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

• ChemBase ID: 382
• Molecular Formular: C11H11F3N2O3
• Molecular Mass: 276.2118496
• Monoisotopic Mass: 276.07217688
• SMILES: FC(F)(F)c1cc(NC(=O)C(C)C)ccc1[N+](=O)[O-]
• Canonical SMILES: O=C(C(C)C)Nc1ccc(c(c1)C(F)(F)F)[N+](=O)[O-]
• InChI: 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)
• InChIKey: MKXKFYHWDHIYRV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
• IUPAC Traditional name: flutamide
• Brand Name: Cebatrol; Eulexin; Niftholide; Niftolide
• Synonyms: Eulexin; Flutamin; Drogenil; FTA; Flutamide USP25; Flutamide; 2-Methyl-N-(4-nitro-3-[trifluoromethyl]phenyl)propanamide; Flutamide; 2-Methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide; N-(Isopropylcarbonyl)-4-nitro-3-trifluoromethylaniline; 4'-Nitro-3'-trifluoromethylisobutyranilide; Drognil; Euflex; Sch 13521; Flutamide; 2-Methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide

Database IDs

• CAS Number: 13311-84-7
• EC Number: 236-341-9
• MDL Number: MFCD00072009
• PubChem SID: 24278446; 46508874; 160963845
• PubChem CID: 3397

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.17286
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.272311
• LogD (pH = 7.4): 3.2723103
• Log P: 3.272311
• Molar Refractivity: 63.4208 cm^3
• Polarizability: 22.133842 Å^3
• Polar Surface Area: 74.92 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.55
• LOG S: -4.69
• Solubility (Water): 5.66e-03 g/l

PROPERTIES

Physical Property

• Solubility: 9.45 mg/L; DMSO; Methanol
• Apperance: Light Yellow Solid
• Melting Point: 110-112°C
• Hydrophobicity(logP): 2.6; 3.335

Safety Information

• Storage Condition: -20°C; Refrigerator
• Storage Warning: Irritant
• RTECS: UG5700000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 63-20/21/22
• Safety Statements: 22-36
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332-H361
• GHS Precautionary statements: P280
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Pharmacology Properties

• Gene Information: human ... AR(367)mouse ... Ar(11835)rat ... Ar(24208)

Product Information

• Purity: 95%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C11H11F3N2O3

DETAILS

DrugBank - DB00499

• Drug Groups: approved
• Description: An antiandrogen with about the same potency as cyproterone in rodent and canine species.
• Indication: For the management of locally confined Stage B2-C and Stage D2 metastatic carcinoma of the prostate
• Pharmacology: Flutamide is a nonsteroidal antiandrogen. In animal studies, flutamide demonstrates potent antiandrogenic effects. It exerts its antiandrogenic action by inhibiting androgen uptake and/or by inhibiting nuclear binding of androgen in target tissues or both. Prostatic carcinoma is known to be androgen-sensitive and responds to treatment that counteracts the effect of androgen and/or removes the source of androgen, e.g. castration. Elevations of plasma testosterone and estradiol levels have been noted following flutamide administration.
• Toxicity: In animal studies with flutamide alone, signs of overdose included hypoactivity, piloerection, slow respiration, ataxia, and/or lacrimation, anorexia, tranquilization, emesis, and methemoglobinemia.
• Affected Organisms: Humans and other mammals
• Biotransformation: Flutamide is rapidly and extensively metabolized, with flutamide comprising only 2.5% of plasma radioactivity 1 hour after administration.
• Absorption: Rapidly and completely absorbed.
• Half Life: The plasma half-life for the alpha-hydroxylated metabolite of flutamide (an active metabolite) is approximately 6 hours.
• Protein Binding: 94-96%
• Elimination: Flutamide and its metabolites are excreted mainly in the urine with only 4.2% of a single dose excreted in the feces over 72 hours.
• References: [Link]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S1908

Research Area: Cancer
Biological Activity:
Flutamide (Eulexin, Flutamin) is an oral nonsteroidal antiandrogen agent primarily used to treat prostate cancer. Flutamide (Eulexin, Flutamin) competes with testosterone and its powerful metabolite, dihydrotestosterone (DHT) for binding to androgen receptors in the prostate gland. By doing so, flutamide (Eulexin, Flutamin) prevents them from stimulating the prostate cancer cells to grow. [1]

Sigma Aldrich - F9397

Biochem/physiol Actions
Flutamide is a non-steroidal anti-androgen.
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.

Toronto Research Chemicals - F598850

Flutamide is a nonsteroidal antiandrogen drug; antineoplastic (hormonal).

REFERENCES

• Link
• http://en.wikipedia.org/wiki/Flutamide
• Neri, et al.: Endocrinology, 91, 427 (1972)
• Sogani, P.C., et al.: J. Urol., 122, 640 (1972)
• Greenway, B.A., et al.: Br. Med. J., 316, 1935 (1972)