CAS 98319-26-7 MFCD00869737-Finasteride 非那雄胺 TAO{mole}

Finasteride 非那雄胺

CAS 98319-26-7 MFCD00869737

化学结构图

SMILES: CC(C)(C)NC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4NC(=O)C=C[C@]4(C)[C@H]3CC[C@@]21C

化学属性

Mol. Formula	C23H36N2O2
Mol. Weight	373
Appearance	白色或类白色结晶性固体。易溶于氯仿、二甲亚砜、乙醇、甲醇或正丙醇，难溶于丙二醇或聚乙二醇400，极微溶于0.1mol/L盐酸、0.1mol/L氢氧化钠溶液或水。熔点约257℃；也有熔点252～254℃。[α] solid D -59°(C=l，甲醇)。
Solubility	DMSO: 32 mg/mL, soluble
Melting Point	253 °C

别名和识别编码

Chemical Name	Finasteride
CAS Number	98319-26-7
Synonym	N-tert-Butyl-3-oxo-4-aza-5α-androst-1-en-17β-carboxamide N-(2-METHYL-2-PROPYL)-3-OXO-4-AZA-5ALPHA-ANDROST-1-ENE-17BETA-CARBOXAMIDE l-652,931 MK-906 N-叔丁基-3-氧代-4-氮杂-5α-雄甾-1-烯-17β-甲酰胺 MK-906 N-(2-甲基-2-丙基)-3-氧代-4-氮杂-5α-雄甾-1-烯-17β-甲酰胺 PROSTIDE 非那甾胺(FTD) N-叔丁基-3-氧代-4-氮杂-5Α-雄甾-1-烯-17Β-甲酰胺 1,(5-ALPHA)-ANDROSTAN-4-AZA-3-ONE-17-BETA-(N-TERT-BUTYL-CARBOXAMIDE) (5alpha,17beta)-(1,1-dimethylethyl)-3-oxo-4-azaandrost-1-ene-17-carboxamide Finasteride FinasterideEdmf/Gmp mk-0906 非那甾铵 17BETA-(T-BUTYLCARBAMOYL)-4-AZA-5-ALPHA-ANDROSTEN-3-ONE 17beta-(n-tert-butylcarbamoyl)-4-aza-5alpha-androst-1-en-3-one 非那甾胺 n-tert-butyl-3-oxo-4-aza-5alpha-an
MDL Number	MFCD00869737
PubChem Substance ID	87560747
Reaxys-RN	4269024
Merck Number	4082
Chemical Name Translation	非那雄胺
Beilstein Registry Number	4269024

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分类

{SNA} Bioactive Small Molecules, Biochemicals and Reagents, Cell Biology, Enzyme Inhibitors, Enzyme Inhibitors by Type, Enzymes, Inhibitors, and Substrates, F, Substrate Analogs
Alphabetic, Analytical Standards, Analytical/Chromatography, Bioactive Small Molecules, Cell Biology, Chromatography, Clinical Standards, F, FA - FL, Hormones, Life Sciences Standards, Market Segments, Neats and Solutions, Pharmacology Standards, Standards for Food and Beverage Analysis, Standards for Pharma Clinical Forensic & Veterinary Analysis
{Chemicalbook} 药物: 其它药物: 其它药物

产品应用

Inhibitor of 5?-reductase, the enzyme which converts testosterone to the more potent androgen, 5?-dihydrotestosterone.

安全信息

RTECSCL5245000

GHS Symbol

WGK Germany3

Signal word Warning

Hazard statements

H302 Harmful if swallowed 吞食有害

Hazard Codes Xn Xn,T

Personal Protective Equipment dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Precautionary statements

P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
P501 Dispose of contents/container to..… 处理内容物/容器.....
P301+P312+P330
P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西，喝水或吸烟。

Risk Statements

R61 May cause harm to the unborn child 可能对未出生的婴儿导致伤害
R60 May impair fertility 可能降低生殖能力
R22 Harmful if swallowed 吞咽有害

Safety Statements

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 418 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Gastrointestinal - ulceration or bleeding from stomach
   Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
   KSRNAM Kiso to Rinsho.

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : >2 gm/kg
TOXIC EFFECTS :
   Skin and Appendages - dermatitis, other (after systemic exposure)
REFERENCE :
   KSRNAM Kiso to Rinsho.  Clinical Report.  (Yubunsha Co., Ltd., 1-5, Kanda
   Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan)  V.1-    1960-
   Volume(issue)/page/year: 28,4091,1994

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 372 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Behavioral - ataxia
   Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
   KSRNAM Kiso to Rinsho.  Clinical Report.  (Yubunsha Co., Ltd., 1-5, Kanda
   Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan)  V.1-    1960-
   Volume(issue)/page/year: 28,4091,1994

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 486 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Behavioral - ataxia
   Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
   KSRNAM Kiso to Rinsho.  Clinical Report.  (Yubunsha Co., Ltd., 1-5, Kanda
   Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan)  V.1-    1960-
   Volume(issue)/page/year: 28,4091,1994

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 3400 mg/kg
SEX/DURATION            : multigeneration
TOXIC EFFECTS :
   Reproductive - Maternal Effects - parturition
REFERENCE :
   TJADAB Teratology, The International Journal of Abnormal Development. (Alan
   R. Liss, Inc., 41 E. 11th St., New York, NY 10003)  V.1-    1968-
   Volume(issue)/page/year: 42,91,1990

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 6720 mg/kg
SEX/DURATION            : male 12 week(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Fertility - post-implantation mortality (e.g. dead and/or
   resorbed implants per total number of implants)
REFERENCE :
   REPTED Reproductive Toxicology.  (Pergamon Press Inc., Maxwell House,
   Fairview Park, Elmsford, NY 10523)  V.1-    1987-  Volume(issue)/page/year:
   5,337,1991

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 1500 mg/kg
SEX/DURATION            : female 6-20 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Paternal Effects - other effects on male
REFERENCE :
   TJADAB Teratology, The International Journal of Abnormal Development. (Alan
   R. Liss, Inc., 41 E. 11th St., New York, NY 10003)  V.1-    1968-
   Volume(issue)/page/year: 42,483,1990

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 3360 mg/kg
SEX/DURATION            : male 12 week(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Fertility - male fertility index (e.g. # males impregnating
   females per # males exposed to fertile nonpregnant females)
REFEREN

其他信息

上游原料:碳酸钠 --> 高锰酸钾 --> 叔丁醇 --> 三苯基膦 --> 乙二醇 --> 环己酮 --> 氢氧化钾溶液 --> 异丙醇铝 --> 3-甲氧基丙酸 --> 二氧化铂 --> 碘酸钠 --> 孕烯醇酮 --> 2,2'-二硫二吡啶
MOL 文件:98319-26-7.mol
治疗男性型脱发药物:非那雄胺也是一种5α–还原酶的特异性抑制剂，属抗性激素类药，它能阻止睾酮转换为二氢睾酮，从而减少双氢睾酮的合成，降低头皮毛囊和血清中双氢睾酮的含量，使已经受抑的毛囊乳头生发功能恢复，促进头发生长并防止继续脱发，非那雄胺是目前美国食品与药品管理局FDA批准的惟一用于治疗男性型脱发的口服药品，推荐剂量为一次1mg。
治疗前列腺增生:非那雄胺是我国治疗前列腺增生和前列腺炎的一种基础药物，它是合成的4–氮甾体激素化合物，属抗性激素药物，可选择性抑制5α–还原酶，使睾酮转化成5α–双氢睾酮(DHT)的过程变阻，前列腺细胞内雄性激素水平下降，血清中的前列腺特异抗原降低，增大的前列腺体积缩小，尿流率增加，从而减轻患者症状，达到治疗前列腺增生的目的。该药的作用特点是能选择性地阻断雄激素对前列腺的刺激作用，却很少影响男子的性功能。前列腺增生又叫前列腺肥大，它导致膀胱颈部和后尿道受压迫，引起尿路梗阻以及其他症状和并发症，使患者深感痛苦，多发于50岁以上的男性人群。
Sigma Aldrich:98319-26-7(sigmaaldrich)
用途二:5α-还原酶抑制剂，可抑制睾酮转化为二氢睾酮。用于良性前列腺增生症的治疗。
非那雄胺价格(试剂级):更新日期产品编号产品名称包装价格 2011/04/16 F0675 非那甾胺 Finasteride 200MG 800元 2011/04/16 F0675 非那甾胺 Finasteride 1G 4000元
用途一:用于治疗男子前列腺肥大及秃发等病症
方法一:以孕烯醇酮为原料。先和吡啶作用，再和甲醇钠反应得3-羟基-5-雄甾烯-17β-羧酸甲酯(Ⅲ)。再和异丙醇铝在甲苯和环己酮中，回流。过滤，洗涤，干燥，减压浓缩。加入石油醚，于5℃搅拌，抽滤得氧化产物(Ⅳ)，收率74.6%。该氧化产物和95%乙醇及10%氢氧化钾溶液，在氮气保护下回流。减压蒸去乙醇后，用6mol几盐酸调至Ph值约为3。抽滤，滤饼用水洗至中性，干燥得水解产物(V)，收率96.4%。水解产物溶于叔丁醇中，搅拌下加入无水碳酸钠的水溶液，回流下滴加高碘酸钠和高锰酸钾的水溶液，加毕回流。冷却，过滤。滤液减压蒸去大部分叔丁醇后，冰浴下用6mol/L盐酸调至Ph值约为2。乙酸乙酯提取，提取液用饱和氯化钠洗，干燥。减压蒸干，乙酸乙酯重结晶得开环产物(Ⅵ)，收率66%。在冰浴冷却下，往乙二醇中通入氨气，加入开环产物，缓慢升至180℃反应。冷却，加水，用6mol／I。盐酸调至Ph值约为2。滤集固体，水洗至中性，用二甲基甲酰胺重结晶，得环合产物(Ⅶ)，收率62.1%。该环合产物和二氧化铂、醋酸及少量高氯酸，在85℃和常压下氢化。滤去催化剂后，减压浓缩至干。残留物用二甲基甲酰胺重结晶，得氢化产物(Ⅷ)，收率92.9%。该氢化产物和三苯基膦、甲苯及2，2’-二吡啶二硫化物(DPDS)混合，室温搅拌。柱层析分离得吡啶硫化物(Ⅸ)，收率79.0%。该硫化物和无水四氢呋喃及叔丁胺，室温搅拌过夜，加入二氯甲烷，用2mol/L盐酸和饱和氯化钠洗，干燥，减压浓缩。残留物用乙酸乙酯重结晶，得酰胺产物(X)，收率77.1%。该酰胺和苯亚硒酸酐及氯苯一起，回流并缓慢蒸出溶剂和生成的水。柱层析分离，粗品用乙酸乙酯重结晶，得白色的非那雄胺晶体，收率52.3％，熔点253～255℃。