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タダラフィル

タダラフィル 化学構造式
171596-29-5
CAS番号.
171596-29-5
化学名:
タダラフィル
别名:
タダラフィル;タダラフィル (JAN)
英語化学名:
Tadalafil
英語别名:
afiL;TadaL;Calai;IC 351;CIALIS;Calais;hyjskn;Adcirca;cialisr;ICOS 351
CBNumber:
CB2236841
化学式:
C22H19N3O4
分子量:
389.4
MOL File:
171596-29-5.mol

タダラフィル 物理性質

融点 :
298-300°C
比旋光度 :
D20 +71.0°
沸点 :
679.1±55.0 °C(Predicted)
比重(密度) :
1.51±0.1 g/cm3(Predicted)
闪点 :
2℃
貯蔵温度 :
Sealed in dry,2-8°C
溶解性:
DMSO: soluble20mg/mL, clear
外見 :
powder
酸解離定数(Pka):
16.68±0.40(Predicted)
色:
white to beige
光学活性 (optical activity):
[α]/D +68 to +78°, c = 1 in chloroform-d
InChIKey:
WOXKDUGGOYFFRN-IIBYNOLFSA-N
CAS データベース:
171596-29-5(CAS DataBase Reference)
安全性情報
  • リスクと安全性に関する声明
  • 危険有害性情報のコード(GHS)
主な危険性  F,Xn
Rフレーズ  11-20/21/22-36
Sフレーズ  16-36/37
WGK Germany  3
RTECS 番号 UQ4431050
HSコード  2934990002
有毒物質データの 171596-29-5(Hazardous Substances Data)
絵表示(GHS)
注意喚起語 Danger
危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード
H225 引火性の高い液体および蒸気 引火性液体 2 危険 P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H315 皮膚刺激 皮膚腐食性/刺激性 2 警告 P264, P280, P302+P352, P321,P332+P313, P362
H319 強い眼刺激 眼に対する重篤な損傷性/眼刺激 性 2A 警告 P264, P280, P305+P351+P338,P337+P313P
H335 呼吸器への刺激のおそれ 特定標的臓器毒性、単回暴露; 気道刺激性 3 警告
注意書き
P210 熱/火花/裸火/高温のもののような着火源から遠ざ けること。-禁煙。
P261 粉じん/煙/ガス/ミスト/蒸気/スプレーの吸入を避ける こと。
P305+P351+P338 眼に入った場合:水で数分間注意深く洗うこと。次にコ ンタクトレンズを着用していて容易に外せる場合は外す こと。その後も洗浄を続けること。
P337+P313 眼の刺激が続く場合:医師の診断/手当てを受けること。
P403+P235 換気の良い場所で保管すること。涼しいところに 置くこと。

タダラフィル 価格 もっと(19)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01COBQA-3248 タダラフィル
Tadalafil
171596-29-5 1g ¥3600 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01COBQA-3248 タダラフィル
Tadalafil
171596-29-5 5g ¥8700 2021-03-23 購入
Sigma-Aldrich Japan Y0001417 European Pharmacopoeia (EP) Reference Standard
Tadalafil European Pharmacopoeia (EP) Reference Standard
171596-29-5 ¥35200 2021-03-23 購入
Sigma-Aldrich Japan PHR1810 Pharmaceutical Secondary Standard; Certified Reference Material
Tadalafil Pharmaceutical Secondary Standard; Certified Reference Material
171596-29-5 500mg ¥24400 2021-03-23 購入
Sigma-Aldrich Japan 1642879 United States Pharmacopeia (USP) Reference Standard
Tadalafil United States Pharmacopeia (USP) Reference Standard
171596-29-5 200mg ¥99800 2021-03-23 購入

タダラフィル 化学特性,用途語,生産方法

用途

タダラフィル(Tadalafil)は、長時間型のホスホジエステラーゼ5阻害剤(英語版)であり、日本での適応は、勃起不全 (ED) 、肺動脈性肺高血圧症、前立腺肥大の排尿障害である。商品名はシアリス、アドシルカ、ザルティアである。

効能

血圧降下薬, 勃起不全治療薬, ホスホジエステラーゼV阻害薬

商品名

アドシルカ (日本イーライリリー); ザルティア (日本イーライリリー); シアリス (日本イーライリリー)

説明

Tadalafil (market name “Cialis” or “Adcirca”) is a kind of PDE5 inhibitor used for the treatment of erectile dysfunction, benign prostatic hypertrophy and pulmonary arterial hypertension. The effect of Tadalafil is relaxing the blood vessels muscles and increasing the blood flow into the corpus cavernosum. The mechanism of action of tadalafil is through inhibiting the activity of the cGMP specific phosphodiesterase type 5 (PDE5). PDE5 degrades cGMP in the corpus cavernosum located around the penis. Therefore, tadalafi leads to the increased concentration of cGMP which further causes the smooth muscle relaxation and increased blood flow into the corpus cavernosum. Some clinical studies also implied that tadalafil could improve endothelia function in men with increased cardiovascular risk and lower the urinary tract symptoms secondary to benign prostatic hyperplasia.

化学的特性

White to Off-White Cyrstalline Solid

Originator

Lilly/ICOS (US)

使用

analgesic, norepinephrine uptake blocker, mu-opiod receptor agonist.A phosphodiesterase 5 inhibitor.Tadalafil is used for the treatment of erectile dysfunction.

使用

Tadalafil is used for the treatment of erectile dysfunction. A phosphodiesterase 5 inhibitor.

定義

ChEBI: A pyrazinopyridoindole that is 2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione substituted at position 2 by a methyl group and at position 6 by a 1,3-benzodioxol-5-yl group (the 6R,12aR

brand name

Cialis (Lilly).

一般的な説明

Tadalafil, (6R-trans)-6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-pyrazino[1', 2' :1,6]pyrido[3,4-b]indole-1,4-dione (Cialis), is a potent PDE5 inhibitor.It received FDA approval for the treatment of erectiledysfunction in December 2003. Because of its half-life of17.5 hours, it is marketed as a 36-hour treatment. Tadalafil ispredominantly metabolized by hepatic enzymes, includingCYP3A4. The concomitant use of CYP3A4 inhibitors suchas ritonavir, indinavir, ketoconazole, as well as moderateCYP3A inhibitors such as erythromycin have been shown toresult in significant increases in tadalafil plasma levels.Much like sildenafil, tadalafil is under clinical investigationfor managing PAH.

作用機序

Tadalafil was the last agent to be released and can be taken on a full stomach without slowing the onset. It has a much longer duration of action, lasting up to 48 hours, compared with sildenafil and vardenafil, which last for approximately 4 hours. The longer half-life of tadalafil results in a lengthened period of responsiveness as compared to sildenafil and vardenafil. This longer therapeutic window requires fewer time constraints for the effectiveness of tadalafil and has been interpreted as being advantageous through providing the option for more spontaneous sexual activity. Because of its long half-life, however, tadalafil, has been detected in plasma even 5 days after oral administration. This suggests the possibility of accumulation if taken regularly and in short intervals, which may result in an increased risk of side effects with the excessive use of this PDE5 inhibitor. The 3,4-methylenedioxy substitution on the phenyl ring was significant for increasing its potency as PDE5 inhibitor. Optimization of the chain on the piperazinedione ring resulted in no significant change in IC50s. Tadalafil is a highly potent PDE5 inhibitor (IC50, 5 nM), with high selectivity for PDE5 versus PDE1 through PDE4. The PDE5/PDE6 selectivity ratio is 85.

薬物動態学

Tadalafil is different in structure from both sildenafil and vardenafil. It is rapidly absorbed and peaks in concentration (378 μg/L after a 20-mg dose) after 2 hours, displaying a long half-life of 17.5 hours. It also is metabolized by the liver (CYP3A4). Notably, its pharmacokinetics is not clinically influenced by alcohol or food intake or by factors such as diabetes or impaired hepatic or renal function.

臨床応用

Tadalafil is one of the two new PDE5 inhibitors launched for the oral treatment of male erectile dysfunction. Tadalafil is a b-carboline derivative and it is structurally distinct from vardenafil (Levitraw) and sildenafil (Viagraw), both of which are PDE5 inhibitors based on a fused pyrimidine core structure. Tadalafil is synthesized in three steps starting from D-tryptophan methyl ester, by first condensing with piperonal in a Pictet-Spengler cyclization reaction to form the tetrahydro-β-carboline derivative, which is followed by chloroacetylation of the piperidine ring nitrogen and cyclization with methylamine. Tadalafil is a potent and highly selective inhibitor of PDE5 (IC50=1 nm). It shows >10,000-fold selectivity for PDE5 versus PDE1, 2, 3, 4, 7, 8 and 9, and >700-fold selectivity versus PDE6. Typically administered at 10 and 20 mg doses, tadalafil is rapidly absorbed and has a tmax of 2 h, which is slightly longer than those of sildenafil (1 h) and vardenafil (0.75 h). Clinically, all of these agents appear to have efficacy for many men within 30–60 min. However, tadalafil distinguishes itself from other PDE5 inhibitors in terms of significantly longer duration of action. The half-life of tadalafil dosed at 20 mg is 17.5 h as compared with 3.8 h for sildenafil (100 mg) and 4.7 h for vardenafil (20 mg). In clinical studies, significant rates of response were reported up to 36 h following drug ingestion. Tadalafil is predominantly metabolized in the liver by CYP3A4 to entities that are not active against PDE5 and excreted mainly as metabolites in the feces and the urine. The pharmacokinetics of tadalafil are unaffected by factors such as intake of food and alcohol, age, the presence of diabetes, and mild or moderate hepatic insufficiency. The most common drug-related adverse events are headache, back pain, dyspepsia, and myalgia. At 10 and 20 mg doses, Tadalafil does not have a significant effect on blood pressure and heart rate and does not result in increased instances of myocardial infarction. Rare reports of prolonged erections greater than 4 h and priapism have been noted with the use of tadalafil. Priapism, if not treated properly, can result in irreversible damage to the erectile tissue. Patients who have an erection lasting greater than 4 h are advised to seek emergency medical attention. Tadalafil has a modest synergistic effect on the nitrate-induced reduction in blood pressure and, as with sildenafil and vardenafil, it is contraindicated for use in patients on nitrate therapy. In diabetic patients, improvement of erectile function by tadalafil is irrespective of the type of diabetes and the type of diabetic therapy.

副作用

Adverse effects related to oral therapy for erectile function are primarily concerned with adverse cardiovascular effects, because PDE5 inhibitors promote vasodilation and, therefore, have an inherent potential to cause hypotension. This is a particular concern for elderly patients with a preexisting condition.

Chemical Synthesis

D-(-)-Tryptophan methyl ester (175) and 1,3- benzodioxole-5-carboxaldehyde (176) were subjected to a modified Pictet-Spengler reaction to form cis- and transtetrahydro- β-carboline tricyclic compounds. The ciscompound 177 was isolated as a white solid in 42% yield. The basic nitrogen in the piperidine ring of 177 was acylated with chloroacetyl chloride (179) to give compound 180 in 93% yield. Finally, the diketonepiperazine ring was formed by adding 180 to 33% methylamine in ethanol under refluxing conditions and yielded tadalafil (XXII) in 77% as a white solid.

参考文献

https://www.drugs.com/tadalafil.html
https://www.drugbank.ca/drugs/DB00820
Roehrborn, C. G., et al. "Tadalafil administered once daily for lower urinary tract symptoms secondary to benign prostatic hyperplasia: a dose finding study." Journal of Urology 180.4(2008):1228.
Rosano, Giuseppe M. C., et al. "Chronic Treatment with Tadalafil Improves Endothelial Function in Men with Increased Cardiovascular Risk." European Urology 47.2(2005):214-222.

タダラフィル 上流と下流の製品情報

原材料

準備製品


タダラフィル 生産企業

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171596-29-5(タダラフィル)キーワード:


  • 171596-29-5
  • TADALAFIL
  • CIALIS
  • IC 351
  • (6R,12AR)-6-(benzo[d][1,3]dioxol-5-yl)-2-methyl-2,3,12,12a-tetrahydropyrazino[1',2':1,6]pyrido
  • GF 196960
  • ICOS 351
  • Tildenafil
  • UK 336017
  • TADALAFIL(CIALIS)
  • Taladafil (cialis)
  • Cialis/taladafil
  • (6r,12ar)-6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione
  • Cialis ,98%
  • Pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione, 6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-, (6R,12aR)-
  • Africa and Ghana tadalafil powder extract
  • (6R,12aR)-6-(1,3-Benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-pyrazino[1',2':1,6]pyridol[3,4-b]indole-1,4-dione
  • 6-Benzo[1,3]dioxol-5-yl-2-Methyl-2,3,6,7,12,12a-hexahydro-pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione
  • Adcirca
  • (6R,12aR)-6-(Benzo[d][1,3]dioxol-5-yl)-2-Methyl-2,3,12,12a-tetrahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4(6H,7H)-dione
  • (2R,8R)-2-(2H-1,3-benzodioxol-5-yl)-6-Methyl-3,6,17-triazatetracyclo[8.7.0.0^{3,8}.0^{11,16}]heptadeca-1(10),11(16),12,14-tetraene-4,7-dione
  • Tadalafil Citrate(Cialis)
  • Calais
  • Tadalafil (Cliais)
  • hanyuanjian
  • tadanafei
  • Soya bean milk essence
  • Crepis base
  • Tadalafil?derivative
  • Tadanafil/Cialis Natural Sex Steroid Hormones Powder Purity 99.5%
  • (6R,12AR)-6-(benzo[d][1,3]dioxol-5-yl)-2-m
  • タダラフィル
  • タダラフィル (JAN)
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