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Chemical Structure| 13311-84-7 Chemical Structure| 13311-84-7

Structure of Flutamide
CAS No.: 13311-84-7

Chemical Structure| 13311-84-7

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Flutamide is a competitive non-steroidal antagonist of androgen receptor.

Synonyms: SCH 13521; Niftolide; Testotard. FLUT.

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Product Details of Flutamide

CAS No. :13311-84-7
Formula : C11H11F3N2O3
M.W : 276.21
SMILES Code : CC(C)C(NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1)=O
Synonyms :
SCH 13521; Niftolide; Testotard. FLUT.
MDL No. :MFCD00072009
InChI Key :MKXKFYHWDHIYRV-UHFFFAOYSA-N
Pubchem ID :3397

Safety of Flutamide

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H332-H362-H372-H411
Precautionary Statements:P201-P260-P263-P264-P270-P271-P273-P304+P340+P312-P308+P313-P391-P501
Class:9
UN#:3077
Packing Group:

Isoform Comparison

Biological Activity

Target
  • Androgen Receptor

    Androgen Receptor, Ki:55 nM

In Vitro:

Cell Line
Concentration Treated Time Description References
HepG2 cells 0.05–300 µM 2 hours To compare the mitochondrial toxicity of flutamide, 2-hydroxyflutamide, and bicalutamide in glucose or galactose-conditioned cells. Flutamide and 2-hydroxyflutamide significantly reduced ATP content in galactose medium, indicating mitochondrial toxicity. Toxicol Sci. 2016 Oct;153(2):341-51.
Mouse primary hepatocytes 10 µM or 50 µM 24 hours FLU elevated Cyp1a1, Cyp1a2, Cyp1b1, Nqo1, and Gsta1 mRNA levels at both 10 and 50 μM, indicating that FLU directly activates the AhR signaling pathway. Biochem Pharmacol. 2016 Nov 1;119:93-104.
HepG2 cells 5 µM, 20 µM, and 100 µM 24 hours FLU significantly increased AhR-dependent luciferase activity at 5 μM and higher concentrations, indicating that FLU can activate AhR. Biochem Pharmacol. 2016 Nov 1;119:93-104.
Hepa-1c1c7 cells 5 µM, 20 µM, and 100 µM 24 hours FLU significantly increased AhR-dependent luciferase activity at 5 μM and higher concentrations, indicating that FLU can activate AhR. Biochem Pharmacol. 2016 Nov 1;119:93-104.
Human keratinocytes (HaCaT) 5 mg/ml 72 hours To investigate the effect of Flutamide on HaCaT cell proliferation, results showed that F-PCL and DF-PCL scaffolds significantly increased HaCaT cell proliferation. FASEB J. 2022 May;36(5):e22310.

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
C57BL/6N C57BL/6N mice Gavage 200 mg/kg Once daily for 28 days After 28 days of FLU treatment, a significant increase in liver weights and liver/body weight ratios was observed, along with elevated bile acid levels in serum and liver, indicating that FLU induced hepatomegaly and disrupted bile acid homeostasis. Biochem Pharmacol. 2016 Nov 1;119:93-104.
BALB/C mice Severe burn wound healing model Topical administration 5 mg/ml Single administration, lasting 28 days To investigate the effect of Flutamide on burn wound healing in mice, results showed that F-PCL scaffolds significantly accelerated wound healing, and DF-PCL scaffolds further promoted wound healing. FASEB J. 2022 May;36(5):e22310.

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

3.62mL

0.72mL

0.36mL

18.10mL

3.62mL

1.81mL

36.20mL

7.24mL

3.62mL

Dissolving Methods
Please choose the appropriate dissolution scheme according to your animal administration guide.For the following dissolution schemes, clear stock solution should be prepared according to in vitro experiments, and then cosolvent should be added in turn:

in order to ensure the reliability of the experimental results, the clarified stock solution can be properly preserved according to the storage conditions; The working fluid for in vivo experiment is recommended to be prepared now and used on the same day;

The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound.
Protocol 1
Protocol 2

References

[1]Luthy IA, Begin DJ, Labrie F. Androgenic activity of synthetic progestins and spironolactone in androgen-sensitive mouse mammary carcinoma (Shionogi) cells in culture. J Steroid Biochem. 1988 Nov;31(5):845-52.

[2]Simard J, Luthy I, et al. Characteristics of interaction of the antiandrogen flutamide with the androgen receptor in various target tissues. Mol Cell Endocrinol. 1986 Mar;44(3):261-70.

[3]Raghow S, Kuliyev E, et al. Efficacious chemoprevention of primary prostate cancer by flutamide in an autochthonous transgenic model. Cancer Res. 2000 Aug 1;60(15):4093-7.

[4]Pu Y, Xu M, et al. Androgen receptor antagonists compromise T cell response against prostate cancer leading to early tumor relapse. Sci Transl Med. 2016 Apr 6;8(333):333ra47.

[5]Wang HX, Liu X, et al. Induction of liver cytochrome P450 1A2 expression by flutamide in rats. Acta Pharmacol Sin. 2005 Nov;26(11):1382-6.

[6]Elzoghby AO, Helmy MW, et al. Novel ionically crosslinked casein nanoparticles for flutamide delivery: formulation, characterization, and in vivo pharmacokinetics. Int J Nanomedicine. 2013;8:1721-32.

[7]Shukla GC, Plaga AR, Shankar E, Gupta S. Androgen receptor-related diseases: what do we know? Andrology. 2016 May;4(3):366-81. doi: 10.1111/andr.12167. Epub 2016 Mar 16. PMID: 26991422.

[8]Simard J, Luthy I, Guay J, Bélanger A, Labrie F. Characteristics of interaction of the antiandrogen flutamide with the androgen receptor in various target tissues. Mol Cell Endocrinol. 1986 Mar;44(3):261-70. doi: 10.1016/0303-7207(86)90132-2. PMID: 3956856.

[9]Marchetti B, Labrie F. Characteristics of flutamide action on prostatic and testicular functions in the rat. J Steroid Biochem. 1988 Jun;29(6):691-8. doi: 10.1016/0022-4731(88)90170-7. PMID: 2838689.

 

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