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KI1079Flutamide1 g$62

Chemical Characteristic

Product NameFlutamide
SynonymsEulexin, SCH 13521
CAS No.13311-84-7
Molecular Weight 276.21
FormulaC11H11F3N2O3
Chemical Name2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
SmilesC(=O)(C(C)C)Nc1cc(c(cc1)[N](=O)O)C(F)(F)F
Chemical Structure

Biological activities

Flutamide is an oral, non-steroidal antiandrogen drug primarily used to treat prostate cancer. Flutamide competes with testosterone and dihydrotestosterone (DHT) for binding to androgen receptors in the prostate gland. In vitro, flutamide (10 µM) prevents androgen up-regulation of arylamine N-acetyltransferase type I (NAT1) in 22Rv1 cells.[1] Flutamide blocks the effect of dihydrotestosterone on hypoxia-inducible factor 1. [2] In male C3H/HeN mice in vivo, treatment with 25 mg/kg body weight flutamide following trauma-hemorrhage results in levels of cytokine release which are comparable with those found in sham-operated animals.[3] In intact mature rats and aged dogs with prostatic hyperplasia, flutamide ignificantly reduces prostate size without altering sexual potency and libido. When administered to castrated rats, flutamide effectively blocks the effects of several androgens on ventral prostate and seminal-vesicle weights. Flutamide inhibits he formation of the nuclear 3S [3H] protein-androgen receptor in addition to decreasing whole-tissue uptake and retention of [3H] testosterone.[4]

Protocols

In vitro: Flutamide is dissolved in DMSO.[2]

References

[1] Butcher NJ, et al. Induction of human arylamine N-acetyltransferase type I by androgens in human prostate cancer cells. Cancer Res. 2007, 67(1): 85-92.
[2] Mabjeesh NJ, et al. Androgens stimulate hypoxia-inducible factor 1 activation via autocrine loop of tyrosine kinase receptor/phosphatidylinositol 3'-kinase/protein kinase B in prostate cancer cells. Clin Cancer Res. 2003, 9(7): 2416-2425.
[3] Wichmann MW, et al. Flutamide: a novel agent for restoring the depressed cell-mediated immunity following soft-tissue trauma and hemorrhagic shock. Shock. 1997, 8(4): 242-248.
[4] Neri R, et al. Anti-androgenicity of flutamide and its metabolite Sch 16423. Biochem Soc Trans. 1979, 7(3): 565-569.

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