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

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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:

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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