FLUTAMIDE
Flutamide
CAS: 13311-84-7
Molecular Formula: C11H11F3N2O3
FLUTAMIDE - Names and Identifiers
| Name | Flutamide |
| Synonyms | Flutamide FLUTAMIDE AURORA KA-860 Flutamide USP25 TIMTEC-BB SBB006930 2-METHYL-N-(4-NITRO-3-[TRIFLUOROMETHYL]PHENYL)PROPANAMIDE N1-[4-NITRO-3-(TRIFLUOROMETHYL)PHENYL]-2-METHYLPROPANAMIDE 2-METHYL-N-(4'-NITRO-3'-(TRIFLUOROMETHYL)PHENYL)PROPANAMIDE 2-Methyl-N-[4-nitro-3-(trifluoromethyl)-phenyl]-propionamide |
| CAS | 13311-84-7 |
| EINECS | 236-341-9 |
| InChI | InChI=1/C11H11F4NO/c1-6(2)10(17)16-7-3-4-9(12)8(5-7)11(13,14)15/h3-6H,1-2H3,(H,16,17) |
FLUTAMIDE - Physico-chemical Properties
| Molecular Formula | C11H11F3N2O3 |
| Molar Mass | 276.21 |
| Density | 1.3649 (estimate) |
| Melting Point | 112 °C |
| Boling Point | 400.3±45.0 °C(Predicted) |
| Solubility | Practically insoluble in water, freely soluble in acetone and in ethanol (96 per cent). |
| Appearance | Pale yellow solid |
| Color | Pale Yellow to Light Yellow |
| Merck | 14,4208 |
| pKa | 13.12±0.70(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.477 |
| MDL | MFCD00072009 |
| Physical and Chemical Properties | Yellow crystalline powder. Slightly insoluble in water. Melting point 111.5-112.5 °c (benzene). Acute toxicity LD50 mice (mg/kg):795.5-898.1 oral. |
| Use | Suitable for the treatment of prostate cancer and prostatic hypertrophy |
FLUTAMIDE - Risk and Safety
| Risk Codes | R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R63 - Possible risk of harm to the unborn child R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S22 - Do not breathe dust. S36 - Wear suitable protective clothing. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S27 - Take off immediately all contaminated clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
| RTECS | UG5700000 |
| HS Code | 29242990 |
FLUTAMIDE - Upstream Downstream Industry
| Raw Materials | Pyridine Isobutyryl chloride |
FLUTAMIDE - Standard
Authoritative Data Verified Data
This product is N-[4-nitro-3-(trifluoromethyl) phenyl]-2-methylpropionamide. The content of C11H11F3N203 shall be between 98.0% and 102.0% based on the dry product.
Last Update：2024-01-02 23:10:35
FLUTAMIDE - Trait
Authoritative Data Verified Data
- This product is light yellow crystal or crystalline powder; Odorless.
- This product is soluble in methanol or ethanol, dissolved in chloroform, almost insoluble in water.
melting point
The melting point of this product (General 0612) is 110~114°C.
absorption coefficient
take this product, precision weighing, plus ethanol dissolution and quantitative dilution to make a solution containing about 20ug per lml, according to UV-visible spectrophotometry (General 0401), the absorbance was measured at a wavelength of 295nm, and the absorption coefficient) was 284 to 302.
Last Update：2022-01-01 13:40:30
FLUTAMIDE - Differential diagnosis
Authoritative Data Verified Data
- take about 20mg of this product, add 1.5ml of newly prepared 5% ferrous ammonium sulfate solution, add 2 drops of dilute sulfuric acid and 1ml of 2mol/L potassium hydroxide methanol solution, shake, A red-brown precipitate should form within 2 minutes.
- take about 0.1g of this product, add 5ml of dilute hydrochloric acid, boil for 1 min, let it cool, filter, add several drops of sodium nitrite solution to the filtrate, shake well, add several drops of alkaline B- naphthol solution, that is, an orange-yellow precipitate was formed.
- the solution under the term of absorption coefficient has the maximum absorption at the wavelengths of 227nm and 295nm as determined by ultraviolet-visible spectrophotometry (General rule 0401), there is minimal absorption at a wavelength of 252nm.
- The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 797).
Last Update：2022-01-01 13:40:31
FLUTAMIDE - Exam
Authoritative Data Verified Data
clarity of ethanol solution
take this product l.Og, add ethanol 10ml to dissolve, the solution should be clarified (General rule 0902 The first method).
sulfate
take this product l. Add 50ml of water, heat and shake fully, cool, filter, take 25ml of filtrate, check according to law (General rule 0802), compare with the control solution made of standard potassium sulfate solution, no more concentrated (0.02%).
fluorine
take this product about 10mg, precision weighing, according to the fluorine inspection method (General 0805) determination, fluorine content should be 18.6% ~ 21.2%.
Related substances
This product is dissolved and diluted with ethanol to make a solution containing 20mg per 1 ml as a test solution; Another 2-nitro-5-aminotrifluorotoluene (impurity I) an appropriate amount of the control was dissolved by adding ethanol and diluted to prepare a solution containing 0.20mg per 1 ml as a control solution. According to the thin layer chromatography (General 0502) test, absorb 15ul of each of the above two solutions, respectively point on the same silica gel GF 254 thin layer plate, with cyclohexane-ethyl acetate (1:1) as the developing solvent, expand, dry, spray with P-dimethylaminobenzaldehyde solution (take 1g of p-dimethylaminobenzaldehyde, add an appropriate amount of ethanol to dissolve, add 23ml of hydrochloric acid, dilute to 100ml with ethanol), check immediately, if the test solution shows impurity spots corresponding to impurity I, the color of the test solution should not be deeper (1.0%) than the main spot of the reference solution.
residual solvent
take an appropriate amount of this product, weigh it accurately, add dimethyl sulfoxide to dissolve and dilute it to make about 0.1g of the solution was used as a test solution; An appropriate amount of benzene and toluene was separately accurately weighed and diluted with dimethyl sulfoxide to prepare a solution containing about 0.2ug of benzene and 89ug of toluene per 1 ml as a reference solution. According to the test for determination of residual solvents (General Principle 0861 third method), the capillary column with 5% phenyl-95% methyl polysiloxane as stationary liquid is used as the chromatographic column, and the sample is determined by non-flow injection, the starting temperature is 50°C, and the retention time is 5 minutes, the temperature was then increased to 175°C at a rate of 8°C per minute and then every minute. The temperature was increased to 260°C at a rate of 35°C for 20 minutes; The inlet temperature was 100°C; And the detector temperature was 260°C. The sample solution and the reference solution were respectively 1u1, injected into the human gas chromatograph, and the chromatogram was recorded. According to the external standard method to calculate the peak area, benzene and toluene residues should be in accordance with the provisions.
loss on drying
take this product and dry under reduced pressure at 60°C for 4 hours, and the weight loss shall not exceed 0.5% (General rule 0831).
ignition residue
take l.Og of this product and check it according to law (General rule 0841). The residue left shall not exceed 0.1%.
Heavy metals
The residue left under the item of taking the ignition residue shall not contain more than 20 parts per million of heavy metal when examined by law (General rule 0821, Law II).
Last Update：2022-01-01 13:40:32
FLUTAMIDE - Content determination
Authoritative Data Verified Data
- measured by high performance liquid chromatography (General 0512).
- chromatographic conditions and system suitability test using eighteen alkyl silane bonded silica gel as filler; Methanol-water (60:40) as mobile phase; The detection wavelength was 230nm. The number of theoretical plates is not less than 2000 calculated from the flutamide peak.
- determination of the appropriate amount of this product, precision weighing, plus mobile phase dissolution and quantitative dilution made per lml containing 0.lmg solution, as the test solution, the precision of 20ul, injection of human liquid chromatograph, record chromatogram; Another flutamide reference substance, the same method for determination. According to the external standard method to calculate the peak area, that is.
Last Update：2022-01-01 13:40:33
FLUTAMIDE - Category
Authoritative Data Verified Data
antineoplastic agents.
Last Update：2022-01-01 13:40:33
FLUTAMIDE - Storage
Authoritative Data Verified Data
light shielding, sealed storage.
Last Update：2022-01-01 13:40:33
FLUTAMIDE - Flutamide Tablets
Authoritative Data Verified Data
This product contains flutamide (C11H11F3N203) should be 93.0% to 107.0% of the label.
trait
This product is a light yellow tablet.
identification
- take an appropriate amount of fine powder of this product (equivalent to 0.2g of flutamide), add 10ml of ethanol, shake to dissolve flutamide, filter, and take the filtrate as the test solution; an appropriate amount of flutamide control was taken, dissolved in ethanol and diluted to prepare a solution containing about 20mg per 1 ml as a control solution. According to the thin layer chromatography (General 0502) test, absorb the above two solutions and put them respectively on the same silica gel GF 254 thin layer plate, with cyclohexane-ethyl acetate (1:1) as the developing solvent, expand, dry, set the UV lamp (254mn) to view, the position and color of the main spot of the test solution should be consistent with the main spot of the reference solution.
- take the test solution under (1), dilute with ethanol to make a solution containing about 20ug of flutamide per 1 ml, and measure by UV-Vis spectrophotometry (General rule 0401) it was determined that there was a maximum absorption at wavelengths of 227nm and 295nm and a minimum absorption at a wavelength of 252nm.
examination
- dissolution the dissolution medium was 1000ml of phosphate buffer solution containing polysorbate 80 (pH 0931) according to the dissolution and release determination method (general rule, second method), speed is 75 rpm, according to the law, after 45 minutes, take the solution 10ml filtration, precision take the filtrate 5ml, put the 50ml flask, with phosphate buffer (pH 6.8) dilute to the scale, shake, as a test solution; Take an additional 24mg flutamide control, precision weighing, 100ml flask, add a small amount of ethanol to dissolve, dilute to the scale with dissolution medium, shake well, take 5ml accurately, put it in a 50ml measuring flask, dilute to the scale with phosphate buffer (pH 6.8), shake well, and use it as a reference solution; the absorbance of each of the above two Solutions was measured at a wavelength of 0401 nm by ultraviolet-visible spectrophotometry (general), and the elution amount of each tablet was calculated. The limit is 75% of the labeled amount and shall be in accordance with the provisions.
- others shall be in accordance with the relevant provisions under the item of tablets (General rule 0101).
Content determination
Take 10 tablets of this product, precision weighing, fine grinding, precision weighing an appropriate amount (about 0.1g equivalent to flutamide), put it in a 100ml measuring flask, add an appropriate amount of mobile phase, shake to dissolve flutamide, dilute to the scale with mobile phase, shake, filter, take the filtrate 5ml accurately, put it in a 50ml measuring flask, dilute to the scale with mobile phase, shake well, as a test solution. Measured and calculated according to the method under the item of flutamide content determination.
category
Same as flutamide.
specification
0.25g
storage
light-shielded, sealed, and stored in a dry place.
Last Update：2022-01-01 13:40:34
FLUTAMIDE - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| overview | flutamide is a non-steroidal androgen antagonist, which belongs to acyl aniline and is the first-line treatment for prostate cancer. It was first designed and synthesized by Schering -Ploug h Company in the United States and was first listed in the United States in 1989 as a drug for prostate cancer. Since flutamide itself does not have any hormonal activity, it has a good effect on prostate diseases, has no effect on the cardiovascular system, and can maintain the sexual function of patients. At present, it has gradually become a commonly used drug for the treatment of prostate cancer and prostate hyperplasia in European and American countries. It can also be used for non-prostate diseases related to androgens. There have been a lot of studies in the world. Moreover, the incidence of adverse reactions of flutamide is low, and patients can tolerate it well when taken orally for many times at low doses, so it is widely used. |
| pharmacological effects | this product competes with androgens for androgen receptors in tumor sites, blocks cell uptake of androgen, and inhibits the combination of androgen and target organs. This product binds to androgen receptors to form receptor complexes, which enter the nucleus and bind to nuclear proteins, thereby inhibiting the growth of tumor cells. |
| pharmacokinetics | this product is absorbed orally, and most of it is metabolized rapidly 1 hour after oral administration. the main metabolite is Flu-tamide hydroxylase, and the metabolite has antiandrogen activity equivalent to that of the original drug, and the serum t1/2 of the two is 5-6 hours. The peak concentration of tissue drug was reached in rats after 6 hours of oral administration, with the highest concentration in gastrointestinal tract, liver and kidney. Twenty-four hours after oral administration of 200mg, the 28% drug was excreted from urine, and the daily output decreased rapidly for the next 4 days. The drug excreted in feces was about 0.9% of the daily dose. |
| Synthesis | 1. Acylation reaction isobutyric anhydride and 3-trifluoromethylaniline in the 30% sodium hydroxide as adsorbent, toluene as solvent (toluene can be recycled), acylation reaction to obtain 2-methyl-N-[(3-trichloromethyl) phenyl] propionamide. Figure 1 shows the synthesis of 2-methyl-N-[(3-trichloromethyl) phenyl] propanamide 2. Nitration reaction at -10 to -5°C, nitrification with mixed acid to obtain flutamide. (2015-11-16) |
| indication | is suitable for prostate cancer and is effective for both newly treated and retreated patients. dermatology is mainly used for hirsutism and acne. |
| adverse reactions | 1. male breast feminization, breast tenderness, sometimes accompanied by galactorrhea, can disappear if the dose is reduced or the drug is stopped. A small number of patients may have diarrhea, nausea, vomiting, increased appetite, insomnia and fatigue. 3. Rare decreased libido, transient abnormal liver function and decreased sperm count. 4. The potential effect of this product on cardiovascular system is smaller than that of diethylstilbestrol. 5. Fetal contact can cause pseudohermaphroditism. |
| precautions | 1. liver function and sperm count should be checked regularly when taking this product for a long time. in case of abnormality, the dose should be reduced or the drug should be stopped, and it can generally return to normal. 2. This product can increase the plasma concentration of testosterone and estradiol, which may cause fluid retention. 3. This product can be used alone, or combined with luteinizing hormone releasing hormone analogs and chemotherapy drugs. 4. It also has certain curative effect on benign prostatic hyperplasia. 5.FDA classified the pregnancy safety of this drug as grade D. |
| contraindications | 1. those who are allergic to this drug are prohibited. 2. Women, children and those with severe liver damage are prohibited. |
| Drug interaction | 1. Gonadotropin-releasing hormone analogs (such as leuprolide acetate, etc.) can inhibit testosterone secretion, and combined with this drug can increase the efficacy. 2. When combined with warfarin can increase bleeding tendency, the dose of warfarin should be adjusted. |
| specification | tablet: 0.25g. Capsule: 0.125g;0.25g. |
| Use | Non-steroidal male hormone antagonists can inhibit the conversion of testosterone to dihydrotestosterone, and can block the cell level in the prostate The binding of dihydrotestosterone to receptors in the nucleus can inhibit the growth stimulating effect of androgen on the prostate. It is effective orally. It is used for the treatment of prostate cancer and prostatic hypertrophy and luteinizing releasing hormone-lianpu, which can treat advanced prostate cancer and prostatic hypertrophy. Suitable for the treatment of prostate cancer and prostatic hypertrophy Uses: anticancer drugs and antiandrogen drugs. It is used to treat advanced prostate cancer and prostatic hypertrophy that cannot be treated with surgery or radiotherapy. |
| Production method | Trifluoromethyl benzene is nitrated to generate m-nitrotrifluoromethyl benzene, reduced to generate m-trifluoromethyl aniline, and isobutyryl chloride After the reaction, nitrification produces flunitrosamide. Or obtained by acylation of 3-trifluoromethyl-4-nitroaniline and isobutyryl chloride. |
Last Update：2024-04-09 02:00:06
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Product Name: 2-Methyl-N-[4-Nitro-3-(Trifluoromethyl)Phenyl]Propionamide Visit Supplier Webpage Request for quotationCAS: 13311-84-7
Tel: 18301782025
Email: 3008007409@qq.com
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QQ: 3008007409
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Product Name: Flutamide Request for quotation
CAS: 13311-84-7
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Email: 2308653804@qq.com
Mobile: 13901914741,13636699301
QQ: 2308653804Send QQ message
CAS: 13311-84-7
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Email: 2308653804@qq.com
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View History
Raw Materials for FLUTAMIDE