コルチゾン

Cortisone

HCID 222786CAS 53-06-5

基本情報

標準SMILES
C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2C(=O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO
InChIKey
MFYSYFVPBJMHGN-ZPOLXVRWSA-N
分子式
C21H28O5
平均分子量
360.4 g/mol
単同位体質量
360.19367399

名称と識別子

優先名称
Cortisone
IUPAC
(8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,11-dione
現地名
コルチゾン
英語名
CORTISONE
分子式
C21H28O5
分子量
360.44

名称と別名

cortisone53-06-5Kendall's compound EReichstein's substance FAWintersteiner's compound F17-Hydroxy-11-dehydrocorticosterone11-Dehydro-17-hydroxycorticosteronePregn-4-ene-3,11,20-trione, 17,21-dihydroxy-Cortisona17,21-Dihydroxypregn-4-ene-3,11,20-trioneCortisonumKortison
名称をさらに表示
コルチゾンライヒシュタイン物質Fa化合物EKendall化合物EコルトンWintersteiner化合物FコルチサートReichstein物質Fa17,21-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(1R,3aS,3bS,9aR,9bS,11aS)-1-ヒドロキシ-1-(2-ヒドロキシアセチル)-9a,11a-ジメチル-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-シクロペンタ[a]フェナントレン-7,10-ジオンKECortisonCorlinCORTONE17A 21-DIHYDROXY-4-PREGNEN-3 17 20-TRIONE(8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,11-dione(8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,6,7,8,9,10,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-3,11(2H)-dioneCortonAdreson
4-Pregnene-17alpha,21-diol-3,11,20-trione17alpha,21-Dihydroxypregn-4-ene-3,11,20-trioneDTXSID5022857Pregn-4-en-17alpha,21-diol-3,11,20-trione17alpha,21-Dihydroxy-4-pregnene-3,11,20-trioneNSC-9703V27W9254FZDTXCID102857

データベース識別子

CAS
53-06-5
PubChem CID
222786
DTXSID
DTXSID5022857
ChEMBL
CHEMBL1499
ChEBI
CHEBI:16962
UNII
V27W9254FZ
EC Number
200-162-4
Nikkaji
J4.139D

物性

構造計算による物性

XLogP
1.5
極性表面積
91.7 Ų
水素結合供与体数
2
水素結合受容体数
5
回転可能結合数
2
重原子数
26

実験および物理化学的性質

LogP1.47
Solubility0.28 mg/mL at 25 °C
Melting Point222 °C
Physical DescriptionSolid
Collision Cross Section · 6 件

257.2 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID5022857]

180.07 Ų [M-H2O-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)];188.6 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

172.48 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];186.07 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];182.86 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

184 Ų [M+H]+ [CCS Type: TW]

184.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

213.2 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)];191.4 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)];188.3 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

物理化学的性質

融点
223 · 223-228 °C (dec.)(lit.)
比旋光度
25 · 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 · 412.46°C (rough estimate)
比重(密度)
1.28 · 1.28±0.1 g/cm3 (20 ºC 760 Torr)
屈折率
210 ° · 210 ° (C=1, EtOH)
闪点
9 ℃ · 9℃

化学的性質

化学的特性Off-White Crystalline Powder

安全と法規制

GHS分類

GHS Classification · 5 件

Warning

H361 (98%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 51 reports by companies from 5 notifications to the ECHA C&L Inventory.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

危険有害性情報

Regulatory InformationCortisone: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Pregn-4-ene-3,11,20-trione, 17,21-dihydroxy-: Human health tier I assessment;IMAP assessments - Pregn-4-ene-3,11,20-trione, 17,21-dihydroxy-: Environment tier I assessment
Hazard Classes and CategoriesRepr. 2 (98%)

毒性情報

Effects During Pregnancy and Lactation · 1 件

◉ Summary of Use during Lactation;Cortisone is a normal component of breastmilk that passes from the mother's bloodstream into milk and might have a role in intestinal maturation, the intestinal microbiome, growth, body composition or neurodevelopment, but adequate studies are lacking. Concentrations follow a diurnal rhythm, with the highest concentrations in the morning at about 7:00 am and the lowest concentrations in the late afternoon and evening. Cortisone has not been studied in breastmilk after exogenous administration in pharmacologic amounts. Although it is unlikely that dangerous amounts of cortisone would reach the infant, a better studied alternate drug might be preferred. Medium to large doses of corticosteroids given systemically or injected into joints or the breast have been reported to cause temporary reduction of lactation.;◉ Effects in Breastfed Infants;None reported with any corticosteroid.;◉ Effects on Lactation and Breastmilk;Published information on the effects of cortisone on serum prolactin or on lactation in nursing mothers was not found as of the revision date. Medium to large doses of corticosteroids given systemically or injected into joints or the breast have been reported to cause temporary reduction of lactation.;A study of 46 women who delivered an infant before 34 weeks of gestation found that a course of another corticosteroid (betamethasone, 2 intramuscular injections of 11.4 mg of betamethasone 24 hours apart) given between 3 and 9 days before delivery resulted in delayed lactogenesis II and lower average milk volumes during the 10 days after delivery. Milk volume was not affected if the infant was delivered less than 3 days or more than 10 days after the mother received the corticosteroid. An equivalent dosage regimen of cortisone might have the same effect.;A study of 87 pregnant women found that betamethasone given as above during pregnancy caused a premature stimulation of lactose secretion during pregnancy. Although the increase was statistically significant, the clinical importance appears to be minimal. An equivalent dosage regimen of cortisone might have the same effect.

法規制情報

Regulatory InformationCortisone: Does not have an individual approval but may be used under an appropriate group standard

安全データ

F
18
wgk
3
rtecs
GM9020000
ridadr
UN1230 - class 3 - PG 2 - Methanol, solution
hs_code
2937210000
risk_code
11-23/24/25-39/23/24/25-63

化学と産業

薬理情報

ATC Code · 4 件

H - Systemic hormonal preparations, excl. sex hormones and insulins;H02 - Corticosteroids for systemic use;H02A - Corticosteroids for systemic use, plain;H02AB - Glucocorticoids;H02AB10 - Cortisone

S - Sensory organs;S01 - Ophthalmologicals;S01B - Antiinflammatory agents;S01BA - Corticosteroids, plain;S01BA03 - Cortisone

QH - Systemic hormonal preparations, excl. sex hormones and insulin;QH02 - Corticosteroids for systemic use;QH02A - Corticosteroids for systemic use, plain;QH02AB - Glucocorticoids;QH02AB10 - Cortisone

QS - Sensory organs;QS01 - Ophthalmologicals;QS01B - Antiinflammatory agents;QS01BA - Corticosteroids, plain;QS01BA03 - Cortisone

FDA Pharmacological Classification · 5 件

V27W9254FZ

CORTISONE

Established Pharmacologic Class [EPC] - Corticosteroid

Mechanisms of Action [MoA] - Corticosteroid Hormone Receptor Agonists

Cortisone is a Corticosteroid. The mechanism of action of cortisone is as a Corticosteroid Hormone Receptor Agonist.

MeSH Pharmacological ClassificationSubstances that reduce or suppress INFLAMMATION.
Tissue LocationsAdipose Tissue;Adrenal Cortex;Adrenal Gland;Epidermis;Fibroblasts;Intestine;Kidney;Neuron;Placenta;Skeletal Muscle;Testis;Thyroid Gland
Cellular LocationsEndoplasmic reticulum;Extracellular;Membrane
Metabolite Pathways · 1 件

11-beta-hydroxylase deficiency (CYP11B1);17-alpha-hydroxylase deficiency (CYP17);21-hydroxylase deficiency (CYP21);3-Beta-Hydroxysteroid Dehydrogenase Deficiency;Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase Deficiency;Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia due to 17 Alpha-hydroxylase Deficiency;Apparent mineralocorticoid excess syndrome;Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH;Corticosterone methyl oxidase I deficiency (CMO I);Corticosterone methyl oxidase II deficiency - CMO II;Total 11 pathways, visit the HMDB page for details

用途と製造

UsesCalculated removal (%): 45.8
Use Classification · 2 件

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Pharmaceuticals -> Steroid hormones

応用分野 · 4 件

解説コルチゾン,白色の結晶.融点215 ℃.[α]D25"+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.森北出版「化学辞典(第2版)

用途薬理研究用。

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

一般的な説明Cortisone is a corticosteroid produced in the adrenal glands. Cortisone is administered for short term pain relief and to reduce swelling from inflammation. This Certified Spiking Solution is applicable in LC-MS/MS applications for endocrinology, clinical chemistry and neonatal screening.

調製方法

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.]

サプライヤー50 社

南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
阿诺西(上海)生物技术有限公司400-1107768 15058188853 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
盐城通铭生物科技有限公司15195160625 · [email protected]

補足説明

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.

関連反応

3 件

関連ノート

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