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F9397

Sigma-Aldrich

Flutamide

Synonym(s):

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

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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

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. It has also been used to study the effects of flutamide on anogenital distance and nipple retention.

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.

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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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
Flutamide-induced hepatotoxicity: ethical and scientific issues
Giorgetti R, et al.
European Review for Medical and Pharmacological Sciences, 21(1 Suppl), 69-77 (2017)
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)
Santiago Rolon et al.
Physiological reports, 9(1), e14663-e14663 (2021-01-05)
Hypoxia is common with preterm birth and may lead to long-term effects on adult pancreatic endocrine function and insulin sensitivity. This phenomenon may be sexually dimorphic due to the hypoxia-induced augmentation of the neonatal androgen surge in male newborns. We
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
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