents in non-metastatic castration- resistant prostate cancer: A Taiwanese perspective. PLoS One. 2024 Aug 7;19(8):e0306900. doi: 10.1371/journal.pone.0306900. PMID: 39110673; PMCID: PMC11305548. 3: Sen A, Khan S, Rossetti S, Broege A, MacNeil I, DeLaForest A, Molden J, Davis L, Iversrud C, Seibel M, Kopher R, Schulz S, Laing L. Assessments of prostate cancer cell functions highlight differences between a pan-PI3K/mTOR inhibitor, gedatolisib, and single-node inhibitors of the PI3K/AKT/mTOR pathway. Mol Oncol. 2024 Aug 2. doi: 10.1002/1878-0261.13703. Epub ahead of print. PMID: 39092562. 4: Ning S, Armstrong CM, Xing E, Leslie AR, Gao RY, Sharifi M, Schaaf ZA, Lou W, Han X, Xu DH, Yang R, Cheng J, Mohammed S, Mitsiades N, Liu C, Lombard AP, Wu CY, Cheng X, Li PK, Gao AC. LX1 Targets Androgen Receptor Variants and AKR1C3 to overcome Therapy Resistance in Advanced Prostate Cancer. Cancer Res. 2024 Aug 1. doi: 10.1158/0008-5472.CAN-24-0440. Epub ahead of print. PMID: 39088701. 5: Zhou T, Nguyen S, Wu J, He B, Feng Q. LncRNA LOC730101 Promotes Darolutamide Resistance in Prostate Cancer by Suppressing miR-1-3p. Cancers (Basel). 2024 Jul 20;16(14):2594. doi: 10.3390/cancers16142594. PMID: 39061232; PMCID: PMC11274508. 6: Urabe F, Imai Y, Goto Y, Tashiro K, Hashimoto M, Yoshihara K, Yamamoto S, Hara S, Miyajima K, Fukuokaya W, Enei Y, Iwatani K, Kayano S, Igarashi T, Aikawa K, Yanagisawa T, Kimura S, Tsuzuki S, Murakami M, Hata K, Shimomura T, Yamada H, Miki J, Kimura T. Real-world evidence of triplet therapy efficacy in patients with metastatic castration-sensitive prostate cancer: a Japanese multicenter study. Jpn J Clin Oncol. 2024 Jul 22:hyae098. doi: 10.1093/jjco/hyae098. Epub ahead of print. PMID: 39037966. 7: Patke R, Harris AE, Woodcock CL, Thompson R, Santos R, Kumari A, Allegrucci C, Archer N, Gudas LJ, Robinson BD, Persson JL, Fray R, Jeyapalan J, Rutland CS, Rakha E, Madhusudan S, Emes RD, Muyangwa-Semenova M, Alsaleem M, de Brot S, Green W, Ratan H, Mongan NP, Lothion-Roy J. Epitranscriptomic mechanisms of androgen signalling and prostate cancer. Neoplasia. 2024 Jul 20;56:101032. doi: 10.1016/j.neo.2024.101032. Epub ahead of print. PMID: 39033689; PMCID: PMC11295630. 8: Campodonico F, Foppiani L, Campodonico V, Introini C. Practical implications of androgen receptor inhibitors for prostate cancer treatment. Explor Target Antitumor Ther. 2024;5(3):543-550. doi: 10.37349/etat.2024.00234. Epub 2024 May 28. PMID: 38966166; PMCID: PMC11220289. 9: Pérez Fentes D, Willisch P, Martínez Breijoo S, Domínguez M, Anido U, Álvarez C, Gómez Caamaño A. Controversies in prostate cancer management: Consensus recommendations from experts in northern Spain. Actas Urol Esp (Engl Ed). 2024 Jul 1:S2173-5786(24)00083-0. English, Spanish. doi: 10.1016/j.acuroe.2024.06.005. Epub ahead of print. PMID: 38960063. 10: Oh C, O'Callaghan M. Seminal Papers in Urology: Darolutamide and survival in metastatic, hormone-sensitive prostate cancer. BMC Urol. 2024 Jul 1;24(1):135. doi: 10.1186/s12894-024-01507-7. PMID: 38951868; PMCID: PMC11218282. 11: Moore C, Naraine I, Zhang T. Complete remission following pembrolizumab in a man with mCRPC with both microsatellite instability and BRCA2 mutation. Oncologist. 2024 Aug 5;29(8):716-720. doi: 10.1093/oncolo/oyae156. PMID: 38920278; PMCID: PMC11299937. 12: El-Taji O, Taktak S, Jones C, Brown M, Clarke N, Sachdeva A. Cardiovascular Events and Androgen Receptor Signaling Inhibitors in Advanced Prostate Cancer: A Systematic Review and Meta-Analysis. JAMA Oncol. 2024 Jul 1;10(7):874-884. doi: 10.1001/jamaoncol.2024.1549. PMID: 38842801; PMCID: PMC11157448. 13: Morgans AK, Grossman JP, Paracha N, Ladino D, Tyas E, Rodriguez-Santamaria F, Shore N. Within-trial hospitalization resource utilization and budget impact analysis for darolutamide in metastatic hormone-sensitive prostate cancer using ARASENS. J Manag Care Spec Pharm. 2024 May 28:1-10. doi: 10.18553/jmcp.2024.24045. Epub ahead of print. PMID: 38807035. 14: Gasperoni L, Giunta EF, Montanari D, Masini C, De Giorgi U. New-generation androgen receptor signaling inhibitors (ARSIs) in metastatic hormone-sensitive prostate cancer (mHSPC): pharmacokinetics, drug-drug interactions (DDIs), and clinical impact. Expert Opin Drug Metab Toxicol. 2024 Jun;20(6):491-502. doi: 10.1080/17425255.2024.2353749. Epub 2024 May 22. PMID: 38778707. 15: Sargos P, Bellera C, Bentahila R, Guerni M, Benziane-Ouaritini N, Teyssonneau D, Vuong NS, Ploussard G, Roupret M, Roubaud G. Short-term Darolutamide (ODM-201) Concomitant to Radiation Therapy for Patients with Unfavorable Intermediate-risk Prostate Cancer: The Darius (AFU-GETUG P15) Phase 2 Trial Protocol. Eur Urol Oncol. 2024 May 15:S2588-9311(24)00116-0. doi: 10.1016/j.euo.2024.04.023. Epub ahead of print. PMID: 38755095. 16: Borque-Fernando Á, Zapatero A, Manneh R, Alonso-Gordoa T, Couñago F, Domínguez-Esteban M, López-Valcárcel M, Rodríguez-Antolín A, Sala-González N, Sanmamed N, Maroto P; en representación del Grupo Guard de Investigación Multidisciplinar en Tumores genitourinarios. Recommendations on the treatment of metastatic hormone-sensitive prostate cancer: Patient selection. Actas Urol Esp (Engl Ed). 2024 May 11:S2173-5786(24)00068-4. English, Spanish. doi: 10.1016/j.acuroe.2024.05.008. Epub ahead of print. PMID: 38740263. 17: Hussain M, Fizazi K, Shore ND, Heidegger I, Smith MR, Tombal B, Saad F. Metastatic Hormone-Sensitive Prostate Cancer and Combination Treatment Outcomes: A Review. JAMA Oncol. 2024 Jun 1;10(6):807-820. doi: 10.1001/jamaoncol.2024.0591. PMID: 38722620. 18: Saad F, Hussain MHA, Tombal B, Fizazi K, Sternberg CN, Crawford ED, Nordquist LT, Bögemann M, Tutrone R, Shore ND, Belkoff L, Fralich T, Jhaveri J, Srinivasan S, Li R, Verholen F, Kuss I, Smith MR. Deep and Durable Prostate- specific Antigen Response to Darolutamide with Androgen Deprivation Therapy and Docetaxel, and Association with Clinical Outcomes for Patients with High- or Low-volume Metastatic Hormone-sensitive Prostate Cancer: Analyses of the Randomized Phase 3 ARASENS Study. Eur Urol. 2024 Apr 20:S0302-2838(24)02264-4. doi: 10.1016/j.eururo.2024.03.036. Epub ahead of print. PMID: 38644146. 19: Wang SS, Bian XJ, Wu JL, Wang BH, Zhang S, Ye DW. Network meta-analysis of combination strategies in metastatic hormone-sensitive prostate cancer. Asian J Androl. 2024 Jul 1;26(4):402-408. doi: 10.4103/aja20242. Epub 2024 Apr 12. PMID: 38624195; PMCID: PMC11280209. 20: Yoshida S, Kajiwara D, Seki M, Tayama M, Tanaka Y, Mizutani H, Fujita R, Yamamura K, Okajima S, Asai M, Minamiguchi K. TAS3681, an androgen receptor antagonist, prevents drug resistance driven by aberrant androgen receptor signaling in prostate cancer. Mol Oncol. 2024 Aug;18(8):1980-2000. doi: 10.1002/1878-0261.13641. Epub 2024 Apr 10. PMID: 38600681; PMCID: PMC11306513.
Wei J, Yin L, Li J, Wang J, Pu T, Duan P, Lin TP, Gao AC, Wu BJ. Bidirectional Cross-talk between MAOA and AR Promotes Hormone-Dependent and Castration-Resistant Prostate Cancer. Cancer Res. 2021 Aug 15;81(16):4275-4289. doi: 10.1158/0008-5472.CAN-21-0198. Epub 2021 Jun 24. PMID: 34167949; PMCID: PMC8373824.

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