6-[(7S)-7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl]-N-methyl-2-naphthalenecarboxamide
- Product Name
- 6-[(7S)-7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl]-N-methyl-2-naphthalenecarboxamide
- CAS No.
- 566939-85-3
- Chemical Name
- 6-[(7S)-7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl]-N-methyl-2-naphthalenecarboxamide
- Synonyms
- CS-517;Orteronel;(S)-Orteronel;TAK-700 (S-form);Orteronel, >=98%;TAK-700 (Orteronel);TAK700 (S-Enantiomer);TAK-700;TAK700;TAK 700;TAK-700/Orteronel (s-isomer);CYP17A1 Inhibitor II, TAK-700 - CAS 566939-85-3 - Calbiochem
- CBNumber
- CB12589726
- Molecular Formula
- C18H17N3O2
- Formula Weight
- 307.35
- MOL File
- 566939-85-3.mol
6-[(7S)-7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl]-N-methyl-2-naphthalenecarboxamide Property
- Boiling point:
- 685.1±45.0 °C(Predicted)
- Density
- 1.35
- storage temp.
- -20C
- solubility
- Soluble in DMSO
- form
- White solid
- pka
- 13.46±0.20(Predicted)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 5.32371
- Product name
- CYP17A1 Inhibitor II, TAK-700 - CAS 566939-85-3 - Calbiochem
- Packaging
- 5mg
- Price
- $184
- Updated
- 2022/05/15
- Product number
- 24191
- Product name
- Orteronel
- Purity
- ≥98%
- Packaging
- 5mg
- Price
- $178
- Updated
- 2024/03/01
- Product number
- 24191
- Product name
- Orteronel
- Purity
- ≥98%
- Packaging
- 10mg
- Price
- $319
- Updated
- 2024/03/01
- Product number
- 24191
- Product name
- Orteronel
- Purity
- ≥98%
- Packaging
- 25mg
- Price
- $704
- Updated
- 2024/03/01
- Product number
- O697600
- Product name
- Orteronel
- Packaging
- 25mg
- Price
- $210
- Updated
- 2021/12/16
6-[(7S)-7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl]-N-methyl-2-naphthalenecarboxamide Chemical Properties,Usage,Production
Uses
Orteronel is an androgen synthesis inhibitor that selectively inhibits enzyme CYP17A1, which is expressed in testicular, adrenal and prostatic tumor tissues.
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].
target
17,20-lyase
IC 50
orteronel inhibited monkey 17,20-lyase and 17-hydroxylase activities with ic50 values of 27 and 38 nmol/l, respectively [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.
6-[(7S)-7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl]-N-methyl-2-naphthalenecarboxamide Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 6-[(7S)-7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl]-N-methyl-2-naphthalenecarboxamide manufacturers
- Product
- Orteronel 566939-85-3
- Price
- US $15.00-10.00/KG
- Min. Order
- 1KG
- Purity
- 99%+ HPLC
- Supply Ability
- Monthly supply of 1 ton
- Release date
- 2021-07-10
- Product
- Orteronel 566939-85-3
- Price
- US $15.00-10.00/KG
- Min. Order
- 1KG
- Purity
- 99%+ HPLC
- Supply Ability
- Monthly supply of 1 ton
- Release date
- 2021-07-09