WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H200724
CAS#: 566939-85-3 (s-isomer)
Description: Orterone, also known as TAK-700, is an orally bioavailable non-steroidal androgen synthesis inhibitor of steroid 17alpha-monooxygenase (17,20 lyase) with potential antiandrogen activity. TAK-700 binds to and inhibits the steroid 17alpha-monooxygenase in both the testes and adrenal glands, thereby inhibiting androgen production. This may decrease androgen-dependent growth signaling and may inhibit cell proliferation of androgen-dependent tumor cells.
Hodoodo Cat#: H200724
Name: Orteronel
CAS#: 566939-85-3 (s-isomer)
Chemical Formula: C18H17N3O2
Exact Mass: 307.13
Molecular Weight: 307.353
Elemental Analysis: C, 70.34; H, 5.58; N, 13.67; O, 10.41
Related CAS #: 426219-18-3 (racemic) 566939-85-3 (s-isomer)
Synonym: TAK700; TAK-700; TAK 700; Orteronel
IUPAC/Chemical Name: (S)-6-(7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide
InChi Key: OZPFIJIOIVJZMN-SFHVURJKSA-N
InChi Code: InChI=1S/C18H17N3O2/c1-19-17(22)14-3-2-13-9-15(5-4-12(13)8-14)18(23)6-7-21-11-20-10-16(18)21/h2-5,8-11,23H,6-7H2,1H3,(H,19,22)/t18-/m0/s1
SMILES Code: O=C(NC)C1=CC=C2C=C([C@@]3(O)CCN4C=NC=C43)C=CC2=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, not in water
Shelf Life: >5 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: Related CAS# 426219-18-3 (Orteronel, racemic mixture) 566939-85-3 (Orteronel, S-isomer)
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The following data is based on the product molecular weight 307.35 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: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Zainuddin M, Vinod AB, Gurav SD, Police A, Kumar A, Mithra C, Dewang P, Kethiri RR, Mullangi R. Preclinical assessment of Orteronel(®), a CYP17A1 enzyme inhibitor in rats. Eur J Drug Metab Pharmacokinet. 2016 Feb;41(1):1-7. doi: 10.1007/s13318-014-0229-2. PubMed PMID: 25297456.
2: Goto A, Moriya Y, Takeuchi T, Mandai T, Tagawa Y, Kondo T, Asahi S. Pharmacokinetics and Urinary Excretion Mechanism of Orteronel (TAK-700), A Novel 17,20-Lyase Inhibitor, in Animals. Drug Res (Stuttg). 2016 Apr;66(4):217-22. doi: 10.1055/s-0035-1564118. PubMed PMID: 26418412.
3: Cathomas R, Crabb SJ, Mark M, Winterhalder R, Rothermundt C, Elliott T, von Burg P, Kenner H, Hayoz S, Vilei SB, Rauch D, Roggero E, Mohaupt MG, Bernhard J, Manetsch G, Gillessen S; Swiss Group for Clinical Cancer Research SAKK.. Orteronel Switch Maintenance Therapy in Metastatic Castration Resistant Prostate Cancer After First-Line Docetaxel: A Multicenter, Randomized, Double-Blind, Placebo-Controlled Trial (SAKK 08/11). Prostate. 2016 Dec;76(16):1519-1527. doi: 10.1002/pros.23236. PubMed PMID: 27457964.
4: Lu C, Suri A, Shyu WC, Prakash S. Assessment of cytochrome P450-mediated drug-drug interaction potential of orteronel and exposure changes in patients with renal impairment using physiologically based pharmacokinetic modeling and simulation. Biopharm Drug Dispos. 2014 Dec;35(9):543-52. doi: 10.1002/bdd.1919. PubMed PMID: 25264242.
5: Petrylak DP, Gandhi JG, Clark WR, Heath E, Lin J, Oh WK, Agus DB, Carthon B, Moran S, Kong N, Suri A, Bargfrede M, Liu G. Phase 1/2 study of orteronel (TAK-700), an investigational 17,20-lyase inhibitor, with docetaxel-prednisone in metastatic castration-resistant prostate cancer. Invest New Drugs. 2015 Apr;33(2):397-408. doi: 10.1007/s10637-014-0199-x. PubMed PMID: 25556680; PubMed Central PMCID: PMC4390470.
6: Saad F, Fizazi K, Jinga V, Efstathiou E, Fong PC, Hart LL, Jones R, McDermott R, Wirth M, Suzuki K, MacLean DB, Wang L, Akaza H, Nelson J, Scher HI, Dreicer R, Webb IJ, de Wit R; ELM-PC 4 investigators.. Orteronel plus prednisone in patients with chemotherapy-naive metastatic castration-resistant prostate cancer (ELM-PC 4): a double-blind, multicentre, phase 3, randomised, placebo-controlled trial. Lancet Oncol. 2015 Mar;16(3):338-48. doi: 10.1016/S1470-2045(15)70027-6. PubMed PMID: 25701170.
7: Fizazi K, Jones R, Oudard S, Efstathiou E, Saad F, de Wit R, De Bono J, Cruz FM, Fountzilas G, Ulys A, Carcano F, Agarwal N, Agus D, Bellmunt J, Petrylak DP, Lee SY, Webb IJ, Tejura B, Borgstein N, Dreicer R. Phase III, randomized, double-blind, multicenter trial comparing orteronel (TAK-700) plus prednisone with placebo plus prednisone in patients with metastatic castration-resistant prostate cancer that has progressed during or after docetaxel-based therapy: ELM-PC 5. J Clin Oncol. 2015 Mar 1;33(7):723-31. doi: 10.1200/JCO.2014.56.5119. PubMed PMID: 25624429; PubMed Central PMCID: PMC4879718.
8: Suzuki K, Ozono S, Yamaguchi A, Koike H, Matsui H, Nagata M, Takubo T, Miyashita K, Matsushima T, Akaza H. A phase 1 multiple-dose study of orteronel in Japanese patients with castration-resistant prostate cancer. Cancer Chemother Pharmacol. 2015 Feb;75(2):373-80. doi: 10.1007/s00280-014-2654-y. PubMed PMID: 25537627; PubMed Central PMCID: PMC4305367.
9: Yamaoka M, Hara T, Araki H, Kaku T, Hitaka T, Tasaka A, Kusaka M. Effect of an investigational CYP17A1 inhibitor, orteronel (TAK-700), on estrogen- and corticoid-synthesis pathways in hypophysectomized female rats and on the serum estradiol levels in female cynomolgus monkeys. J Steroid Biochem Mol Biol. 2013 Nov;138:298-306. doi: 10.1016/j.jsbmb.2013.07.002. PubMed PMID: 23856460.
10: Suri A, Pusalkar S, Li Y, Prakash S. Absorption, Distribution, and Excretion of the Investigational Agent Orteronel (TAK-700) in Healthy Male Subjects: A Phase 1, Open-Label, Single-Dose Study. Clin Pharmacol Drug Dev. 2016 May;5(3):180-7. doi: 10.1002/cpdd.234. PubMed PMID: 27163496.
11: Van Hook K, Huang T, Alumkal JJ. Orteronel for the treatment of prostate cancer. Future Oncol. 2014 Apr;10(5):803-11. doi: 10.2217/fon.14.35. PubMed PMID: 24799061; PubMed Central PMCID: PMC4148348.
12: Hara T, Kouno J, Kaku T, Takeuchi T, Kusaka M, Tasaka A, Yamaoka M. Effect of a novel 17,20-lyase inhibitor, orteronel (TAK-700), on androgen synthesis in male rats. J Steroid Biochem Mol Biol. 2013 Mar;134:80-91. doi: 10.1016/j.jsbmb.2012.10.020. PubMed PMID: 23146910.
13: Suri A, Pham T, MacLean DB. A Phase 1, Randomized, Single-Dose Crossover Pharmacokinetic Study to Investigate the Effect of Food Intake on Absorption of Orteronel (TAK-700) in Healthy Male Subjects. Clin Pharmacol Drug Dev. 2016 May;5(3):188-95. doi: 10.1002/cpdd.233. PubMed PMID: 27163497.
14: Kumar A, S VK, Gurav S, Zainuddin M, Dewang P, Kethiri RR, Rajagopal S, Mullangi R. Development and validation of an RP-HPLC method for the quantitation of Orteronel (TAK-700), a CYP17A1 enzyme inhibitor, in rat plasma and its application to a pharmacokinetic study. Biomed Chromatogr. 2013 Dec;27(12):1590-4. doi: 10.1002/bmc.2964. PubMed PMID: 23788266.
15: Rampurwala M, Wisinski KB, Burkard ME, Ehsani S, O'Regan RM, Carmichael L, Kim K, Kolesar J, Tevaarwerk AJ. Phase 1b study of orteronel in postmenopausal women with hormone-receptor positive (HR+) metastatic breast cancer. Invest New Drugs. 2016 Nov 8. [Epub ahead of print] PubMed PMID: 27826831.
16: Hussain M, Corn PG, Michaelson MD, Hammers HJ, Alumkal JJ, Ryan CJ, Bruce JY, Moran S, Lee SY, Lin HM, George DJ; Prostate Cancer Clinical Trials Consortium, a program of the Department of Defense Prostate Cancer Research Program and the Prostate Cancer Foundation.. Phase II study of single-agent orteronel (TAK-700) in patients with nonmetastatic castration-resistant prostate cancer and rising prostate-specific antigen. Clin Cancer Res. 2014 Aug 15;20(16):4218-27. doi: 10.1158/1078-0432.CCR-14-0356. PubMed PMID: 24965748.
17: Yamaoka M, Hara T, Hitaka T, Kaku T, Takeuchi T, Takahashi J, Asahi S, Miki H, Tasaka A, Kusaka M. Orteronel (TAK-700), a novel non-steroidal 17,20-lyase inhibitor: effects on steroid synthesis in human and monkey adrenal cells and serum steroid levels in cynomolgus monkeys. J Steroid Biochem Mol Biol. 2012 Apr;129(3-5):115-28. doi: 10.1016/j.jsbmb.2012.01.001. PubMed PMID: 22249003.
18: Dreicer R, MacLean D, Suri A, Stadler WM, Shevrin D, Hart L, MacVicar GR, Hamid O, Hainsworth J, Gross ME, Shi Y, Webb IJ, Agus DB. Phase I/II trial of orteronel (TAK-700)--an investigational 17,20-lyase inhibitor--in patients with metastatic castration-resistant prostate cancer. Clin Cancer Res. 2014 Mar 1;20(5):1335-44. doi: 10.1158/1078-0432.CCR-13-2436. PubMed PMID: 24418642.
19: Gurav S, Police A, Zainuddin M, Farooqui JH, Reddy G K, Kethiri RR, Rajagopal S, Mullangi R. Development and validation of a highly sensitive LC-ESI-MS/MS method for the determination of Orteronel® (TAK-700) in rat plasma: application to a pharmacokinetic study. Bioanalysis. 2012 Jun;4(12):1471-80. doi: 10.4155/bio.12.107. PubMed PMID: 22793031.
20: Zhu H, Garcia JA. Targeting the adrenal gland in castration-resistant prostate cancer: a case for orteronel, a selective CYP-17 17,20-lyase inhibitor. Curr Oncol Rep. 2013 Apr;15(2):105-12. doi: 10.1007/s11912-013-0300-1. Review. PubMed PMID: 23371447.
