532371 CYP17A1 Inhibitor II, TAK-700 - CAS 566939-85-3 - Calbiochem

532371
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      Overview

      Replacement Information

      Key Specifications Table

      Empirical FormulaCAS #
      C₁₈H₁₇N₃O₂ 566939-85-3

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          Glass bottle 5 mg
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          Description
          OverviewA cell-permeable, orally bioavailable, nontoxic, nonsteroidal naphthylmethylimidazole compound that as a potent, selective and reversible inhibitor of 17,20-lyase (IC50 = 140 nM, 27 nM, and 1.2 µM in human, monkey, and rat, respectively) and reduces the weight of androgen-dependent organs. At higher concentrations, affects 17α-hydroxylase (IC50 = 760, 38 and > 10,000 nM in human, monkey and rat, respectively) activity with minimal effect on 11β-hydroxylase. Suppresses testosterone (IC50 = 640 nM) and androstenedione (IC50 = 210 nM) production without affecting the synthesis of corticosterone or aldosterone in rats (up to 30 µM). Displays desirable pharmacokinetic properties (t1/2 - 3.8 h; Tmax = 1.7 h; AUC = 0.727 mg h/ml following an oral dose of 1 mg/kg in monkey).

          Please note that the molecular weight for this compound is batch-specific due to variable water content.
          Catalogue Number532371
          Brand Family Calbiochem®
          Synonyms6-((7S)-7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide, Orteronel, TAK700
          References
          ReferencesDreicer, R., et al. 2014. Clin. Cancer Res. 20, 1335.
          Yin, L. and Hu, Q., 2014. Nat. Rev. Urol. 11, 32.
          Hara, T., et al. 2013.J. Steroid Biochem. Mol. Biol. 134, 80.
          Yamaoka, M., et al. 2012. J. Steroid Biochem. Mol. Biol. 129, 115.
          Kaku, T., et al. 2011. Bioorg. Med. Chem. 19, 6383.
          Product Information
          CAS number566939-85-3
          FormWhite solid
          Hill FormulaC₁₈H₁₇N₃O₂
          Chemical formulaC₁₈H₁₇N₃O₂
          ReversibleY
          Applications
          Biological Information
          Primary Target17,20-lyase
          Secondary target17α-hydroxylase
          Purity≥98% by HPLC
          Physicochemical Information
          Cell permeableY
          Dimensions
          Materials Information
          Toxicological Information
          Safety Information according to GHS
          Safety Information
          Product Usage Statements
          Storage and Shipping Information
          Ship Code Ambient Temperature Only
          Toxicity Standard Handling
          Storage -20°C
          Protect from Light Protect from light
          Do not freeze Ok to freeze
          Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
          Packaging Information
          Packaged under inert gas Packaged under inert gas
          Transport Information
          Supplemental Information
          Specifications

          Documentation

          CYP17A1 Inhibitor II, TAK-700 - CAS 566939-85-3 - Calbiochem SDS

          Title

          Safety Data Sheet (SDS) 

          References

          Reference overview
          Dreicer, R., et al. 2014. Clin. Cancer Res. 20, 1335.
          Yin, L. and Hu, Q., 2014. Nat. Rev. Urol. 11, 32.
          Hara, T., et al. 2013.J. Steroid Biochem. Mol. Biol. 134, 80.
          Yamaoka, M., et al. 2012. J. Steroid Biochem. Mol. Biol. 129, 115.
          Kaku, T., et al. 2011. Bioorg. Med. Chem. 19, 6383.
          Data Sheet

          Note that this data sheet is not lot-specific and is representative of the current specifications for this product. Please consult the vial label and the certificate of analysis for information on specific lots. Also note that shipping conditions may differ from storage conditions.

          Revision19-December-2014 JSW
          Synonyms6-((7S)-7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide, Orteronel, TAK700
          DescriptionA cell-permeable, orally bioavailable (Tmax/Cmax/AUC = 1.7 h/147 ng·mL-1/727 ng·h·mL-10-24 h/monkey & 1.7 h/39 ng·mL-1/177 ng·h·mL-10-8 h/rat; 1 mg/kg p.o.), nonsteroidal, optically active naphthylmethylimidazole compound that acts as a potent, reversible, substrate-competitive inhibitor against the 17,20-lyase activity (IC50/[substrate] = 19 nM/10 nM 17α-hydroxypregnenolone/rhP450c17, 27 nM/5 µM 17α-hydroxypregnenolone/monkey adrenal microsomes, 48 nM/10 nM 17α-hydroxyprogesterone /rat testicular microsomes, 140 nM/5 µM 17α-hydroxypregnenolone/rhP450c17, 1.2 µM/5 µM 17α-hydroxyprogesterone /rat testicular microsomes) of cytochrome P450 17A1 (CYP17A1; P450c17), while inhibiting only human & monkey, but not rat, CYP17A 17α-hydroxylase activity (IC50/[substrate] = 38 nM/5 µM pregnenolone/monkey adrenal microsomes, 760 nM/5 µM pregnenolone/rhP450c17, >10 µM/5 µM progesterone/rat testicular microsomes) and exhibiting much reduced or little potency against 11β-hydroxylase activity (IC50 >1 µM/rat testicular microsomes & >10 µM/monkey adrenal microsomes) or 9 other human CYP isoforms (IC50 = 14 µM/2C19 & >30 µM/1A2, 2A6, 2B6, 2C8, 2C9, 2D6, 2E1, 3A4). Consistent with its enzyme inhibition activity, TAK-100 is shown to cause cellular progesterone built-up and reduce dehydroepiandrosterone (DHEA) & androstenedione production in human adrenocortical tumor cell NCI-H295R (IC50 = 37 & 54 nM, respectively), ATCH-stimulated primary monkey adrenal cell (IC50 = 110 & 130 nM, respectively), and hCG-stimulated primary rat testicular cell (IC50 = 210 nM against androstenedione production) cultures with greater potency and selectivity than Ketoconazole (Cat. No. 420600). Oral administration is reported to result in reduced serum steroid levels in vivo among male cynomolgus monkeys (0.3 to 10 mg/kg for single & 3 to 15 mg/kg/12 h for multiple oral dosing) with or without castration and hypophysectomized male rats (30 to 300 mg/kg for single & 37.5 to 600 mg/kg/8 h for multiple oral dosing).
          FormWhite solid
          Intert gas (Yes/No) Packaged under inert gas
          CAS number566939-85-3
          Chemical formulaC₁₈H₁₇N₃O₂
          Purity≥98% by HPLC
          SolubilityDMSO (10 mg/ml)
          Storage -20°C
          Protect from light
          Do Not Freeze Ok to freeze
          Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
          Toxicity Standard Handling
          ReferencesDreicer, R., et al. 2014. Clin. Cancer Res. 20, 1335.
          Yin, L. and Hu, Q., 2014. Nat. Rev. Urol. 11, 32.
          Hara, T., et al. 2013.J. Steroid Biochem. Mol. Biol. 134, 80.
          Yamaoka, M., et al. 2012. J. Steroid Biochem. Mol. Biol. 129, 115.
          Kaku, T., et al. 2011. Bioorg. Med. Chem. 19, 6383.