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F9397

Sigma-Aldrich

Flutamide

Synonym(s):

2-Methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide

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1 G
$49.70
5 G
$170.00

About This Item

Empirical Formula (Hill Notation):
C11H11F3N2O3
CAS Number:
13311-84-7
Molecular Weight:
276.21
EC Number:
236-341-9
MDL number:
MFCD00072009
UNSPSC Code:
51111800
PubChem Substance ID:
24278446
NACRES:
NA.77

$49.70

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Quality Level

100

originator

Schering Plough

SMILES string

CC(C)C(=O)Nc1ccc(c(c1)C(F)(F)F)[N+]([O-])=O

InChI

1S/C11H11F3N2O3/c1-6(2)10(17)15-7-3-4-9(16(18)19)8(5-7)11(12,13)14/h3-6H,1-2H3,(H,15,17)

InChI key

MKXKFYHWDHIYRV-UHFFFAOYSA-N

Gene Information

human ... AR(367)
mouse ... Ar(11835)
rat ... Ar(24208)

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Application

Flutamide has been used to effect of testosterone on Glial cell-derived neurotrophic factor (Gdnf) mRNA production in vitro.[1] It has also been used to study the effects of flutamide on anogenital distance and nipple retention.[2]

Biochem/physiol Actions

Flutamide is a non-steroidal anti-androgen drug. It consists of a nitroaromatic structure. Flutamide is a potent competitor of testosterone and dihydrotestosterone receptors. It is a potent hepatotoxin.[3]

Features and Benefits

This compound was developed by Schering Plough. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

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Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Carc. 2 - Repr. 2 - STOT RE 2

target_organs

Liver

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW9761
MKCT5085
MKCR8700
MKCP9859
MKCL6929

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Flutamide-induced hepatotoxicity: ethical and scientific issues
Giorgetti R, et al.
European Review for Medical and Pharmacological Sciences, 21(1 Suppl), 69-77 (2017)
N A Spry et al.
Prostate cancer and prostatic diseases, 16(1), 67-72 (2012-08-22)
To examine changes to whole body and regional lean mass (LM) and fat mass (FM) over 33 months of intermittent androgen suppression therapy (IAST). Phase II cohort study of 72 prostate cancer patients without metastatic bone disease. Patients received flutamide
Shuchen Gu et al.
Cellular signalling, 25(1), 66-73 (2013-01-15)
Actin cytoskeleton reorganization initiated by testosterone conjugates through activation of membrane androgen receptors (mAR) has recently been reported in colon tumor cells. This mAR-induced actin reorganization was recognized as a critical initial event, controlling apoptosis and inhibiting cell migration. The
Anthony Schroeder et al.
General and comparative endocrinology, 281, 7-16 (2019-05-07)
Sex steroids are involved in sex determination in almost all vertebrates, including species with temperature-dependent sex determination (TSD). It is well established that aromatase and estrogens are involved in ovary determination in TSD species. In contrast, the role of non-aromatizable
Combined exposure to anti-androgens exacerbates disruption of sexual differentiation in the rat
Hass U, et al.
Environmental Health Perspectives, 115(Suppl 1), 122-128 (2007)
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Questions

  1. How Can I prepare 1nM solution of flutamide? flutamide dissolves in ethanol? AFTER DISSOLVING flutamide IN ETHANOL , WHATS the storage conditions and useful life?

    1 answer

    1. Flutamide is soluble in ethanol (50 mg/ml) with heat as needed, yielding a clear to hazy, yellow to yellow-green solution. It is also soluble in acetone, ethyl acetate, methanol, chloroform, and ether.

      The molecular weight of flutamide is 276.21, and this value can be used to calculate the amount needed to make a 1nM solution in the desired volume:
      https://www.sigmaaldrich.com/support/calculators-and-apps/mass-molarity-calculator

      Using freshly made solutions whenever possible is always recommended, but storing them at -20°C in non-diluted aliquots should maintain their stability for at least one month.

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