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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 724
実験および物理化学的性質
Collision Cross Section
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℃
- 貯蔵温度
- -20 °C · -20°C Freezer
- 溶解性
- クロロホルム(微量、加熱、超音波処理)、DMSO(微量)、エタノール(微量、He
- 外見
- 個体
- 酸解離定数(Pka)
- 12.37 · 12.37±0.60(Predicted)
- 色
- ホワイト~ペールベージュ
- 水溶解度
- 229.9 mg/L · 229.9mg/L(25℃)
- Merck
- 2539 · 2539
- 主な用途
- 臨床検査臨床検査
- InChIKey
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N
- SMILES
- O[C@]1([C@@]2([C@H]([C@H]3[C@@H]([C@]4(CCC(=O)C=C4CC3)C)C(=O)C2)CC1)C)C(=O)CO
- LogP
- 1.47 · 1.470
- CAS データベース
- 53 · 53-06-5(CAS DataBase Reference)
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
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
毒性情報
Effects During Pregnancy and Lactation
◉ 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
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
- hazard_code
- F,T,Xn
- safety_code
- 22-24/25-45-36/37-16-7
- Hazard Classifications
- Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1
- ストレージクラス
- 3 - Flammable liquids
化学と産業
薬理情報
ATC Code
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
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.
Metabolite Pathways
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
Use Classification
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
Pharmaceuticals -> Steroid hormones
応用分野
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.]
上流・下流製品情報
上流原料
下流製品
サプライヤー50 社
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
関連ノート
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