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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.

Brochure

Title
NPI Flyer- Epigenetics and Nuclear Function Feature
New Products - Antibodies, Small Molecule, Inhibitors

Technical Info

Title
White Paper: Further considerations of antibody validation and usage.
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.