CAS 53-03-2|(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|Prednisone|prednisone|Liquid Pred|Deltasone|Orasone...

基本信息

化学结构

分子式

C₂₁H₂₆O₅

分子量

358.42814

精确质量

358.17802393

电荷

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

Canonic 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

Isomeric 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

计算属性

JChem

LogD (pH = 7.4)

1.66

LogD (pH = 5.5)

1.66

Log P

1.66

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

true

Acid pKa

12.58

极化表面积

91.67

极化性

38.20

摩尔折射率

97.57

LOG S

-3.38

数据来源

名称和标识

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 (1R,3aS,3bS,9aR,9bS,11aS)-1-hydroxy-1-(2-hydroxyacetyl)-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-7,10-dione

别名

PrednisoneLiquid PredDeltasoneOrasoneAdasonePrednisona [INN-Spanish]Prednisonum [INN-Latin]PRDDehydrocortisone1,4-Pregnadiene-17α,21-diol-3,11,20-trione去氢可的松17Α,21-二羟基-1,4-孕甾二烯-3,11,20-三酮Prednisone泼尼松17α,21-Dihydroxy-1,4-pregnadiene-3,11,20-trione强的松1-可的松(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)-dione1-Cortisone17α, 21-Dihydroxypregna-1,4-dien-3,11,20-trione1,4-Pregnadiene-17α,21-diol-3,11,20-trionePrednisonumDeltacortisoneLiquid Pree泼尼松17,21-Dihydroxypregna-1,4-diene-3,11,20-trioneUltracortenAncortoneΔ1-DehydrocortisoneApo-PrednisoneBicortonePrednicortPrednicormRetrocortine1,2-DehydrocortisoneSone(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-dioneDehydrocortisone1,4-Pregnadiene-17alpha,21-diol-3,11,20-trioneprednisone1,2-Dehydrocortisone17,21-Dihydroxypregna-1,4-diene-3,11,20-trioneprednison

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

Prednisone IntensolDacortenPrednicortMeticortenSonePrecortPrednitonePanafcortDecortinCortancylDelcortinSterapredAdasoneRetrocortineDecortancylBetaparPrednisonDecortisylPrednicen-MDelta-cortisoneCartancylBicortoneAncortoneDelta-cortelanServisoneDeltacortenePrednizonNizonParmenisonDeltisonParacortDeltraSupercortilCortanPronison

国际非专利药品(INN)

prednisonumprednisoneprednisona

名称和标识

数据登录号

PubChem SID

16096398046508166248987482488784956352934

EC号

PubChem CID

CAS号

Beilstein号

MDL号

Chemspider ID

CHEMBL

ATC码

维基百科标题

KEGG ID

CHEBI ID

Medline Plus

美国药典/FDA物质标识码

DrugBank ID

专利号

US2008261978WO2005073221US2005043330US2006199789US2007231410US2008221161WO2005073203WO2005075447WO2008153701WO2005007628WO2005077925WO2007123765EP1913942EP1900742

BRENDA Ligand数据库

145980145066102926104334

CompTox数据库

DTXSID4021185

BRENDA数据库

4.1.99.37.6.2.21.14.13.541.1.1.1461.1.1.2131.3.99.41.1.1.501.14.15.8

PubMed文献链接

1043897423093541233952811897157015859934

MetaboLights数据库

MTBLS205MTBLS2145MTBLS673MTBLS2825MTBLS3487MTBLS586MTBLS3750

SABIO-RK数据库

240810117

Reaxys Registry

2065301

BKMS React数据库

104334102926145066145980

SureChEMBL数据库

SCHEMBL3288

Drug Central Database

2,253

数据登录号

化合物性质

分子相关蛋白质

暂无数据

点击上传数据

分子图谱

暂无数据

点击上传数据

描述信息

DrugBank

DB00635

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

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]

MP Biomedicals

02102718

Crystalline

05218172

MP Biomedicals Rare Chemical collection

Wikipedia

Prednisone

Sigma Aldrich

P6254

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

286990

包装
5 g in glass bottle

TRC

P703780

Adrenocortical steroid. Glucocorticoid, antiinflammatory.

ChEBI

CHEBI:8382

A synthetic glucocorticoid drug that is particularly effective as an immunosuppressant, and affects virtually all of the immune system. Prednisone is a prodrug that is converted by the liver into prednisolone (a beta-hydroxy group instead of the oxo group at position 11), which is the active drug and also a steroid.

描述信息

参考文献

PubChem文献

数据源提供

• 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)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, PLZ000; PLZ100

• Gambertoglio, J.G. et al., J. Pharmacokinet. Biopharm., 1980, 8, 1, (rev)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 587B, (nmr)

• Herzog, H.L. et al., Tetrahedron, 1962, 18, 581, (synth)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6213

• Ger. Pat., 1960, 1 090 208; CA, 55, 26044b, (sulfate)

• Ger. Pat., 1960, 1 089 755; CA, 55, 20008, (succinate)

• Nobile, A. et al., J.A.C.S., 1955, 77, 4184, (synth)

• Pickup, M.E., Clin. Pharmacokinet., 1979, 4, 111, (rev)

• Herzog, H.L. et al., Science (Washington, D.C.), 1955, 121, 176, (struct)

• Hickey, J.P. et al., J. Magn. Reson., 1980, 38, 501, (cmr)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 738

• Gardi, R. et al., Gazz. Chim. Ital., 1963, 93, 431, (ir, uv)

参考文献

生物活性

PubChem BioAssay

生物活性

描述信息

DrugBank

DB00635

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

Pharmacology

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]

S1622

Crystalline

MP Biomedicals Rare Chemical collection

Wikipedia

Prednisone

Sigma Aldrich

P6254

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

286990

包装
5 g in glass bottle

TRC

P703780

Adrenocortical steroid. Glucocorticoid, antiinflammatory.

ChEBI

CHEBI:8382

参考文献

PubChem文献

数据源提供

• http://en.wikipedia.org/wiki/Prednisone

• Lennon, V., et al.: Lancet, 364, 2106 (2004)