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2mg |
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5mg |
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10mg |
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25mg |
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50mg |
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100mg |
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250mg |
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500mg |
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Other Sizes |
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Purity: ≥98%
Orterone (aslo known as TAK-700; TAK 700; TAK700) is an orally bioavailable non-steroidal androgen synthesis inhibitor of human 17,20-lyase inhibitor with potential anticancer activity. It inhibits human 17,20-lyase with IC50 of 38 nM, and exhibits >1000-fold selectivity for human 17,20-lyase over other CYPs (e.g. 11-hydroxylase and CYP3A4). It is a novel hormonal therapy developed by Takeda company for the treatment of prostate cancer.
ln Vitro |
Orteronel has an IC50 of 110 nM for androstenedione and 110 nM for DHEA, which are both produced in monkey adrenal cells in response to ACTH stimulation. Also, with an IC50 of 37 nM, ortersteronel significantly reduces the synthesis of DHEA in human adrenocortical tumor line H295R cells[1]. With an IC50 of 54 nM for rat steroid 17,20-lyase and 38 nM for human steroid 17,20-lyase, respectively, orteronel has strong inhibitory activity against either enzyme in vitro. Orteronel does not appreciably impact CYP3A4 or 11-hydroxylase, among other CYP isoforms. Compared to the other CYP isoforms, Orteronel has a higher inhibitory impact on 17,20-lyase in microsomes expressing human CYP isoforms, with an IC50 of 19 nM1.
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ln Vivo |
Favorable pharmacokinetic characteristics are obtained with ortionel (1 mg/kg, po), with Tmax, Cmax, t1/2, and AUC0-24 hours of 1.7 hours, 0.147 μg/mL, 3.8 hours, and 0.727 μg/mL, respectively[1]. Oral administration of 1 mg/kg of orally administered Orteronel significantly lowers the levels of DHEA and serum testosterone in cynomolgus monkeys[2].
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Animal Protocol |
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References |
[1]. Yamaoka M, et al. 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.
[2]. Kaku, Tomohiro., et al. Discovery of orteronel (TAK-700), a naphthylmethylimidazole derivative, as a highly selective 17,20-lyase inhibitor with potential utility in the treatment of prostate cancer. From Bioorganic & Medicinal Chemistry (2011), 19(21), 6 |
Molecular Formula |
C18H17N3O2
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Molecular Weight |
307.35
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CAS # |
566939-85-3
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Related CAS # |
426219-18-3 (racemic);566939-85-3 (s-isomer);
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Appearance |
Typically exists as solids (or liquids in special cases) at room temperature
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SMILES |
O=C(NC)C1=CC=C2C=C([C@@]3(O)CCN4C=NC=C43)C=CC2=C1
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InChi Key |
OZPFIJIOIVJZMN-SFHVURJKSA-N
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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
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Chemical Name |
(S)-6-(7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide
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Synonyms |
TAK700; TAK-700; TAK 700; Orteronel (s-isomer);
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HS Tariff Code |
2934.99.9001
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Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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Solubility (In Vitro) |
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Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 1.43 mg/mL (4.65 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 14.3 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 1.43 mg/mL (4.65 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 14.3 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 1.43 mg/mL (4.65 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 0.5% methylcellulose: 30 mg/mL |
Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
1 mM | 3.2536 mL | 16.2681 mL | 32.5362 mL | |
5 mM | 0.6507 mL | 3.2536 mL | 6.5072 mL | |
10 mM | 0.3254 mL | 1.6268 mL | 3.2536 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration: mg/mL;
Method for preparing DMSO stock solution: mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation::Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
NCT03211052 | Terminated | Drug: TAK-700 and LHRH agonist | Prostate Cancer | Centre of Experimental Medicine | February 18, 2013 | Phase 2 |
NCT00569153 | Completed | Drug: TAK-700 | Prostatic Neoplasms | Millennium Pharmaceuticals, Inc. | April 2008 | Phase 1 Phase 2 |
NCT01808040 | Completed | Drug: Larotrectinib Sulfate Procedure: Bone Scan |
Post Menopausal, Hormone Receptor Positive Breast Cancer |
University of Wisconsin, Madison | November 2012 | Phase 1 |
NCT01046916 | Completed | Drug: TAK-700 | Prostate Cancer | Millennium Pharmaceuticals, Inc. | May 2010 | Phase 2 |