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53-03-2 分子结构
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(1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-diene-5,17-dione

ChemBase编号:517
分子式:C21H26O5
平均质量:358.42814
单一同位素质量:358.17802393
SMILES和InChIs

SMILES:
O[C@]1([C@@]2([C@H]([C@H]3[C@@H]([C@@]4(C(=CC(=O)C=C4)CC3)C)C(=O)C2)CC1)C)C(=O)CO
Canonical SMILES:
OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)CC(=O)[C@H]1[C@H]2CCC2=CC(=O)C=C[C@]12C
InChI:
InChI=1S/C21H26O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h5,7,9,14-15,18,22,26H,3-4,6,8,10-11H2,1-2H3/t14-,15-,18+,19-,20-,21-/m0/s1
InChIKey:
XOFYZVNMUHMLCC-ZPOLXVRWSA-N

引用这个纪录

CBID:517 http://www.chembase.cn/molecule-517.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
(1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-diene-5,17-dione
(1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-diene-5,17-dione
IUPAC传统名
prednisone
(1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-diene-5,17-dione
商标名
Delta-cortelan
Delta-cortisone
Delta-cortone
Delta-dome
Adasone
Ancortone
Apo-prednisone
Betapar
Bicortone
Cartancyl
Colisone
Cortan
Cortancyl
Cortidelt
Cotone
Dacorten
Dacortin
Decortancyl
Decortin
Decortisyl
Dekortin
Delcortin
Dellacort
Dellacort A
Delta Cortelan
Delta E
Deltacortene
Deltacortisone
Deltacortone
Deltasone
Deltison
Deltisona
Deltisone
Deltra
Di-Adreson
Diadreson
Econosone
Encorton
Encortone
Enkorton
Fernisone
Fiasone
Hostacortin
In-Sone
Incocortyl
Juvason
Lisacort
Me-Korti
Metacortandracin
Meticorten
Nisona
Nizon
Novoprednisone
Nurison
Orasone
Origen Prednisone
Panafcort
Panasol
Paracort
Parmenison
Pehacort
Precort
Predeltin
Prednicen-M
Prednicorm
Prednicort
Prednicot
Prednidib
Prednilonga
Prednison
Prednisone Intensol
Prednitone
Prednizon
Prednovister
Presone
Pronison
Rectodelt
Retrocortine
Servisone
Sone
Sterapred
Supercortil
Ultracorten
Ultracortene
Winpred
Wojtab
Zenadrid
别名
1-可的松
17Α,21-二羟基-1,4-孕甾二烯-3,11,20-三酮
去氢可的松
强的松
泼尼松
泼尼松
1,4-Pregnadiene-17α,21-diol-3,11,20-trione
17α,21-Dihydroxy-1,4-pregnadiene-3,11,20-trione
Prednisone
Liquid Pree
Deltacortisone
Prednisonum
Prednisona [INN-Spanish]
Prednisonum [INN-Latin]
PRD
Dehydrocortisone
Prednisone
Deltasone
Liquid Pred
Orasone
Adasone
(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-3H-cyclopenta[a]phenanthrene-3,11(6H)-dione
1-Cortisone
17α, 21-Dihydroxypregna-1,4-dien-3,11,20-trione
1,4-Pregnadiene-17α,21-diol-3,11,20-trione
17,21-Dihydroxypregna-1,4-diene-3,11,20-trione
1,2-Dehydrocortisone
Ancortone
Apo-Prednisone
Bicortone
Prednicorm
Prednicort
Retrocortine
Sone
Ultracorten
Δ1-Dehydrocortisone
(1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-diene-5,17-dione
CAS号
53-03-2
EC号
200-160-3
MDL号
MFCD00003608
Beilstein号
2065301
PubChem SID
160963980
46508166
24887849
24898748
PubChem CID
5865
CHEBI ID
8382
ATC码
A07EA03
H02AB07
CHEMBL
635
Chemspider ID
5656
DrugBank ID
DB00635
KEGG ID
C07370
美国药典/FDA物质标识码
3EN3HG4WSW
维基百科标题
Prednisone
Medline Plus
a601102

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 12.576199  质子受体
质子供体 LogD (pH = 5.5) 1.6585041 
LogD (pH = 7.4) 1.6585013  Log P 1.6585041 
摩尔折射率 97.5681 cm3 极化性 37.495747 Å3
极化表面积 91.67 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 2.07  LOG S -3.51 
溶解度 1.11e-01 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
312 mg/L expand 查看数据来源
Dioxane expand 查看数据来源
DMSO expand 查看数据来源
Ethanol expand 查看数据来源
Pyridine expand 查看数据来源
外观
White Solid expand 查看数据来源
熔点
220-225°C expand 查看数据来源
236-238 °C(lit.) expand 查看数据来源
253 - 255°C expand 查看数据来源
decomposes 233-235 °C expand 查看数据来源
比旋光度
[α]25/D +169°, c = 0.5 in dioxane expand 查看数据来源
疏水性(logP)
0.6 expand 查看数据来源
1.661 expand 查看数据来源
保存条件
-20°C expand 查看数据来源
Refrigerator expand 查看数据来源
Room Temperature (15-30°C) expand 查看数据来源
RTECS编号
TU4154100 expand 查看数据来源
欧盟危险性物质标志
有害性(Harmful) 有害性(Harmful) (Xn) expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
危险公开号
63 expand 查看数据来源
安全公开号
36/37/39-45 expand 查看数据来源
GHS危险品标识
GHS08 expand 查看数据来源
GHS警示词
Warning expand 查看数据来源
GHS危险声明
H361 expand 查看数据来源
GHS警示性声明
P281 expand 查看数据来源
个人保护装置
Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand 查看数据来源
给药途径
Oral, Nasal, Rectal, Injection, IV expand 查看数据来源
生物利用度
70% expand 查看数据来源
排泄
Renal expand 查看数据来源
半衰期
1 hour expand 查看数据来源
代谢
prednisolone (liver) expand 查看数据来源
法定药品分级
Rx Only (US) expand 查看数据来源
妊娠期药物分类
C expand 查看数据来源
生物活性机理
ACTH antagonist expand 查看数据来源
ACTH secretion inhibitor expand 查看数据来源
Calcium mobilizer expand 查看数据来源
Corticosteroid expand 查看数据来源
Gluconeogenesis promoter expand 查看数据来源
Glycogen deposition inhibitor expand 查看数据来源
Phosphorus mobilizer expand 查看数据来源
纯度
≥98% expand 查看数据来源
95% expand 查看数据来源
98% expand 查看数据来源
级别
Ph Eur expand 查看数据来源
成盐信息
Free Base expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
应用领域
Antiinflammatory expand 查看数据来源
Immunosuppressive expand 查看数据来源
药典
testing & handling conforms to Pharmacopeia expand 查看数据来源
Pharmacopeia Traceability
traceable to BP 553 expand 查看数据来源
traceable to PhEur P2900000 expand 查看数据来源
traceable to USP 1559006 expand 查看数据来源
Empirical Formula (Hill Notation)
C21H26O5 expand 查看数据来源

详细说明

详细说明

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals -  05218172 external link
MP Biomedicals Rare Chemical collection
MP Biomedicals -  02102718 external link
Crystalline
DrugBank -  DB00635 external link
Item Information
Drug Groups approved
Description A synthetic anti-inflammatory glucocorticoid derived from cortisone. It is biologically inert and converted to prednisolone in the liver. [PubChem]
Indication For the treatment of drug-induced allergic reactions, perennial or seasonal allergic rhinitis, serum sickness, giant cell arteritis acute rheumatic or nonrheumatic carditis, systemic dermatomyositis, systemic lupus erythematosus, atopic dermatitis, contact dermatitis, exfoliative dermatitis, bullous dermatitis herpetiformis, severe seborrheic dermatitis, severe (Stevens-Johnson syndrome) erythema multiforme, mycosis fungoides, pemphigus, severe psoriasis, acute adrenocortical insufficiency, Addison's disease, secondary adrenocortical insufficiency, congenital adrenal hyperplasia, hypercalcemia associated with neoplasms, nonsuppurative thyroiditis, ulceratice colitis, Crohn's disease, acquired hemolytic anemia, congenital hypoplastic anemia, erythroblastopenia, adult secondary thrombocytopenia, adult idiopathic thrombocytopenia purpura, acute or subacute bursitis, epicondylitis, acute nonspecific tenosynovitis, acute or chronic lymphocytic leukemia, Hodgkin's or non-Hodgkin's lynphomas, Waldenstrom's macroglobulinemia, primary brain tumors (adjunct), nephrotic syndrome, tuberculous meningitis, multiple sclerosis, myasthenia gravis. cerebral edema, chorioretinitis, diffuse posterior choroiditis, aleergic conjunctivitis, Herpes zoster ophthalmicus, anterior segment inflammation, iridocyclitis, iritis, keratitis, optoc neuritis, sympathetic ophthalmia, corneal marginal allergic ulcers, symptomatic sarcoidosis, Loeffler's syndrome not manageable by other means, berylliosis, fulminating or disseminated pulmonary tuberculosis when used concurrently with appropriate antituberculous chemotherapy and aspiration pneumonitis.
Pharmacology Prednisone, the most commonly-prescribed corticosteroid, is used to treat allograft rejection, asthma, systemic lupus erythematosus, and many other inflammatory states. Prednisone has very little mineralocorticoid activity.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic.
Absorption Readily absorbed from the gastrointestinal tract.
Half Life 2 to 3 hours
Protein Binding Extensively bound to plasma proteins.
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals -  S1622 external link
Research Area: Immunology
Biological Activity:
Prednisone(Adasone) is a synthetic corticosteroid agent that is particularly effective as an immunosuppressant compound. Prednisone(Adasone) is used to treat certain inflammatory diseases and (at higher doses) some types of cancer, but has significant adverse effects. Because prednisone (Adasone) suppresses the immune system, prednisone (Adasone) leaves patients more susceptible to infections. Prednisone(Adasone) is usually taken orally but can be delivered by intramuscular injection or intravenous injection. Prednisone(Adasone) has a mainly glucocorticoid effect. Prednisone (Adasone) is converted by the liver into prednisolone, which is the active compound and also a steroid. [1]
Sigma Aldrich -  P6254 external link
Biochem/physiol Actions
Prednisone is a synthetic glucocorticoid with anti-inflammatory and immunosuppressive activity.
包装
1 g in poly tube
5, 10, 25 g in poly bottle
Sigma Aldrich -  286990 external link
包装
5 g in glass bottle
Toronto Research Chemicals -  P703780 external link
Adrenocortical steroid. Glucocorticoid, antiinflammatory.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • http://en.wikipedia.org/wiki/Prednisone
  • Lennon, V., et al.: Lancet, 364, 2106 (2004)
  • Wingerchuk, D., et al.: Neurology, 66, 1485 (2004)
  • Fliri, A.F., et al.: J. Med. Chem., 52, 8038 ((2004)
  • Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 587B, (nmr)
  • Nobile, A. et al., J.A.C.S., 1955, 77, 4184, (synth)
  • Herzog, H.L. et al., Science (Washington, D.C.), 1955, 121, 176, (struct)
  • Ger. Pat., 1960, 1 089 755; CA, 55, 20008, (succinate)
  • Ger. Pat., 1960, 1 090 208; CA, 55, 26044b, (sulfate)
  • Herzog, H.L. et al., Tetrahedron, 1962, 18, 581, (synth)
  • Gardi, R. et al., Gazz. Chim. Ital., 1963, 93, 431, (ir, uv)
  • Pickup, M.E., Clin. Pharmacokinet., 1979, 4, 111, (rev)
  • Hickey, J.P. et al., J. Magn. Reson., 1980, 38, 501, (cmr)
  • Gambertoglio, J.G. et al., J. Pharmacokinet. Biopharm., 1980, 8, 1, (rev)
  • Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6213
  • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 738
  • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, PLZ000; PLZ100
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专利

专利

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