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

Orteronel, TAK-700, 17,20-Lyase Inhibitor, [566939-85-3]

MSDS (material safety data sheet) or SDS, CoA and CoQ, dossiers, brochures and other available documents.

Synonyms: 6-((7S)-7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide, Orteronel, TAK700

Primary Target: 17,20-lyase
532371
  
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      Overview

      Replacement Information

      Key Spec Table

      CAS #Empirical Formula
      566939-85-3C₁₈H₁₇N₃O₂
      Description
      Overview

      This product has been discontinued.



      A 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
      Quality LevelMQ100
      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
      Global Trade Item Number
      Catalogue Number GTIN
      532371 0

      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 Protect from light
      -20°C
      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.