CAS 51333-22-3|16,17-Butylidenebis(oxy)-11,21-dihydroxypregna-1,4-diene-3,20-dione|budesonide|(1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-propyl-5,7-dioxapentacyclo[1...

基本信息

化学结构

分子式

C₂₅H₃₄O₆

分子量

430.53386

精确质量

430.23553881

电荷

InChI

InChI=1S/C25H34O6/c1-4-5-21-30-20-11-17-16-7-6-14-10-15(27)8-9-23(14,2)22(16)18(28)12-24(17,3)25(20,31-21)19(29)13-26/h8-10,16-18,20-22,26,28H,4-7,11-13H2,1-3H3/t16-,17-,18-,20+,21?,22+,23-,24-,25+/m0/s1

InChIKey

VOVIALXJUBGFJZ-KWVAZRHASA-N

Canonic Smiles

CCCC1O[C@H]2[C@](O1)(C(=O)CO)[C@@]1([C@@H](C2)[C@@H]2CCC3=CC(=O)C=C[C@@]3([C@H]2[C@H](C1)O)C)C

Isomeric Smiles

CCCC1O[C@@H]2C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@@]5([C@H]4[C@H](C[C@@]3([C@@]2(O1)C(=O)CO)C)O)C

计算属性

JChem

LogD (pH = 7.4)

2.73

LogD (pH = 5.5)

2.73

Log P

2.73

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

13.75

极化表面积

93.06

极化性

46.88

摩尔折射率

116.11

LOG S

-4.73

数据来源

名称和标识

别名

16,17-Butylidenebis(oxy)-11,21-dihydroxypregna-1,4-diene-3,20-dioneBudesonideRespulesLisoflamBudesonideBidienPreferidBudesomideRhinocort(11β,16α)-16,17-[Butylidenebis(oxy)]-11,21-dihydroxypregna-1,4-diene-3,20-dioneBudenofalkTurbuhalerOlfexNebuampulSpirocortS 1320CortiventRhinocort AquaEntocortMicronylBudesonPulmaxanPrederidInflammidePulmicortDemotestNohalonBudamax(11beta,16alpha)-16,17-(Butylidenebis(oxy))-11,21-dihydroxypregna-1,4-diene-3,20-dionebudesonide

IUPAC传统名

budesonide (1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-propyl-5,7-dioxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosa-14,17-dien-16-one (1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-propyl-5,7-dioxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-14,17-dien-16-one

IUPAC标准名

(1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-propyl-5,7-dioxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosa-14,17-dien-16-one (1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-propyl-5,7-dioxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosa-14,17-dien-16-one

国际非专利药品(INN)

budesonide

名称和标识

数据登录号

化合物性质

安全信息

德国WGK号

RTECS编号

TU3723000

个人保护装置

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

MSDS下载

下载链接

-20°C Freezer

药理学性质

相关基因信息

human ... IFNG(3458), IL5(3567)rat ... Nr3c1(24413)

生物活性机理

Glucocorticoid steroid

化合物性质

分子相关蛋白质

暂无数据

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分子图谱

暂无数据

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描述信息

Sigma Aldrich

B7777

Biochem/physiol Actions
Budesonide is a second generation glucocorticoid with low systemic absorption. It is used as an anti-inflammatory agent in the treatment of asthma, rhinitis, and inflammatory bowel disease. It inhibits the expression of chemokine mRNA and production of eotaxin and RANTES protein in primary human bronchial epithelial cells. Budesonide is currently in clinical trials for the prevention of lung cancer. It shows inhibitory effects on benzo[a]pyrene-induced carcinogenesis of the lung in mice.

PHR1178

General description
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34.
Other Notes
Values of analytes vary lot to lot.
Biochem/physiol Actions
Budesonide is a second generation glucocorticoid with low systemic absorption. It is used as an anti-inflammatory agent in the treatment of asthma, rhinitis, and inflammatory bowel disease. It inhibits the expression of chemokine mRNA and production of eotaxin and RANTES protein in primary human bronchial epithelial cells. Budesonide is currently in clinical trials for the prevention of lung cancer. It shows inhibitory effects on benzo[a]pyrene-induced carcinogenesis of the lung in mice.

TRC

B689490

A non-halogenated glucocorticoid related to triamcinolone hexacetonide. Used as an antiinflammatory agent.

ChEBI

CHEBI:3207

A glucocorticoid steroid having a highly oxygenated pregna-1,4-diene structure. It is used mainly in the treatment of asthma and non-infectious rhinitis and for treatment and prevention of nasal polyposis.

描述信息

参考文献

PubChem文献

数据源提供

• Clissold, S.P., et al.: Drugs, 28, 485 (1979)

• Ryrfeldt., A., et a.: J. Steroid Biochem., 10, 317 (1979)

• Roth, G., et al.: J. Pharm. Sci., 69, 766 (1979)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 1034

• Spencer, C.M. et al., Drugs, 1995, 50, 854, (rev, pharmacol)

• Hvizdos, K.M. et al., Drugs, 2000, 60, 1141-1178, (rev)

• Clissold, S.P. et al., Drugs, 1984, 28, 485; 1992, 44, 375, (rev)

• Albertsson, J. et al., Acta Cryst. B, 1978, 34, 3027-3036, (cryst struct)

• Brattsand, R. et al., J. Steroid Biochem., 1982, 16, 779, (pharmacol)

• Thalen, A. et al., Acta Pharm. Suec., 1984, 21, 109; 145; 1987, 24, 97, (synth, pmr)

• Gauvreau, G.M. et al., Am. J. Resp. Crit. Care Med., 1996, 154, 1267, (pharmacol)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, BOM520

• McGavin, J.R. et al., Drugs, 2001, 61, 71-78, (rev)

• Wikby, A. et al., J. Chromatogr., 1978, 157, 65

• Thalen, A. et al., Arzneim.-Forsch., 1979, 29, 1687, (synth, pharmacol)

• Ryrfeldt, A. et al., Biochem. Pharmacol., 1989, 38, 17-22, (pharmacol)

• Korn, S.H. et al., Am. J. Resp. Crit. Care Med., 1997, 155, 1117, (pharmacol)

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

别名

IUPAC传统名

IUPAC标准名

国际非专利药品(INN)

budesonide

描述信息

Sigma Aldrich

B7777

PHR1178

TRC

B689490

A non-halogenated glucocorticoid related to triamcinolone hexacetonide. Used as an antiinflammatory agent.

ChEBI

CHEBI:3207

参考文献

PubChem文献

数据源提供

• Clissold, S.P., et al.: Drugs, 28, 485 (1979)

• Ryrfeldt., A., et a.: J. Steroid Biochem., 10, 317 (1979)

• Roth, G., et al.: J. Pharm. Sci., 69, 766 (1979)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 1034

• Spencer, C.M. et al., Drugs, 1995, 50, 854, (rev, pharmacol)

• Hvizdos, K.M. et al., Drugs, 2000, 60, 1141-1178, (rev)

• Clissold, S.P. et al., Drugs, 1984, 28, 485; 1992, 44, 375, (rev)

• Albertsson, J. et al., Acta Cryst. B, 1978, 34, 3027-3036, (cryst struct)

• Brattsand, R. et al., J. Steroid Biochem., 1982, 16, 779, (pharmacol)

• Thalen, A. et al., Acta Pharm. Suec., 1984, 21, 109; 145; 1987, 24, 97, (synth, pmr)

• Gauvreau, G.M. et al., Am. J. Resp. Crit. Care Med., 1996, 154, 1267, (pharmacol)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, BOM520

• McGavin, J.R. et al., Drugs, 2001, 61, 71-78, (rev)

• Wikby, A. et al., J. Chromatogr., 1978, 157, 65

• Thalen, A. et al., Arzneim.-Forsch., 1979, 29, 1687, (synth, pharmacol)

• Ryrfeldt, A. et al., Biochem. Pharmacol., 1989, 38, 17-22, (pharmacol)

• Korn, S.H. et al., Am. J. Resp. Crit. Care Med., 1997, 155, 1117, (pharmacol)

生物活性

PubChem BioAssay

化合物性质

安全信息

德国WGK号

RTECS编号

TU3723000

个人保护装置

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

MSDS下载

下载链接

-20°C Freezer

药理学性质

化合物信息

ID:132753