F9397

Sigma-Aldrich

Flutamide

Synonym(s):
2-Methyl-N-4-nitro-3-(trifluoromethyl)phenylpropanamide
Empirical Formula (Hill Notation):
C11H11F3N2O3
CAS Number:
Molecular Weight:
276.21
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77
Pricing and availability is not currently available.

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.

Packaging

1, 5 g in poly bottle

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 is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.
This compound was developed by Schering Plough. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. F9397.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Pictograms

Exclamation markHealth hazard

Signal Word

Warning

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

Xn

Risk Statement

63-20/21/22

Safety Statement

22-36

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Vasantha Padmanabhan et al.
Endocrinology, 156(7), 2678-2692 (2015-04-29)
Prenatal T excess induces maternal hyperinsulinemia, early puberty, and reproductive/metabolic defects in the female similar to those seen in women with polycystic ovary syndrome. This study addressed the organizational/activational role of androgens and insulin in programming pubertal advancement and periovulatory...
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)
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...
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...
Palakkil Mavilavalappil Sandeep et al.
Metabolic syndrome and related disorders, 13(6), 248-254 (2015-04-29)
Polycystic ovary syndrome (PCOS) is a major hyperandrogenic disorder. Many drugs prescribed specifically to treat PCOS have side effects; however, previous studies suggest that natural therapeutics including botanicals may be less invasive and equally effective for the management of PCOS....

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