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Merck
CN

F9397

Flutamide

Non-steroidal anti-androgen drug

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

Key Documents

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Product Name

Flutamide,

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.

Signal Word

Warning

Hazard Statements

H302,H351,H361,H373,H411

Hazard Classifications

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

Target Organs

Liver

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW9761
MKCT5085
MKCR8700
MKCP9859
MKCL6929

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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)
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
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.
Kai Xue et al.
Molecular endocrinology (Baltimore, Md.), 26(12), 2004-2015 (2012-10-03)
Nuclear receptor subfamily 4 group A member1 (NR4A1), an orphan nuclear receptor, is involved in the transcriptional regulation of thecal cell androgen biosynthesis and paracrine factor insulin-like 3 (INSL3) expression. Androgens are known to play an important regulatory role in
View All Related Papers

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Product Information Sheet - F9397

Product Information Sheet

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