| Field | Specification |
|---|---|
| Target | |
| Alternative names | TAK-700 |
| CAS no. | |
| Applications | |
| Molecular weight | |
| Molecular formula | C18H17N3O2 |
| Purity | |
| SMILES | |
| Form | Solid |
| Storage | |
| Shipping | |
| Catalog no. (Mfr.) | |
| Main SKU |
Compound Overview
Orteronel, also known as TAK-700, is a highly selective inhibitor of human 17,20-lyase (CYP17), with an IC50 of 38 nM. It shows more than 1000-fold selectivity over other CYPs such as 11-hydroxylase and CYP3A4[1][2]. It is supplied as a white to light brown solid (C18H17N3O2, MW 307.35) at 99.90% purity.
Physical & Chemical Properties
| CAS Number | 566939-85-3 |
|---|---|
| Molecular Formula | C18H17N3O2 |
| Molecular Weight | 307.35 g/mol |
| Purity | 99.90% |
| Appearance | Solid |
| Color | White to light brown |
| SMILES | O=C(C1=CC=C2C=C([C@@]3(O)CCN4C=NC=C43)C=CC2=C1)NC |
| Target | CYP17 |
| Signaling Pathway | Metabolic Enzyme/Protease |
| Solubility | In Vitro: DMSO: 25 mg/mL (81.34 mM; Requires sonication; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO) |
| Storage | Powder: -20°C, 3 years; 4°C, 2 years. In solvent: -80°C, 2 years; -20°C, 1 year. |
| Shipping | Room temperature in continental US; may vary elsewhere. |
Literature Cited
Sources cited in this description and in the In Vitro & In Vivo Data tab. Peer-reviewed publications that used this product are listed under References.
Safety
For Research Use Only. Not for use in diagnostic or therapeutic procedures, and not for human or veterinary use. Handle in accordance with the Safety Data Sheet and your institution's chemical hygiene plan.
In Vitro
| Solvent | Solubility | Notes |
|---|---|---|
| DMSO | 25 mg/mL (81.34 mM) | requires sonication; use freshly opened DMSO (absorbed moisture lowers solubility) |
Aliquot the stock solution and store it at -80°C (up to 2 years) or -20°C (up to 1 year); avoid repeated freeze-thaw cycles.
In Vivo
Choose the formulation that suits the animal model and route of administration; percentages are volume ratios of the final working solution. Start from a clear DMSO stock (see In Vitro above), add the co-solvents one at a time in the order listed, mixing after each addition, and prepare the working solution fresh on the day of dosing. If precipitation or phase separation occurs, gentle warming or sonication can help.
Protocol 1
| Composition | 10% DMSO + 40% PEG300 + 5% Tween-80 + 45% saline |
|---|---|
| Result | ≥ 1.43 mg/mL (4.65 mM); clear solution |
| How to prepare | Gives a clear solution at ≥ 1.43 mg/mL (saturation not determined). For 1 mL of working solution: add 100 μL DMSO stock (14.3 mg/mL) to 400 μL PEG300; then 50 μL Tween-80; then 450 μL saline to bring the volume to 1 mL. Saline: dissolve 0.9 g sodium chloride in ddH2O and make up to 100 mL. |
Protocol 2
| Composition | 10% DMSO + 90% (20% SBE-β-CD in saline) |
|---|---|
| Result | ≥ 1.43 mg/mL (4.65 mM); clear solution |
| How to prepare | Gives a clear solution at ≥ 1.43 mg/mL (saturation not determined). For 1 mL of working solution: add 100 μL DMSO stock (14.3 mg/mL) to 900 μL 20% SBE-β-CD in saline. 20% SBE-β-CD in saline: dissolve 2 g SBE-β-CD powder in 10 mL saline until clear (4°C, store up to one week). |
Protocol 3
| Composition | 10% DMSO + 90% Corn Oil |
|---|---|
| Result | ≥ 1.43 mg/mL (4.65 mM); clear solution |
| How to prepare | Gives a clear solution at ≥ 1.43 mg/mL (saturation not determined). Use with caution if continuous dosing will exceed two weeks. For 1 mL of working solution: add 100 μL DMSO stock (14.3 mg/mL) to 900 μL corn oil. |
Data provided by the manufacturer.
In Vitro
In monkey adrenal cells, orteronel suppresses ACTH-stimulated production of DHEA and androstenedione, with IC50 values of 110 nM and 130 nM, respectively. Orteronel also potently suppresses DHEA production in the human adrenocortical tumor line H295R cells, with an IC50 of 37 nM[1]. In vitro, orteronel potently inhibits rat and human steroid 17,20-lyase, with IC50 values of 54 nM and 38 nM, respectively. Orteronel does not significantly affect other CYP isoforms, including 11-hydroxylase and CYP3A4. Using microsomes that express human CYP isoforms, Orteronel inhibits 17,20-lyase more strongly than the remaining isoforms, with an IC50 of 19 nM[2].
In Vivo
Orteronel (1 mg/kg, p.o.) gives favorable pharmacokinetic parameters, namely Tmax 1.7 hours, Cmax 0.147 μg/mL, t1/2 3.8 hours and AUC0-24 hours 0.727 μg/mL[1]. Oral Orteronel at 1 mg/kg markedly lowers serum testosterone and dehydroepiandrosterone (DHEA) levels in cynomolgus monkeys[2].
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
Animal Administration[2]
House adult male cynomolgus monkeys in a temperature-controlled room (23±2°C) under a 12:12 h light/dark cycle, with illumination from 7:00 am to 7:00 pm, for the single dosing experiments. Suspend the test compounds (+)-Orteronel and (−)-Orteronel in 0.5% methylcellulose and administer orally at 1 mg/kg. Collect blood samples just before dosing and at 8 h (preliminary study) or at 2, 5 and 10 h after dosing. Store serum at −30°C until assayed by radioimmunoassay. Determine testosterone and DHEA concentrations with a Testosterone I-125 kit and a DHEA RIA kit, respectively.
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
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Dihydrotestosterone synthesis pathways from inactive androgen 5α-androstane-3β,17β-diol in prostate cancer cells: Inhibition of intratumoural 3β-hydroxysteroid dehydrogenase activities by abiraterone. Sci Rep 2016 Aug 26:6:32198.
Plumbagin improves the efficacy of androgen deprivation therapy in prostate cancer: A pre-clinical study. Prostate 2017 Dec;77(16):1550-1562.
PMID: 27561382
