ChemicalBook > CAS DataBase List > 6-[(7S)-7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl]-N-methyl-2-naphthalenecarboxamide

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
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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)
color 
White to light brown
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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.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
5.32371
Product name
CYP17A1 Inhibitor II, TAK-700 - CAS 566939-85-3 - Calbiochem
Packaging
5mg
Price
$184
Updated
2022/05/15
Cayman Chemical
Product number
24191
Product name
Orteronel
Purity
≥98%
Packaging
5mg
Price
$178
Updated
2024/03/01
Cayman Chemical
Product number
24191
Product name
Orteronel
Purity
≥98%
Packaging
10mg
Price
$319
Updated
2024/03/01
Cayman Chemical
Product number
24191
Product name
Orteronel
Purity
≥98%
Packaging
25mg
Price
$704
Updated
2024/03/01
TRC
Product number
O697600
Product name
Orteronel
Packaging
25mg
Price
$210
Updated
2021/12/16
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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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6-[(7S)-7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl]-N-methyl-2-naphthalenecarboxamide Suppliers

Shanghai Boyle Chemical Co., Ltd.
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sales@boylechem.com
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China
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J & K SCIENTIFIC LTD.
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GIHI CHEMICALS CO.,LTD
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AdooQ Bioscience CHINA
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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

Zhuozhou Wenxi import and Export Co., Ltd
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
Zhuozhou Wenxi import and Export Co., Ltd
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

566939-85-3, 6-[(7S)-7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl]-N-methyl-2-naphthalenecarboxamideRelated Search:


  • 6-[(7S)-7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl]-N-methyl-2-naphthalenecarboxamide
  • Orteronel
  • TAK-700 (S-form)
  • TAK-700 (Orteronel)
  • Orteronel, >=98%
  • (S)-Orteronel
  • CYP17A1 Inhibitor II, TAK-700 - CAS 566939-85-3 - Calbiochem
  • TAK-700;TAK700;TAK 700
  • CS-517
  • 2-Naphthalenecarboxamide, 6-[(7S)-6,7-dihydro-7-hydroxy-5H-pyrrolo[1,2-c]imidazol-7-yl]-N-methyl-
  • TAK700 (S-Enantiomer)
  • TAK-700/Orteronel (s-isomer)
  • (S)-6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide
  • 566939-85-3
  • Inhibitors