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Finasteride

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Finasteride Basic information
Treatment of benign prostatic hyperplasia Drugs for the treatment of male pattern alopecia Chemical property Uses Methods of production
Product Name:Finasteride
Synonyms:PROSCAR;PROSTIDE;N-(2-METHYL-2-PROPYL)-3-OXO-4-AZA-5ALPHA-ANDROST-1-ENE-17BETA-CARBOXAMIDE;MK-906;(5alpha,17beta)-(1,1-dimethylethyl)-3-oxo-4-azaandrost-1-ene-17-carboxamide;17beta-(n-tert-butylcarbamoyl)-4-aza-5alpha-androst-1-en-3-one;4-azaandrost-1-ene-17-carboxamide,n-(1,1-dimethylethyl)-3-oxo-,(5-alpha,17-be;4-azaandrost-1-ene-17-carboxamide,n-(1,1-dimethylethyl)-3-oxo-,(5alpha,17beta
CAS:98319-26-7
MF:C23H36N2O2
MW:372.54
EINECS:
Product Categories:Active Pharmaceutical Ingredients;API;Biochemistry;Steroids;Steroids (Others);Intermediates & Fine Chemicals;Pharmaceuticals;Vitamin Ingredients;Intracellular receptor;Steroid and Hormone;PROSCAR;Hormone Drugs
Mol File:98319-26-7.mol
Finasteride Structure
Finasteride Chemical Properties
mp 253 °C
storage temp. Store at RT
solubility DMSO: 32 mg/mL, soluble
form solid
Water Solubility insoluble
Merck 4082
CAS DataBase Reference98319-26-7(CAS DataBase Reference)
Safety Information
Hazard Codes Xn,T,Xi
Risk Statements 22-61-60-36/37/38
Safety Statements 36/37/39-45-53-36-26
WGK Germany 3
RTECS CL5245000
Hazardous Substances Data98319-26-7(Hazardous Substances Data)
MSDS Information
ProviderLanguage
SigmaAldrich English
Finasteride Usage And Synthesis
Treatment of benign prostatic hyperplasiaFinasteride is China a benign prostatic hyperplasia and prostatitis based drug treatment, it is 4 - nitrogen steroid hormone compounds of the synthesis, belonging to resistance hormone drugs, can be selective inhibition of 5α- reductase, enable the conversion of testosterone into resistance 5α dihydrotestosterone (DHT), front row in glandular cells of the male hormone levels drop, reduce the serum prostate specific antigen, reduce the prostate volume increased, urine flow increased, thereby reducing symptoms to achieve the purpose for the treatment of benign prostatic hyperplasia.
Prostatic hyperplasia is called hypertrophy of the prostate, leading to the bladder neck and urethra oppressed, causing urinary tract obstruction and other symptoms and complications, so that patients feel pain, multiple men over the age of 50.
The above information is edited by the chemicalbook Han Ya.
Drugs for the treatment of male pattern alopeciaFinasteride is a 5α- reductase inhibitor, is hormone resistant drugs, it can prevent converts testosterone to dihydrotestosterone (DHT), so as to reduce of DHT synthesis, reduce the content of scalp hair and serum dihydrotestosterone. Germinal function recovery has been suppressed follicular papilla, promoting hair growth and preventing hair loss, finasteride is currently approved by the U.S. Food and Drug Administration (FDA) only for male pattern hair loss of oral drug treatment, the recommended dose is 1mg.
Chemical propertyIt is white or white crystalline solid. Soluble in chloroform and dimethyl sulfoxide, ethanol, methanol and propanol, hardly soluble in propylene glycol or polyethylene glycol 400, very slightly soluble in 0.1 mol / L hydrochloric acid, 0.1mol/L NaOH solution or water. Melting point is about 257℃; also melting is 252 ~ 254℃ [α]D-59° (C = L, methanol).
Uses1. 5αreductase inhibitors can inhibit the conversion of testosterone to dihydrotestosterone. Used for the treatment of benign prostatic hyperplasia.
2. Use for the treatment of male diseases such as prostate hypertrophy and alopecia.
Methods of productionUse pregnenolone as raw material. First it acted with pyridine and then with methanol reaction to sodium 3- hydroxy -5- androstenes -17βmethyl esters (III). Then it is reaction with aluminum isopropoxide in toluene and cyclohexanone, reflux, filtering, washing, drying, vacuum concentration. With petroleum ether at 5 ℃, stirring, filtering to oxidation products (IV), the yield is 74.6%.The oxidation products and 95% ethanol and 10% potassium hydroxide solution, reflux under nitrogen protection. After removing the ethanol distillation, with 6mol hydrochloride to pH value is about 3. Filtration, filter cake was washed to neutral, drying the hydrolysate (V), the yield is 96.4%. Hydrolysate solution in TERT butanol, adding anhydrous sodium carbonate aqueous solution under stirring, reflux drip heightening iodate sodium and potassium permanganate solution, Add reflow. Cooling and filtering. The filtrate is vacuum steaming most of tert butyl alcohol, ice bath with 6mol/L hydrochloric acid to pH value of 2. Use ethyl acetate extraction, extraction liquid with saturated sodium chloride wash, dry. Evaporated, ethyl acetate recrystallized to obtain the ring opening products (VI), the yield is 66%. In ice bath cooling, into the ethylene glycol through into the ammonia and join the open ring products, slow rise to 180℃ to react. Cooling, add water, with 6 mol / I. hydrochloride was adjusted to pH value is about 2. Filter set solid, washing to neutral, recrystallized by dimethyl formamide, the cyclization product (VII), the yield is 62.1%.The product of cyclization and two platinum oxide, acetic acid and a small amount of perchloric acid were hydrogenated at 85 under atmospheric pressure. To filter the catalyst after decompression concentrated to dry. Residues with N,N-dimethylformamide recrystallizationt to get hydrogenation product (VIII), the yield is 92.9%.The hydrogenated products and three phenyl phosphine, toluene and 2, 2 '- two pyridine two sulfide (DPDS) mixture, stirring at room temperature. Chromatographic separation of pyridine sulfide (IX), the yield is 79%. The sulfide and anhydrous tetrahydrofuran (THF) and tert butylamine were stirring at room temperature overnight, the addition of dichloromethane, washed with 2 mol / L hydrochloric acid and saturated sodium chloride, dry and concentrated under reduced pressure. The residue is used with ethyl acetate recrystallization, amide product (X), the yield is 77.1%. The amide, Benzeneseleninic anhydride and chlorobenzene are together, and slowly evaporating solvent and reflux water generated. Separate by Column chromatography, crude with ethyl acetate recrystallization, white finasteride crystal, the yield was 52.3%, the melting point is 253 to 255℃.
Chemical PropertiesOff-White Crystalline Powder
UsageInhibitor of 5α-reductase, the enzyme which converts testosterone to the more potent androgen, 5α-dihydrotestosterone. Antialopecia agent.
Usageanti-androgen, alpha-reductase inhibitor
UsageTreatment of benign prostatic hyperplasia and androgenetic alopecia
UsageInhibitor of 5a-reductase, the enzyme which converts testosterone to the more potent androgen, 5a-dihydrotestosterone. Antialopecia agent
Biological ActivityAntiandrogen that inhibits type II 5 α reductase (IC 50 = 65 nM). Suppresses the conversion of testosterone to dihydrotestosterone. Reduces prostatic dihydrotestosterone levels and prostate size in vivo . Orally active.
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