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コルチゾン

コルチゾン 化学構造式
53-06-5
CAS番号.
53-06-5
化学名:
コルチゾン
别名:
コルチゾン;ライヒシュタイン物質Fa;化合物E;Kendall化合物E;コルトン;Wintersteiner化合物F;コルチサート;Reichstein物質Fa;17,21-ジヒドロキシプレグナ-4-エン-3,11,20-トリオン;17α,21-ジヒドロキシプレグナ-4-エン-3,11,20-トリオン;ウィンターシュタイナー化合物F;コルチビット;コルトゲン;アドレナレックス;コーチゾン;コルチソン;ケンダル化合物E;コンパウンドE;コルチゾン, 結晶
英語化学名:
CORTISONE
英語别名:
KE;Corlin;Corton;Adreson;CORTONE;Andreson;Cortisal;Cortison;Cortogen;Incortin
CBNumber:
CB6413305
化学式:
C21H28O5
分子量:
360.44
MOL File:
53-06-5.mol

コルチゾン 物理性質

融点 :
223-228 °C (dec.)(lit.)
比旋光度 :
D25 +209° (c = 1.2 in 95% alcohol); 25546 +269° (c = 0.125 in benzene); 25546 +248° (c = 0.1 to 0.2 in alcohol)
沸点 :
412.46°C (rough estimate)
比重(密度) :
1.28±0.1 g/cm3 (20 ºC 760 Torr)
屈折率 :
210 ° (C=1, EtOH)
闪点 :
9℃
貯蔵温度 :
-20°C Freezer
酸解離定数(Pka):
12.37±0.60(Predicted)
水溶解度 :
229.9mg/L(25 ºC)
Merck :
2539
CAS データベース:
53-06-5(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,T,Xn
Rフレーズ  11-23/24/25-39/23/24/25-63
Sフレーズ  22-24/25-45-36/37-16-7
RIDADR  UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany  3
RTECS 番号 GM9020000
18
HSコード  2937210000
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
H370 臓器の障害 特定標的臓器有害性、単回暴露 1 危険 P260, P264, P270, P307+P311, P321,P405, P501
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。
P260 粉じん/煙/ガス/ミスト/蒸気/スプレーを吸入しないこ と。
P280 保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。
P301+P310 飲み込んだ場合:直ちに医師に連絡すること。
P311 医師に連絡すること。

コルチゾン 価格 もっと(15)

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) W01MPB02190172 コルチゾン, 結晶
Cortisone, Crystalline
53-06-5 250mg ¥5400 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01MPB02190172
Cortisone, Crystalline
53-06-5 1g ¥6000 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01CHDASB-00003795 コルチゾン
Cortisone
53-06-5 100mg ¥13400 2018-12-26 購入
東京化成工業 C1317 コルチゾン >97.0%(HPLC)
Cortisone >97.0%(HPLC)
53-06-5 10g ¥13500 2020-09-21 購入
東京化成工業 C1317 コルチゾン >97.0%(HPLC)
Cortisone >97.0%(HPLC)
53-06-5 1g ¥3100 2021-03-23 購入

コルチゾン 化学特性,用途語,生産方法

外観

白色~わずかにうすい褐色, 結晶性粉末~粉末

溶解性

メタノール, エタノール, アセトン, クロロホルムに易溶、水に不溶。

解説

17α,21-dihydroxypregn-4-one-3,11,20-trione.C21H28O5(360.44).副じん皮質ホルモンの一つ.1936年,O. WintersteinerとJ. Pfiffnerによりウシの副腎からはじめて結晶状に単離されたが,同年,T. Reichstein(ライヒシュタイン),E.C. Kendall(ケンダル)らも抽出?結晶化に成功した.また,1950年,J.J. Schneiderは男子尿より単離している.1949年にP.S. Hench(ヘンチ)とKendallは,リウマチ性疾患に特効性を有することを報告した.デオキシコール酸,ジオスゲニン,ヘコゲニン,スチグマステロール,エルゴステロールなどの原料から合成されている.白色の結晶.融点215 ℃."+209°(エタノール).水にほとんど不溶,エタノール,アセトンに可溶,エーテル,ベンゼンに難溶.グルココルチコイド作用が強く,ミネラルコルチコイド作用は弱い.副腎皮質機能不全,リウマチ性疾患,アレルギー性疾患,皮膚疾患などの治療に用いられる.コルチゾンのエステル誘導体ではコルチゾン21-アセタートが知られている.[CAS 53-06-5]"
森北出版「化学辞典(第2版)

用途

薬理研究用。

効能

抗炎症薬, グルココルチコイド受容体作動薬

化学的特性

Off-White Crystalline Powder

Originator

Cortone Acetate,MSD,US,1950

使用

Cortisone is used for inflammatory processes, allergies, and adrenal insufficiency.

使用

Glucocorticoid, anti-inflammatory agent

使用

antiinflammatory, glucocorticoid

使用

Anticoagulant

定義

ChEBI: A C21-steroid that is pregn-4-ene substituted by hydroxy groups at positions 17 and 21 and oxo group at positions 3, 11 and 20.

Manufacturing Process

The following technique is described in US Patent 2,541,104. A solution of 2.0 g of 3(α)-hydroxy-21-acetoxy-11,20-diketo-pregnane, which can be prepared as described in Helv. Chim. Acta 27, 1287 (1944), is treated in a mixture of 25 cc of alcohol and 6.4 cc of acetic acid at 0°C with 6.0 g of potassium
cyanide. The solution is allowed to warm to room temperature and after 3 hours is diluted with water. The addition of a large volume of water to the alcohol-hydrogen cyanide mixture precipitates a gum which is extracted with chloroform or ethyl acetate. The extract is washed with water, and evaporated to small volume under reduced pressure. The crystalline precipitate (1.3 g) consists of 3(α),20-dihydroxy-20-cyano-21-acetoxy-11-keto-pregnane; dec. 175° to 185°C.
A solution of 0.60 g of chromic acid in 1.2 cc of water and 11 cc of acetic acid is added to a solution containing about 1.2 g of 3(α),20-dihydroxy-20-cyano- 21-acetoxy-11-ketopregnane at room temperature. After 1 hour, water is added and the product, which precipitates, is filtered and recrystallized from ethyl acetate to produce 3,11-diketo-20-hydroxy-20-cyano-21-acetoxypregnane; dec. 214° to 217°C.
0.40 cc of phosphorus oxychloride is added to a solution containing about 950 mg of 3,11-diketo-20-hydroxy-20-cyano-21-acetoxy-pregnane dissolved in 3 cc of pyridine. After standing at room temperature for 24 hours, the solution is poured into water and dilute hydrochloric acid, extracted with benzene and concentrated to dryness. The crude product, after chromatography gives one main constituent, namely δ17-3,11-diketo-20-cyano-21-acetoxy-pregnene; MP 189° to 190°C.
A solution of 1.0 g of δ17-3,11-diketo-20-cyano-21-acetoxy-pregnene in 10 cc of benzene is treated with 1.0 g of osmium tetroxide and 0.43 g of pyridine. After standing at room temperature for 18 hours, the resulting solution is treated successively with 50 cc of alcohol, and with 50 cc of water containing 2.5 g of sodium sulfite. The mixture is stirred for 30 hours, filtered, and the filtrate acidified with 0.5 cc of acetic acid and concentrated to small volume in vacuo. The aqueous suspension is then extracted four times with chloroform, the chloroform extracts are combined, washed with water and concentrated to dryness in vacuo. Recrystallization of the residue from acetone gives 9°C. This compound is then treated with acetic anhydride and pyridine for 15 minutes at room temperature to produce 3,11,20-triketo-17(α)-hydroxy-21-acetoxypregnane or cortisone acetate.

Therapeutic Function

Glucocorticoid

危険性

Damaging side effects, e.g., sodium retention from ingestion.

薬物動態学

Following oral administration, cortisone acetate and hydrocortisone acetate are completely and rapidly deacetylated by first-pass metabolism. Much of the oral cortisone, however, is inactivated by oxidative metabolism before it can be converted to hydrocortisone in the liver. The pharmacokinetics for hydrocortisone acetate is indistinguishable from that of orally administered hydrocortisone. Oral hydrocortisone is completely absorbed, with a bioavailability of greater than 95% and a half-life of 1 to 2 hours (23).

臨床応用

Cortisone is administered orally or by intramuscular (IM) injection as its 21-acetate (cortisone acetate).Cortisone acetate or hydrocortisone usually is the corticosteroid of choice for replacement therapy in patients with adrenocortical insufficiency, because these drugs have both glucocorticoid and mineralocorticoid properties.

Chemical Synthesis

Cortisone, 17α,21-dihydroxypregn-4-en-3,11,20-trione (27.1.26), is also synthesized in various ways from compounds already having the steroid skeleton. One of them is very similar to a method of making hydrocortisone described above, in which it is synthesized from progesterone, which undergoes microbiological oxidation, forming 11α-hydroxyprogesterone (27.1.9). The hydroxyl group of the last is oxidized by chromium(VI) oxide in acetic acid, giving 11-ketoprogesterone (27.1.10). This is reacted with diethyloxalate in the presence of sodium ethoxide, forming the corresponding α-ketoester in the form of a sodium enolate 27.1.11, which undergoes bromination with two equivalents of bromine, giving a dibromoketone 27.1.12. The resulting dibromoketone undergoes a Favorskii rearrangement, but the product is not hydrolyzed, and the unsaturated acid is isolated in the form of a methyl ester 27.1.20. Reacting this with pyrrolidine gives a dienamine 27.1.21, which undergoes reduction by lithium aluminum hydride, which results in that, the keto-group on C11 transforms into a hydroxyl group, and the carbmethoxy group to a primary alcohol, forming the compound 27.1.22. Acidic hydrolysis of the product and subsequent acetylation gives an acetate 27.1.23, and the hydroxyl group at C11 in which it is oxidized with chromium(VI) oxide to a ketone, forming the compound 27.1.24. This undergoes a reaction with osmium tetroxide, and the resulting osmate is oxidized by magnesium dioxide in N-methylmorpholine, giving cortisone acetate 27.1.25. Hydrolysis of the acetyl group using sodium bicarbonate leads to the formation of cortisone (27.1.26).

代謝

The metabolism of hydrocortisone has been previously described. Cortisone acetate is slowly absorbed from IM injection sites over a period of 24 to 48 hours and is reserved for patients who are unable to take the drug orally. The acetate ester derivative demonstrates increased stability and has a longer duration of action when administered by IM injection. Thus, smaller doses can be used. Similarly, hydrocortisone may be dispensed as its 21-acetate (hydrocortisone acetate), which is superior to cortisone acetate when injected intra-articularly.

純化方法

Crystallise cortisone from 95% EtOH or acetone. The UV has 14,000 M-1cm -1 at 237nm (EtOH). [Beilstein 8 IV 3480, Hems J Pharm Pharmacol 5 409 1953, Beilstein 8 IV 3480.]

コルチゾン 上流と下流の製品情報

原材料

準備製品


コルチゾン 生産企業

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53-06-5(コルチゾン)キーワード:


  • 53-06-5
  • 17,21-Dihydroxy-4-pregnene-3,11,20-trione
  • 17,21-Dihydroxypregn-4-ene-3,11,20-trione
  • 20-trione,17,21-dihydroxy-pregn-4-ene-11
  • Adrenalex
  • Adreson
  • Andreson
  • Corlin
  • Cortadren
  • Cortandren
  • Cortisal
  • Cortisate
  • Cortison
  • Cortistal
  • Cortivite
  • Cortogen
  • delta(sup4)-pregnene-17alpha,21-diol-3,11,20-trione
  • Incortin
  • KE
  • Kendall's compound
  • Pregn-4-en-17alpha,21-diol-3,11,20-trione
  • Pregn-4-ene-3,11,20-trione, 17,21-dihydroxy-
  • Reichstein Fa
  • Scheroson
  • (8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-diMethyl-7,8,9,10,12,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,11(2H,6H)-dione
  • Cortisone solution
  • Cortisone-[2H7]
  • NSC 9703
  • 4-Pregnen-17a,21-diol-3,11,20-trione-d2
  • 11-DEHYDRO-17-HYDROXYCORTICOSTERONE
  • 17A 21-DIHYDROXY-4-PREGNEN-3 17 20-TRIONE
  • コルチゾン
  • ライヒシュタイン物質Fa
  • 化合物E
  • Kendall化合物E
  • コルトン
  • Wintersteiner化合物F
  • コルチサート
  • Reichstein物質Fa
  • 17,21-ジヒドロキシプレグナ-4-エン-3,11,20-トリオン
  • 17α,21-ジヒドロキシプレグナ-4-エン-3,11,20-トリオン
  • ウィンターシュタイナー化合物F
  • コルチビット
  • コルトゲン
  • アドレナレックス
  • コーチゾン
  • コルチソン
  • ケンダル化合物E
  • コンパウンドE
  • コルチゾン, 結晶
  • ステロイド
  • ヒドロキシケトステロイド
  • 生化学
  • グルココルチコイド
  • 抗アレルギー薬
  • 抗リウマチ薬
  • 消炎薬
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