6-[(7S)-7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl]-N-methyl-2-naphthalenecarboxamide
Synonym(s):6-((7 S)-7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide, Orteronel, TAK700;6-((7S)-7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide, Orteronel, TAK700;CYP17A1 Inhibitor II, TAK-700 - CAS 566939-85-3 - Calbiochem
- CAS NO.:566939-85-3
- Empirical Formula: C18H17N3O2
- Molecular Weight: 307.35
- MDL number: MFCD20528078
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-07-02 08:55:00
What is 6-[(7S)-7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl]-N-methyl-2-naphthalenecarboxamide?
The Uses of 6-[(7S)-7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl]-N-methyl-2-naphthalenecarboxamide
Orteronel is an androgen synthesis inhibitor that selectively inhibits enzyme CYP17A1, which is expressed in testicular, adrenal and prostatic tumor tissues.
What are the applications of Application
TAK-700 is a steroid 17,20-lyase inhibitor with efficacy in rat, monkey, and human cells
Biological Activity
orteronel is an androgen biosynthesis inhibitor. it selectively inhibits the enzyme cyp17a1 which is expressed in testicular, adrenal, and prostatic tumor tissues. cyp17 catalyzes two sequential reactions: (a) the conversion of pregnenolone and progesterone to their 17α-hydroxy derivatives by its 17α-hydroxylase activity, and (b) the subsequent formation of dehydroepiandrosterone (dhea) and androstenedione, respectively, by its 17,20-lyase activity ).
in vitro
orteronel potently suppresses androgen production in monkey adrenal cells but only weakly suppresses corticosterone and aldosterone production; the ic50 value of orteronel for cortisol was about 3-fold higher than that for dhea. moreover, in human cyp17a1 and human adrenal tumor cells, orteronel inhibited 17,20-lyase activity 5.4 times more potently than 17-hydroxylase activity in cell-free enzyme assays and dhea production 27 times more potently than cortisol production in human adrenal tumor cells, suggesting greater specificity of inhibition between 17,20-lyase and 17-hydroxylase activities in humans vs monkeys [1].
in vivo
after orteronel single oral dosing, serum levels of dhea, cortisol, and testosterone were rapidly suppressed in intact cynomolgus monkeys. in castrated monkeys treated twice daily with orteronel, suppression of dhea and testosterone persisted throughout the treatment period. these findings suggest that orteronel may be an effective therapeutic option for diseases where androgen suppression is critical, such as androgen sensitive and crpc [1].
References
[1] yamaoka m, hara t, hitaka t, kaku t, takeuchi t, takahashi j, asahi s, miki h, tasaka a, kusaka m. 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;129(3-5):115-28.
Properties of 6-[(7S)-7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl]-N-methyl-2-naphthalenecarboxamide
Boiling point: | 685.1±45.0 °C(Predicted) |
Density | 1.35 |
storage temp. | -20C |
solubility | Soluble in DMSO |
pka | 13.46±0.20(Predicted) |
form | White solid |
color | White to light brown |
Safety information for 6-[(7S)-7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl]-N-methyl-2-naphthalenecarboxamide
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 6-[(7S)-7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl]-N-methyl-2-naphthalenecarboxamide
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